Feb 26, 2019 · 27m · a16z
a16z Podcast | Stories and Lessons in Enterprise Sales
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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 a16z Podcast episode recorded for military veterans, tech veterans Mark Leslie and Peter Levine discuss the fundamentals of enterprise sales, authentic executive leadership, and company culture. They share strategic advice and personal war stories on building sales teams, handling startup crises, and bridging the divide between engineering and sales organizations.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The host holds 2.2% of the talking time here. How this is scored →
The host as informed peer 1.9 Guest teaching 4.2 Guest disagreement 0.7 The host pushing back 0.3
speaking balance: gold is the host, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 2:44 Mark rejects the idea that authenticity or character can be taught
Mark explicitly disagrees with the host's inquiry about teaching authenticity, asserting that human character and entrepreneurial drive are immutable.
Hardest push from the host ▶ 2:29 Peter questions whether authenticity is innate or trainablePeter presses Mark on his definition of authenticity, challenging him to explain how someone knows if they are authentic and whether it can be learned.
Biggest teaching moment ▶ 9:33 Mark explains engineering time and March 32nd deadlinesMark educates the audience and host on the inherent trade-offs in software delivery, humorously defining engineering chronology.
The host holds their own ▶ 10:06 Peter highlights his own enterprise sales career and domain expertisePeter demonstrates his hands-on sales background by sharing how he transitioned from writing code at Veritas to chasing sales prospects across the globe.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The host as informed peer | Guest teaching | Guest disagreement | The host pushing back | Why |
|---|---|---|---|---|---|---|
| Defining Authenticity in Entrepreneurship and Organizational Leadership | 2 | 5 | 2 | 2 | Peter introduces the concept of authenticity and asks whether it can be taught. Mark reframes the premise, arguing that core character and entrepreneurship cannot be taught or changed, educating the host on leadership dynamics. | |
| How Technical Founders Should Approach Sales and Selling | 2 | 5 | 1 | 0 | Peter prompts Mark on how technical founders with zero sales background should approach selling. Mark walks through the progression of selling partners, investors, hires, and customers, highlighting that early sales cannot be outsourced. | |
| What Makes a Great Salesperson and Sales Careers | 3 | 5 | 1 | 1 | Peter asks about sales career entry points and tension between sales and engineering. Mark breaks down compensation structures, rejection resilience, and jokes about engineering time management. | |
| Sales War Stories and the Power of Persistence | 6 | 2 | 0 | 0 | Peter shares his own transition from Veritas engineer to persistent salesman, showing his domain experience. Mark collaborates by recounting Peter's famous persistence war stories in South Carolina and the UK. | |
| Building Organizational Loyalty, Trust, and Company Culture | 2 | 5 | 0 | 0 | Peter asks how military-style loyalty transfers to corporate culture. Mark provides a masterclass on transparency, the bank of trust concept, and defining culture during dark times. | |
| Navigating Crisis and Handling Major Enterprise Client Cancellations | 2 | 6 | 0 | 0 | Peter asks for a specific leadership trial Mark faced. Mark tells the story of Sequin Computers canceling a major order right after their IPO and how humbling themselves saved the quarter. | |
| Designing Simple and Effective Sales Compensation Incentive Plans | 0 | 5 | 1 | 0 | An audience member asks about sales compensation alignment. Mark explains keeping incentive plans simple enough to fit on a 3x5 card and shares the Sun Microsystems Rolex story. | |
| Recruiting Top Sales Talent and Structuring Sales Forces | 0 | 5 | 1 | 0 | An audience member asks about balancing glamour when recruiting top sales talent. Mark contrasts coin-operated infantry salespeople with Delta Force early-stage sales hires. | |
| Podcast Conclusion and Final Acknowledgments | 0 | 0 | 0 | 0 | Peter briefly wraps up the session and thanks Mark. |
Statements from this episode (15)
Mark Leslie: Founders solving unexperienced problems face lower success rates
“I think that the probability of success is much lower when you're trying to solve a problem that you've never personally experienced.”
Mark Leslie: You cannot teach someone to become an entrepreneur
“You can teach an entrepreneur How to go start and build a company, but you can't teach someone to be an entrepreneur who's not an entrepreneur.”
Mark Leslie: Leaders cannot change people's behavior because character is immutable
“I think character, my personal opinion, is as immutable. I don't believe that you can change behavior of people.”
Mark Leslie: Founders cannot subcontract early-stage startup sales
“At this point in time, there is nobody better equipped in a startup company to talk about the beauty and the benefits of the product, and the vision of the future that we're painting. There's nobody better equipped to do that than the founders who started the …”
Mark Leslie: Technical founders struggle with asking for customer orders
“So one of the things that technical founders, you know, they're pretty good usually at the vision thing. They're not so good at asking for the order, right?”
Mark Leslie: Typical enterprise sales account executive OTE is $300,000
“So the typical, what they call OTE, on target earnings, is today around 300,000 dollars. Half in base, half in incentive.”
Mark Leslie: Engineering projects cannot be on time, fully featured, and high-quality
“So my experience with engineering projects is that they can either be on time, they can be fully featured, or they can be high quality. I've never seen it all come together on the same day.”
Peter Levine: Startups that survive deep crises emerge much stronger
“Every company goes through some cathartic event, right, where it's the pit of despair, right, like nothing can go well, and the companies that pull out of that actually come out much stronger as a result. It is not A straight line up and to the right by any st…”
Mark Leslie: Organizational trust operates like a bank account with no loans
“I think of trust, I think of it as a bank of trust. So in a bank of trust, you can make a deposit, meaning you can express trust and give people that sense. In times of need, when things are bad and you need people to stand by you can make a withdrawal from th…”
Mark Leslie: Company culture is defined by crisis decisions, not published values
“Culture in a company has nothing to do with the values that are published. Culture in a company has to do with what happens in a company when things get bad and people have to make decisions on how do they react.”
Mark Leslie: Dysfunctional sales behavior stems from flawed comp plans, not salespeople
“And the reason that salespeople don't behave right relative to their compensation plan, it's not the salesman, it's the compensation plan.”
Mark Leslie: Enterprise sales compensation plans should fit on a 3x5 card
“I think a compensation plan should be on a three by five card. This is what your base is. This is how much you're getting. These are the, you know, kind of notches as you go up the thing. And here's what we're paying you for.”
Mark Leslie: Sun Microsystems offered top salespeople Rolexes to break comp plans
“So, they got their five top salesmen in the world, and they brought them into the home office, and they said, the guy who breaks the compensation plan most significantly gets a gold Rolex. It worked. They found out all the holes in the plan.”
Mark Leslie: Set sales quotas so 75% of reps hit 100%
“It's my belief that you want to have a company where 75% of the people get to a hundred percent. Then you have a reputation as this is a company where people make money.”
Mark Leslie: Early-stage startups need adaptable sales reps over process-driven hires
“But when you're just starting out, You want delta force. You want resourceful people who have minimal resources, and can react in a way, and can pull other people in the company, and can do amazing things that you can't, that you don't, you know, a big sales f…”