Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034

1. 0:00 – 1:13

   Who is Kevin Egan

   1. KEKevin Egan0:00

      I think when I'm closing a candidate, I'm, I'm interested if I'm giving them a fair comp plan, are they really interested about the long-term journey at this company? 'Cause this comp plan only represents this moment in time for the next year or two. Um, if we're both successful, the company will, um, increase in size. Our jobs will be different. Our jobs will be bigger. So what, how do they view the o- the long-term journey at this company? And are they excited about the company and the journey, or is it about the comp plan? It's really about a total rewards element, which is you're, you're joining a rocket ship. Uh, you're gonna love this job and it's gonna, you know, really benefit your career overall.

   2. HSHarry Stebbings0:36

      Kevin, I have heard so many great things from Maggie, from Kim, from Renu. But I wanna start in the beginning. So it hit me, how did you make your way into the world of sales first? Let's start there.

   3. KEKevin Egan0:47

      So I was lucky to join Oracle in the mid-'90s, and I started, um, in the data center in a technical support role, and quickly made my way over to the sales engineering side of the house, uh, supporting database technologies, again, at Oracle in the late '90s in their DMD organization, which was a fast-moving, fantastic place to learn, learn both sales and technology.

   4. HSHarry Stebbings1:12

      You know,

2. 1:13 – 4:35

   Lessons from Salesforce, Dropbox & Slack

   1. HSHarry Stebbings1:13

      I, I thought it'd be really cool, uh, but also a little bit unfair if I started with a quickfire round, 'cause you've had some incredible companies where you've been an essential part of their sales teams and often led them, Salesforce, Dropbox, and Slack. And I thought there's gonna be, like, one or two lessons from each that really shaped how you think. And so I wanted to delve into each in a quickfire round. So if we take Salesforce, what was the biggest takeaway for you? And how did that shape how you think?

   2. KEKevin Egan1:40

      Salesforce does not get enough credit for being one of the original product-led growth companies. If you look at Salesforce and what Benioff did in the early days, we were one of the first companies to ever allow companies, or our, uh, potential clients to use a trial of our service at no charge for 30 days. And during that trial, the sales team was obsessed with, what are the business problems that this customer's trying to solve? How do I c- help configure the Salesforce service to help solve those business problems? And it led to incredible conversion rates. So the idea that if we're gonna put the product in our customers' hands, we gotta give them help in terms of how they solve their problems, uh, as a, as a key accelerant. So that was an amazing element of Salesforce, and, and one I just don't think they got enough credit for. Uh, Salesforce remains an incredibly customer-centric company. Uh, so lots to learn there overall.

   3. HSHarry Stebbings2:34

      Let's move to Dropbox. You then spent four years, a little over four years at Dropbox. What was the biggest takeaway for you from your time there? And how did it shape your mindset?

   4. KEKevin Egan2:43

      My biggest takeaway from Dropbox was the importance of getting it right, the, th- that being, how do we provide a product that end users really love, but that large enterprises can trust from a security and operations standpoint? So the balance between end user love and an enterprise security posture is a really difficult one to strike. And I think Dropbox was one of the first companies to go from a B2C company into the B2B realm, and really work hard to get the, the enterprise posture and the security and controls right, which is no small task. And it's, uh, somewhat of an unsexy pursuit, uh, but it's much necessary in order for large companies to trust you and to bring you in, uh, and allow you to expand within their domain.

   5. HSHarry Stebbings3:24

      I mean, we're gonna dive into that later. I'm gonna pepper you with questions, so have no fear. We- we're gonna, we're gonna fully embrace that one. Final one there before we do dive in, Slack, such a hyper growth story that you were, you know, core and central to. What was your biggest takeaway from your time at Slack? And how did that impact your mindset?

   6. KEKevin Egan3:41

      Well, I think Slack coming a little bit later had the benefit of watching other companies go before us from that, that marriage of end user love and virality and the enterprise posture. If you think about Slack, the, the power of Slack comes, the bigger the team, the, and the, the more employees you can get engaged in that platform, the more value they drive to their customers. So Slack, from day one, had an appetite to work with large teams and large customers. Uh, yet they had an incredibly engaging platform. So that ability to marry end user love with the enterprise posture right out of the gates, focused on large teams and all the security controls that were necessary there, was something that was, uh, truly unique at the time, and, uh, very enjoyable. It, it led to, uh, as you said, hyper growth.

   7. HSHarry Stebbings4:29

      It did, and also, that's where I heard so many great stories, as I said, from Maggie, Kim, and Renu. Now, I do wanna

3. 4:35 – 7:30

   The Sales Playbook

   1. HSHarry Stebbings4:35

      start at the core crux of a lot of the discussions I have with founders, which is a sales playbook. Can I just wanna get some nomenclature right? How do you define sales playbook, Kevin?

   2. KEKevin Egan4:45

      Well, that's an interesting question, Harry. I don't typically use the word playbook. I know a lot of people do, and, and I don't have a problem with it. But playbook, to me, seems like just a simple one, two, three, and you follow these steps and you're gonna close the deal. When I think of a playbook, I actually just think of sales motions. I prefer the, the term sales motions. And understanding really who is the buyer? What's the user persona that we're selling to? What's the industry that they're in? What are the business problems that they're faced with? And how does our product and our service uniquely solve that problem? And talking in terms of the unique solution to that problem is where I think strong sellers really shine. Um, and, and not talking about product features, but really the solution that, uh, overall would drive your business value. So that's a motion more than it is a, uh, one, two, three playbook in my mind.

   3. HSHarry Stebbings5:37

      So when we think about that motion, is it the founder that needs to be the one who creates the different motions? Or are they able to hire a first sales leader, a first sales hire to create the motions for them?

   4. KEKevin Egan5:51

      I think when you listen to a founder speak to their product and how it solves business problems, it's the job of the sales leader to pull from that-... and codify it, and put it into, into writing and, and explain that these are our sales motions. So I think it's the CEO and the founder's job to provide the inspiration and the high level talking points and, and the, the kind of the idea matching as they're talking about, uh, other executives. But it's the sale- it's the sales VP's job to really kind of nail it. (clears throat)

   5. HSHarry Stebbings6:23

      (laughs) No. I, I totally agree. I think nailing also kind of create re- repeatability in it for others to really take hold of. If we think about PLG versus enterprise, something that I see a lot of today is founders chasing PLG and enterprise kind of from day one. Can you do both at the same time, do you think, Kevin?

   6. KEKevin Egan6:43

      I think you can, but I think it's extremely difficult. I think Slack was able to do it. I think they nailed PLG first, uh, and then enterprise. But they always had a, an eye towards enterprise. The reason why I say it's extremely difficult is to capture the end user's imagination, capture that end user love is one thing. But to build out the enterprise security set, the future set, and the enterprise posture, all the processes and controls that are necessary to really go big in enterprise, uh, takes many, many years. So I think, uh, it is... If I had to pick a path, it's probably more sequential. PLG first, gathering that end user love, and then adding on the enterprise layers following that.

   7. HSHarry Stebbings7:24

      I, I mean, we're gonna delve into that. I just have to ask. You mentioned Slack nailing PLG first there and then moving to

4. 7:30 – 13:35

   When to Movie Into Enterprise

   1. HSHarry Stebbings7:30

      enterprise. I, I just chatted to Kim before this show, and she said, "I had to ask, how did you know it was the right time to move into enterprise when you did with Slack?"

   2. KEKevin Egan7:40

      If you're a product that's generating enough end user value and it starts to spread within companies, you're gonna get pulled in by those companies to enterprise. And you're gonna get to user counts that are so significant, you're gonna get on the radar of procurement and legal, and they say, "If this many people are using this product, I want the right terms in place so that I can feel comfortable using the product." So you're gonna feel a real pull if you're getting it right and that virality is happening within companies. And I think that's what happened at Slack. They had, in, in some cases, tens of thousands of users within single companies that said, "Hey, look, we need to come to the table and operate. You need to operate as more of a strategic partner than a rogue service, uh, that my end users love."

   3. HSHarry Stebbings8:26

      I, I absolutely love that. But then we come to that realization, we're getting pulled into enterprise, we're getting pulled into procurement. I think there's a maybe naivety sometimes around what needs to change when you move to enterprise. What are the biggest elements, Kevin, that need to change when you're scaling from a PLG motion to an enterprise motion?

   4. KEKevin Egan8:44

      Well, I think number one is scale and reliability. They need to know that if they're, if this becomes business critical, that you're gonna be, you know, providing the SLAs and the 99.99 uptime. Uh, there's data geography requirements around data residency. If I'm gonna use a service in Japan or if I'm gonna use it in Europe, I need to know that you have got local data centers. Uh, there's process controls. Tell me, you know, they wanna know how your engineers control data, who has access to that data, what c- what security and protocols you use around that data. They have encryption requirements, data loss prevention requirements. Uh, so it, it gets pretty deep. And I think the one thing to emphasize there is that there's no finish line. It's not like, as a, uh, PLG company, you can dip your toe into enterprise and deliver these three or four features. It's, it's a lifelong pursuit that you need to be in partnership with your customers. If you look at today and just the changes in the, uh, data requirements around GDPR, like, that's a full-time job for someone to be looking at that and saying, "Okay. Well, how are we running our service? And is it compliant in Europe?" So it is a, uh... It's naive to think it's just a few features, uh, because in fact, it is a lifelong pursuit to, to make sure that you're staying up with the, the most, uh, stringent requirements that are coming out of enterprises today.

   5. HSHarry Stebbings10:03

      I totally agree. You can't dip your toe in. Those are the quite technical

   6. NANarrator10:06

      Yeah.

   7. HSHarry Stebbings10:06

      ... gnarly aspects of what needs to be done. There's also just the a- actual ability to move there in the first place. When you think about structuring your sales team as well, does the sales team carbon copy from PLG to enterprise? Should we change the structure? Should it be, you know, more formal from AE to SDR to you name it? Like, how does the structure of sales teams change when moving from PLG to enterprise?

   8. KEKevin Egan10:32

      Well, I think at first, the sales team is, is obviously there for revenue growth, but almost even more importantly, providing customer feedback into the product group. Giving the product team that they're working with a sense for, why do these people gravitate to this service? What business problem is it solving? How would you, down the line, translate this into ROI for the end user? And once they start doing that... So it's a, it's kind of at the be- early days, it's creating a, a major feedback loop, which you can build that repeatability on. Once you have that repeatability, then you can start to build sales teams that are more traditional with the EDR, um, core sellers focused on just revenue numbers, uh, supported by sales engineers and so forth.

   9. HSHarry Stebbings11:19

      Can I ask you a bit of a weird one? But like, when you're doing PLG, you kind of know if sales teams are good. You see very quickly the velocity that they close customers. The sales cycles are shorter. It's easier to tell effectiveness. When you're scaling into enterprise, sale cycles are longer, conversations take more time. How do you determine rep effectiveness when moving into enterprise?

   10. KEKevin Egan11:41

       In a PLG world, I think rep effectiveness... The best companies out there are doing a lot of AB testing. Atlassian is famous for AB testing, "What happens if I put this account in the hands of a rep versus my, my regular, uh, online channels?" And I'd say the most effective way is that testing.

   11. HSHarry Stebbings12:03

       Okay. Should we test from the start? Should we layer the testing in? When we say, like, testing, if I'm a founder listening, test with what? A rep versus customers- uh, uh, what- what is the alternative to testing? Do you see what I mean?

   12. KEKevin Egan12:17

       Yeah. So if you're doing an A/B test, you have your market, you have your online channels. You've got chat, you've got your website, and you've got your e-commerce engine and so forth. So that's one channel. And then the other would be sales rep handle, where you can kind of measure what they're doing through their activities in Salesforce and opportunities that are being created. So you simply have a cohort of customers that are managed through, uh, the web channels and another cohort that are managed through sales reps. And if you see outsized growth in the ones managed through sales reps, hopefully you do, uh, then that'll tell you that you have strong effectiveness.

   13. HSHarry Stebbings12:52

       One way to tell effectiveness is also, like, when you hire multiple at the same time.

   14. KEKevin Egan12:55

       Yeah.

   15. HSHarry Stebbings12:56

       You can tell... Do you agree with the hiring two or three at the same time, or actually do you think that's unnecessary?

   16. KEKevin Egan13:02

       Well, coming into Salesforce and Dropbox and Slack and Atlassian, there were, there were already small teams built out. But I do favor hiring two to three at a time if you can afford it. I think that, that is a great indicator of sales rep ef- real sales rep effectiveness, and the comparison on, on the reps, uh, is very effective and will tell you, number one, "Can my reps accelerate?" And number two, "Within my sales rep base, uh, who's really carrying the water up the hill and making it happen?"

   17. HSHarry Stebbings13:28

       I totally agree, if you can afford it. I think it's a very, very good way to tell effectiveness. If we dive into that hiring process,

5. 13:35 – 21:27

   How to Identify & Hire Talent

   1. HSHarry Stebbings13:35

      I heard that you are incredible when it came to identifying talent.

   2. KEKevin Egan13:39

      (laughs)

   3. HSHarry Stebbings13:40

      Um, how do you structure the hiring process for new sales hires? And if I'm a founder that you've angel invested in, how would you advise me? I've never done it before and I need that help and guidance.

   4. KEKevin Egan13:51

      I think that hiring s- great salespeople is about process and it's about discipline and process. When I was at Salesforce, I had the benefit of being a part of a process that came together that we really invested in. As Marc Benioff said, he, he wanted to see everybody have hiring fatigue. Everybody should be interviewing it all the time, whether it be for a job opening that you have today or one that you might have down the line. To hire well, you really need to put a multi-step process in to get to know the, the, the candidate, to get to know how they approach a customer, understand business problems, and then present to those business problems in a differentiated way. No hire that I've made at, uh, my past companies have gotten the job until they've presented a, uh, a mock scenario around a fictitious company, uh, and a business problem that they're trying to solve. So we really put the rep on the, on the spot, so to speak, to show how they deliver in the moment, uh, if we're talking to a customer about how they'll uniquely solve their business problem. So this is, again, we're... And by the time a rep gets a, a job with one of these companies, they should have met with five or six different people and five or six different steps. And, uh, that stand and deliver moment, I think, is important and tells you who can really, uh, command the conversation.

   5. HSHarry Stebbings15:05

      Kevin, help me out here. Mock scenario, what does that look like? So one, like, often people either give, like, the mock scenario of the company where the rep's at now or the company that the hirer's at, which is kind of biased, I find, in- in either direction. How do you think about which company that they should, like, sell against or, like, sell for? Um, how long do you give them? Who's in that mock scenario meeting? What makes the best ones? Can you just help me understand what- what that looks like for me?

   6. KEKevin Egan15:35

      Sure. So I could go either way on that. At Salesforce, we gave them a fictitious company and a business, set of business problem that they were to solve using the Salesforce set of solutions. At Slack, we were comfortable with them positioning their own service. Uh, and so I think both have their advantages. I just think it's of- what's important is really to really lay out what the business problems are, how this rep is gonna solve them, and how they're gonna kind of command the room, so to speak, when they're trying to get it over the finish line.

   7. HSHarry Stebbings16:04

      Can I ask, I, I, I'm... Respectfully, and this is gonna sound incredibly arrogant, I don't, I struggle with that one. Again, you're the hailed business leader, so I'm like, you know, being very bold here. But if you have, you know, years at a company, I know back to front how to articulate my business solution. I know back to front every aspect of it. I can pull the wool over your eyes in seconds. If you give me a new company and say, "You got 24 hours, sell me this pen," I've already gotta think on my feet about different customer personas, different customer needs, how to position that in market competitively. I've really gotta show my skill on the spot in real time, like sales leaders need to. Do you not think that actually it's a bit easier if you give them what they already know?

   8. KEKevin Egan16:49

      Good question. I think if they're selling you what they already know, then the audience should be delivering much harder questions and, uh, harder objections. So I- I think you can accommodate for that in terms of the tone that you take in that meeting.

   9. HSHarry Stebbings17:05

      So, like, what do we think about good versus great? How do the best do in these mock scenarios, and are there any red flags that you look for?

   10. KEKevin Egan17:13

       The most curious part of the interview process is when they get through final interviews and you're assuming that they're just gonna crush the mock scenario. And sometimes they'll just come in and it'll be a flop and you'll say, "Wow, I just never saw that coming." And that comes down to what's their comfort level being in front of a room, being in front of an audience that's gonna throw up real objections? So sometimes you're surprised. Uh, good versus great comes down to are they consistent throughout the whole process, right? Do they, do they crush the interviews and then just come in with a level of confidence, uh, during the mock scenario that just wins you over and makes a ton of sense? So I th- I'd say overall it's consistency. When you start to see inconsistency across the different steps of the process, uh, that's definitely a red flag.

   11. HSHarry Stebbings17:57

       Does the type of person that you need change dependent on whether you're running a PLG or an enterprise motion, Kevin?

   12. KEKevin Egan18:04

       I'm not sure I differentiate so much on enterprise versus PLG. To me, it's a little bit more about the timing of the company. How old is the company and where are they in their journey? Uh, early days of hiring reps, you're gonna need renascence reps that have a very wide breadth of, of skillsets, uh, who enjoy the building process. And as things go on and you start to sale- scale your sales team, you're gonna see reps that are there for, really to make a living and are more concerned with what's the paycheck and what's the quota, uh, and that is, that's a different rep. So I think it's, to me, it's a little bit over time, how the reps change, a little bit less PLG versus enterprise. But, uh, certainly as you go into enterprise and you've been there longer, that rep that is gonna be successful there has more experience and is more focused on wha- what are my set of accounts and how do I crush my number?

   13. HSHarry Stebbings18:56

       Can I ask, do you think it's a fair description-

   14. KEKevin Egan19:00

       (laughs) .

   15. HSHarry Stebbings19:01

       ... that sales reps are coin-operated, and is that a bad thing even? I hear founders sometimes say, "Oh, I'm a bit worried about how focused they are on the comp, on the OTE, on the bonus." Is that a bad thing?

   16. KEKevin Egan19:14

       Again, going back to timing, it does not pay to have coin-operated sales reps in the early days. They are gonna be overly focused on quotas and, and, and crushing their number to, to get to a certain outcome. The early days are really about who is creating the best connection between my developing product and my potential customer. But I think in the later years, or as you build out your sorg- sales organization, while I don't like to term coin-operated, uh, people do become more specialized as you get bigger as a company, and the specialization of the sales rep is to bring in customers and grow revenue, and they need to make a living and, and so, um, I would be concerned about coin-operated early days but n- but not later.

   17. HSHarry Stebbings19:54

       I hear a lot of founders say that biggest mistake they made when hiring sales teams was hiring for logos. My question to you is, do you... How do you advise founders on the logo hires? So often I see startups and they go, "Ooh, amazing name from..." You name it, big company. Microsoft, Oracle, you name it. Um, and they say that's their big mistake. How do you advise on logo hires and what to look for?

   18. KEKevin Egan20:21

       I think for a founder who's hiring, I could absolutely see where the big logo hire does not work out. Uh, I think, again, what you're looking for there is intellectual range, and that often doesn't just show up from, by the fact that they worked at Microsoft or came from Google or what have you. Um-

   19. HSHarry Stebbings20:40

       What do you mean by intellectual range, Kevin?

   20. KEKevin Egan20:42

       What I mean by intellectual range is this person, this initial sales leader, is gonna have a lot on their plate. Uh, they're not gonna have a, a big marketing team that's, that they can outsource all of the, uh, the writing and the messaging to. They're not going to have all the resourcing from product management and so forth. So they're gonna need to do a lot of different things. And so, they're gonna need to have energy and range to do everything from writing to messaging, to closing, and, um, providing that customer feedback, you know, the voice of the customer back in the product. So that range as we get... As the companies become bigger and more specialized, uh, starts to narrow, if you will. But in early days, it's really about how much stuff are you willing to take on? And, and that's, that's what I'm referring to when I talk about range.

6. 21:27 – 26:00

   How to Structure Comp Packages

   1. KEKevin Egan21:27

   2. HSHarry Stebbings21:27

      Can I ask you, Kevin, you've hired some of the best across many different organizations. Comp packages are pretty hard to understand if it's your first time and to know what's good, what's fair. What have been some of your biggest lessons on effective comp package giving when rearing?

   3. KEKevin Egan21:44

      Well first, your comp plan needs to be fair, and there's plenty of market data out there that you can get to understand, am I in range of market to provide a fair comp plan? I think when I'm closing a candidate, I'm, I'm interested if I'm giving them a fair comp plan, are they really interested about the long-term journey at this company? 'Cause this comp plan only represents this moment in time for the next year or two. Um, if we're both successful, the company will, um, increase in size, our jobs will be different, our jobs will be bigger. So what... How do they view the o- the long-term journey at this company, and are they excited about the company and the journey or is it about the comp plan? Sometimes if it becomes, uh, too much about the comp plan, then that, then that's a red flag because it is... It's really about a total rewards element which is, you're, you're joining a rocket ship, uh, you're gonna love this job and it's gonna, you know, really benefit your career overall. So that's kind of what I'm looking for, but comp plans certainly need to be fair. If you're not providing a fair comp plan, you, you can't, uh, expect to hire the best.

   4. HSHarry Stebbings22:41

      I, I totally agree with you in terms of the importance of fairness there, front and center. Uh, e- I... Uh, one of my favorite, uh, mentors says, "You're never wrong to do the right thing." And I always think back to that on fairness. Um, it's a lovely one. Can I ask you though, uh, you know, again, we mentioned, like, working with amazing people. Again, spoke to so many that worked with you and they said once you hired them, you were incredible when it came to trust building. And I wanted to ask you, how do you think about building trust with new hires and them building trust in you? Both ways. What works for you?

   5. KEKevin Egan23:19

      Well, I think on the journey of, of people joining a company, in the early days, they, they wanna have clear expectations and you as a leader need to be a little bit more directive on what are the expectations and how they... How, of how you're gonna get there. And then as they become competent and, and ramped up in their job, it's a little bit more of a partnership and here's what, here's what we're going to do. I wanna hear more ideas from them on what they see, uh, as the next steps for the organization. So, it goes from directive to more of a partnership. So I think that's an important element. Um, the job and the, the manager-employee relationship changes over time. Uh, so that's one thing I try to focus on.

   6. HSHarry Stebbings24:02

      It changes over time. How do you retain a sense of hierarchy? I think one thing that I've got wrong, Kevin, as a manager, honestly, I'm young, is I try to be people's friend.And I'm not your friend. Like, I am your boss at the end of the day and I know we don't like hierarchies or boss, but like you, you are someone's boss, and everyone has a boss. How do you retain that hierarchy, but also trust and proximity?

   7. KEKevin Egan24:29

      So I think the word hierarchy is interesting. I think the employee really needs to appreciate that their manager has more on their plate, that their manager is dealing with a level of complexity that they may not have to deal with, right? If I go up and if I look at my manager, Cameron, he's got more on his plate than myself. And they need to appreciate that you've got a lot going on, and when you're with them, you're focused on, in their world and what's important to them. But they need to s- they need to have a sense for, "If I was to take your job, here are the four or five things that I would need to ramp up to have a grasp on." If they feel like you're doing the same job as them, then you're in trouble and the hierarchy is gonna break down. So I think it's about how much work, role, and responsibility that we're putting at every level so that people can be their best, and how do we ramp them into the next job, and do they have an appreciation for that there is a ramp? If they do, then I think hierarchy works and there's an appreciation. Um, secondly with hierarchy, I think you're not gonna exercise hierarchy every day. But there are moments, uh, throughout the year where you have to be very direct with your employees on what the expectations are, and if they're not h- uh, meeting those expectations, you certainly need to deliver that news in plain speak and they need to know where they stand. So I think hierarchy also breaks down if the leader is not available or comfortable providing direct feedback.

   8. HSHarry Stebbings25:58

      I mean, I'm glad you said about direct feedback.

7. 26:00 – 31:25

   How to Give Feedback

   1. HSHarry Stebbings26:00

      I heard that you were very good at providing direct feedback, which again, is something that I honestly struggle with, um, and I like to avoid conflict. What would you advise founders on how to provide effective direct feedback?

   2. KEKevin Egan26:14

      When I think of direct feedback, I think of it in terms of a ratio. So there's the day-to-day work that we're trying to get done, there's the challenges that we're facing, and we should be enjoying those challenges and having fun with it. Uh, but there's also times where we need to get better or we have our blinders on and we need to be thinking more broadly, and it's the job of the manager to, to break that news, so to speak. Uh, but it ha- it is a, a portion of the relationship. It is not a constant, uh, feedback loop that's happening every day. It's a moment in time. People will kind of dust them, you know, sit up a little bit straighter, dust themselves off, and off we go. We're back to more of a, a con- congenial, fun working relationship. But again, you can't be afraid to provide that feedback. And if, if you're not providing it, I think the employees sense that, uh, and they are disappointed when they don't get feedback 'cause it's something that everybody I've worked for is looking for.

   3. HSHarry Stebbings27:11

      What are the biggest mistakes sales leaders make with feedback?

   4. KEKevin Egan27:14

      When I think of feedback, if you... Liz Wiseman's book, Multipliers, really nailed it. Like, is the feedback diminishing and is it overbearing and is it too frequent, or is it just the right amount and is it geared towards the priorities that we're trying to get after? So I think it's about frequency, uh, and making sure that it's not personal, but it's about, how are we getting after it as a team?

   5. HSHarry Stebbings27:36

      I, I totally agree with that. In terms of how we're getting after it as a team, you need something to get after. How do you think about effective sales forecasting in 2023, a year of such uncertainty?

   6. KEKevin Egan27:48

      In the year 2023, I think sales force- forecasting has gotten a little more difficult. Um, everything is on the table. Every company is looking for areas to trim or reasons not to spend. So as a rep or a sales team, you better be crystal clear on the business problem that your sol- your pro- your solution is solving and why the cus- company would spend money on it and what are they expecting in terms of return. If you don't have those things, you may not have a deal that's forecastable.

   7. HSHarry Stebbings28:17

      How do you think about CFOs being in every deal now? The deal cycles have changed so significantly in my mind. The buyers have changed so significantly. Everything about the way that we used to sell has changed with the complexity that now is inherent within cycles. Do you agree, and how does that change your process?

   8. KEKevin Egan28:34

      I think when the CFO is involved, w- we welcome it. I think if, if the CFO is involved into your deal and they're spending time on that deal, that tells you that you are strategic to them. So your responsibility to respond to that is giving them the fi- you know, the financial or the value engineering as it's called on the ROI. And that is the, the job of the sales team to do that. Maybe they have resources in a value engineering team, maybe they don't. But really giving the CFO a cris- crystal clear picture of what's the return, um, I think is table stakes these days. And again, uh, we don't... Uh, I, I welcome it because it tells you that they're willing to lean in and work with you as a partner.

   9. HSHarry Stebbings29:18

      Speaking of kind of leaning in and working with you as a partner, when you think about like driving them home to actually closing, how do you think about quite a challenging element which is balancing hitting quarterly revenue targets with longer term pipeline and sales strategy? How do you think about that balance?

   10. KEKevin Egan29:36

       I think the balance between hitting the quarterly number and building long-term pipeline for the... if it's an early stage company who absolutely needs that, that deal, you're probably gonna need your leadership and executive support as a seller on your side to make it clear in the right tone to the prospect that this is an opportunity that would really help the company at that time. Uh, but it needs to be done in a tone that works for the customer. Uh, jamming deals at the end of the quarter is always kind of obnoxious, but, uh, it happens. Uh, it does work, but sometimes there is a detrimental effect to kinda...... cramming deals at the end of the quarter, uh, from a brand standpoint and from a relationship standpoint. So, uh, you know, the magic in all of this is the best reps are creating ample pipeline throughout the year, and they somehow have so much, you know, they create enough pipeline that they're able to hit their quarterly numbers without doing any- anything unnatural to get those deals in. Because if one falls out, they've got another that comes in. So it's around really generating enough pipeline throughout the year so you don't put yourself in that position. Um, now is that possible every time? Probably not, but, uh, for the most part over the long run, uh, pipeline covers all SIMs.

   11. HSHarry Stebbings30:57

       Kevin, do you do discounting, my friend?

   12. KEKevin Egan30:59

       In my current role at Atlassian, we, we don't discount. We try to work on terms that work for our customer, but everything's programmatic. So if our customers were to, uh, speak with any other customer, they know that they're in the same boat and that, um, we're transparent and fair. Uh, at other customer, at other, uh, previous employers, yeah, we would discount and, um, but that was, you know, something that worked well for both the company and the customer.

8. 31:25 – 35:30

   How to Do Discounting

   1. KEKevin Egan31:25

   2. HSHarry Stebbings31:25

      How do you do discounting well? Do you know what I mean? Like, if I wanna get it over the line, I don't wanna seem desperate. I don't wanna give away too much. But how do I do discounting well? And do I need approvals to do discounting? I'm a rep on your team. Can I give a 20% discount? Can I, can I give a 30% discount? Like, what, what stage is acceptable versus unacceptable?

   3. KEKevin Egan31:47

      Good discounting should originate from the office of the CFO. Meaning the CFO knows the margins, they know what they're willing to, uh, what margins they're willing to give away on products at what volumes. What should happen in most companies is sh- CFO should provide a discount matrix that the rep might have a few points to give, the rep's manager might have a few more points to give based on volume, and then all the way up to the sales VP, and then at some level, the exception would come from the CFO. So it should be very well organized, and it should be with an eye towards what can the, uh, company afford to give, uh, based on certain volumes. If it's, if it's distinct or not tied into the CFO's office, then I think you're gonna run in circles and have a lot of problems.

   4. HSHarry Stebbings32:30

      Can I ask, what are the biggest mistakes that you see startups and startup founders make when it comes to discounting?

   5. KEKevin Egan32:36

      For most startups, if you're in with procurement and you're not selling through PLG and through the website and swiping the credit card, so to speak, and you're in with procurement, that procurement agent knows that you're a startup, knows that you are, um, really keen on that revenue and that that revenue matters, and they're gonna push you harder than they might other vendors. And what they're looking for is conviction on your side that you believe in the product, that you have an understanding of the business value, uh, value and the ROI that it's gonna provide, and they're looking for you to make a stand. So, you'll face more pressure to discount, but I think procurement is looking for you to hold the line.

   6. HSHarry Stebbings33:17

      I totally agree, they are. Can I ask, if you don't get a deal over the line, you do a deal review or you do deal reviews generally, but I just wanna focus on that. How often do you deal, do deal reviews? How do you structure them? Who's invited? Can you walk me through how you do deal reviews?

   7. KEKevin Egan33:35

      A deal review is happening at different frequencies based on where you are in the organization. So sales reps having a deal review with their manager, uh, daily. I'm spending two to three hours a week just doing deal reviews. A deal review is, uh, what p- what separates good from great, I think great is organized using MEDDIC or MedPic or some framework for, how do we assess the deal, the people in the deal, the business value, and what are the drivers and how are we gonna get across the finish line? And I think the best sales leaders that I've seen run deal reviews aren't so interested in why the deal is gonna happen, but they're more focused on why the deal won't happen. So it's the job of the manager to kind of see around the corner or see areas of weakness in that deal plan to really get the team to step up and cover any gaps. So it's about why it's not gonna happen, not all the good news about why it is going to happen.

   8. HSHarry Stebbings34:25

      Kevin, I'm on many boards and very often they say, "Ah, you know, it just slipped to next quarter. Just slipped to next quarter." And I never quite know what to say. I'm like, "Well, you know, why?" And they're, "Well, we're not really sure," blah, blah, blah. H- how do you respond when you hear the classic, "Oh, it's slipped to next quarter"?

   9. KEKevin Egan34:45

      When I hear, "It's slipped to next quarter," what I'm looking for is, did you commit it to this quarter? Was... And did you tell the company that it was absolutely coming in and it's actually slipped? Or was it something that you were pursuing that potentially you could pull into this quarter? Those are two very different things. If it was committed to the quarter, uh, and did not come in, then I would, if I'm a startup, I would do a full deal review and understand why it didn't come in. And is it something around our pricing and our, our product or is it something around the sales execution? And I would be looking at those, you know, different sides of the equation to really dig into, where do I have the problem?

   10. HSHarry Stebbings35:25

       I, I totally agree in terms of understanding where you have the problem. I do wanna move into my favorite though, Kevin,

9. 35:30 – 38:52

   Quick-Fire Round

   1. HSHarry Stebbings35:30

      which is a quick fire round. So I say a short statement, and then you suggest, uh, a wonderful answer in about 60 seconds. Does that sound okay?

   2. KEKevin Egan35:37

      That sounds great.

   3. HSHarry Stebbings35:39

      So what sales tactics have not changed in the last five years?

   4. KEKevin Egan35:43

      Written communication that illustrates grasp of what the business problem is and how you're gonna solve it, illustrates the fact that you've got a plan and you can drive, uh, according to that plan.

   5. HSHarry Stebbings35:55

      Tell me, what sales tactics have died a death?

   6. KEKevin Egan35:58

      Sales tactics that have died a death are really around withholding information. When I started at Oracle to get a white paper, you had to email the sales rep and, and to get any technical documation- documentation, so forth. Over time, that has changed dramatically. So withhold- tr- withholding information, um, has died a death. I think transparency across the board is the new normal.

   7. HSHarry Stebbings36:23

      What one piece of advice would you give to a new sales leader starting in your role? So imagine you the night before you joined Atlassian or Slack as a sales leader, what would you have called yourself up and said?

   8. KEKevin Egan36:37

      I'd call myself and say, every environment's different. Uh, watch out for pattern matching from the previous company. Really get to know your peer group and, and the other side of the equation, that being probably the engineering leadership, to understand how they view their product and how their product solves problems. So spending more time with the broader organization and not pattern matching.

   9. HSHarry Stebbings37:02

      What would you most like to change about the world of sales, Kevin?

   10. KEKevin Egan37:05

       What I'd like to most change about sales, I think if there's an opportunity with AI to use technology to help every sales rep understand the best next step for their customers and to show up with more great idea for their customers. So in terms of change, I'd like to see more adoption of AI to help us do that.

   11. HSHarry Stebbings37:26

       What would you most like to change or what's the hardest element of your role with Atlassian today?

   12. KEKevin Egan37:31

       I think the hardest part of the job at Atlassian right now is helping our customers with an opinionated view on how to make them successful. And I don't think that's different than any other company. Um, Jira's been out there a long time. How are we helping engineering teams and broader companies ship better products faster and really getting into the weeds with them and providing an opinionated solution on how our services are helping them, I think is a pursuit that, uh, we're, we're really turning up the, the investment on, uh, but something that we're going to work every day to make happen.

   13. HSHarry Stebbings38:05

       What one company's sales strategy, Kevin, final one, do you most look up to, respect or impressed by recently? Where you literally go, "That was a smart sales strategy. Well done."?

   14. KEKevin Egan38:17

       I'm impressed by Snowflake, uh, from afar. I've, I have not been a buyer of Snowflake technology. But my sense is that that company from the CEO on down, has really great alignment and it's customer-centric. And, again, I don't work there, but I think it's probably a pretty intense environment and they're making it happen every day. So that's a company that if you look at the last five years, they've really made hay. And, and I got, you know, hats off to them in terms of, uh, how much progress they've made.

   15. HSHarry Stebbings38:43

       Kevin, listen, I love doing this. As I said, I had so many good things from Kim, from Rainie, from Maggie. So thank you so much for joining me today, and I so appreciate the time.

   16. KEKevin Egan38:51

       Harry, thanks so much for having me.

Episode duration: 38:53