Jan 2, 2019 · 28m · a16z
a16z Podcast | Getting Sales Right
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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 the a16z Podcast, former LinkedIn VP of Sales Daniel Shapero joins Peter Levine to share insights on scaling enterprise sales to over $1 billion, hiring tactics, performance management, sales forecasting, and transitioning into product leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The host as informed peer 3.1 Guest teaching 5.3 Guest disagreement 1.3 The host pushing back 2.4
speaking balance: gold is the host, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 12:27 Middle-management bravado callout
Dan rejects simple rule-of-thumb firing timelines, arguing that managers who act like firing decisions are easy belong in middle management.
Hardest push from the host ▶ 15:20 Pressing for specific hiring averagesPeter repeatedly presses Dan to commit to a specific hiring success rate percentage across industry sales reps.
Biggest teaching moment ▶ 24:10 Behavioral science behind sales compensationDan uses Cialdini's behavioral research to demonstrate why direct financial incentives work for transactional sales tasks but degrade creative tasks like engineering.
The host holds their own ▶ 22:20 Challenging the premise of sales commissionsPeter forcefully voices the technical founder argument that sales reps should be paid flat salaries with stock options just like software engineers.
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 |
|---|---|---|---|---|---|---|
| Why LinkedIn Built a Massive Enterprise Sales Team | 3 | 5 | 1 | 2 | Peter asks why a viral product like LinkedIn needed a massive sales team. Dan reframes sales not as product peddling, but as consultative guidance to help enterprise clients transform their recruiting operations. | |
| Operationalizing Sales Leadership and Executive Time Management | 2 | 4 | 0 | 1 | Peter prompts Dan to describe the operational reality of running a 1,200-person organization. Dan details how executive focus shifts from product positioning to scaling systems, and highlights the need to plan 18 months ahead. | |
| Strategic Sales Hiring and the Mock Call Method | 2 | 4 | 0 | 1 | Peter asks for advice on initial sales hires for early-stage companies. Dan outlines his strategy of overhiring for foundational roles and implementing mock sales calls early in the interview process. | |
| Managing Low Performance and Decisions on Offboarding | 3 | 6 | 3 | 2 | Peter asks about strict quarterly metrics for offboarding underperforming sales reps. Dan dismisses quick-fire mentalities as middle-management bravado, arguing that high-potential reps require nuanced evaluation and self-imposed decision deadlines. | |
| Sales Hiring Batting Averages and Leadership Selection | 4 | 5 | 2 | 4 | Peter attempts to pin Dan down to a baseline hiring success percentage. Dan resists a single metric, explaining how success rates vary wildly depending on whether the role is outbound prospecting, account management, or executive leadership. | |
| Sales Forecasting as a Driver for Company Growth | 3 | 6 | 1 | 3 | Peter inquires about the real purpose of strict sales forecasting. Dan explains that accurate sales forecasting is vital because it gives executive leadership the confidence to fund engineering investments up to a year early. | |
| Structuring Sales Compensation and Preserving Corporate Culture | 5 | 7 | 2 | 4 | Peter articulates the classic technical founder critique regarding why salespeople receive commission while engineers receive flat salaries. Dan provides a comprehensive psychological breakdown covering constant rejection, measurable individual outputs, Cialdini behavioral science, and promotion-based culture building. |
Statements from this episode (20)
Dan Shapiro: Enterprise hiring products generate 60 percent of LinkedIn revenue
“About 60% of how LinkedIn makes money is through serving enterprises to help them hire great people”
Dan Shapiro: Talent Solutions grew from $40M to $1B in four years
“When I inherited it was Probably about a forty million dollar business and grew it to over a billion dollars in the span of about four years.”
Dan Shapiro: Direct enterprise sales teams capture higher pricing than self-serve
“And my guess is that for most products, you could actually find a price that you could, the product would, you know, in theory actually sell itself at scale. Truth is that we found that price to be materially lower than the value we can communicate to the mark…”
Dan Shapiro: Most LinkedIn enterprise buyers reject self-serve for human reps
“You can actually go and buy LinkedIn's enterprise product suite online by yourself with a credit card, and the truth is that most people don't because they want someone to help them make the right decision about what to buy in a consultative way.”
Dan Shapiro: Two days in person beats a year of phone calls
“You can learn more in two days in an office than you can talking to them over the phone for a year.”
Dan Shapiro: Company culture is defined by hiring, promotion, and firing decisions
“Those moments are where the organization learns what the culture really is. Who do you hire? Who do you promote? Who do you let go? Like, that's where culture gets defined, from my perspective.”
Dan Shapiro: Sales leaders fail by focusing on quarters instead of scaling
“I think where a lot of people get struggle is where the top leader is basically thinking about the business three to six months out. And I think a lot of sales leaders do because they grew up in a quarter to quarter individual rep capacity versus thinking abou…”
Dan Shapiro: LinkedIn always over-hired talent when launching new products or offices
“Any time that we launched a new office or a new product, and we basically need to hire the first person to go seed the opportunity, we've always over hired.”
Dan Shapiro: The best way to assess salespeople is having them sell
“I think beyond that, I think probably the biggest lesson I learned about hiring salespeople is the easiest way to assess a salesperson is to get them to sell to you.”
Dan Shapiro: Good salespeople ask great questions; bad ones talk too much
“Good sales person asks good questions, bad sales, people talk a lot.”
Dan Shapiro: Leaders who think firing is easy belong in middle management
“Anyone that acts like, has the bravado to act like, oh, it's easy for them to know when to fire someone, I think that those people, ah, are in middle management. They're sort of relegated to middle management, right?”
Dan Shapiro: Slow-ramping sales hires often have the highest long-term potential
“Some of the people that took the longest to mature as salespeople had the highest potential in the long run.”
Dan Shapiro: Default to firing underperformers if still uncertain at the deadline
“I always set a time period for myself, so I say, okay, great. It is July. By October, I'm gonna make a decision, and in October, even if I still feel in the middle ground, it's a no.”
Dan Shapiro: Early startup sales hunting roles have high performance variance
“Some roles, like hunting roles, early in a startup's career, have tremendous variance of success. Some people crush it, a lot of people don't, and you're probably going to have to cycle through people pretty quickly.”
Dan Shapiro: Hiring enterprise sales leaders into early-stage startups often fails
“And at least in a startup, most people, like, the thought process that we've seen is, you know, okay, we're at 50 people. We need to be at 500 people. Who has managed a 500, been a manager in a 500 person org? Okay, great. Let's go bring them into our org. Oka…”
Dan Shapiro: The ultimate purpose of tech sales is funding engineering
“If you want to take a super Silicon Valley view of sales, our goal is to fund engineering, and my ability to do that successfully requires me to be a good forecaster.”
Dan Shapiro: Applying rigid sales forecasting to new products is counterproductive
“I think forecasting goes a little awry, where you essentially apply forecasting rigidity to new businesses, and the conversation is, you're just launching a new product, and it's, you said you were gonna do three million, and you did two and a half, and why we…”
Dan Shapiro: Explicit output compensation hurts creative work like engineering
“Sort of, the other thing that I think if you're a fan of I think is Bob Cialdini, the guy that wrote the Influence book basically says that for creative, expansive type of tasks, giving people explicit compensation is actually really counterproductive. They te…”