Feb 2, 2022 · 46m · 20sales
20 Sales: How To Build Sales Teams with a Product-Led-Growth GTM, What is a Sales Hiring Scorecard and How To Construct Yours & How To Structure the Onboarding Process for all New Sales Hires with Dannie Herzberg, Partner @ Sequoia Capital
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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 20 Sales, host Harry Stebbings interviews Sequoia Capital Partner Danny Herzberg on scaling enterprise sales teams in Product-Led Growth (PLG) environments, evaluating high-velocity sales talent, and structuring effective onboarding processes.
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 31.6% of the talking time here. How this is scored →
Harry as informed peer 2.7 Guest teaching 3.1 Guest disagreement 0.8 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:31 Asserting control over the interview agenda
Dannie directly interjects before Harry can finish his question to pivot the discussion back to reference checks, declaring them the single most important part of the process.
Hardest push from Harry ▶ 16:23 Challenging external sales hiring with a guest quoteHarry explicitly challenges Dannie's view on hiring external sales heads by quoting a previous guest's claim that top sales leaders never join early startups.
Biggest teaching moment ▶ 29:21 Coaching the host on personal leadership weaknessesDannie steps into a mentor role to advise Harry on overcoming his need for approval, sharing a story about her former manager placing a 'need for approval' sticky note on her desk.
Harry holds his own ▶ 26:24 Citing a $6B anti-portfolio mistake on reference checksHarry demonstrates deep investor experience by using his own multi-billion dollar deal mistake to illustrate the dangers of over-indexing on negative reference checks.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Danny Herzberg's Background and Entry into Tech | 1 | 2 | 0 | 0 | Harry opens with a warm welcome and asks standard conversational questions about Dannie's entry into tech. Dannie shares a detailed narrative of her path from a Soviet refugee family background to working at HubSpot based on her waitressing experience. | |
| HubSpot Learnings: Culture, Community, and Evaluating Startups | 2 | 3 | 0 | 1 | Harry asks how Dannie evaluates startup culture, citing his own observations at Hopin. Dannie outlines her framework around intentional culture codes and user community engagement, using Notion as a prime example. | |
| Scaling Enterprise Sales at Slack and Product-Led Growth Lessons | 1 | 3 | 0 | 0 | Harry asks for key lessons from scaling Slack's enterprise org from $100M to $1B. Dannie explains the importance of personal empathy across functions and breaks down three structural lessons for product-led growth sales. | |
| When and How Founders Should Transition Sales Playbooks | 3 | 3 | 1 | 2 | Harry asks sharp questions about whether early founders should build sales playbooks themselves or hire a leader. Dannie gently reframes the sequence, arguing founders must be day-one sales heads before transitioning to player-coaches. | |
| Identifying 10x Sales Leaders and Internal vs External Hiring | 4 | 3 | 2 | 4 | Harry challenges Dannie with a counter-perspective from a previous guest who claimed decacorn sales leaders rarely join early startups. Dannie offers a nuanced response distinguishing between CROs and senior directors who have seen high growth. | |
| Managing Organizational Change and Avoiding Rigid Playbooks | 4 | 3 | 1 | 3 | Harry probes into practical interview structures and asks whether simulated calls or customer calls reveal more talent. Dannie explains interview scorecards, unscripted business acumen questions, and keeping candidates in their comfort zone. | |
| Conducting Rigorous Reference Checks and Trusting Intuition | 5 | 3 | 2 | 4 | Dannie interrupts to emphasize reference checking as the most critical step. Harry counters by sharing a personal investment mistake where a negative reference caused him to pass on a company now worth six billion dollars. | |
| Choosing Respect Over Likability in Leadership | 2 | 5 | 1 | 2 | Harry candidly confesses his personal weakness of needing to be liked and asks Dannie for coaching. Dannie takes on a mentor role, sharing advice on prioritizing respect over approval and recounting a sticky-note lesson from her early manager. | |
| Structuring Sales Onboarding and Early Red Flags | 3 | 4 | 2 | 3 | Harry presses on a common complaint in SaaS that product-led growth sales reps are reluctant to do cold outbound. Dannie reframes top PLG reps as extroverted user researchers who proactively synthesize customer feedback for executives. | |
| Building Seller Confidence and Aligning Sales with Product and CEO | 3 | 3 | 0 | 1 | Harry inquires about early red flags, building representative confidence, and cross-functional alignment. Dannie outlines practical tactics like bringing product teams into sales QBRs and creating positive feedback loops. | |
| Quick Fire Round: Sales Tactics, Personal Stories, and Insights | 2 | 2 | 0 | 1 | Harry runs a quick-fire round covering obsolete sales tactics, parenting impacts, and founder hiring mistakes. Dannie shares lighthearted anecdotes, including cold messaging her husband on OkCupid using outbound sales principles. |
Statements from this episode (29)
Slack grew revenue from $100M to $1B during Herzberg's tenure
“Danny is a partner at Sequoia Capital, and prior to entering the world of venture, Danny spent four years at Slack, As their head of enterprise sales at Slack, Danny built and scaled the self-serve, mid-market, and enterprise sales orgs across the Americas, as…”
Herzberg: In 2010, HubSpot was mostly a media site with little product
“If you're not familiar with what HubSpot was back in 2010, it was basically a media site with a little bit of a product.”
Herzberg: Treating company culture as a product requires dedicated budget and leadership
“We treated culture as a product. So we were constantly shipping new features. It had a budget. It had resources. There was even a senior leader to make sure that we got it right.”
Herzberg: Slack initially harbored internal cynicism toward sales
“To be honest, there was a bit of cynicism around sales in the beginning at Slack, and I totally got that.”
Herzberg: Product is the primary top-of-funnel driver in PLG
“Specifically in PLG, product is the most important component of the top of the funnel.”
Herzberg: Expansion dictates most sales revenue in PLG companies
“Expansion dictates most of the sales driven revenue, which means the sales and success need to work in lockstep with one another, which means you need to build customer relationships for the long run and figure out how to engage exact sponsors, even if a custo…”
Herzberg: Founders must sell the product themselves before hiring sales staff
“So the founder needs to sell the product before anyone else can. So day one, founder equals head of sales.”
Herzberg: First post-founder sales hire should be a player-coach
“The next one could be a player coach who can roll up his or her sleeves, do the selling while simultaneously taking the lead on hiring the next four account executives.”
Herzberg: Startups only need a CRO after proving sales formula
“You need a CRO when you're past the zero to one phase. So the sales formula is working. It's time to scale it to the next level.”
Herzberg: Early startups in low $10Ms ARR should hire VPs, not CROs
“So if you're an earlier stage company, let's say in the low two Tens of millions. I would hire a VP or an SVP so that they have something to grow into. We with sales DNA are very internally competitive, so it's always good if there's something to work toward.”
Herzberg: Sales leaders unable to name followers present a red flag
“If they don't have Three or four people off the top of their head that would follow them. To me, that's a yellow flag, maybe a red flag about who they are as a leader.”
Herzberg: Startup employees must embrace handing off processes to scale
“At a hyper growth startup, the company is changing so quickly that you need to take pride in being the person who stands something up, allows it to run pretty well, and then hands it off for someone else to scale it.”
Herzberg: Sales leaders who cannot explain past tactic failures lack flexibility
“And if that person cannot name what won't fit a new culture as opposed to what worked in their old one, they're not showing any flexibility. And my hunch is they're going to be a playbook person, takes a carbon copy and brings it from one place to the other. T…”
Herzberg: Behavioral interview questions yield scripted answers for sales candidates
“If you ask hypothetical and behavioral questions, like what's your 30, 60, 90 plan, you are going to get really articulate, well-scripted answers that do not help you vet the candidate in earnest.”
Herzberg: Sales hiring scorecards should cap at five core attributes
“When I work with founders on creating a sales interview process, we start by creating a scorecard. That scorecard has no more than five must-have Attributes and skills”
Herzberg: Testing sales candidates in their comfort zone yields better evaluations
“I want to see what it looks like when they are in their absolute Comfort zone. And I want to see them rock it in their comfort zone. So I would say, pitch me your product, or let's do a discovery call, because I think that's more telling than a pitch.”
Herzberg: Reference checks are the single most important step in hiring
“The most important thing is digging into references, and I'm saying this because I was on a reference call recently for someone who was getting hired into an executive role at a publicly traded company, and the reference was conducted by the search firm, and I…”
Stebbings passed on a $6B company due to a bad reference check
“I missed a company like a five million pre that's now a six billion dollar company because I listened to the reference on the founder, and they said he was a shit employee, and he was, you know, Opinionated and rude and all these things. And it was wrong. He w…”
Herzberg: Trust hiring intuition over isolated negative reference checks
“Your intuition matters. References are critical, but they aren't everything. And if your intuition is saying, I had a good connection with this person, I've heard plenty of good things around them, and sure, they may have frustrated one person or been a really…”
Herzberg: Striving for approval undermines leadership courage
“And what I realized is if you're striving for people to like you don't have the courage to say hard things, to challenge your peers, to challenge someone you work for.”
Herzberg will hire candidates she dislikes if they have high integrity
“So for that reason, I'm totally okay hiring someone who I don't like per se, so long as I respect the way that they think, and I think that they are a high integrity human being.”
Herzberg: New Sales Reps Should Onboard by Pitching Discarded Leads
“Find a pool of discarded leads. Maybe the company focuses up market, but there's a bunch of SMBs who have raised their hands and we don't bother selling to them. Take that pool of SMB leads, start calling them, and just practice the discovery, practice the pit…”
Herzberg: Effective PLG Sales Reps Act Like Extroverted User Researchers
“A good seller within a PLG company is kind of like an extroverted user researcher. So they may have talked to 10 different users on the front lines who are effusive about the product, and then they're synthesizing those user interviews, putting those into some…”
Herzberg: Sales leaders must speak with new customers weekly
“If a leader had not gotten in front of a customer, if he or she was sitting in virtual or physical conference rooms for their first two months and wasn't talking to one new customer at minimum every single week, that is a major flag for me about customer orien…”
Herzberg: Product teams own the pipeline in PLG companies
“If it's a product-led growth company, then product essentially owns the pipeline number.”
Herzberg: Hour-long sales slide decks are dead
“Slide decks. No hour-long slide decks. They're boring. This is a world where people want to see the product, feel it, see it customized to their context.”
Herzberg: Founders wait too long to hire revenue ops and sales enablement
“They wait way too long to hire revenue ops and sales enablement teams to make the team successful. So they invest all this time and money Into hiring a sales leader, maybe some sales reps, and they don't have the support systems to set them up to thrive and sc…”