Frank Fillmann: How I Boosted Revenue by $500M at Salesforce; Tips for Hiring Salespeople | E992

Frank Fillmann is CRO/Country Leader Australia for Salesforce where he is responsible for responsible for the overall strategy, execution, success, and growth of the $1B+ Australian market across all industries. Prior to Salesforce, Frank was SVP/GM @ Tableau where he was responsible for the strategy, execution, and growth of Tableau's Top Accounts. Over the last 10 years at Salesforce, Frank's accomplishments include $500M+ new revenue closed in 5 years and $1B+ revenue managed. As a result, Frank has been awarded #1 Sales VP of the Year, North America, 3 times! Huge thanks to Zhenya Loginov @ Miro for the intro to Frank today. _______________________________________________ Timestamps: 0:00 How did Frank get into sales? 3:54 How do you define a sales playbook? 8:42 How to assemble a top sales team? 12:37 Advice on Hiring Sales Reps 16:38 How to Negotiate a Sales Deal 22:08 Hiring Mistakes 28:35 Sales Rep Onboarding 33:49 How to Convert on Sales 38:30 Has consumer psychology changed? 43:26 How to Do Weekly Reviews 55:07 Quick Fire Round _______________________________________________ Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Frank Fillmann on Twitter: https://twitter.com/FillmannSFDC Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact _______________________________________________ #FrankFillman #Salesforce #HarryStebbings #SalesLeader #salesrep

Frank FillmannguestHarry Stebbingshost

Mar 22, 20231h 1mWatch on YouTube ↗

EVERY SPOKEN WORD

140 min read · 27,939 words

0:00 – 3:54
How did Frank get into sales?
1. FFFrank Fillmann
  ... what you find is the best people, they wanna teach. They're proud of their craft, they're proud of what they tried and worked. They wanna help the new gal or the new guy. (instrumental music plays)
2. HSHarry Stebbings
  Frank, let's do this, my friend. I've been excited for this one. We had such a good chat beforehand, and I was like, "Shit, I wish we were recording this chat." But thank you-
3. FFFrank Fillmann
  Yeah.
4. HSHarry Stebbings
  ... so much for joining me today.
5. FFFrank Fillmann
  Yeah, great to be here, Harry. Thanks for having me.
6. HSHarry Stebbings
  Not at all. And I said excited, and Zhenya said the most wonderful things. So I wanna start with a little bit on you. You've run some of the most incredible sales orgs. What was the entry into sales for you, Frank?
7. FFFrank Fillmann
  Well, look, I knew I wanted to be in sales straightaway. In college, I worked for a company selling knives in people's homes. Like, the opposite of the job you'd ever go for. I ended up running, uh, an office as a college student. I was 20 years old. I had 75 people working for me in Palm Beach, Florida. It was like getting a PhD in sales. So in undergrad, I'm in finance. It's an overloaded, uh, degree. Everyone's getting it. So I started to pick up some programming classes just to try to find some separation, and then IBM picked me up. They love the intersection of, like, you know, sales and programming. And I, I tell you one thing, as soon as I got to sales training, I realized most people didn't have any proper sales experience, and I was really excited that I had the hustle and grind of that, of that experience. Um, and then my first role at IBM was a competitive sales rep. So every account I talked to didn't wanna talk to me. So you get to kinda have this, like, bulletproof skin on you, which is a really, really great way to get into sales.
8. HSHarry Stebbings
  If only I had that in dating. (laughs) Um ... (laughs)
9. FFFrank Fillmann
  (laughs)
10. HSHarry Stebbings
  Um, I wanted to start, though ... And again-
11. FFFrank Fillmann
  (clears throat)
12. HSHarry Stebbings
  ... we said, uh, we said off schedule. I'm going straight for it. You said-
13. FFFrank Fillmann
  All right.
14. HSHarry Stebbings
  ... it was like a PhD in sales.
15. FFFrank Fillmann
  Yeah.
16. HSHarry Stebbings
  What did you learn in that PhD of sales very early on?
17. FFFrank Fillmann
  Uh, I th- if, if I were to stack rank, uh, recruiting, like the art and science of recruiting, a big part of it is how do you recruit a college student to, to go sell knives? You sell them to your mom, your aunt, their friend, and then at some point they end up fizzling out. But the, the ability to, to recruit people to go do it, if you can recruit good people, uh, you're gonna have a lot of success. And that, that's carried on with me my entire career, which is if I get the best people and I treat them great, by definition they hit their goals, I'm hitting my goals, and the company's happy. So I think, like, the idea of recruiting the best people, and it stuck with me. And then I was an intern, uh, for a recruiting firm, and I enjoyed that a lot. So it's like, that's kind of the bedrock of my whole approach as a sales leader.
18. HSHarry Stebbings
  When we chatted before, you said how you handle tragedy defines you. And I didn't know whether it was okay for me to ask this, but can you unpack-
19. FFFrank Fillmann
  (laughs)
20. HSHarry Stebbings
  ... this for me? And I, I don't know, I, I-
21. FFFrank Fillmann
  We're going, we're going deep. We're going right in.
22. HSHarry Stebbings
  I, I, I, I caviated with it. I don't know if it's okay, but I'm going to anyway. Uh, can you unpack this for me and how you feel on this one?
23. FFFrank Fillmann
  Uh, like, it's about resistance and persistence. I think, you know, my job every day is to solve problems, and I think i- if you, if you have a problem with a problem, you're not gonna persevere. If you're okay tackling something that's super difficult, how you respond to that is gonna help define you. So, like, for me personally, when I was a kid, my father passed away when I was eight. My mom remarried. I picked up an incredible stepfather, and then years later my brother passed when I was 30. But what it does is it makes you really grateful for what you do have, to look for the positive, but it always kind of produced a chip on my shoulder and a feeling of being unstoppable. And it's like, "Hey, I made it through that. Let's go." And that's just carried, carried on with me through my professional career.
24. HSHarry Stebbings
  Can I ask, has it ever got you in trouble?
25. FFFrank Fillmann
  You know, I, I don't know if I have a, a silver bullet on that one, but I do think that it, it creates a bold mindset and encourages you to go for jobs, for example, that you're unqualified for or go for deals that you're not in a position to win. But I think, like, the best teams take three-point shots, and it encourages you to take three-point shots. So yeah, you're gonna take more risks. I, I would argue the outcome is gonna be significantly better than if you have a more conservative mindset in your career. So I think it just encourages a lot of, uh, risk-taking.
26. HSHarry Stebbings
  Boom. We've gone for an early sports analogy. Good to, good to get the different demographics in there, Frank. Well done. Um, I wanna start, though, on one of my favorites 'cause I, I go back and forth on this. People tell me I'm wrong. Uh, people tell me I'm right. Um,
3:54 – 8:42
How do you define a sales playbook?
1. HSHarry Stebbings
  I wanna first understand, how do you define a sales playbook?
2. FFFrank Fillmann
  Uh, repeatable and relevant maybe, if I'm just gonna, like, boil it down. There's a lot of process and MBA words that, that get lost in there sometimes. Repeatable and relevant. So I think first it's client relevance. So clients don't care about you, your gear, your product, your organiza- ... they care about them, their metrics, their firm. And so it's gotta be client-oriented. And then for the rep, it's really hard to ramp in a new firm. Like, probably 50% of reps out there, they're something new. It's a new company. It's a new team. It's a new client. It's a new industry. And so it takes six to 12 months to ramp up. If you can have something that's super relevant, it allows the client to get in- uh, immediate interest in the firm, and it allows the rep to, um, to ramp way faster. So, like, for me, I always start with the money and I work backward, and I focus on TAM, and then I start to build the playbook back from there. So at least I know if I'm on a treasure hunt and I've got a shovel and we've got people digging, are they digging in the right spot? And I think that's the question that a lot of, um, sales teams miss. They find it later in the year when it's a bit too late. That make sense?
3. HSHarry Stebbings
  I, uh ... Do you know what? I would love to actually just dig in there so I understand. So you said you start with the money and you work back from there.
4. FFFrank Fillmann
  Mm-hmm.
5. HSHarry Stebbings
  I'm a founder. Help me out. Uh, what do I do, and what did you mean by that?
6. FFFrank Fillmann
  All right. So I, a lot of it, I kind of picked up from Geoffrey Moore. He's got some really great material, and I made it mine over time. I think of TAM, it's like there's three elements to it. It's either, um, near or far, right? It's either big or small, and it's either known or unknown. And so it ... That might be like overly simple, but let's, let's break that down. It's either near or far. So I'm either gonna go on a, on a 12, 18-month sales cycle for a larger deal, or there's-
7. HSHarry Stebbings
  Mm-hmm.
8. FFFrank Fillmann
  ... some create and close. Customer needs something, and I'm gonna go sell it to them. It's either big or small in the sense that I'm either gonna take down something that helps my quarter, or am I gonna have a great year, I probably need to go for a transformational deal that might take er- a year or two. And I wanna prioritize and run an and business where I'm, at all times, going for something big, but I'm chipping away along because, you know, you can't always count on a big deal hitting. And the third part is the part that I never hear people talk about, and it drives me kind of nuts, which is it's either known or unknown. So, like, when Steve Jobs creates the, uh, the iPhone, goes out and does the keynote, no one ever knew they had it, and then they had to immediately have what, what he offered. And so it's about identifying problems a customer has that they don't know how to solve, creating a vision, and then encouraging them that you have an opportunity to solve that problem for them.And now you're hunting for a way larger pot of money, and you're actually aligned to what they're solving for, and you immediately differentiate. 'Cause then it's not you versus a competitor. You're the only one that's gonna solve it because you actually uncovered the opportunity for them, and you're bringing them along in a journey and building a vision. And I think that kind of goes back to the iPhone analogy of-
9. HSHarry Stebbings
  (laughs)
10. FFFrank Fillmann
  ... I didn't know I need it, and now I have, I can't live without it.
11. HSHarry Stebbings
  Do you have more patience with your sales team for that unknown element? Because you're also then engaging in a process of customer education, which is just traditionally another three to six months at least. Do you have more patience with that, and how do you think about the customer education as an additional challenge to, "Oh, I get it. I'm replacing something on my budget"?
12. FFFrank Fillmann
  Yeah, so I think, like when I think about, like an industry playbook, right, what I do is... Think about the first quarter as a sales, the sales rep. The first thing that you're asked to do is create an account plan. And that's good. It gets you organized. It gets the whole squad and team organized. I would argue that you wanna have an account hypothesis, and you wanna go back and finish that in Q1. So let's, let's like, let's take this apart piece by piece. First, you wanna identify where the TAM is. Where is everyone gonna mobilize and drive an AND business, right? So where are the dollars? Known, unknown, big, small, near, far. From there, then you wanna have a set of industry, um, sort of assets. So-
13. HSHarry Stebbings
  Right.
14. FFFrank Fillmann
  ... if you wanna drive client relevance, um, and you're gonna show up to an insurance firm and you're gonna work with, uh, like an insurance claims adjuster, they don't wanna see a demo of technology. They wanna know, how do you make the life of an, a claims adjuster easier? How do you get to the scene of the accident faster? How do you detect fraud? How do you ensure payment comes faster? So tran- like Rosetta Stoning everything from technology into the use case and the persona of the person, now, boom, you have an immediate set of client relevance where they go, "Wow, this person really understands my industry." And on the, on the rep side, they're not thinking, uh, so much about the technology. They're immediately identifying, is there a problem? Can I solve it? And then you're s- you're, you're ramping them in weeks instead of months and quarters, and now you jump to stage two in the sales process. So the, the funny thing is if you identify the TAM, and you create a vision, and you put an industry lens on it, the client gets engaged faster and the rep gets to go a lot faster. It actually compresses the sales cycle. And now you're finding where the dollars are in April, May, or June, not in September or October. You actually have a shot at a good year.
15. HSHarry Stebbings
  So I totally get you. What y- re- is required there is a specialization of sales teams, the verticalization into-
16. FFFrank Fillmann
  Uh-huh.
17. HSHarry Stebbings
  ... industry-specific so they are
8:42 – 12:37
How to assemble a top sales team?
1. HSHarry Stebbings
  able to get up to speed with the customer, the customer problems, demands. How do you think about advising founders on how to specialize sales teams? When's enough customer demand? And if you were them, w- what would you advise them?
2. FFFrank Fillmann
  Yeah, I think it's about, you know, like assembling a good team is really, really hard, like, you know, chemistry and talent, and is this person with this experience gonna do really well? So you asked the word patience. Yeah, that's a big part of it, and, like, stepping them through it, working with them. But I think the fastest and easiest way to do it is let's say you're gonna have an established team that has two or three people in it. You're gonna get someone up front leading like the quarterback that owns the whole process that's been there, done that. You're gonna take the high potentials, put 'em inside that team. And then over time, they're naturally gonna learn that process because they're following the leader, and they're gonna get there a whole lot faster. So doing it one by one as a sales leader would be really hard to like literally teach every seller. But if you selectively build teams in the right way, then you're having the team teach the team. And that starts to drive scalability and repeatability, and you're not doing everything yourself, right? So I think that's the way that, that, that you do that at scale. And also if you get really good people that care about each other and they're competitive, even if they're not on the same team, they wanna help each other, and you wanna reward that and incent that and ask people to step up and help you, what, what you find is the best people, they wanna teach. Like they're proud of their craft. They're proud of what they tried and worked. They wanna help the new gal or the new guy.
3. HSHarry Stebbings
  Can I ask, do you think that you should hire two reps at the same time? Jason Lamkin always says that you need to understand, like y- you need to have two at the same time. Otherwise, it could just be a shit rep.
4. FFFrank Fillmann
  Um.
5. HSHarry Stebbings
  I often hear from ... Is that true?
6. FFFrank Fillmann
  I don't know. It's like, uh, it's like a, uh, it's a... Uh, I guess we go back to the football analogy. Do you have like two quarterbacks that compete every... I, here's a challenge. If you want the environment where people perform at their best, you need safety. If you want safety, they have to know that you're trusting them, that you've got their back. And if you have two different people kind of competing in the same environment, I don't know if that creates the right environment. I would prefer to go all in and have their back. And if need be, I'll go on sales calls. I'll do all the work with them until they're ready to go out on their own. And that takes a lot of effort. But if you get the right person with the right potential, absolutely I'll invest in that person for a few quarters or a year, and then they're off on their own. So I- I- I would probably just go with one. That's my, that's just my gut.
7. HSHarry Stebbings
  That is fascinating. (laughs) You're like, "What the fuck, Harry?" You sent the schedule-
8. FFFrank Fillmann
  (laughs)
9. HSHarry Stebbings
  ... and you're like, "Yeah, whatever."
10. FFFrank Fillmann
  (laughs)
11. HSHarry Stebbings
  (laughs) Um, but you see why I was like, don't bother preparing.
12. FFFrank Fillmann
  Yeah.
13. HSHarry Stebbings
  Um, it's fascinating, you said about safety there, though. Because especially in sales, I get it, but you also want a bit of, well, a lot of healthy competition. You want real quarters-ending efficiency, drive, urgency. How do you create safety with a little bit of fear of not hitting targets?
14. FFFrank Fillmann
  Look, if you hire the right people that are, um, that are just super competitive, right? It's like athletes on the field. Y- you don't have to worry about that. Like they're, they have the inner drive and the competitiveness that's gonna far exceed any pressure that you could ever apply, full stop. That's just the way that I operate. I think it goes back to some of the things we started this conversation with. And so like for me, if you get the right people involved, a lot of those problems go away. So how do you find fast horses? You hire a fast horse, and guess who they run with. They run with fast horses. Go find the best sales rep that you're gonna go find and see who they hang out with in the office and socially. They hang out with top performers. They hang out with winners. And so whenever you're in the interview cycle, the, the first question I always ask, full stop, is, "Hey, top rep, who are your friends, and should I have an opportunity to meet them?" Because they are always gonna know the best talent. And I think when you bring them in and you drive that competitiveness, all those problems go away.
15. HSHarry Stebbings
  How did I meet you, my friend?
16. NANarrator
  (laughs)
17. FFFrank Fillmann
  (laughs)
18. HSHarry Stebbings
  I went to Shenya and I said, "Who's the best sales rep?" And he was like, "Oh, Frank."
19. NANarrator
  (laughs)
20. HSHarry Stebbings
  Uh, so I know your game. I know your game. Um, but you mentioned about hiring many, many times. We're gonna get back to playbooks and accounts. But I just wanna touch on it 'cause we're so on it
12:37 – 16:38
Advice on Hiring Sales Reps
1. HSHarry Stebbings
  now. How do you advise me on the hiring process for sales reps? Uh, let's start there.
2. FFFrank Fillmann
  I think fit. It's like how do you, how do you buy a suit? Uh, it doesn't really matter, like, the color or the fa- It's like, does it fit you? Was it bespoke? Was it made for your frame, right? So for me, it depends on the account. And so you look at a spectrum of, like, SMB to strategic sales, the answer's gonna be wildly different. I'll probably talk about the enterprise component, which is top in a commercial to, to strategic. Uh, so for me, it's about fit. So if I've got, if I've got an account that has multiple reps on it, um, the team chemistry is really difficult, but I always want the closer up front, because they have to carry it all the way from one end of the field all the way down. But I'm also gonna wanna bring in, like, a visionary. Sometimes they're more academic, they're super right-brained, very creative. They can build a vision and bring the organization along. They may not be as comfortable closing. And then, and the third profile of, of people I wanna pick up is the person that wants to go hunt and take down every deal. Let's, like, see a bear, shoot a bear. That's on, that's on something that I was, like, super talented at. I, I wanted to go kind of big game hunting. But you, if you're gonna run an AND business, you need a collection of those different skills and you put 'em all together. So, like, I, uh, y- you wanna find those people, and then at a chemistry level figure out, can they work together or do you have two alphas? If you have two alphas, it's never gonna work. And so, like, uh, and I've s- and I've screwed this up a few times, by the way.
3. HSHarry Stebbings
  We're gonna... I, I wanna touch on how you screwed it up. But I just wanna stay on the hiring specifically. So when you're-
4. FFFrank Fillmann
  Yep.
5. HSHarry Stebbings
  ... interviewing reps, do you try and not box them, but put them in a bucket and understand, you're a visionary, you're a killer bear, shooter bear, you're a closer?
6. FFFrank Fillmann
  Yeah.
7. HSHarry Stebbings
  Like, how do you advise me on hiring these three different profiles?
8. FFFrank Fillmann
  Yeah, it's like, uh, if you ask someone what their passions are, um, what they're most proud of, like, what's a deal where, um, they create a demand that never existed before, you're, and someone's either gonna get excited and passionate or they're gonna look at you like you've got two heads. Uh, you ask those qualifying questions, it's very easy to determine, like, segmentation wise, where do they fit in? And b- uh, 'cause you always need people that are gonna go do create and close. That, that's required full stop for any software firm. But if you're gonna move into the enterprise and, and do material deals that are gonna break records, you've gotta have a closer that's super passionate. So I just ask those qualifying questions and people will, will make that answer super easy to follow.
9. HSHarry Stebbings
  You said create demand that's never existed before. When we chatted before, you said this was som- one of the most important skills you look for. Can you just explain what that means to me and, and how I should look for it?
10. FFFrank Fillmann
  Yeah, so when we talked about the TAM example where demand is known or unknown, and I think, like, how do you create money that doesn't exist? You go look at the demand that, uh, that's inbound, and then you look at the, the latent demand that doesn't exist. That's an immediate way to increase the TAM that you're pursuing without hiring any more people. And so, like, when I think of, um, creating demand that doesn't exist, and you ask someone that, what I mean by that is, what problems does a customer have that they don't understand how to solve where you've created an answer to them? So go back to, like, the Frank Slootman example, right, of he works with, he worked with different firms where he'd ask clients what they thought about the product and they were using it in very diverse ways that surprised the organization. So at a product level, they're like, "Hey, we didn't design it that way, but customers are using it here." Well, like, lean in on that and ask them, "Well, how are you using it and why are you using it that way?" You go back and align that to the long-range plans of the organization, chances are there's a big gap in execution where they've got a big vision and a big target and they don't know how to get there. So how do you take a malleable platform and create a vision around it that says, "Oh, you're trying to align and move up market. What if you had better insight into the customer profile that you're pursuing?" And then you align a malleable platform and create a solution that says, "We can help you get better visibility into how to pursue that." So you're chasing larger deals and you're moving up market to the enterprise segment, and now all of a sudden you're a consultant. And you're not starting with tech, you're ending with technology. So for me, it's like every conversation starts with through the lens of the customer and great empathy, what are they trying to do and then how do we reverse engineer the product to fit it? It never starts with product.
16:38 – 22:08
How to Negotiate a Sales Deal
1. FFFrank Fillmann
2. HSHarry Stebbings
  Talk to me about negotiation in that process. You know, people often think that that comes first. Where does negotiation sit in that process of, like, you know, customer discovery, customer understanding for you?
3. FFFrank Fillmann
  So I, I think the biggest mistake is when you just send a price over, right, and then you end up arguing about numbers. So you ever see this, you send a proposal, and whether it's, like, a percentage savings or the absolute number, it's, like, human nature in negotiation to, to look at that and then want that number to be smaller. And so sometimes you get lost on all the wrong details. So if it's me, my preference would always be start with a blank canvas, find your buyer, and spend some quality time. And I think you'd ask questions of her like this. Number one, how are you measured? What are the metrics that you as an organization, as an individual are measured by and at the organization level? And you start to really unpack how they define value and values and what their priorities are. And then you go, like, a level deeper. What's most important? Is it cash flow? Is it TCO? Is it year one fees? Is it exit fees? And you can start to kind of profile, like, what financial levers do you have to play with that matter to them? And I think, commensurately, you've got to be super transparent with your organization. Here's how we're measured. Here's how we report. These are the prioritized levers that we have. Here's what we want. And so if you do that and then you start to align on deal structure, right, um, whether it's, like, is it a flat or is it a ramp, um, w- when you start to, like, really categorize all the different ways to package a solution, if you do your job right and you're authentically looking for ways to create a win for them while being transparent about what a win for you looks like, then by the time they get the first offer, it's gonna land well because it's very predictable.
4. HSHarry Stebbings
  That's great.
5. FFFrank Fillmann
  And then when they counter or you counter, it should be very predictable 'cause they've already told you what they're interested in and so have you. And it takes some of, like, the gamesmanship out of it where you're just trying to find a win on both sides.And it's hard to do, but, uh, when you start with price, it's really hard to get there.
6. HSHarry Stebbings
  You said communicate about what a win looks like for you. I've had founders say to me before, "I never wanna tell the customer what a win is for me 'cause I, I almost want them to feel I'm, I'm in hardship almost. I don't want them to think that I'm profiting." Um, how does one communicate what a win is for them in a way that's beneficial for the progression of the deal?
7. FFFrank Fillmann
  Well, it's like, you know, we talked a little bit about what sales tactics have changed over the last 20 years. Protectionism. I think, like, things are a lot more transparent. Customers have access to all kinds of data about your organization, about products, about negotiation. So, like, the idea of being close then to, like, you have all the information and you don't wanna share it, that's just evolved. Like, we're 20 years past that. And so for me, it's about being really transparent. But i- if it starts with you, it, it's... I don't think it's really authentic. It's gotta always start with them. So, like, I was reading a book called The Go-Giver, and it's like, how do I serve, how do I serve the person I'm working with and s- and working for genuinely as the priority, and then you back into what's good for you? So I start with, what are your priorities? What... Like, what are the mistakes? What do you not wanna see? What's really gonna irritate you? Um, if you're gonna try to solve this internally, where are you gonna catch a lot of flack? And then I say, great, now that I understand this, here's how we are generally measured, and here's some overlap, and then what I wanna do im- immediately upfront here is say, like, one of the friction points that we could acknowledge, we're probably gonna bump heads here, so let's just identify it. We'll try to work through those with a very unique solution. A- and I think if you do that authentically, someone's gonna say, "All right, like, they're showing up, trying to help me out." Um, and, and I don't know that every negotiation starts that way, but the best ones I've been involved in start that way.
8. HSHarry Stebbings
  It's probably also one where they self-select. And what I mean by that is, like-
9. FFFrank Fillmann
  (laughs)
10. HSHarry Stebbings
  ... the ones who are willing to engage with those harder topics are ones who actually are closer to conversion versus the ones that actually will never convert. Do you know what I mean?
11. FFFrank Fillmann
  Yeah. Yeah, and you can, you can tell that immediately. You know, some people, they don't wanna share, and, and that's okay. Like, that... Uh, no negotiation's always gonna go flawlessly, and, and you're not always gonna get transparently b- transparency, but I try, and, and I become more predictable, and, uh, it takes some of the emotion out of it, I think.
12. HSHarry Stebbings
  So many people on the show have said before about the importance of, like, recording sales calls for training purposes. How do you think about the importance of that whilst also retaining the humanity and the, the truth elements, which often people will feel less comfortable sharing when there's a recording?
13. FFFrank Fillmann
  Uh, I guess that's probably predicated on the fact that we do a lot of video calls. I mean, here we are. You know, you're in London. I'm in the States. We're doing a video call. Um, I, I, I really miss face-to-face sales. I'm glad that we're getting back there, by the way. But, like, that's a, that's a different topic. Um, for me, I think, like, the feedback loop, which is, I think, where you're going, um, it's less about recording and dissecting. Um, it's also less about waiting a whole quarter and giving feedback, which I think it's really hard, and it never lands well. I, I like to do, like, an obsessive, in-the-trenches process with my team, where we spend a lot of time prepping, we do a lot of time role-playing. We go to the meeting together, and the first thing we do when, when we're done is we go debrief. And the first thing is like, uh, "All right, give me some criticism. What did I do wrong?" So it's not like me, as a leader, talking down to someone. Like, all of us have an opportunity to learn. And then it's like, "All right, we're all, we're all in this thing together," versus, like, you know, "How am I being evaluated or critiqued?" 'Cause, like, you go back to safety. If I feel like I'm being critiqued, I'm gonna get defensive, and I'm not gonna get the best output. So I don't like the formal process. I like just to say, like, "How do we get better at our craft, so next time it's gonna land even better," right?
22:08 – 28:35
Hiring Mistakes
1. FFFrank Fillmann
2. HSHarry Stebbings
  I, I totally get you. Speaking of kind of how you can improve, you mentioned before with, you know, the closers, the killer bear, shooter bear, um, and the visionary, uh, that you've made some mistakes. What are some of the glaring mistakes that you made there?
3. FFFrank Fillmann
  Yeah, I've, I've certainly, you know, over my whole career, um-
4. HSHarry Stebbings
  (laughs)
5. FFFrank Fillmann
  ... this goes back, this goes back to being 20 years old. Um, you know, hiring people, it's really, it's really hard as well. You know, some people are great interviewers, and, uh, you know... But then all those... Th- that doesn't always translate through. So I think for me, uh, I'd say the biggest mistake I've made was trying to team people together that were both alphas. And, and, like, I think being an alpha in sales is really, really good. You want the natural leader. But, um, if they do it at the expense of other people, and there's an ego involved, and then you have two of those together, it will crash and burn immediately. So, like, stylistically, that's where the, the hair on the back of my neck stands up, and I say, "I don't wanna go through that again." Um, and, and I wanna be able to pair that person with someone who might say, "You know what? I don't have as much at-bats. Like, I don't have the experience. Pair me with them, and they're gonna, they're gonna exponentially learn. They're gonna get three years of education in a year when they get paired up with the alpha." So it's healthy. It's just not healthy together. (laughs)
6. HSHarry Stebbings
  I, I, I totally get you in terms of not being healthy together. I'm thinking about, like, you know, high-alpha, high-ego people, and I think about very experienced and also very high potential when I hear that as a potential conflict. How... And this was actually from one of your friends, Matt. He said, "How do you rank high potential versus high experience on the spectrum of importance when hiring leaders?"
7. FFFrank Fillmann
  Uh, so th- that's, that's an easy one for me. Um, it's always hypo, one, experience two. The- there's always an exception to that, though. I think when you have, like, a big, mature, uh, customer and a big brand with a lot of visibility, you'll always have to take experience first. You don't want someone learning on the job in a very high-profile environment, because then you might be setting them up for failure. And that's, like, not f- fair to them as a sales rep. So with the exception of that, I'll always hire for potential. Um, and, and I wanna take someone who's got, um, a tremendous amount of adaptability and, and, um, and future potential, give them a job they might be a year away from, watch them be a little bit nervous and stumble for a quarter. But what's gonna happen is they're gonna get there way faster. So I, I'll always go potential first.
8. HSHarry Stebbings
  I agree with you totally. My question is, what's a stumble, and what's a stumble too far?
9. FFFrank Fillmann
  Yeah, I think when you, um...It's almost like when you outsource to someone to say, "Hey, I think you're really good. You've got good potential. There's a big meeting coming up, you've got this." That's crazy. So like for me, what I wanna do, whether it's me or one of my leaders, it doesn't matter who in the stack does this, someone who's more experienced, get in the trenches with that person and say, "Look, you've never had a CEO meeting before. Let's figure out how they're gonna operate and run the meeting. First off, they might run the meeting and you're just gonna have to go along with it. So whatever you're gonna plan for, you can just toss right out the window." And you don't know that until you go through it. And so for me, it's like during the preparation and the role playing, um, having that senior leader step by step with them to say, "Here's an experience I went through," but also ideally you have a senior leader go with them on that meeting, and they play the role, right? So maybe they're teeing them up with a softball question that they can hit out of the park, or they're there in case it goes off the rails, they can hop in. But I think having sort of, like, someone riding shotgun with you in the car, uh, and then, and then giving the freedom to go take the wheel a little bit is really important. But, um, once you get through that handholding process, you get a few at bats, you'll find the rep's like, "I think I got this." And then you go, "Great, you've demonstrated the experience. Go." But I think if you start there, you're kind of leaving them out in the wind and that's not fair for them.
10. HSHarry Stebbings
  Can I ask, you know, I was thinking about high potential but maybe not quite there yet. O- One thing I- I do struggle with often in enterprises, like enterprise sales cycles are long and measuring rep effectiveness is naturally harder. How do you think about measuring rep effectiveness in strategic sales with much longer sales cycles?
11. FFFrank Fillmann
  Let's take two examples. One a- one example is you've got a big account that you're pursuing, um, and i- you've got two or three reps. The first thing I do is grab the hypo and put them inside of that organization, right? So they're, they're, they're teaming along with it. Uh, if not, I think there's a, there's a level of, uh, babysitting, and I say that as a positive term, not a negative term, where I'm gonna sit side by side with that rep and... So, like, a big part of my day is I clear two to three hours that I have no plans for specifically so a rep says, "Hey, I've got a big account meeting coming up and I feel stuck," or, "I have a, an account meeting coming up and I want you to join." I can immediately, and I will immediately clear my calendar and say, "Let's get in the, let's get in the trenches." So I'm literally personally teaching them and bringing them along, um, and never letting them out on their own until they're ready to go. So, like, that... And, and so there, I don't think there's any substitute for on, like, handholding on-the-ground training. And so the only way that you do that is personally getting involved, and so that's why we just run a super flat organization. I could care less what my title is or what yours is. We all have the client's interests in mind, let's get together and go. So like, "I'm a rep, put me to work," and that's my mentality, and I think the team appreciates that, um, y- you know, you're not sitting in the ivory tower, like, you're out there with them.
12. HSHarry Stebbings
  But six months in, I haven't closed a dollar. Are you going, "Shit, Harry's not great"?
13. FFFrank Fillmann
  Um-
14. HSHarry Stebbings
  How do we know whether I'm good or not? 'Cause the sales cycles are so long.
15. FFFrank Fillmann
  Yeah, I guess, you know, it's a really good point, especially, you know, if you think about what the... You know, I wonder what the enter- enterprise sales cycle is. Probably, what, 12 months?
16. HSHarry Stebbings
  12 to 18.
17. FFFrank Fillmann
  6 to 24. 12 to 18 months. Um, I, I think, like, first off, you gotta set them up for success. If it's a big account and, and they're gonna do a big buy every couple of years, you can cyclically understand what the odds are of that person coming in. And I think if it's a one to two year sale cycle and you have someone new, maybe it's more of an 18 to 24 month sales cycle. So if you put them in with the hope that they're gonna land it in the first year, you're setting them up for failure. So I think you can prohibit some of that. Um, so I think you either give that account to them in year two, um, or you don't give that account to them at all. So I think, I think that what... I, I think measuring the effectiveness along the way is predicated on setting them up for success at the beginning of the year. But I also think that if you're a team and you're going on sales calls together, you know if they're doing the job or not, right? Like, there's no escape from, from that if you're actually giving them ample time to prep, to go on a meeting with them and to debrief. Like, your job as a leader is to spot that. It shouldn't be hard.
18. HSHarry Stebbings
  You said about setting them
28:35 – 33:49
Sales Rep Onboarding
1. HSHarry Stebbings
  up for success there. It's one thing that I find a lot of founders really struggle wi- with, which is, like, new rep onboarding, especially when they haven't really done it before. I'm joining your team today. What does my rep onboarding look like for you in an ideal fashion?
2. FFFrank Fillmann
  It's a little bit contrarian, and we talk- we've talked about a couple pieces, but, like, let's take Humpty Dumpty apart and look at Q1. The first thing I wanna do is I wanna build, uh, an account plan, but let's call that a hypothesis. That way we're immediately starting to take action, we're mobilizing both the sales team and the extended team. But immediately from there I'm gonna pause and say, "Great, let's go do the TAM analysis," and we've talked about that. We broke that down already. Like, where's the money? Where's the opportunity? From there, I'm then gonna align the sales process to where that revenue opportunity is. And if I'm doing my job right, I'm running an and business. I'm gonna pick off some of the small deals along the way, I'm gonna go for the big bat, and ideally there's a path to hit my quota both ways. So at the end of the year if I intersect and both hit, I'm gonna have a monster year. If one of the two hit, I'm gonna have a pretty good year. From there, the third step is we're gonna create, like, an industry playbook. I think playbook, it's sort of like this ambiguous term, so I don't mean like the PhD version of a playbook. What I mean is I'm a sales rep, I'm about to go on a call. Um, what I don't want to do is go prepare all the materials, I just wanna go out and make the sales call. So let's say you're walking out... Like, I've got four kids. So one of my kids is walking out, uh, in the morning to go to school. They don't wanna prepare their meal, they don't wanna pack the lunch. They wanna get the Capri Sun, the apple, the sandwich, put it in a paper bag, go out and they wanna eat. And so if I'm a new rep, I don't wanna go figure out everything about my product, everything about the industry and the customer and go build this whole thing that, by the way, all of their peers did.
3. HSHarry Stebbings
  Yeah.
4. FFFrank Fillmann
  Like, you gotta drive a level of repeatability. So what we do is we build industry playbooks. So if we're covering an insurance company and the insurance adjuster, that example we used earlier, we're gonna put together five slides. In the industry, with 80% accuracy, these are the problems they're faced with. These are the solutions where we fit. These are examples where it works. These are the outcomes of customers who have solved the problem with our technology and the outcome of it. And then here's a success plan to get there.And what it does is, it doesn't replace discovery but it gives them a framework to say with 80% accuracy you're probably gonna land well if you use this process.
5. HSHarry Stebbings
  Yeah.
6. FFFrank Fillmann
  So number, number one, you know where the money is. You, you're making the right sales call, you're talking to the right person, you're pursuing the right opportunity. And when you show up, you're talking the love language of the client. Immediately you're relevant, immediately you get ramped and you know you've qualified out the opportunity isn't worth pursuing or it is, and you've jumped along in the sales cycle. Now you race back at the end of the quarter, and you rebuild your top account, uh, playbook. You rebuild your count- account plan, and then now you've got three quarters to find and close the revenue, versus finding out in Q2 or Q3 and now you, now you're in a race to the end of the year. And I think when you're in a race, it's really hard to perform. So how do you, how do you, like, ramp them and give them some space to run? That's how you do it. So I think what you do in Q1 completely determines the success of your year.
7. HSHarry Stebbings
  How do you create the slides? I know it sounds stupid, but is this like Google Slides? And then how do you share them across the team? 'Cause I love that. In terms of a way to ram people efficiently, it's fantastic. But what do you use in practice?
8. FFFrank Fillmann
  Um, so, so first off, I drive people crazy. So like I did this personality test a few years ago with my coach and what I found out is I'm, I'm off, I'm, I'm full-blown left brain and right brain at the same time. N- normally someone's very dominant on one side or the other and I have both, which means I drive people crazy. I have a lot of ideas that I want to execute. And so in the absence of focus, I'm everywhere. Like, I'm the absent-minded professor. And so what I have to do is get really, really focused on, um, what's the idea, how do we prioritize, stay on message and then execute with focus. So that's one of those learnings as a leader that I've, that I've tried to get better at over time. So a big part of what we do as a team is we wanna bring the creative energy and we wanna bring the right people, not to conform to our group, but bring in a lot of diverse set of, uh, of experiences and personalities and, and perspectives. So we do, like, a lot of right brain creative whiteboard-y stuff to, to come together on, "Hey, we tried these five different points with a customer. Three failed, two worked. Let's go in on those two." So it's very much trial and error, so, like, mistakes, very encouraged in our group. So if you screwed up and the client meeting went poorly, great. Like tell us so we don't go do that again. And so whenever we build the playbook, it'll end up in slides, but the way that we build it, we call it, you know, by the people, for the people. I'll literally bring in my industry team, my sales reps, my engineers, me, and we'll sit down and say, "Let's bring together the last six months of learnings and let's go rebuild the industry playbook based on what's actually working, what's monetizable." And, and look, like, even with COVID, the world's changed a lot in two years. If you're not adapting your cycle, like, it's gonna be stale, so you have to do that. And then we put together five very simple, very, um, like, point and shoot slides that, like, a fifth grade, a fifth grader could read and understand. And then you take that and you say, "This isn't the end all, be all. It's a template. Make it yours." Like, make the questions yours, but let it inform the discovery so when you're asking questions, the buyer's like, "Wow, they did their homework. I appreciate that. I wanna lean in and help this person."
33:49 – 38:30
How to Convert on Sales
1. HSHarry Stebbings
  I love that as a first step. You can tell that the buy would resonate when someone comes in prepped. We're moving to the end of the cycle. People are slow to convert. We both know this.
2. FFFrank Fillmann
  (laughs)
3. HSHarry Stebbings
  How do you create urgency in a sales cycle where there might not be urgency on the buy side?
4. FFFrank Fillmann
  Yeah. I think, um, I think if it starts with you as an organization and what's in the interest of the firm trying to sell it, I think it's go- uh, they're gonna see through that. I don't think it's gonna work. I think it's gotta be to the lens of the client, like full stop. So let's take an example. I'm the customer, I'm trying to stand up a new program, um, that's always gonna require people, process and tech, but tech's gotta enable something to get stood up and they go, "Hey, we have to go live next July. We don't need it yet. This is Q4. Like, come back in six months." Well, we go, "Great. You need it in July. When do you do user testing?" "Well, we're gonna do user testing in May." "So when do you need to adminis- minister the technology?" "Well, we'd probably do that in February or March." "Great. So when would you need to stand up to technology and have a contract in place?" "Well, maybe, like, January, February." And if you actually take that very logical objection of, not now, we're six months away, and you programmatically work back and you create a success plan based on their timeline, chances are they need to get going right now. But, like, you can't make the assumption they understand it 'cause this is what your job is, not theirs. So you've gotta build out this here's the success plan over the next six months and requires you to start now, and by the way, take advantage of your enterprise buying power and our fiscal year end to get the best technology financial deal that aligns to your success. And if you, if you focus on their success and their outcomes and a faster ROI table, then tho- they might believe you and wanna lean in and buy earlier, but I think if you do it based on what's in the best interest of the firm that you're representing, I don't know that it's gonna land as well.
5. HSHarry Stebbings
  So the biggest reason I'm on many boards, the biggest reason for companies not hitting targets is, hey, they loved it, they loved it, really, they're super keen, but it just slipped into next quarter. That happens all the time. What would you say if you were on the board of that enterprise sales company?
6. FFFrank Fillmann
  Yeah, I'd say two things. Number one, in this environment I- the first question is have you adapted a lens on the buying cycle for the CFO to review it? Like, is there a, is there a quant element of value in- inside the proposal that a CFO who's never met with you, who will never meet with you, who's never used the technology could look at, understand and say, "I like what I'm seeing financially." Because that's, like, the new... We have a new buyer in the cycle that was never there, that's the CFO, and they're props- probably gonna get personally involved in an enterprise deal that's material, and if you haven't evaluated that and, and haven't, like, role-played that, then you're gonna fail. That's number one.
7. HSHarry Stebbings
  So sorry, what, what do we... Sorry, just so we do it at a time.
8. FFFrank Fillmann
  Yeah.
9. HSHarry Stebbings
  What do we need to do there? Like, create a doc specially for the CFO that says, "I love you, CFO." You know?
10. FFFrank Fillmann
  Yeah. No, that's, that's a good one. So I... Here's the way I would do it. You know, after you go through what are your value and values? What is the problem we're solving? What is the solution? What is the success and roadmap?... what is the value, and then what is the pricing, and what is the next step. Like, that's the logical process. Before you get to pricing is the value, and I think the value slide has a few different pieces to it. A- and yeah, like, if you're being, like, really specific, Harry, it's a Google Slide, right? Um, but you've gotta think through a few lenses. One is the economic value of buying. Are they getting a good deal? Are they avoiding cost? Are they saving money? And part of that is fee reduction, right, as an example. Another part is how do you consolidate and do cost reduction in this cycle where, hey, I have 15 vendors. How do I standardize on one? So cost reduction or cost savings has a lot of different, uh, pieces. The other piece of that is value. How do they drive value to the organization? Now if you've done your homework right and you've asked the questions, you know how they're measured, you've read the 10-K, you know what, um, what is important to that organization financially, and you've built a value framework that either says time to value is faster, R- ROI is there, uh, this is gonna drive shareholder value in these meaningful ways. And then I think the qualitative value, which I don't think a CFO's really gonna buy into, is-
11. HSHarry Stebbings
  Mm-hmm.
12. FFFrank Fillmann
  ... as a side benefit, you might raise sales. As a side benefit, you might have happier people. As a side benefit, you might reduce your carbon footprint because you've moved to the cloud. Now these are things that, like, a CFO would look at and say, first, they've done their homework. Second, my team has validated this. Third, now I wanna lean in and not object to it but maybe ask some questions. You're avoiding all of these inhibitors to a sale and maybe, maybe enlisting the support of someone that only care about is financial value. So if you skip it, I think it's, it's gonna be problematic to a sale cycle.
13. HSHarry Stebbings
  Do you
38:30 – 43:26
Has consumer psychology changed?
1. HSHarry Stebbings
  notice the language and the priorities of your buyers is changing in a new economic cycle? Whereas before they would care about ESG, they would care about gr- team collaboration and m- morale, and now it's like save me fucking dollars.
2. FFFrank Fillmann
  Yeah, it's, you know, it's interesting and, and I think, like, in any, um, in any cycle like this, and who knows how long it works, but we saw it in 2008, 2009. It's like, we've all been through this before. Absolutely, they wanna do more with less. Cost matters. Efficiency matters. And I think, like, this is when you're gonna get more financial buyers as part of the process. If you haven't organized your story around these new evolving priorities, shame on you, because their, like, their priorities have shifted. Your messaging and your value prop should absolutely be shifting in alignment with them, or you're gonna be irrelevant. And that's, th- then that's your fault.
3. HSHarry Stebbings
  I, I totally agree with you. The other question I have to ask, kind of given the, the very influx times, is really planning and forecasting, who fucking knows? That's why VCs aren't investing is 'cause no one wants to catch a falling knife. As a sales leader today, and I know it's very different for different segments, different j- go-to-market motions, but just for you, how do you think about forecasting where it's like, I don't know, there might be war, there might be hyperinflation, Biden re- might remember the day of the week, might not, uh, England may have a new prime minister tomorrow. Like, you know, how do you plan with such uncertainty?
4. FFFrank Fillmann
  Um, I think there's three pieces. Uh, y- one is you need, like, a, a, a very left brain math model that looks at all the historicals and says, you know, like, on an average ratio, this is our close rate, the pipe... Like, there's basic math that everyone should include as part of the cycle. Number two, everyone should be layering in AI to be able to, at a predictable level, at s- if you're a big organization, at scale, understand trends, because if everyone else in the organization is seeing a downfall in forecast, technology's gonna pick that up. Where if you've got a team of five people in a small territory, you're not. Like, you don't have a chance to pattern match 'cause you're not talking to a thousand reps, but the tool is. The third is I think you need to have, like, a right brain qualitative review of everything in your cycle. So what we do is we do a bottoms up, deal-by-deal analysis, and then we go back and compare it to the math model and whatever AI says, and, and we go, do we believe the truth of this? And I think if you're really involved in your business, if you're, like, out talking to customers and listening to them and asking qualifying questions, i- i- I think between those three or four dynamics, you should be able to call your business. But I, I think when you look at the, The Wall Street Journal, you can, you can tell when there's gonna be more cost pressures. So, like, we spent a lot more time forecasting and, like, truing up and doing, like, checks and balances now, as you should in this cycle, um, so you're never gonna, like, remediate all of the, uh, the risk. But I tell you what you can do is you can microwave it a little bit and take it out of the cycle and have a more predictable forecast.
5. HSHarry Stebbings
  It's so funny. So then kind of about, kind of, you know, the, the reps. I, I, I remember before the show when we chatted, you said even the best sales leaders want to be super reps, and I thought it was kind of confusing 'cause I thought the point was that reps wanted to be sales leaders and sales leaders didn't wanna go back down to being super reps. So why do the best sales leaders want to be super reps, Frank?
6. FFFrank Fillmann
  Well, there's two kind of super reps, right? There's the good and the bad, right? So just go with me here. So I think, like, if you're a controller into leader where you've always gotta be, you know, the person in the meeting or, like, "Hey, I did this," or, you know, "I'm gonna get overly involved," or, "I'm gonna, like, micro this person," that's not great. Um, but, but I do think, like, i- if you wanna understand how to drive success in the field, I think if you look at your job as internal and, and the sales rep as external, and you're, and you're, uh, and you're too far removed from the customer, that's terrifying to me. So I wanna be, like, all of our big deals, we do a weekly review. Uh, full stop every single week. What are the biggest deals in the week or the quarter, the month, or the year? And what I'm gonna do is I'm gonna get really, really involved, and the second I see something go off the rails, great, I have a two-hour block in my calendar. Cancel whatever you got, let's get on the phone, and we're gonna spend time rebuilding your enti- entire value prop. And then next week, I wanna see how that goes. And so I think, like, that's, that's the way that, that I get sort of micro, but it's in the interest of the, of the rep. And the first question, the first question I ask on a big deal review is, "What's your goal, not your quota? What's your goal?"What do you need to be financially successful this year? Great. Now how do we get there? Here's this proposal. You're not gonna get there with this proposal. Let's work together to bridge the gap so you hit your goal. And I think if you do that authentically, you're helping that person and you're not being critical, you're not looking over the shoulder. You're just trying to drive increased odds of success. But in so doing, you've gotta be, like, really in there with the rep, right? So you gotta be like a leader and a sales rep. I don't... And you just have to be able to fluctuate back and forth.
7. HSHarry Stebbings
  You said
43:26 – 55:07
How to Do Weekly Reviews
1. HSHarry Stebbings
  about the weekly review there. I really wanna dig in on this.
2. FFFrank Fillmann
  Okay.
3. HSHarry Stebbings
  When do you do it? How long does it last? Who sets the agenda? Who's invited? Just walk me through it. Again, I'm an angel investment of yours. I have no idea about weekly reviews.
4. FFFrank Fillmann
  Yeah. So, you know, every team's probably dependent. I- I think if I were to, like, generalize, it's an hour and a half a week, right? Um, the first 30 minutes is freeform, which is, you know, maybe it's because there's an urgent deal and we just need to, like, pivot into whatever senior leadership might need that week, or I have, you know, a house on fire we need to solve. Great, let's identify it and swarm. Uh, the second hour is very structured, and it's a little bit more looking forward. So I might have an hour and broken into 20-minute slots, and I've got three reviews, right? Maybe that's this quarter or next quarter. And what they're gonna do, very pro- programmatically, is show me two slides. One is the why slide and one is the big deal review slide. In the why slide, what I'm gonna do is say, "I want you to tell me exactly through the lens of the CEO's long-range priorities..." Maybe it's a CIO or a CDO or a chief operating officer, but let's take the CEO for an example and say, "What are- what are their long-range plans?" And then you say, "Great, what's gonna inhibit them from hitting that? What would be the value of, of accomplishing those goals? How would you quantify the value of solving that problem?" And you kinda go left to right where what's important to them is paramount, and far off on the right, you know, if you have- if you use your binoculars, is the technology that solves the problem. But it forces the rep to think through the client problem through the lens of the customer, not the lens of product, right? And so it's gonna force to say, "If you're gonna build a vision or a story to solve a problem for them, let's start with what's important to them." Great news, it's a public firm. Grab their 10-K, do some discovery. This isn't hard. The second thing I'm gonna do is a big deal review template, which is gonna be a slide that's gonna tell me all the mechanics. Who are the players? What's the solution? What's the product? What are the needs? Who's involved? What's the next step? You get the point. And I can true up the right brain, artistic, industry-oriented lens of how do we solve a big, scary problem, and then you true that up with the fundamentals of what they're doing day-to-day in the field. And then the third component is I want the entire team on that call, the industry team, the value team, the solution team, and the sales management. And we don't go in, like, you know, picking away at this. We go in as peers saying, "How do we elevate our game?" And I think taking the fear out of that call and saying, like, "No one's judging. Come in with crappy ideas. Like, bring all of 'em." Um, where people genuinely know you're trying to help them hit their goal. You can drive criticism and provoke people in a really good, healthy, competitive way that elevates everyone's game.
5. HSHarry Stebbings
  You said about the variance of inputs there from your side, from the seller side.
6. FFFrank Fillmann
  Yeah.
7. HSHarry Stebbings
  In terms of buyer side, like multithreading... Brilliant word. I love how kind of intellectual it sounds. Um, but when we think about multithreading, often I hear this as well. We said about slipping deal cycles, like, "Ah, our champion left." Um, and you're like, "Well, build multiple champions." Um, how do you think about the right way to multithread, at what stage it makes sense, and often mistakes that you see?
8. FFFrank Fillmann
  Yeah. So it's like, um, it's like... I think this goes back to customer-obsessed. If you- if you've got a rep with two accounts or if you've got three people covering one account, the common denominator is you've got time to be completely immersed in that company, right? So let's go through the example. Um, you're dealing with, uh, an organization that sells cell phones, right? Well, you're a consumer. Go buy the cell phone. Uh, or if it's a pub- public firm, go buy the stock and sit in the shareholder meeting. Um, go on... Like, go into the inside sales organization, put on a headset. Bring them donuts, bring them some, some stuff to, like, say thank you for their time, and listen in to what their customers are challenging them with. So Harry, you were asking about multithreading. You know, how do you do it? I think it starts with customer obsession, right? And so if you really wanna understand what the customer needs, I think, like, a traditional sales cycle of thoughtful discovery and a few meetings and being single-threaded into, like, one buying unit or one person, that's scary. Like, what if someone leaves the organization? Or like you said, what if the sponsor leaves? Like, that drives problematic approaches. So if you really wanna get to know the account, you've gotta be obsessed. Buy the share. Um, if you're selling to a phone organization, go buy the cell phone, go into the store, talk to the retail sales associate. And so, like, you get to really understand broadly the challenges across the organization, um, in a multifaceted way. Number two, you wanna start threading in conversations from, like, IT to data to the line of business all the way across. The other thing you wanna do is have really good top-to-top alignment. And I don't mean when it's deal time. I mean, like, before it's deal time. Where does a thoughtful conversation of aligning, whether it's the CEOs together or the CIOs together or line of business executives together? But I think, um, if you take this customer-obsessed mindset, you're gonna have that entire organization wired top to bottom. But it's not in your interest. It's in theirs. If sometone's stuck, have the backbone to call your peer, who's my boss. That drives transparency, 'cause at all times, they know they have ultimate access to your organization. And when that happens, um, and there's risk in the cycle, you don't have to worry about it because you've got the entire place wired. And so I think if you've got, like, an obsessed mindset, you're gonna have every angle covered, and when one predictably falls astray, great news. You- you remediate that, but everything else is gonna stay in place.
9. HSHarry Stebbings
  I- I- I totally get you. Can I ask, when you think about, like, you said alignment there, um, selling into very strategic large accounts takes a lot of challenges from a product perspective, whether it's SOC2 or any of the security requirements. Where do you think are the biggest...... not misalignments, but alignment gaps that sales faces. Is it with product? Is it with legal? Is it with, um, design? Is it with customer success? Where are the biggest misalignments that pr- sales has with other functions within the org?
10. FFFrank Fillmann
  You know, it's interesting as, as, as I've started... as my career's grown, what I've noticed is a big part of my job is, um, is dealing with all of my parallel... my peers, the extended team. Like, that's in some cases the majority of my job. By the way, the first question I always ask every time I meet with those leaders is, "How are you measured? What do you need from me? And this is, these are the three things I need from you. And do we have agreement and alignment on what those priorities are for both of us and what the expectations are? So every time we talk, I don't wanna go through everything else. Let's start there, and then we'll cover the rest of it." So I think, like, an area where it's, um, it's really hard right now is customer success because they're kind of like the customer might beat them up, the sales team has very different goals than they do. And what I find is a lot of time the sales team doesn't understand how success is measured and paid, uh, they don't appreciate, uh, the challenges of how hard it is to be a success manager 'cause everybody wants something from you and you've gotta be everywhere. But if you're measured against everything, you're measured against nothing. And so I think one way to, to make it that, um... to kind of make that problem smaller, bring success on the sales calls with you. Make sure they're client-facing. Have them come in and don't do a quarterly business review, have a success review and, and elevate them, put them on a pedestal, put a spotlight on them, make them successful. The client's going to appreciate that because you're not just trying to sell, you're trying to drive value, and now they're critical path in the cycle, and what otherwise would be a lagging function that's trying to run and chase up and make everybody happy, now they're critical path. And if you have a big customer and they do a big buy, now you're gonna have to gr-... otherwise you'll grab the success person and bring them in and say, like, "I need you to do all this stuff." And they don't... Like, "I don't even know what they bought." And so how do you make them successful? You bring them along during the process and treat them like a teammate and make sure they know that you're helping them hit their metrics, and that's gonna be one way to help them.
11. HSHarry Stebbings
  Final one for you, uh, (laughs) which we stuck so much to the schedule. So glad we had that.
12. FFFrank Fillmann
  (laughs)
13. HSHarry Stebbings
  I literally spend hours on these schedules. I don't know why I literally bother anymore. But anyway-
14. FFFrank Fillmann
  (laughs)
15. HSHarry Stebbings
  ... I think it informs my mindset or some bullshit. Um, compensation wise, how do you think about constructing the right sales comp plans? I have a lot of early first-time founders that are like, "I hit, like, five to one, like, I don't know." Uh, how, how do I think about the right sales comp plan for my sales team?
16. FFFrank Fillmann
  I think the biggest challenge you wanna solve is alignment with how the company, um, reports to their shareholders, whether that's a private or a public company. How is the company measured? And then make sure there's alignment all the way down to how the sales rep is paid. Like, I think in the absence of that, there's gonna be a tension point where what the customer wants and what the rep wants is wildly different from what leadership wants. And then you take the salespeople, whether it's a, a first or second line manager, they're in the middle getting squeezed, where the people above and below them want wildly different things, and that creates a lot of tension in the cycle. If you've got full alignment that this is how the organization is being measured, this is how the rep's being paid, you're driving aligned incentives, and then everything starts to work a lot better. So I think if that, like, fundamental principle is there, um, the other problems start to work themselves out.
17. HSHarry Stebbings
  What's your biggest challenge today, Frank? When you look at your role, what's the hardest part?
18. FFFrank Fillmann
  Yeah. I think when you think about talent, bringing the right people in, um... Okay, let me ask you a question. Harry, have you ever, you ever bought a house?
19. HSHarry Stebbings
  Yeah. Uh, apartment.
20. FFFrank Fillmann
  Okay.
21. HSHarry Stebbings
  Yeah.
22. FFFrank Fillmann
  Apartment. So you go through the process. Um, when I bought my house, it was, um... it was, it was nice foundation, terrible color, terrible decoration, right? And so what happens is most people would go through this process of buying a house and they look at it, and if they can't see the end state, they don't have the vision to do so, they're not gonna buy it. So I literally told my agent when I bought my house, I was like, "I'm so glad this color of this house was rust red." She goes, "No one else said that. I'm so surprised to hear you." I said, "Well, if it was white, it would have been sold a year prior and, like, I wouldn't have been able to afford it." So quite literally, the idea that, um, people that can visualize the end state, that's a very powerful tool and it's very rare to be able to do that. And by the way, customers have a hard time doing that.
23. HSHarry Stebbings
  Huh.
24. FFFrank Fillmann
  Not because they're not intelligent, it's because they're busy. They're stressed out. They've got a million things to do. Finding people that can be visionary, that can, that can imagine the end state, and then creatively reverse back engineer through the lens of the customer the challenges, um, that they're gonna see and then how to re-... how to remediate that, and then bring that to life and take the customer on the journey and inspire them and excite them and then get them to the state mentally where they believe you and they see what the outcomes can be, that is an art that is extremely difficult to find. And when you can find someone who has it, you grab them, you bring them over, and you, and you just... and, and, and you just give them all the resources possible and you try to retain them as long as possible. That is a skill and a value that's very difficult to find. That and teaching people to communicate with senior executives. Those are just, like, hard to find skills. And so I appreciate that when I see it.
25. HSHarry Stebbings
  Man, all of my career I've been told I'm not experienced enough, I'm not smart enough, I haven't put the yards in. And I'm like, "I get it. But what if I can?" Like, what if I... what if you're wrong and I'm right? And it's like the visualization of, "I get you, but let's see, like, in my mind what it looks like if I'm right." And I think I am. Do you see what I mean? And so it's like, uh, seeing what others don't in terms of the uncapped.
26. FFFrank Fillmann
  Here's the deal here, that's a competitive advantage, right? And so you recognize that, that, like, very few people do that. What they wanna do is just hire more people. Like, the ability to, I think, to capitalize on that is rare. And so if you get really good at something other people don't pay attention to, I think that's probably one of the things that makes you great.
27. HSHarry Stebbings
  Man, I can talk to you all day. I wanna move into a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay?
28. FFFrank Fillmann
  Let's go.
55:07 – 1:01:46
Quick Fire Round
1. HSHarry Stebbings
  So what sales tactics have not changed over the last five years?
2. FFFrank Fillmann
  Um, listening, discovery, personal relationships, face-to-face.
3. HSHarry Stebbings
  COVID? Right? That, that changed a little bit, no?
4. FFFrank Fillmann
  Well, it changed, but, like, the need for it didn't change, right? So now that we're cycling back to face-to-face, what I'm finding is, it's really difficult to build relationships when you're remote. Um, it's easier to retain them over time. But I think, like, what I'm finding is, the absence of face-to-face, something misses, something is missing from the cycle. You've got to find a way to recreate that, acknowledging that it wasn't there for a while. We've got to bring that back.
5. HSHarry Stebbings
  How, how did your sales approach change remote with COVID?
6. FFFrank Fillmann
  I'd say there's two things that I learned during COVID. One is if you're, if you're a hunter rep, if you're like an SMB, it's really, really hard. You're trying to build a relationship from scratch. Fortunately, we were in the enterprise space so we didn't have that. But in the enterprise space, I think, like, one thing that we would do is we'd build, like, a big executive briefing and we would send Uber Eats gift cards to everyone who would be a part of that briefing and we would have like a really nice digital experience. And we were trying to sort of, like, bring in the events team and get really kinda, uh, clever and crafty and make it fun and exciting for the customer. Um, and then on the internal side, we would do a lot of virtual happy hours. Like, right at the very, very beginning when people are scared, just like how do you kind of bring morale up, but people, get people connected? Um, but I think now that we're on the, the back end of COVID, um, I think the value of face-to-face when you can do it and it's safe, I think we need to bring that back.
7. HSHarry Stebbings
  I totally agree with you. I, um, desperately miss the face-to-face, I have to say. (laughs) Tell me, what sales tactics have died a death, Frank?
8. FFFrank Fillmann
  Uh, I think, um, hiding information, right? Like, uh, the idea of solution selling which is like, "I have information you don't and I'm gonna tell you what you need." Um, people have wild access to information on your firm and the organization and, and the product. I think recognizing that and being super transparent and coming in saying, "Tell me what you know about it." And w- like, and, and being really authentic with that. Um, I, I think h- hiding information and trying to be protective, that's 20 years ago.
9. HSHarry Stebbings
  What would you say is the biggest mistake that founders make when hiring sales teams today?
10. FFFrank Fillmann
  Um, I, I think there's go- there's a maturity curve of an organization going from a few customers to really, really big in scale. And I think, um, as you start to hire the sales team, you're gonna get to a maturity point where y- you wanna move up market, customers have a different expectation, and I think trying to train folks that don't have the enterprise experience and convert them over, I don't think it's setting them up for success. I think you need to be able to find folks that have done this before that bring in the top end of the game and then having really, really good segmentation, SMB, commercial, enterprise, and then alignment by industry. I think you need to hire the proven team that's got experience doing that. Your customers expect it. Um, but you still want the other team to be able to manage the lower end of the business because they really know the organization and the product. So I think it's, it's a complement to those two things.
11. HSHarry Stebbings
  What's more important, my friend, experience on deal size or experience on industry specific?
12. FFFrank Fillmann
  I think, uh, everything starts and ends with the customer. If you understand their needs, um, I think everything else is gonna work better. I do think, like, in some particularly large deal cycles, you know, you don't want to give someone an at bat, they, where they've never really been in the big game before. That's not really fair. But if I had to stack rank that, um, industry experience and driving client trust and relevancy. You can reverse engineer everything a lot easier than having big experience on a deal but not understanding what's gonna make your customer successful.
13. HSHarry Stebbings
  What advice would you give to a sales leader starting a new role today?
14. FFFrank Fillmann
  It's not about you, it's about your team. So I always think that you wanna put the customer first, I think you gotta put the employee first before the customer. It's always been kinda wild to me that, um, that folks would, would, would be self-focused as a, as a sales manager, 'cause by definition you're as successful as your team is. And so, like, I was just reading the book The Go-Giver. Um, I want my team to be more successful than I ever have been. I want them to be able to create wealth for their families. Uh, and, and so I think the more that I work for them, I serve them and they know that and I'll do anything they need for me to do. Um, so I think just, like, running a very flat organization, um, being very selfless, um, and driving their success, what I found is not only do they end up producing, it creates a level of incredible loyalty that you really weren't planning on where sometimes they don't wanna leave the nest even when they need to. So it's, it's kinda simple, but I don't see it enough.
15. HSHarry Stebbings
  What would you most like to change about the world of sales today, Frank?
16. FFFrank Fillmann
  Uh, I think, like, uh, empathy. I think we, we need to, like, really remember how hard it is for our team. Um, g- go look at the last two years. How hard is it to be a, a, a sales rep who might have joined an organization and after two years never actually went into an office? Like, the, to be able to, like, get in the mindset of a, of a sales rep who's never actually been in, they haven't met their comrades, they haven't met the customer face-to-face, and remembering just how hard that is. And as you go farther up in the organization, more and more of our job as sales leaders is internal. But, like, if you get too far away from the customer or you get too far away from the rep, you forget how dang hard it is to do their jobs. And so being empathetic and spending quality time with them keeps you humble, keeps you relevant. So that's probably the one thing I'd change.
17. HSHarry Stebbings
  I agree. I, I think sales is a fucking brutal job. Um...
18. FFFrank Fillmann
  (laughs)
19. HSHarry Stebbings
  (laughs) Well done. Um, I have final one for you, Frank. I love this. (laughs) What one company sales strategy have you been most impressed by recently?
20. FFFrank Fillmann
  Uh, I, for me it's Miro. So now that everything's been remote and, of course, we're trying to, like, ramp that back, um, I'm super right brain, super creative. I like to grab a whiteboard in an office and, and, like, work through stuff. I'm super visual. It's really hard to do remote. I, I put, like, a, a whiteboard up in my office, my wife throws it away. Um, and so Miro is, like, the technology that enables the ability to feel connected as a team, have a, have a connected sort of set of tools that bring all these disparate ideas together and allow the, allow the team to rally when you're remote. And then that's now a digital format that you can bring into the office and extend it when you're in person. So that's really been something that's, that's helped us, um, in the last couple years.
21. HSHarry Stebbings
  Allows you to feel connected. Love this little girl bound routine on the hands movements, uh.
22. FFFrank Fillmann
  (laughs)
23. HSHarry Stebbings
  (laughs) Uh, Frank, I've loved this. You are a hero. You put up with so much shit from me.
24. FFFrank Fillmann
  (laughs)
25. HSHarry Stebbings
  I honestly, I honestly really love this. It's shows like this which make me love what I do. So thank you for being amazing and you were fantastic.
26. FFFrank Fillmann
  Um, yeah, well, listen, I've never done this before. I'm, I'm, like, not anxious but I'm excited to see what the outtakes look like. (laughs) Uh, appreciate you having-

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