Jul 12, 2023 · 38m · news
Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, Harry Stebbings interviews Kevin Egan, Head of Global Enterprise Sales at Atlassian, to explore how high-growth startups can successfully transition from product-led growth to enterprise-grade sales. Egan delivers actionable advice on structuring recruiting pipelines, aligning sales talent with organizational maturity, and establishing healthy managerial boundaries.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 28.4% of the talking time here. How this is scored →
Harry as informed peer 3.1 Guest teaching 3.7 Guest disagreement 1.4 Harry pushing back 2.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 4:45 Premise Rejection on Playbooks
Kevin politely but firmly rejects Harry's framing of 'sales playbooks', explicitly stating he avoids the term in favor of 'sales motions'.
Hardest push from Harry ▶ 16:04 Challenging Mock Sales FormatsHarry directly confronts Kevin's mock scenario preference, arguing that candidates presenting their current product can easily pull the wool over interviewers' eyes.
Biggest teaching moment ▶ 4:45 Sales Motions vs. Step-by-Step PlaybooksKevin dismantles the common industry notion of 1-2-3 sales playbooks, instructing Harry on how real solution-selling focuses on buyer personas and business problems.
Harry holds his own ▶ 16:04 Harry Demonstrates Interviewing ExpertiseHarry uses his experience assessing sales talent to offer a sharp counter-argument about candidate evaluation and real-time critical thinking.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Entering the World of Sales | 2 | 3 | 1 | 1 | Harry opens the conversation and transitions into a fast-paced overview of Kevin's career across Oracle, Salesforce, and Dropbox. Kevin provides foundational insights on product-led growth history while Harry maintains a friendly, structured interviewing stance. | |
| Slack Takeaway - Virality and Enterprise Scale | 2 | 4 | 3 | 1 | When Harry asks for a definition of a sales playbook, Kevin gently rejects the premise and term, explaining why he prefers 'sales motions' focused on user personas and business problem solutions. | |
| Timing the Transition from PLG to Enterprise | 3 | 4 | 1 | 1 | Harry asks informed questions citing specific former colleagues about when Slack knew to move into enterprise. Kevin details the technical, compliance, and data sovereignty hurdles required for enterprise readiness. | |
| Restructuring Sales Teams for Enterprise | 3 | 3 | 1 | 4 | Harry probes deeper into sales effectiveness measurement, pushing Kevin to clarify what A-B testing cohorts actually looks like in practice rather than leaving it at a high-level concept. | |
| Structuring the Hiring Process and Mock Scenarios | 5 | 3 | 3 | 7 | Harry explicitly pushes back against Kevin's stance on mock interview scenarios, arguing forcefully that allowing reps to present their existing product makes it too easy for them to deceive interviewers. | |
| Renaissance Reps vs. Specialized Reps and Compensation | 3 | 4 | 2 | 2 | Harry questions whether reps are inherently coin-operated and asks about logo hires. Kevin outlines the concept of 'intellectual range' required for early sales leaders versus specialized reps. | |
| Compensation Packages and Long-Term Value Alignment | 3 | 5 | 1 | 2 | Harry admits his own management vulnerability regarding maintain workplace hierarchy versus friendship. Kevin educates on how clear expectations and direct feedback sustain hierarchy without unnecessary friction. | |
| The Art of Delivering Direct Feedback | 3 | 4 | 1 | 2 | Harry asks about feedback mistakes and CFO involvement in modern sales cycles. Kevin reframes CFO presence as a positive indicator of deal strategic importance. | |
| Balancing Quarterly Targets and Pipeline Generation | 4 | 4 | 1 | 2 | Harry asks tactical questions about discounting execution and authority levels. Kevin contrasts Atlassian's strict no-discounting policy with traditional discount matrix governance originating from the CFO. | |
| Structuring Deal Reviews and Handling Slippage | 4 | 4 | 1 | 2 | Harry shares board-level frustrations regarding slipped deals. Kevin lays out a rigorous deal review structure centered on why deals won't close rather than optimistic forecasts. | |
| Quick Fire Round & Conclusion | 2 | 3 | 1 | 1 | In the quickfire round, Kevin shares concise observations on sales tactics that have died, AI adoption, and admiration for Snowflake's alignment. Harry closes with warm appreciations. |
Statements from this episode (27)
Egan: Prioritize Candidate Long-Term Commitment Over Immediate Compensation Plans
“I think when I'm closing a candidate, I'm interested if I'm giving them a fair comp plan, Are they really interested in about the long-term journey at this company? Because this comp plan only represents this moment in time for the next year or two.”
Egan: Salesforce Is Underrated as an Early Product-Led Growth Innovator
“Salesforce does not get enough credit for being one of the original product-led growth companies.”
Egan: Dropbox was among first B2C companies transitioning to B2B enterprise
“I think Dropbox was one of the first companies to go from a B to C company into the B to B realm and really work hard to get the enterprise posture and the security and controls right.”
Egan: Slack Uniquely Combined Enterprise Security With End-User Engagement From Launch
“So Slack from day one had an appetite to work with large teams and large customers yet they had 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 securit…”
Egan: Founders set sales vision; sales VPs codify repeatability
“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. So I think it's the CEO and the founder's job to provide the inspiration and the high level talking points and the kind of th…”
Egan: Startups Must Master PLG Before Layering On Enterprise Sales
“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. The reason why I say it's extremely difficult is to capture the end user'…”
Egan: Slack Reached Tens of Thousands of Organic Users Per Company
“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.”
Egan: Enterprise sales transition requires continuous compliance, not just key features
“It's naive 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.”
Egan: Early Enterprise Sales Teams Must Prioritize Product Feedback Over Revenue
“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 t…”
Egan: A/B Test Rep Accounts Versus Digital Channels to Measure Effectiveness
“In a PLG world, I think rep effectiveness, the best companies out there are doing a lot of A-B testing. Atlassian is 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 effect…”
Egan: Hire Sales Reps in Cohorts of Two or Three for Benchmarking
“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 effectiveness and the comparison on, on the reps is very effective and will tell you. Number one, Can my reps accelerate? And number two, within …”
Kevin Egan never hires sales reps without a mock presentation
“No hire that I've made at my past companies have gotten the job until they've presented a mock scenario around a fictitious company and a business problem that they're trying to solve.”
Salesforce and Slack used different sales candidate mock scenarios
“At Salesforce, we gave them a fictitious company and a business set of business problems that they would solve using the Salesforce set of solutions. At Slack, we were comfortable with them positioning their own service, and so I think both have their advantag…”
Egan: Early-stage startups need generalist sales reps before scaling specialized ones
“Early days of hiring reps, you're going to need Renaissance reps that have a very wide breadth of skill sets who enjoy the building process. And as things go on and you start to sell, scale your sales team, you're going to see reps that are there for really to…”
Egan: Early-Stage Startups Should Avoid Hiring Coin-Operated Sales Reps
“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. The early days are really about who is creating the best connection between my developing pr…”
Egan: Early startup sales hires require intellectual range over big-company logos
“I think for a founder who's hiring, I could absolutely see where the big logo hire 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 worked at Microsoft or ca…”
Egan: Hierarchy breaks down if employees feel managers do their job
“If they feel like you're doing the same job as them, then you're in trouble, and the hierarchy is going to break down.”
Egan: Avoidance of direct feedback degrades managerial hierarchy
“So I think hierarchy also breaks down if the leader is not available or comfortable providing direct feedback.”
Egan: Direct feedback should be periodic, not a daily loop
“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. But there's also time…”
Egan: Enterprise sales deals are unforecastable without clear ROI metrics
“As a rep or a sales team, you better be crystal clear on the business problem that your problem, your solution is solving and why the 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 h…”
Egan: CFO time investment indicates a deal is strategic
“If the CFO is involved in your deal and they're spending time on that deal, that tells you that you are strategic to them.”
Kevin Egan: End-of-quarter deal cramming harms brand and customer relationships
“Jamming deals at the end of the quarter is always kind of obnoxious, but it happens. It does work, but sometimes there is a detrimental effect to kind of Cramming deals at the end of the quarter from a brand standpoint and from a relationship standpoint.”
Kevin Egan: Top sales reps maintain enough pipeline to avoid unnatural deals
“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 fal…”
Egan: Atlassian Does Not Discount Software Prices for Any Customers
“In my current role at Atlassian, 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 speak with any other customer, they know that they're in the same boat and that we're transparent…”
Egan: Enterprise sales discounting must originate from the CFO
“Good discounting should originate from the office of the CFO. Meaning, the CFO knows the margins. They know what they're willing to what margins they're willing to give away on products at what volumes. What should happen in most companies is the CFO should pr…”
Egan says withholding product documentation in enterprise sales is dead
“The 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 to get any technical documentation, documentation, so forth. Over time that has changed dramat…”
Sales leaders must avoid pattern-matching previous playbooks when starting new roles
“I'd call myself and say every environment's different. Watch out for pattern matching from the previous company. Really get to know your peer group and the other side of the equation of that being probably the engineering leadership to understand how they view…”