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Sean Murray: Why Discovery Today is F***** & How to Scale Into Enterprise Effectively | E1107

Brex automates and accelerates spend management, with easy-to-use corporate cards, travel, expense management, and bill pay — all on one AI-powered platform. Ready to join them? Switch to AI-powered spend management at brex.com/ ----------------------------------------------- Sean Murray is the CRO @ Greenhouse which is the fourth company Sean has scaled successfully into the enterprise. Sean’s prior roles include revenue leadership positions at Saleloft (CRO), Xactly (VP Sales), and CEB, now Gartner (Head of MID Global Sales). ----------------------------------------------- Timestamps: (0:00) Intro (00:02:25) Sales-Marketing Blend (00:06:00) Top CMO Traits (00:08:00) Marketing & Sales Impact (00:11:33) Customer Education Tactics (00:15:54) Sales Challenges Today (00:18:41) Innovative Sales Methods (00:22:08) Renewal & Upsell Tactics (00:28:05) Sales Tech Improvements (00:31:41) Customer Success in Enterprise (00:35:09) Sales Commitment Balancing (00:38:58) Customer Relations Management (00:48:23) Sales Team Dynamics (00:59:49) Sales Compensation Insights (01:09:20) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Sean Murray 1. The Origin Story: Is a Love of Sales Born: How did Sean first fall in love with Sales? What does Sean know now that he wishes he had known when he started his career in sales? What is Sean’s biggest advice to a young person entering the sales world today? 2. Sales has Changed; You Need to Change with It: Why do CMOs need to be good sellers and CROs need to be good marketers today? Have we seen the total blending of sales and marketing today? Should we get rid of all sales teams and just have content marketing teams? 3. How to Move into the Enterprise Successfully: What are the three biggest mistakes startups make when scaling into the enterprise? What easy wins can they do early in the sales process to enterprises to get a good start? How important are logos? Does social validity really work in enterprise? How should sales teams use discounting in enterprise sales most effectively? What is the right way for sales leaders and CROs to budget for enterprise? Is there a way to test enterprise without committing the company and a lot of resources? 4. How to Build the Best Sales Team Today: What is the right hiring process for all new sales hires? What are the questions you have to ask in the interviews? What do the case studies entail? What are signals of the best reps? What are the biggest mistakes teams make when hiring new sales reps? What have been Sean’s biggest lessons on comp and negotiation with new reps? ----------------------------------------------- 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 Greenhouse Software on Twitter: https://twitter.com/Greenhouse Follow 20VC on Instagram: https://www.instagram.com/20vchq 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 ----------------------------------------------- #harrystebbings #20vc #business #venturecapital #startup #SeanMurray #greenhouse

Sean MurrayguestHarry Stebbingshost
Jan 24, 20241h 13mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:25

    Intro

    1. SM

      Discovery as we know it is (censored) .

    2. HS

      This is Sean Murray, CRO at Greenhouse. He is an expert in helping startups move into enterprise, and here are his tips on overcoming the three biggest challenges.

    3. SM

      First, the credibility. No one knows who you are, especially in the enterprise. The second is do you have real product-market fit? Because those big companies, they all believe that they're special snowflakes. And third, your financial, because as you move up market, they just don't trust you. They don't trust that you can survive.

    4. HS

      Sean, I am so excited for this. I heard so many good things from Maggie beforehand. So, thank you so much for joining me today.

    5. SM

      Harry, uh, it's such a treat to finally meet you and have this conversation. I've been looking forward to this conversation for the entire week. And before we get started, I have to thank you for what you're doing to our overall craft of selling in 20 Sales. I'm learning so much. I've been listening to the conversations, and we are accelerating the craft. So, thank you for all that you do.

    6. HS

      I can't believe I get paid for this, Sean.

    7. SM

      (laughs) I mean...

    8. HS

      I'm- I'm just waiting for someone to catch me. But I wanna start with your falling in love with sales. I- I often find there's a moment. When did you fall in love with sales? And when was that like, "Aha, I really wanna do this as a career"?

    9. SM

      Uh, so I wish I had a really elegant answer. I listened to Eagan's, um, conversation. It was like very intentional. And similar to say Mark, um, from Grammarly, I'm an accidental salesperson. Now, I'm a son of a salesperson. My father, my late father was, uh, dedicated salesperson. So, I was never gonna get into sales. So, through undergrad, uni, and graduate school, I was a bartender. And it was great, right? But when all of my smarter friends were taking up internships, I was slinging cocktails. So, I got my first assignment at the Corporate Executive Board, CEB. And my job title was marketing associate. Well, it turns out that I was making 300 cold calls a day to C-suite executives in the Fortune 1000. I was what's now called a sales development rep, a sale- an SDR. And that's when I fell in love with sales. I had this moment where I said, "Wait a minute, if I make more phone calls and book more meetings for my account executive, they'll just give me more money." I'm like, "Yeah." It's like, "Okay, this is amazing." And it tapped into my competitive spirit, trying to be on top of the stack rankings. And I've been basically an SDR ever since. This is like 22, 23 years later. But that's when I fell in love with sales.

  2. 2:25 – 6:00

    Sales-Marketing Blend

    1. SM

    2. HS

      Can I ask you? And I'm ju- w- we said it was conversational. I just think so much about the blurring between marketing and sales today, because I think if people don't know your brand when you first speak to them, really it's on the fold of marketing and brand awareness. How do you think about the blending of sales and marketing in that way, and actually whether there is a chasm between the two today almost?

    3. SM

      Yes. Well, the blend couldn't be more relevant today. And I view my role right now as the head of selling, when I used to be the head of sellers. So, the CMO, the marketer must be very effective at selling, and the head of sales must be very effective in marketing. And the primary reason why is because of the buyer. When on an inbound lead to your business, the seller now gets 9% of that buyer's time to evaluate whether they're gonna go with you or not. And Harry, in that 9%, this is according to Gartner, in that 9%, you must split that time with the other partners or vendors in that process for the buyer. So, the reason why this is- that's such a great question is that how do you grab their attention, their buy attention? How do you teach them about your product? How do you teach them about what you do when they're not talking with you? So, there's much of more of a blend today than ever before.

    4. HS

      Okay, let's unpack that. There's two sides there. CMOs that need to be good sellers, and, um, you know, heads of sales or CROs that need to be good marketers. What does it mean to be a good marketer coming from the sales side with that hat on first?

    5. SM

      Yeah, there are two, two big elements pop out to me. The most important is messaging. What problem are we solving, and what's the problem behind that problem that we're solving? Many sellers, you're just deployed, go and produce more revenue, and then come back with all of the revenue. But now, we must think differently about demand generation. The second being branding. How do we attract more people into our sales process? So, that demand generation piece is what's most relevant to me right now.

    6. HS

      But is that not marketers? Like, as a sales rep, and as a SDR on your team, do I not go to you, my boss, "Sean, but that's their job. Don't look at me for that. I'm here to make the calls to the leads that come in."

    7. SM

      Yes. And, and that model has long been gone, right? Where my role right now is to make those SDR conversations much easier. And how do I generate more inbound demand for what we do, rather than having just to completely go outbound? Now, I grew up, Harry, and, uh, 98% of my pipeline was completely outbound. Creating the category, creating the demand. But now there's a much smarter way to do it. And there's some really cool technologies that's available to enable those SDRs or those account executives to have those better conversations.

    8. HS

      Okay. Sorry, I'm sure this is great. (laughs) But if, if SDRs and sales teams are doing messaging and brand, well, what the fuck are marketing doing?

    9. SM

      (laughs) Well, marketing is holding our hand throughout the entire process. So, marketing, looking at our digital spend, the brand excellence, making sure we show up where our buyers hang out, whether it be at events or online or through social. We're all one big team. And, and I'm not just, I'm not just talking shit about this either. Like, the sales and marketing organization is very, very tight. And that's how you enjoy the most success today when that is one whole unit.

    10. HS

      Okay.

  3. 6:00 – 8:00

    Top CMO Traits

    1. HS

      And if we put the other hat on, I'm just gonna, I'm getting in so much trouble for this. I mean, dude, there are so few good...... marketers who are good at marketing. I mean, the CMO generation is one dearth and my, yeah, very few talented people. Sorry. Um, oh, Jesus, if we're expecting them to be good at selling as well, we're in the real minutiae. I mean, fuck. (laughs) So, what does it mean for a CMO to be a good seller on the flip side?

    2. SM

      So, Karen VanBuren is a CMO I get to work with. What Karen, or what the best CMOs do, that I get to work with and I have worked with, they know our buyer better than anyone else. They spend time with their customers. CMOs don't spend time with the customers, right? That's just kind of like, that's like a- a head fake. But the best CMOs understand deeply the pains of the buyer, what makes them tick, what drives business value and personal value for the buyer, and that's what makes the best CMOs today. Because when you know that, then you become a great seller, right? Because people, they don't wanna be sold to, but they do want to buy.

    3. HS

      Do you combine those meetings? 'Cause you can't spend too much time with the customer. If I'm your customer, I'm like, "Oh, Jesus, I've gotta spend time with the CMO, the- the CRO." My question is like, do you combine them together? Do you join calls together? What's the right way for you... 'cause you both need to have that interaction with customer?

    4. SM

      Yeah. Yeah. It's a great question, and it's probably a sense of all of the above. So for example, our marketing organization, they run our customer advisory board, so our core key customers that help drive our product and drive our innovation, that's a marketing-generated event.

    5. HS

      Mm-hmm.

    6. SM

      And so that's one example how they spend time with our customers, and we invest heavily in conversation intelligence as a technology. And so our marketers, they're frequently listening to our customer calls, listening to our prospect calls. They're very in touch with what's going on in our existing... in the personas of who we are engaging with.

    7. HS

      Can I ask

  4. 8:00 – 11:33

    Marketing & Sales Impact

    1. HS

      you, as the CRO, how do you measure the effectiveness of a marketing team? Is it on num- 'cause you can always gamify success. Number of leads, converted pie, it- it can all be gamified to some extent. How do you measure success of marketing teams?

    2. SM

      We have a full dashboard on how we measure the success of marketing, and it's inbound generation, the demand-

    3. HS

      Mm-hmm.

    4. SM

      ... but it's also, we go all the way down to our customer journey because our marketing organization is very heavily involved with our existing customers. NPS, gross retention, net retention, we do measure our marketers on the full suite of everything that I am measured with. Our marketing organization, we hold them as accountable to the revenue as I am. So for example, if you were to ask my marketers at the last two or three companies where I've engaged and helped build, they would know the revenue numbers as tight as I know.

    5. HS

      Wow. That's impressive. That's rare for marketing teams. Uh, I can... (laughs) I'm r- I'm really getting in trouble here. Uh, and I- I- I wanna start, you know, we mentioned kind of dialing for dollars and the outbound nature. I, I speak to so many companies a day and they're all going, "Ugh, it is so hard." Just to place this in context, are we in a recession from a sales environment do you think, and how does it compare to prior environments you sold through?

    6. SM

      I don't know if it's a recession. However, we are right-sizing, and maybe, maybe that we all shouldn't have grown as fast as we did. Like, the valuations of businesses and companies when we were raising, let's say, in 2020, 2021, those valuations are, they're- they're beautiful. Don't get me wrong, 'cause I benefited from some of those valuations. However, they just were over inflated. No pun intended. So, I do believe we're in- in a right-sizing type environment, but it does feel harder now than it has in the past.

    7. HS

      So, is that right-sizing the reason why so many teams are struggling with new logos?

    8. SM

      No, um, I'm personally, uh, I'm experiencing the opposite where new logo sales are actually fairly strong, and, say, some customer churn might be a little bit more difficult. But, uh, new logo sales has always been hard. And the best sellers right now, they are adjusting. They're just changing how they go into the market. And yeah, don't get me wrong, I would prefer fish to jump in the boat with inbound leads. Yeah, that was a lot more, like, easier. But I don't think that's a primary reason why selling is hard right now.

    9. HS

      How are, how are they adjusting? Everyone says all budgets are going back to CFOs, and CFOs aren't buying technology. That's what everyone says. How are they adjusting, and do you agree with that?

    10. SM

      I do agree with that. The CFO in different personas, huh, there are functions people have never even heard of that are getting involved in the sale right now, right? So I agree with that sentiment, and I also agree that it is harder. Hard sell. But what the best sellers are doing now, and I geek out with a lot of other sellers, and what I'm finding that the best sellers are doing right now, they're revisiting their ideal customer profile.

    11. HS

      Mm-hmm.

    12. SM

      They're revisiting their target accounts, who they want to go and pursue and engage with. They're adjusting their messaging, right? Like, Harry, you and I both know growing up that there, there was a monster under the bed, right? We both knew that, right? And that's how many sellers talk about their problems, like, "Oh, there's a monster under the bed." But you know what? The better sellers, they're talking about the monster that's down the hall, through the other door, and hiding in the closet. They're teaching. They're teaching-

    13. HS

      Mm-hmm.

    14. SM

      ... their buyer about that monster. Not about the obvious monster that's under the bed. So, I think the better sellers are adjusting.

    15. HS

      So, that- that's

  5. 11:33 – 15:54

    Customer Education Tactics

    1. HS

      really interesting. I always say when you have to educate your customer, it's so much harder. It's just so much harder. It's like when you're fundraising and your VC doesn't know anything about the space you're in. Good luck. (laughs) Do you agree or not, given the fact that the best educate?

    2. SM

      I do believe the best educate. And in fact, in my sales process internally, third company in a row, the first stage of the sales process is called teaching. Teaching. Hypothesis-based selling. I mean, look, if you are a seller today-... and you engage a potential buyer, and you're wasting your time asking about what fucking CRM that they use or where they're located or who they do business with or how they make money, you're fucked. You just-

    3. HS

      (laughs) .

    4. SM

      Just don't even call, right?

    5. HS

      Yeah.

    6. SM

      So the first stage is teaching. If I can teach you more about your business, if I can teach you something about your business that you might not even be thinking about, you will engage with me. And so I- I- I agree to the- to this- to your sentiment of what you're saying, but that teaching component is critical.

    7. HS

      Has how you sell changed given the fact that, bluntly, bottoms-up buying has now largely evaporated and CFO centralization of budget has largely taken place?

    8. SM

      But, Harry, what changed more than just selling is buying. Buying is changing. And the comment I made earlier that if I'm engaging in a- if I'm gonna go buy something, literally, according to Gartner, 9% of that entire process is actually engaged with the seller. So what's changed more in selling is how people buy. And so how selling has changed here is my comment about marketing earlier, which is, how can I teach the market, the shoppers about what I do and the value I create when I'm not even talking to them? And it's hard.

    9. HS

      Isn't that why content marketing is the most important thing that you can do today, and then should all sales teams not just be a team of content marketers? If you're the only final 9%, then surely you should just have a amazing content marketing team and fuck it, they'll tip over for the final 9%.

    10. SM

      Well, there- I've got good news for the sellers out there. I've got good news, 'cause here's- he- he- according to Gartner, Harry, um, 43% of buyers, according to Gartner, 43% of buyers that had a digital-only experience in purchasing have a 1.65X higher regret rate, right? So the best sales cycle is when it is rep-enabled. Like, the rep is part of that process. In fact, you reduce buyer regret by half if the rep is involved in the process.

    11. HS

      Whoa.

    12. SM

      So what the rep does... So to your point, yeah, yeah, like, content marketing's super important. Teaching things when no one's around, yeah, yeah, yeah, you gotta do that. But the good news for the sellers, right, is that we get to be there to make sense, to bring the human context to what they're buying and so they can ax- ask, uh, actual questions.

    13. HS

      How do you think about what ACV is the right level ACV for sales reps and teams to interject versus let them be self-serve? Like, is it above 10K? Is it above 50K? But then, you know, someone from, you know, a huge company can come in and sign up for one seat. But it could be a... How do you determine?

    14. SM

      I have sellers where I prioritize, um, the SMB segment. I do, right? Because those sexy startup companies that are in Silicon Valley or in London or in Paris, wherever they are, they grow up to be enterprise customers.

    15. HS

      Mm-hmm.

    16. SM

      So I still want human engagement. And that ACV is, say, 9, 10K US. Like, it's not a- it's not a big ticket. But those customers are still valuable. And if I just automate that whole process, which I think we're moving toward as a craft, don't get me wrong. I think we're moving there. But I'm not ready to concede to my competitors that have not automated that segment. So it's- it's tricky, really depends. I don't have like a great answer of when is that moment. But let me- what I'm gonna do say, I am constantly looking at automation, different technology on how I make it easier for buyers to buy on their own and renew on their own and engage with our company on thei- on their own. The- there's a lot of innovation happening with that like 15, 20K-ish ACV.

  6. 15:54 – 18:41

    Sales Challenges Today

    1. SM

    2. HS

      You- you said that by constantly looking. I think another reason why so many are struggling with new logos is just the broken nature of discovery. How do you think about discovery today? Like, is it totally fucked? Is it actually in good shape? Wh- what is your thoughts?

    3. SM

      Discovery is fucked.

    4. HS

      (laughs) And for anyone listening with kids in the car, so are you (laughs) .

    5. SM

      That's how I'm gonna rework right now because my kids are home from school for the holiday break, so I can't swear the way I like to when I'm around my kids as often. Um, but l- l- let me make sure I clarify. Discovery as we know it is fucked, right?

    6. HS

      Mm-hmm.

    7. SM

      And wh- when discovery, I took out the word discovery from the sales process and I inserted the word teaching. And words matter, turns out. And what I would prefer my organization, what they do when they engage with a potential buyer is they teach them. Teach them about their company, teach them about their category, teach them about their craft instead of asking the lazy, dumb questions that they can find out on their own. What- that's the discovery that is dead because technology allows you to understand so much about your buyer before you talk with them within minutes.

    8. HS

      Do you think you need specialization on a vertical playbook basis then? Because if you can teach me more about my business, Sean, I'm either incredibly stupid or you should be leading fucking Microsoft.

    9. SM

      (laughs)

    10. HS

      Like... So- so, uh, how are you gonna get smarter than me on my business?

    11. SM

      And- and it might not be about your specific business, but it could be about the investor world. And the key word that we try and use is reframing the prob- reframing, right? So in your world, whether you're investing, you're looking for certain types of companies before you make an investment, whether it'll be LTV to CAC, whatever metrics that you're looking in. But we wanna reframe it to be about something different, something you might not be thinking about. And that could be your voice internal survey results from your employees. Do they have happy employees? It could be what their customers are saying about the company you might invest in. Now I'm not- I'm not giving you an insight right now, but if I'm selling to VC firms, I talk to 30 VC firms in a month.... and fuck me if I don't have some insight about the VC community that you might not be exposed to in the last month.

    12. HS

      Do you know the most interesting thing you could do actually, you could do an analysis of like talent churn within portfolio companies of a specific VC. You could say, "Hey, I took five of your out performers. When I looked at head count variation across them, actually these two have a much higher churn rate than these other three. Maybe it might be something there is to talk about. Do you wanna hop on a 10-minute call?"

  7. 18:41 – 22:08

    Innovative Sales Methods

    1. HS

    2. SM

      If I can tell you a two-minute story, I promise it's worth it.

    3. HS

      Oh, yeah.

    4. SM

      Okay. There's a company called DENTSPLY. This is from CEB now Gartner, right? There's this company called DENTSPLY. DENTSPLY is located here in the United States. Like $2 billion in revenue, right? They make, when you go to the dentist, they make all the tools and the drills and the things that you go to when you go to the dentist, right? I'll make this fast. They produce these drills, the most ergonomic light drills that were gonna take the world by storm. 500 sales reps go out and try to sell these drills to these dentists' office, right? They couldn't sell them. You know why? 'Cause all the dentists were saying, "No, no, no. You sold me these drills three years ago and they worked just fine," until one rep did something differently, that one rep did research. The rep found out that 30% of dental hygienists were out of work each year, 30% of the time of absenteeism, and found out they were out of work through absenteeism because of carpal tunnel, 'cause if you're like a dental hygienist, you're in these like fucking weird positions all day working on, on people's mouths, right?

    5. HS

      Huh.

    6. SM

      So anyway, that rep did the math and figured out, because if you cancel your appointment to go to the dentist, the family took the whole day off of work to go to the dentist. It's an expensive problem. To the tune of a small business, dentist shop, to the tune of about $700,000 and- and a year of lost business.

    7. HS

      Wow.

    8. SM

      So this one sales rep goes back to the dentist's office, explains his problem in a new way. The problem with absenteeism with, uh, uh, with these folks being out of office or being out of the, uh, um, the, the dentist's office, and the, the dentist would just say, "No, no, that's just part of doing business. That's just cost of doing business. How can we fix this?" Well, the rep said, "If I gave you a way that you could avoid your hygienist to suffer from carpal tunnel, absenteeism, would you buy these drills?" "Well, that," he's like, "That doesn't exist." Lo and behold, these most ergonomic drills that were the lightest ever, that would prevent absenteeism.

    9. HS

      (laughs)

    10. SM

      So you see what I'm doing here, right? It's like reframing the problem that you think that you're solving, and that's what I mean about teaching your buyer something different about their business.

    11. HS

      I totally get you and I, I totally agree with you. Um, how do you do that though when it's horizontal? Like it's easy when you sell dentist drills. It's like that's all you sell. Um, I, you know, bluntly at Greenhouse, you sell talent in it. But when you sell Airtable, Notion, fuck.

    12. SM

      Yeah.

    13. HS

      Could be anyone.

    14. SM

      Well, i- and that's it because we are, let- let's just use hiring software as an example.

    15. HS

      Mm-hmm.

    16. SM

      Let's use sales engagement software, like lots of different categories. But if we're talking about hiring software, it's persona-based. I'll go sell to a retail, manufacturer, tech company and a biotech business. But many of the problems are still the same within talent acquisition.

    17. HS

      Mm.

    18. SM

      Right? There are ver- there- there are parallels that you can draw and what many talent organizations, what they're thinking about differently right now is, let's say DE&I, diversity, inclusion in their businesses, not just hiring. And so I can go in and teach different industries about how other industries are visualizing inclusion...

    19. HS

      Oh.

    20. SM

      ... and diversity hiring in their business, right? So it can be done in horizontal or vertical, but it's not easy.

    21. HS

      Yeah, I get you, but actually, CFOs across a SaaS company probably have similar thoughts to CFOs across a fintech company, and actually on a per role basis, you might get some luck there as well.

  8. 22:08 – 28:05

    Renewal & Upsell Tactics

    1. HS

      Okay. So if we have that on new logos, so one thing that is also very apparent is kind of renewals are harder than ever. Uh, Steve, your, your successor at Saleslofter, yes, uh, said that every renewal is a new deal. Um, do you agree and are renewals harder than ever?

    2. SM

      Renewals are, I do agree, renewals are harder than they've been in the past.

    3. HS

      Yeah.

    4. SM

      And what creates these renewals to be more difficult, there is a lack of consensus. There's dysfunctional consensus when new personas enter that renewal process. I do agree with the sentiment, Harry, that CFOs, IT, functions I'd never even heard of show up in renewal conversations today. And we now must prove not just ROI anymore, but it's time to value what we're gonna do differently for them. And no one really feels comfortable making solid decisions right now, which creates this dysfunction within the consensus buying at the renewal point because budgets are tight. People aren't spending, and it- it's just difficult.

    5. HS

      What do you think, if there's one or two things that you most need to prove, what do you think they are across the board?

    6. SM

      Oh, first is the data. Proof.

    7. HS

      Okay.

    8. SM

      You must prove that you are helping your customer get measurably better at whatever is the problem that you are solving.

    9. HS

      Yeah.

    10. SM

      So I would say data probably one and data probably number two. It's really in the proof, it's- it's in that proof points. And what's the next problem that they have in the coming year that you can solve for?

    11. HS

      Do you have to change your team structure to accommodate the changing data requirements of your customers in order for them to upsell? Before, people just came back and said, yeah, Henry Schuck at ZoomInfo came on the show and said, "Oh, before everyone just came back and was like, 'Yeah, sure, we'll take it again, and why not buy 10 more seats, 20 more seats, 30 more seats?' Now it's like they need so much more." He's like, "We changed our whole customer success team to be like data first to prove upsells." Do you need to do that or is that a step too far?

    12. SM

      I do not think that is a step that's too far at all.Our customers are leaving breadcrumbs throughout our product at all times, and making sure that we get the right sets of data in the right hands at the right moment is critical. And so, I don't know if it requires a full restructure. However, what I do know today within customer success or account management, whatever the structure looks like, um, everyone should be in customer success and in sales at the same time.

    13. HS

      Huh. What does that mean? Like, how do you actually do that? Does that mean sales teams spend time in CS, and CS in sales? Like, just unpack that for me, and if I'm a founder listening, what should I do?

    14. SM

      No. It, it's, it's a great equation to go and solve for. What I'm finding now is that in customer success, you have fewer touch points with your customer.

    15. HS

      Mm-hmm.

    16. SM

      And the product must synch for you at some point, of course. Right? But when you're having those customer conversations, can you also weave in the commercial component of upsale and/or cross-sale? Because in customer success, you're building trust. You're building that relationship. And in some models, of one of which I'm part of and have been part of, is you have this, like, awkward, high-tension moment where a salesperson comes on and is like, "But wait. I got more things for you." But to have that process a bit more, um, centralized is, is probably the best part. So if I'm a founder right now, you must find people that care greatly. I just saw a post by Jason Lipkin that was spot on. Like, your first few CS hires, someone that cares greatly about your product, they're passionate, they're smart, and everything else will sort itself out. But if I'm a founder right now, I would think about combining those roles a bit within CS and account management, but separate that from your new logo hunters. Make sure that's separated.

    17. HS

      Okay. So how do you manage the t- challenging element of the handoff? "Hey, Sean, I've sold you, and now you've just, you've learned to love me. Meet my colleague, Sarah," And you're like, "Whoa. What?" Uh. How do you handle that?

    18. SM

      We handle that, how I'd handled the past, is through technology. That handoff should be flawless. So to the founders that are listening, ensure that you should have a hunter organization that chases new logos. I firmly believe it. By the way, Harry, I got, I was able to... One of the highlights of my sales career is I was able to launch the sale of the Challenger Sale. Have you heard of the Challenger Sale?

    19. HS

      No.

    20. SM

      Oh, Harry, this is a must-read for you. Um, it's a must-read. Anyways, Brent Adamson, Matt Dickin- Dixon, they are the authors and the researchers behind a lot of the content. But the argument is, and I firmly believe this to this day, you have an organization that secures new logos, so long as you have the runway and the TAM to support it, and then you have a customer-facing organization. You separate those two. But to answer your question, the technology-

    21. HS

      Whoa. No. Wait. That, that's too good. So, w- wait. You have someone to secure new logos. What, what, what does that mean? Like, they go out and they pull together a, a list of names that could be good targets and... Just help me understand how that works.

    22. SM

      Yes. Okay. Let's slow down. Uh, you have the new logo organization and their, their, their only purpose in life is to go get more new customers.

    23. HS

      Mm-hmm.

    24. SM

      Right? So when they get an, an order form signed... By the way, no one's signing order forms anymore. Uh, it's digital.

    25. HS

      (laughs)

    26. SM

      But when you get that order form signed, you pass it off to a customer-facing team, whether that be called account management, customer success, customer support, whatever you wanna call 'em. But these are two distinct different teams. Harry, when you have those, those roles combined, the research is profound. When you combine those roles, it doesn't work very well. So long as you have the TAM, the total addressable market, and you have, you have the green field available where you can go and secure new logos, you've got that runway, those roles should be separated.

    27. HS

      Okay. So they're separated.

  9. 28:05 – 31:41

    Sales Tech Improvements

    1. HS

      W- and then we have the handoff, where you bring in technology. How does technology help a handoff? Like, conversational intelligence? Help me understand how, you know, Gong will help our sales and CS teams make a seamless transition.

    2. SM

      So a big plug for Gong. We are Gong... But the AI that they are building within the conversation intelligence is remarkable. So if I'm a customer success person, and I'm inheriting a new customer, I can go into Gong and just look for quick highlights, quick moments that were important during the sales process on how I'm gonna absorb and learn about that customer. It's brilliant. It's really smart. And so that's how that transition now happens flawlessly.

    3. HS

      So, so, so you would then expect your CS person to come into the calls, learn, and then me, as a CS, hop on that handoff call and say, "Sean," you're the customer in this case, uh, "How are your daughters doing? I know that you're going to Taylor Swift." And you go, "Oh, wow." Like, they've got that relationship-based sell already. Is that what you want?

    4. SM

      In the enterprise, the short answer is yes.

    5. HS

      Hmm.

    6. SM

      Right? So I pursue... Um, the last three companies I've helped build, I pursue every segment, from SMB startups all the way up to the 20,000 employee mega companies. And in the enterprise segment, that level of personalization makes a difference, and very important. So to answer your question, yes. We expect our teams... Maybe not that, "I'm gonna go to a Taylor Swift concert in London with my daughter." Maybe not that far, but certainly what my top three problems are that I must solve in this current year, that level of detail, yes. Now, at scale, maybe in the SMB, where it's a bit more automated, not as much personalization is required.

    7. HS

      Okay. So then we have that, and you're like, "Yeah, I like this CS person. They're, they're... That's good, that's good." And now I'm going, "Hmm." As the CS person, "We can upsell him." Uh, how do I bring in the salesperson back into the process when I've now built quite a good relationship with CS?

    8. SM

      Yes. And, and that's the conversation we were having earlier where you have account managers or salespeople that are also talking to your customers-

    9. HS

      Mm-hmm.

    10. SM

      ... along with these customer success relationship builders that are typically measured on NPSs. My argument is to combine those rules.

    11. HS

      Hmm.

    12. SM

      That's my argument that I see today. Leverage technology, leverage the data on when you know customers should be up for expansion, should be up for cross-selling. Your data should tell you that. Whether you're using Gainsight or Gong, whatever technology you're using, you should be able to see that and allow the frictionless sales environment to happen within the customer organization.

    13. HS

      So CS is sales?

    14. SM

      Yes.

    15. HS

      Okay. If CS is sales, is that not a misalignment? You're one of my cu- and now I totally get... Uh, d- let me just... Uh, hear me out here. You're one of my customers. "You know what? You may not quite be ready for our full enterprise AI product yet, but I think you could be soon. And so why don't I sell it to you now because it's nearly the end of the quarter and I really want that bonus? So, you know what, Sean? You need it now."

    16. SM

      (laughs) It's just that easy. But really, Harry, I believe, and I have a bit of a bias, we're all in sales. Come on. We're all in sales when we're serving our customer. We are. And, uh, the good news, the customers expect it.

    17. HS

      Mm-hmm.

    18. SM

      Right? They expect it. They expect to be

  10. 31:41 – 35:09

    Customer Success in Enterprise

    1. SM

      sold to.

    2. HS

      Do you think they do?

    3. SM

      (laughs)

    4. HS

      Do you think in CS they don't feel like it's a safe space where you do just want them to m- be made as successful as possible? Maybe I'm ignorant and naive.

    5. SM

      No, you're not ignorant, because my CS organization today, they are not in sales. They are not. I wanna make an argument that we should be.

    6. HS

      Mm-hmm.

    7. SM

      But today they are not in sales. Many customer success organizations do not have a quota, right? They sit in positive revenue or COGS and they do not have a quota, and they focus on adoption, using the product. That's very... That's a classic model.

    8. HS

      Uh, if, if they're not but you would want them to be, why are they not?

    9. SM

      That's the question. That's the question.

    10. HS

      Can you not, can you not stomp your feet and say?

    11. SM

      Well, well, I, I am, you know, b- banging my hand against the desk. Uh, I gotta be better at my persuasion.

    12. HS

      Yeah.

    13. SM

      But really also, Harry, it depends also on the product. Because if the product is easier to adopt, you probably need less customer success. So the innovation of the product makes the difference.

    14. HS

      Mm-hmm.

    15. SM

      And if you have a heavy people or human-oriented customer success organization, ugh, could be a red flag for the buyer.

    16. HS

      Yeah. No, I get that. You said about kind of the range of customers you sell to and you have sold to over your career.

    17. SM

      Mm-hmm.

    18. HS

      I mean, I'm invested in many companies and kind of the Holy Grail is like, "Well, we're gonna scale into enterprise," and then hundreds of thousands of dollars of ACVs will just magically open up, and it doesn't happen like that, and there's this real naivety. What do you think customers or founders get wrong about moving into enterprise?

    19. SM

      A lot. Okay, there is a lot to get wrong. The three biggest hurdles in taking that Holy Grail of moving up into the enterprise, those massive ACVs, the sexy LTV to CAC, those sexy logos that you could talk about. But the hardest problems, first, the credibility.

    20. HS

      Mm-hmm.

    21. SM

      No one knows who you are, especially in the enterprise. IT will destroy you, right?

    22. HS

      Mm-hmm.

    23. SM

      The second is, do you have real product market fit for those big companies? Because those big companies, they all believe that they're special snowflakes.

    24. HS

      (laughs)

    25. SM

      And so they need things that are just different because you've built an SMB or mid-market platform that's there to scale, right?

    26. HS

      Mm-hmm.

    27. SM

      And third is somewhat related to both, but your financial and your financials, because as you move upmarket, they just don't trust you. Very similar to credibility, but they just don't trust that you'll be around. They don't trust that you can survive as a, as a startup for that long. So I think those are the three, um, probably not so insightful insights that I've experienced in moving up.

    28. HS

      I wanna ask.

    29. SM

      So-

    30. HS

      Okay, so IT will kill you. Why? Why will IT kill me? What did we get wrong here?

  11. 35:09 – 38:58

    Sales Commitment Balancing

    1. HS

      um, that's one. Uh, two, I'm a special snowflake and I deserve special attention. Will you do customization for me to land my contract? How do you advise founders on the willingness to customize versus not in order to secure a contract?

    2. SM

      I love this, Harry. So this is the most friction a founder will experience in their life, right?

    3. HS

      (laughs)

    4. SM

      You can al-

    5. HS

      Not, not, not marriage. No.

    6. SM

      No, no, no. Marriage is easy-

    7. HS

      (laughs)

    8. SM

      ... compared to this friction. But this is going to be the real friction, is when they are moving up that market and how they're going to differentiate those two on a customization of sales debt. Because the sales organization is gonna say, "Hey, look. We've gotta go create 15 different bells and 20 different whistles to make this company work for us." And I refer to that as sales debt.

    9. HS

      Mm-hmm.

    10. SM

      And so the lesson learned is how do you balance sales debt? Because every once in a while, you're gonna wanna take down Adobe as a customer so you can say you've got Adobe as a customer, or the snowflakes with those sexy logos, Slack, Salesforce, whatever.... but you must balance that sales debt, and just know when to walk away from deals because the biggest pain point when you move into the enterprise is they want you all to be special, and they want customization, and it's gnarly. So, as one example, Harry, uh, Greenhouse, where, where I'm building now, I really cap it at 10,000 employees, but I try not to pursue much more above that. And it's mostly because it just gets so difficult above that threshold. And I don't think... The, the big money really isn't with those companies anyways. They actually, there aren't many companies that have over 10,000 employees, but when you get to that level, it gets gnarly.

    11. HS

      Can I ask you, have you made any mistakes in terms of taking on sales debt too much with a specific customer?

    12. SM

      Yes.

    13. HS

      It's easy to.

    14. SM

      Yes. Many, many, many mistakes, and it's less about over-promising. It's being upfront about what we can and can't do or what we can try to do, but the biggest mistake is the time I can't get back.

    15. HS

      Mm-hmm.

    16. SM

      So, I went to go after one of those sexy logos, and I went back to my product and my engineers and was like, "Look, this is gonna be easy. You gotta trust me. I've never been an engineer before, but this sounds really easy." And I had my product team and my engineering team invest a year of their time trying to make it work, and it didn't. And so I can't get that time back, and with founders, that time is too precious. And so those are the big mistakes. It's not about, um, being false or lying to your customer, but it's the time that you can't get back.

    17. HS

      Oof. Yeah, I mean, that's a very accommodating product team, to be fair, to actually engage for that long and to let you roll with it. Um, yeah. No, I'm totally sure. Yeah, you mentioned the sexy logos. Do they really make a difference? Like when companies come and say, "Hey, we've got Slack and Dropbox," and you name it, do they make a difference or not when closing?

    18. SM

      Um, if... It's a good question. The short answer is it does make a difference. Now every salesperson in the world pitches and they over-pitch those enterprise logos, but the first problem that I mentioned when moving upmarket is you lack credibility. And the reason why those logos do matter is I need to show you... So, Harry, you're my enterprise customer, and you're looking at me like, "Fuck you. You can't do half the shit that you're talking about." But what I need to be able to say is you, Ha- it's like, "Harry, look. I'm gonna set you up with the folks at Slack, DocuSign, and Snowflake, and they're gonna tell you a story of how they use my product." I need that. You need that.

    19. HS

      That's, that's very impressive and different though. There's a difference between, "Hey, look at these sexy logos, now buy," and, "Hey, why don't you speak to existing customers and they'll be references for us?" Do you see what I mean?

    20. SM

      Yes.

  12. 38:58 – 48:23

    Customer Relations Management

    1. SM

      Yes, but they're, they're two and the same, right? Which is, the hurdle you're jumping over is the credibility hurdle.

    2. HS

      Do you worry about asking existing customers to sell for you? Do you worry that it's too much to ask, that they don't have time?

    3. SM

      It depends. Because, okay, Harry, we're role playing again.

    4. HS

      Yeah.

    5. SM

      Now, Harry, you as my enterprise customer, I'm not gonna ask you for your time to help me go sell to other big companies. But if you do, maybe I'll give you a little bit of a discount on renewal. I'll do something for you, right? So, um, I, I do ask in advance. So, when I'm moving upmarket, I make these concessions as part of my negotiation when I'm closing a deal, which is-

    6. HS

      Huh. Okay, so you'll say, "Hey, if you can help on up to three different cu- potential customers, we can have a wiggle room of 10% on a renewal."

    7. SM

      Correct, right? So, as I'm moving upmarket, so the founders that are listening that have aspirations to go be bold and move up into the enterprise, do it, but think very carefully, um, when you're negotiating these terms with your first 25, say, enterprise customers, give and gets. You're gonna need their help to get this going, so give them the concessions that they need. Make it worth their while and get it in writing.

    8. HS

      Mm-hmm.

    9. SM

      Get it in writing so that you can use it.

    10. HS

      O- Okay. Another area where they're like, not only, yes, everyone wants customization, especially now everyone wants a discount, and some are like, "You know what? We don't discount. We know the value of our product," and others are like, "Pfft, of course we discount." (laughs) Um, what's the right approach to discounting for founders listening, thinking about that scale into enterprise?

    11. SM

      Discounting is okay.

    12. HS

      Hmm.

    13. SM

      It's fine. And in different environments, it's important that you adjust when you need to. We all believe that our products are the best, especially those founders that are listening, I know, but there are moments that when everyone on the block is charging $80 for a beautiful steak, and then the market goes south, and then the rest of the street is selling those steaks for $20, you can't keep charging $80 for your steak. You can, but you're going to lose.

    14. HS

      Mm-hmm.

    15. SM

      The worst deal is the one that takes too long. Drop your price and go get the fucking deal and move on. Just move on. Go get the next deal. So, I have been a big advocate of flexibility. Maybe not discount. I'm reframing it a little bit. It, it's flexibility in negotiating terms. It's not necessarily just discounting and dropping your price, but go get something different. So, as an example, if my price is 100K, I will do this deal for 60, and then, Harry, what I expect from you is a, a story about how you love my product. Harry, I want you on the stage of my annual conference raving about my product, and I want two social posts from you raving about my product. And then we'll do the deal for 60. So it's not a discount; it's a trade.

    16. HS

      I like that. I'll do the trade. Yeah, okay. Fair. You said that... I loved it. You said there about kind of the time is the biggest killer, and if it takes too long, move on. Do you think you know upfront if a deal will take a long time? And what are signals that a potential prospect is gonna be a slow mover?

    17. SM

      Yes. There are many indicators, and having a data-driven process teaches you about what those clues are.

    18. HS

      Okay. What are they?

    19. SM

      Uh, there's probably a list of about 40.

    20. HS

      (laughs)

    21. SM

      The, the level of consensus that's required, the level of approvals that are required, any-

    22. HS

      Okay. Okay. So let's just take those. Sorry, I like to go. P- are people honest? Everyone likes to feel important. When you say, "Hey, you know, who, uh, uh, are you a decision maker for, for buying Greenhouse?" "Of course I am. Yeah, yeah, yeah, yeah, it's me. You're, you're speaking to the right person."

    23. SM

      (laughs)

    24. HS

      How do you... How do you know?

    25. SM

      Yeah. It... That's a great call-out, and you are right. That happens nine times out of ten. And frankly, they are not the person that can sign the order form, so you, you are right. Um, the question to ask maybe differently is who should I engage early because, Harry... Role play again, okay? Harry, buyers like you, I have 7,000 customers and buyers that look and feel just like you. What happens at the end of this process is the CFO will get involved, the head of procurement will get involved, IT will get involved. Harry, I don't think your company's gonna be any different. So, in order to be a good steward of your time, let's get them involved now because then I can set you up for success. Harry, you want this product, I know you do. But in order for you to be successful, let's get these players involved and so-

    26. HS

      Do you not dam- do you not damage their ego? I'm sitting here thinking, "Fuck you. You don't fucking believe that I'm the buyer."

    27. SM

      No. No, I do-... Uh, if I do, fuck it, right? But what I have is credibility on my shoulder, Harry, because what I said to you, "Harry, companies that look and feel just like you, some of your competitors, companies that are in your ecosystem, this is what happens at the end." My hypothesis is this is what's gonna happen to us at the end. These people are gonna wanna get involved.

    28. HS

      Does competitive selling work? Does saying... Uh, uh, I don't know. I'm taking the most competitive industry, CRMs, you know, monday.com and Pipedrive. Does saying, "Hey, monday.com, we're actually working with Pipedrive and they're seeing incredible success. You don't wanna be left behind," does competitive selling work in that respect?

    29. SM

      I, I, I value the question. The short answer would be yes. Wh- what I will say about with the competition and selling against your competition is when I'm directly the seller is to not, uh, belittle or throw mud at my competitors. It rarely works. If you roll around with pig... If you roll ar- roll around in the mud with pigs, you just get dirty. And so I teach my sales organizations as best I can to not speak ill of the competitors.

    30. HS

      I totally agree. I think it's the fastest way to lose credibility to chat shit about someone. I think it's... You, uh, you see it often with venture investors too, and it's just like, yeah, that's not a good way to do it. Um, okay. Uh, uh, we missed one crucial thing which is, like, for me, I think a lot of companies actually try and move into enterprise way too soon. A million in ARR? Uh, y- SMB market's a lot bigger than that, okay? So we're, if you, if you wanna start there, let's start there proper. When's the right time to move into enterprise? You know, you've done three now. When are you like, "Okay, this is ready to ramp"?

  13. 48:23 – 59:49

    Sales Team Dynamics

    1. SM

    2. HS

      Yeah. Do you say, "Hey, like, it's not working," and just cut it? Like, how often are reps repairable versus just let 'em go?

    3. SM

      But the right answer is you move on and you bring in new talent. That's the right answer.

    4. HS

      Do you think you're good at hiring sales reps?

    5. SM

      Yes. I'm the best. You know why?

    6. HS

      Why?

    7. SM

      'Cause I've got software. I don't worry about hiring 'cause I've got great software.

    8. HS

      Okay. Well, help me understand that. I'm a founder, I'm hiring my sales team, how do I hire sales reps or sales teams with software?

    9. SM

      Okay. (laughs) There's a lot to unpack here, but I've been leveraging software for many, many years in my hiring effort and when I'm learning about hiring salespeople, the best people, there's a lot more data and science involved than when would think.

    10. HS

      Okay.

    11. SM

      So, it really first starts with how you attract talent to your company. What are the words that you're using in your job description to ensure that you're creating a fair and equitable environment to motivate people to come and work for you? So, that's what really where the process starts for me, is how I'm attracting talent.

    12. HS

      Can I, can I be blunt? "Fair and equitable environment to encourage people to motivate..." Like, do you know what, honestly, sales reps want, Shawn? They want a company that's selling fast and easy, yeah? Where you get high comp and you get good coms and the sales aren't that freaking hard. Doesn't that sound like a dream? That's what... You got two job offers, one where you feel inclusive and you're empowered, and another where sales are easy and coms is high.

    13. SM

      I don't think so, Harry. Now, here's what I've learned in my journey, right? Okay. If you... L- let's go back to that example of attracting talent to your company, okay? Uh, according to Forbes Women, that in gender neutral job posts, right? 74% of women less likely to interview, right? Now, hear me out. When in that same description, uh, in the same source, if there are masculine-related tasks or words, like, you'll crush it, (clears throat) you'll dominate, like those types of words, only 55% of women will apply. Now, hold on. According to Exactly Insights, those that identify as female out-perform their male counterparts by 8%. If you, as a sales manager, have a certain profile that you're most attracted to, right? Then that's probably who you're gonna go and hire.

    14. HS

      Mm-hmm.

    15. SM

      And so, when I feel as though I've perfected sales hiring, it's because I eliminate bias from the process. It's very structured, it's very intentional, it's driven by competencies.

    16. HS

      Okay. So, so we realize that the words matter in terms of how they impact our funnel of applicants on the talent side, so we use gender-neutral words, we use, uh, p- I don't know, personality-neutral words. And then what? Then, and then we have, like, a talent pool. How do we then hire?

    17. SM

      The next step after you've attracted all this talent to your company, right? You're at advantage because you've got this massive pool to choose from, right? So, then what happens next is your proper kickoff and agreeing on, what are the right competencies that we are seeking? What are the right attributes that we are seeking? And then, who is going to do what? So, setting up this structured process to ensure you have consistency through the entire... For the follow-through and the interview process. So, for example, the high-performing reps, they have similar competencies; (clears throat) drive for results, um, persuasion, negotiation, intellectual curiosity. So, you incorporate that in your structured process. And you only get so much time with a candidate.

    18. HS

      Mm-hmm.

    19. SM

      A candidate's only gonna give you, as a hirer, so much time.

    20. HS

      Mm-hmm.

    21. SM

      And what companies fuck up so often is that, let's say there are three or four people that interviewed that candidate. They all ask the same damn questions.

    22. HS

      Huh.

    23. SM

      So, you're not getting enough data from that candidate in the short time allowance that you do have.

    24. HS

      Okay. So, how do you get enough data? And how do you make it different where it's not like, "Oh, tell me about a time when you persuaded someone to do something they wouldn't have otherwise done?"

    25. SM

      Right. Great question. The interview for each person, interviewee, is highly structured, right? So, Harry, you and I, we're on the same interview team. Okay.

    26. HS

      Mm-hmm.

    27. SM

      In our software, here's what I'm going to do. I'm seeking and checking out for negotiation competencies, persuasion competencies, and drive for results. Here are the questions I'm going to ask and here are how they will be assessed. Okay, Harry, you are going to test for these other competencies. Here are the questions you are going to ask and here's how you will assess them. And so, the interview is very structured, and I'm making this up. It's a three-hour process for the candidate, and every candidate is also gonna have the same take-home test.

    28. HS

      Hmm.

    29. SM

      Every candidate is gonna go through the same personality test. Like, so it's very, very structured. There's no room for bias, there's no room for repetitive nature, and you follow that process. So, you, you can get the most data for your candidate in th- that amount of time that you're allowed.

    30. HS

      Okay. So, we have three different interviews over three hours? And w- how are they just divided up, just so I understand? I'm, I'm a founder literally hiring my first salespeople. One is, like, competencies? What's, what are the other two?

  14. 59:49 – 1:09:20

    Sales Compensation Insights

    1. SM

      So, I don't waste-

    2. HS

      Mm-hmm.

    3. SM

      ... my time, I don't waste theirs. Transparent pay. The second lesson I've learned is I've moved to a national pay structure, right? So, if I live in London, um, if I live in New York City, if I live in Cleveland, Ohio, it's still the same job. Right? You're still performing the same tasks. So, that transparent, standard pay doesn't really matter where you live. And I pay on the higher end. I assume you live in London. I assume that you live in New York City, and I will pay you on that high end. Not the highest-paid shop in New York City, but I'll pay you on that high end. So, transparency and one pay structure.

    4. HS

      Okay. What are the biggest mistakes people make when they're negotiating comp?

    5. SM

      They underpay or they overpay. Those are the biggest mistakes.

    6. HS

      Hmm.

    7. SM

      Where, um, there's- there's great data that exists about how much people are paid for certain roles. There's- it's very transparent, but some people, they underpay in a startup, and they just try and overpay, let's say, on the equity side.... right? I get that. But that's a mistake.

    8. HS

      Yeah. What's the right OTE level, do you think?

    9. SM

      So, uh, on the enterprise and national pay, depending on what your quota would be is probably the right place to start, right?

    10. HS

      Yeah.

    11. SM

      So best practice is a five-to-one ratio, so if I'm gonna pay someone 200 Pound Sterling, I want them to have a million quid as a, as a goal or as a quota, right? So, like, thinking about what the, the, um, what that ratio that you're willing to pay. Now in a startup, you may have to sacrifice that a bit, so maybe four to one-

    12. HS

      Okay.

    13. SM

      ... based on what that quota is versus what you're willing to pay. But that's considered best practice, so look at it in that type of way. Then, depending on where you're hiring, you can get plenty of data on what, like, the averages are.

    14. HS

      Yeah. No, I get you totally. How long does it take to ramp to get people to quota? Like, you bring me in. Like second quarter, does Harry tend to hit quota? In third quarter? I know it depends on the ACV, but selling in enterprise with large ACVs, generally speaking, how long does that take?

    15. SM

      Yeah, so if you're selling into the enterprise, and let's just use an ACV of 100K.

    16. HS

      Mm-hmm.

    17. SM

      Right? You wanna let that rep ramp for about six months.

    18. HS

      Hmm.

    19. SM

      Move slow in order to move fast later. But don't wait those six months to measure their performance. Have stage gates along the way those six months. But an enterprise rep, it'll take a good year, right?

    20. HS

      Yeah.

    21. SM

      Because the next six months, you, you ease them into their quota. You want them to be successful at the end of the day, right? And so you want them to-

    22. HS

      The thing that fucking kills companies, though, is churn. When you look at the amount of sales reps that leave after two years, it's so high. And so you actually have, like, six months of productivity in 24 because it takes a year to ramp. The final six, they're thinking about, you know, how they're gonna leave. And so you've got six in the middle where they're productive. Doesn't this kill organizations?

    23. SM

      It, it does if you let it, right? And the conversation we were having a little bit earlier, the piece of the conversation we had earlier, which is, in your sales process, you'll know within the first six months if this rep's gonna cut it in the enterprise or not. You should.

    24. HS

      Yeah.

    25. SM

      And, and when I think founders make a mistake is they wait for how many deals that they get a year and a half later.

    26. HS

      Hmm. Yeah.

    27. SM

      There, there should be more stage gates in those first six months.

    28. HS

      What, what, what, what are the stage gates in the first six months that should be had to understand the effectiveness of a rep in enterprise?

    29. SM

      Uh, certification. So I've always, uh, embedded a certification culture within my revenue organization. And so you're testing these sales pros. You're having them test on your product. You're testing them on your narratives. You're testing them on whatever it is that you want to test them on. And then when they get in sales cycles, are they graduating from stage two to stage three in the sales cycle or not? What's missing? Listening to the Gong conversations or Chorus or SalesLoft or whatever you use, but those first six months in the enterprise are very, very critical.

    30. HS

      Yeah.

  15. 1:09:20 – 1:13:50

    Quick-Fire Round

    1. HS

      process, on the firm, anything that..." And the best always do have many questions.

    2. SM

      Yes.

    3. HS

      Yeah. What sales tactic has died a death?

    4. SM

      Discovery.

    5. HS

      Why?

    6. SM

      Because there's too much information that we can extract on our own that we should know a lot about our buyer before we engage with them.

    7. HS

      What was your favorite question to ask in an interview process for a sales rep?

    8. SM

      Explain a time to me when you were asked to call back in six months. The reason why I love that question, Harry, is you will expose that person and how, and how they operate pretty quickly.

    9. HS

      Do the majority not just say, "I haven't, I haven't been asked to call back in six months"?

    10. SM

      No. The majority say, "Oh, that's great. I'll make sure I put it on my calendar. Here's what I'm gonna do in the interim and I'll call you in six months." I've had the majority say that. Every business-

    11. HS

      Is that a lie?

    12. SM

      Those are the people I don't hire.

    13. HS

      Is that, is that a liar?

    14. SM

      Yeah, I don't hire those.

    15. HS

      What's the best answer?

    16. SM

      The best answer to that question?

    17. HS

      Yeah.

    18. SM

      They reframe the problem and they teach me something that I didn't know about my business right now in that moment.

    19. HS

      What other function does sales has, have the most friction with? Product? CS?

    20. SM

      Sadly, yeah, sadly, it's product and marketing.

    21. HS

      Mm-hmm.

    22. SM

      Because salespeople, uh, they want a product that's applicable for everyone, right? So they complain about the product, which is wrong. And the second reason why sale's wrong is on marketing. They want a fat pipeline of buyers that are ready to buy, and they blame marketing for it, which is also wrong. So that's typically where the most conflict is.

    23. HS

      Take me to a deal you've had to get really creative to win. What did you do, Sean?

    24. SM

      Everything (laughs) . What we were talking about earlier about discounting, it's just not about discounting, it's about give and gets. And I've had some of the biggest companies that I must win, and I must have them as a customer, but they'll sit on my customer advisory board. We will promote them in different ways. We will use their product in new ways. There are ways to get creative to win the business. But basically, people want to buy, they just don't want to be sold to. And so, the way I get creative to win deals is to make it a no-brainer for that buyer to, to, to trust me and to go with me.

    25. HS

      How do you maintain morale when missed goals happen? It always happens at some point. How do you maintain morale?

    26. SM

      Well, first, it's not easy. But second, it's goal visualization. Celebrating these small, quick wins is very important because there are small wins that happen throughout the day. And goal visualization, reminding the team of our purpose and our mission and why we do this every day. Reminding the team of the impact that we're having in the market. As an example, Harry, over this past year when there's a very low hiring volume that's happening right now, right?

    27. HS

      Mm-hmm.

    28. SM

      Greenhouse, we have helped over a million people win the job of their dream by using a fair process leveraging Greenhouse software. So I remind people of really what we're building and what we're doing. We have 7,000 customers, and we've processed over a million offer letters through our software this year when no one's hiring. But to answer your question, don't forget the goal visualization. Yeah, we all wanna make money and hit our quota, uh, all those things, but you gotta go deeper sometimes and get back to what really motivates people. Because not everyone's motivated by money, shockingly.

    29. HS

      What f- final one, what one company sales strategy has most impressed you recently when you look across the landscape?

    30. SM

      20 VC, you.

Episode duration: 1:13:50

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