20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

0:00I do favor hiring two to three at a time if you can afford it. In a PLG world, rep effectiveness, the best companies out there are doing a lot of A .B. testing. Early days of hiring reps, you're going to need renaissance reps that have a very wide rep of skill sets. You all listening to 20 sales with me, Harry Stubbins. Now this is the monthly show where we sit down with the best sales leaders in the world to reveal their tips, tactics and strategies when it comes to scaling sales teams. Today, I'm so thrilled to be joined by Kevin Egan, global head of Enterprise Sales at Atlassian and brings more than 25 years of Enterprise Sales experience and leadership to the company.

0:35And prior to his current role, Kevin served as the vice president of North America Sales at both Slack and Dropbox, and has held various senior sales leadership positions at Salesforce. I'd also want to say thank you to Maggie Hort, Kim Graves and Ray New Gupta, some fantastic questions suggestions today. I so appreciated that. But before we move into the show's day, you might remember in our amazing episode with Maggie Hott. She mentioned a tool she could not live without called Pocus. What is Pocus? Or Pocus is a revenue data platform that makes it easy for go -to -market teams to analyse, visualize and action data about their prospects and customers without needing engineers.

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3:18Kevin, I am so excited for this. I have heard so many great things from Maggie, from Kim, from Reynau, but I want to start at the beginning to hit me. How did you make your way into the world of sales first? Let's start there. So I was lucky to join Oracle in the mid 90s and I started in the data center, a technical support role and quickly made my way over the sales engineering side of the house. Again at Oracle in the late 90s in their DMD organization which was a fast moving, fantastic place to learn. I thought it'd be really cool if I started with a quick fire round because you've had some incredible companies where you've been a central part of their sales teams and often lead them.

3:57Sales force drop box in a slank and I thought there's going to be like one or two lessons from each that really shaped how you think. And so I want When it's delve into each and a quick far round, so if we take Salesforce, what was the biggest takeaway for you and how did that shape how you think? Salesforce does not get enough credit for being one of the original product led growth companies. If you look at Salesforce and what Betty Opt did in the early days, we were one of the first companies to ever allow companies for our potential clients to use a trial at no charge for 30 days. During that trial, the sales team was obsessed with one of the business problems of this customers trying to solve, how do I help configure the sales force service to help solve those business problems and it led to incredible conversion rates.

4:38The idea that if we're going to put the product in our customers hands we got to give them help in terms of how they solve their problems. That was an amazing element of sales force and what I just don't think they got enough product for. Let's move to Dropbox. You then spent four years, a little over four years of Dropbox. What was the biggest takeaway for you from your time there and how did it shape your mindset? My biggest takeaway from Dropbox was the importance of getting it right. How do we provide a product that end users really love, but that large enterprises can trust from a security and operation standpoint?

5:08So the balance between end user love and enterprise security posture is a really difficult one to strike. I think Dropbox is one of the first companies to go from a B2C company into the B2B realm and really work hard to get the enterprise posture of the security and controls right, which is no small task. that's somewhat of an unsexy pursuit, but it's much necessary in order for large companies to trust you and to bring you in and allow you to expand within their domain. I mean, we're gonna dive into that later. I'm gonna peppy you with questions. Slack is such a hyper -grace story that you're the core and central to.

5:40What was your biggest takeaway from your time at Slack and how did that impact your mindset? If you think about Slack, the power of Slack comes, the bigger the team and the more employees you can get and engage in that platform, the more value they drive to their customers. So Slack from day one had it appetite to work with large teams and large customers Yet they have an incredibly engaging platform So that ability to marry end user love with the enterprise posture right out of the gates Focus on large teams and all the security controls that were necessary there was something that was truly unique at the time And very joyful it led to a hyper grow I do want to start at the core crux of a lot of the discussions I have with founders which is a sales playbook and I just want to get some nomenclature right.

6:24How do you define sales playbook, Kevin? Well that's an interesting question, Harry. I don't typically use the word playbook. Playbook to me seems like just a simple one, two, three and you follow these steps and you're going to close the deal. I think it's more than that. When I think of a playbook, I actually just think of sales motions. I prefer that the term sales motions. Understanding who is the buyer, what's the user persona that we're selling to, what's the industry that they're in, one of the business problems that they're faced with and how does our product uniquely solve that problem.

6:53Talking in terms of the unique solution to that problem is where I think strong sellers really shine and not talking about product features but really the solution that overall would drive a business value. So that's a motion where there is a one, two, three playbook in my mind. 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? 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 writing and explain that these are our sales motions.

7:32So I think it's the CEO of the founders job to provide the inspiration and the high -level talking points and the kind of the idea matching as they're talking to other executives, but it's the sales VP's job to really nail it. If we think about PLG vs Enterprise, something that I see a lot of today, found as chasing PLG and Enterprise, kind of from day one, can you do both at the same time, do you think Kevin? 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, and then Enterprise, but they always had an eye towards Enterprise.

8:06The reason why I say it's extremely difficult is to capture the end users imagination, capture that end user love is one thing. But to build out the enterprise security set, the feature set and the enterprise posture, all the processes and controls that are necessary to really go big at enterprise takes many, many years. So I think if I had to pick a path, it's probably more sequential PLG first, gallery that end user love, and then adding on the enterprise layers following that. We're going to delve into that. I just have to ask you mentioned slat nating PLG first there and then moving to enterprise I just sounded 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 slag?

8:45If 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 cows that are so significant you're going to get on the radar per curbing illegal and they say if as many people are using this product I want the right turns in place so that I can feel comfortable using the product. So you're going to 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 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 Rome service that my end users love But then we come to that realization, we're getting pulled into enterprise, we're getting pulled into procurement.

9:30I think there's maybe naivety sometimes around what needs to change when you move to enterprise. All of the biggest elements, Kevin, need to change when you're scaling from a PLG motion to an enterprise motion. I think number one is stale and reliability. They need to know that if this becomes business critical, you're going to be providing the SLA's in the 99 .99 uptime. There's data, geography requirements around data residency. If I'm going to use a service in Japan or if I'm going to use it in Europe, I need to know that you've got local data centers, process controls. You know, they want to know how your engineers control data, who has access to that data, what security protocols you use around that data.

10:09They have encryption requirements, data loss prevention requirements. It gets pretty deep, but I think the one thing to emphasize there is that there's no finish line. It's not like as a PLG company, you can dip your tone at a prize and deliver these three or four features. 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 data requirements around GDPR, like that's a full -time job for somebody to be looking at that and say, okay, well, how are we running our service and is it compliant in Europe? It's now you have to think it's just a few features because in fact it is a lifelong pursuit to make sure that you're staying up with the most stringent requirements that are coming out of enterprises today.

10:46I totally agree and condit buttoon. Those are the quite technical and gnarly aspects of what needs to be done. There's also just the 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 M2 price should we change the structure? Should it be more formal from A to SDR to you name it? How does the structure of sales teams change when moving from PLG to M2 price? Well, I think at first the sales team is obviously there for revenue growth, but almost even more importantly providing customer feedback into the product group.

11:21Giving the product team that they're working with a sense for why do these people gravitate to the service? What business problem is it's solving? How would you down the line translate this into our live for the end user? Early days is creating 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 core sellers focus on just revenue numbers supported by sales engineers and so forth. Can I ask you a bit of a weird one but when you're doing PLG you kind of know if sales teams are good do you see very quickly the velocity that they close customers the sales cycles are shorter it's easier to tell effectiveness.

12:00When you're scaling into enterprise sales cycles a longer conversations take more time how do you determine rapid factiveness when moving into and price. It appeals to world rep effectiveness. The best companies out there are doing a lot of A .B. testing. It's last seen as famous for A .B. testing. What happens if I put this account in the hands of a rep versus my regular online channels? And I'd say the most effective way is that testing. Should we test from the start? Should we layer the testing in? When we say like testing, if I'm a founder, there's a thing, test with what? A rap versus what is the alternative to testing?

12:37Do you see what I mean? Yeah, you need to have this if you're doing an AB 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 handled where you can kind of measure what they're doing Through their activities and sales force and opportunities that are being created So you simply have a cohort of customers that are managed through the web channels and another co -authored that are managed Her sales reps if you see outsized growth in the ones managed her sales reps hopefully you do and that'll tell you that you have strong effectiveness or you're on your way to affect them.

13:10Sales champ. One way to tell effectiveness is also like when you hire multiple at the same time, you can tell it you agree with the hiring two or three at the same time or actually do you think that's unnecessary? I do favor hiring two to three at a time if you get afford it. It is a great indicator of sales rep up back to this and the compares on the reps is very effective and I'll tell you, number one, can my reps accelerate? And number two, within my sales rep base, who's really incurring the water of the Illamaegan app? If we dive into that hiring process, I heard that you're incredible when it came to identifying talent.

13:44How do you stretch 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 helping guidance. I think hiring great salespeople is about process that it's about discipline. And 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 Mark Benioff said, he, he watersy, everybody have hiring fatigue. Everybody should be interviewing it all the time, whether it be for a job opening that you have today or when that you might have down the line.

14:14To hire well, you really need to put a multi -step process in to get to know 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 my past companies have gotten the job until they presented a mock scenario around a fictitious company and a business problem that they're trying to solve. So we really put the rep on the spot so to speak to show how they deliver in the moment. We're talking to a customer about how they'll uniquely solve their business problem. By the time a rep gets a job with one of these companies, they should have met with five or six different people and five or six different steps.

14:51And that's standing in the deliver moment, I think is important and tells you who can really command the car. Kevin, help me out here, moxonario. What does that look like? So one, I often people either give the moxonario of the company where the reps that, no, or all the company that the higher is that, which is kind of biased, I find, in either direction. How do you think about which company that they should like sell against or like sell for? How long do you give them? Who's in that moxonario meeting? What makes the best ones? Can you just help me understand what that looks like for me? Sure, so I could go either way on that.

15:24At Salesforce, we gave them a fictitious company, a business set of business problems that they were solving in Salesforce, set of solutions at Slack, we were comfortable with them positioning their own service. 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 going to solve them, and how they're going to kind of come in the room so to speak when they're trying to get over the finish line. I struggle with that one and you're the hailed business leader. So I'm like, you know, being very bold here.

15:53But 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 all over your eyes in seconds. If you give me a new company and say you've got 24 hours selling me this pen, I've really got to think on my feet about different customer personas, different customer needs, how to position that in market competitive. I've really got to show my skill on the spot in real time like sales leaders need to. Do you not think that art sheets are a bit easier if you give them what they already know? Good question.

16:25I think if they're selling you what they already know, then the audience should be delivering much harder questions and harder objections. I think you can accommodate for that in terms of the tone that you take in that meeting and some of the mock question there. What do we think about Good vs Great? How do the best do in these moxonarios? and are there any rad fliers that you look for? 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.

16:58And that comes down to what's their comfort level being in front of a room, being in front of an audience, it's gonna throw up real objections. So sometimes you're surprised. Good versus great comes down to, are they consistent throughout the whole process, right? Did they crush the interviews and then just come in with a level of confidence during the moxenero that just wins you over makes a ton of sense. I'd say overall it's consistency. When you start to see game consistency across the different steps of the process, that's definitely right flag. Does the type of person that you need change, dependent on whether you're running a PLG or an enterprise motion cabin?

17:31I'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? Early days of hiring reps, you're going to need renaissance reps that have a very wide rep of skill sets of who enjoy the building process. And as things go on, you start to scale your sales team. You're going to 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. 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.

18:04But certainly as you go into enterprise and you've been there longer that rep that is going to be successful there has More experience and is more focused on what are my set of accounts and how do I crush my number? Do you think is a fair description that sales reps a 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 OT on the bonus Is that a bad thing again going back to timing? It does not pay to have coin operated sales reps in the early days. They're going to be overly focused on quotas and crushing their number to get to a certain outcome.

18:40The early days are really about who has created the best connection between my developing product and my potential customer. But I think in the later years or as you build out your sales organization, why don't like the term coin operated? 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 so I would be concerned about coin operated for early days but not later. I hear a lot of founders say that biggest mistake they made when hiring sales teams was hiring for logos.

19:11My question to you is how do you advise founders on the logo hires? So often I see startups and they go, oh amazing name from big company Microsoft Oracle and they say that's their big mistake. How do you advise on logo highs and what to look for. I could absolutely see where the big logo ira does not work out. 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 work to Microsoft or King. What do you mean by intellectual range cabin? What I mean by intellectual range is this person, this initial sales leader is going to have a lot in their play.

19:47They're not going to have a big marketing team that they can outsource all of the writing and the messaging to, they're not going to have all resourcing from product management and so forth. So they're going to need to do a lot of different things. And so they're going to need to have energy and range to do everything from writing to messaging to closing and providing that customer feedback, you know, the voice of the customer back into product. So that range as the company's become bigger and more specialized starts to narrow, if you will. But in the early days, it's really about how much suffer you will end to take on.

20:18And that's sort of referring to when I thought I got range. Can we also see Kevin, you've hired some of the best across many different organizations. Cone 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 Cone Package giving when rearing? I think when I'm closing a candidate, I'm interested if I'm giving them a fair comp plan. Are they really just in about the long term during this company? Because this compaid only represents this moment in time for the next year or two. So if we're both successful, the company will increase in size.

20:50Our jobs will be different. Our jobs will be bigger. So how do they view the long -term journey at this company? And are they excited about the company and the journey? Or is it about the complaint? Sometimes it becomes too much about the complaint that that's a red flag because it's really about a total reward element, which is you're joining a rocket ship and you'll love this job and it's going to really benefit your career overall. That's kind of what I'm looking for, but complaints certainly need to be fair. if you're not providing a fair comp plan, you can't extract a higher of the best. One of my favorite mentors says you're never wrong to do the right thing and I always think about that on fairness.

21:22Can I ask you though, again, we mentioned 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 lives and then building trust in you. Both ways. What works? Well, I think on the journey of people joining a company in the early days, they want to have clear expectations and you as a leader need to be a little bit more directive on one of the expectations and how are you going to get there. And then as they become competent and ramped up in their job, it's a little bit more of a partnership and here's what we are going to do.

22:02Only have more ideas from them on what they see 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 the job and the the manager employee relationship changes over time so that's one thing I try to focus on how do you retain a sense of hierarchy I think one thing that I've got wrong Kevin is a manager on the sea I'm young I tried to be people's friend and I'm not your friend I am your boss at the end of the day and I know we don't like hierarchies or boss you are someone's boss and everyone has a boss How do you retain that hierarchy but also trust and proximity?

22:37The term hierarchy is an interesting one to get buy -in from your employees. They need to appreciate their manager is contending with a lot more issues and has more on their play which is requiring a certain level of skill set and focus and hard work to get done. As I look at my boss, Karen, he's got more of 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. They need to have a sense for it. If I were to take your job here, the four or five things that I would need to ramp up to have a grasp on.

23:14If they feel like you're doing the same job as them, then you're in trouble and the hierarchy's 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 have appreciation for that there is a ramp if they do that I think hierarchy works and there's an appreciation. Secondly, with hierarchy, I think you're not going to exercise hierarchy every day. But there are moments throughout the year where you have to be very direct with your employees on what the expectations are and if they're not meeting those expectations, you certainly need to deliver that when he was in Plainsby and they need to know where they stand.