Jul 2, 2022 · 49m · news
Daniel Yanisse: Biggest Mistakes Founders Make in the Hiring Process | 20VC #903 · 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, Checkr co-founder Daniel Yanisse shares key leadership lessons on scaling a multi-billion-dollar business, highlighting mistakes in executive hiring, the value of CEO coaching, and the realities of board management and fundraising.
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 19.6% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 2.9 Guest disagreement 1.4 Harry pushing back 2.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 41:51 Rejection of host's external blame framing
When Harry prompts Daniel to blame board or market advice for moving into enterprise too early, Daniel firmly rejects the premise, taking full solo accountability.
Hardest push from Harry ▶ 24:54 Harry's vehement rejection of long board meetingsHarry strongly challenges the standard framing of 3-to-4-hour board meetings, calling them egregious and outlining his own strict pre-read standard.
Biggest teaching moment ▶ 13:11 Reframing feedback frameworks beyond tropesDaniel educates Harry on constructive feedback dynamics, dismantling the standard 'shit sandwich' cliché in favor of transparent ratio balancing.
Harry holds his own ▶ 4:24 Harry's specific challenge on delegation boundariesHarry demonstrates startup operational knowledge by pressing Daniel on what truly requires a founder's attention versus what should be delegated to functional leads.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Origin Story and Taking the Entrepreneurial Risk | 4 | 2 | 1 | 4 | Harry asks standard origin questions but introduces pushback at 04:24 by challenging Daniel's view on delegation, arguing product managers can handle product launches. | |
| Hiring Mistakes and the Challenges of Executive Fit | 3 | 4 | 1 | 2 | Daniel educates Harry on the structural reasons executive hires fail and why FAANG leaders struggle when transitioning to early-stage chaos. | |
| The Art of Feedback and Graceful Offboarding | 3 | 5 | 2 | 3 | Harry asks about the 'shit sandwich' feedback technique, and Daniel reframes the concept, explaining why simply balancing positive and constructive feedback works better than sugarcoating. | |
| Fostering Leadership Unity and Team Building | 2 | 2 | 0 | 1 | A collaborative segment on leadership team unity where Daniel outlines practical habits like daily standups and informal messaging group chats. | |
| The Transformative Impact of CEO Coaching | 2 | 3 | 2 | 1 | Daniel candidly shares how CEO coaching transformed his style and bluntly dismisses founders who claim they do not have time for a coach. | |
| Effective Board Management and Strategic Alignment | 6 | 3 | 1 | 7 | Harry forcefully rejects long board meetings as egregious and wasteful, presenting a tight alternative blueprint for board efficiency. | |
| Balancing Confidence, Ego, and Startup Adversity | 2 | 2 | 1 | 2 | Daniel reflects on personal confidence versus humility, describing how business setbacks in 2019 and 2020 served as essential humbling experiences. | |
| Valuations, Capital Efficiency, and Fundraising Pitfalls | 5 | 4 | 2 | 4 | Harry challenges Checkr's high valuation history and raises hiring friction at high valuations, but Daniel counters that Checkr has maintained capital efficiency and profitability. | |
| Founder Personality Types and Late-Stage Fundraising Realities | 3 | 3 | 1 | 2 | Daniel contrasts intense versus empathetic founder personality types and explains why late-stage fundraising requires public-market forecasting precision. | |
| Strategic Decisions: Enterprise Failure, API Success, and M&A | 3 | 3 | 2 | 3 | When Harry asks if external pressures led to an ill-timed enterprise expansion, Daniel explicitly rejects blaming others and accepts full founder accountability. | |
| Quick-Fire Round and Looking Ahead | 2 | 1 | 2 | 1 | During a fast-paced quick-fire round, Daniel criticizes speculative web3/crypto developments while praising real-world engineering metrics. |
Statements from this episode (19)
Yanisse: Checkr co-founders started the company while on H-1B visas
“We also were on H-one B immigrant visas in the US. So our visa was tied to our current job.”
Yanisse: Founders must keep control of executive hiring, vision, fundraising, and customer relations
“So I completely agree that the highest leverage activities you can do as a founder is hiring the best bench and C-suite and VPs you can. Setting the vision. That's only something you can do, you know, finding the values and the purpose of the company or missio…”
Yanisse: Checkr has fired over 20 failed executive hires
“I think I hired over 20 plus, I kind of stopped counting leaders over time and that didn't work out for one reason or another after some time.”
Yanisse: 25% to 50% of executive hires fail at any company
“I think between one and two and one in four executives don't really work out in any company.”
Yanisse: Startups should hire executives for their two-year scale target
“I think you have to hire them for what you need in the next two years. So if you look at the scale that they've operated at and you project yourself one or two years in the future, that that's, you know, let's say if you have a hundred people in the revenue te…”
Yanisse: Give underperforming executives 3 to 6 months to course-correct
“You do need to give them some time and, you know, also founders, I would say suck at giving feedback. There's many reasons why For some days it's hard to give, you know, constructive feedback to senior leaders, but you do need to give them feedback to talk abo…”
Checkr's executive team holds a 30-minute standup meeting every single morning
“So when COVID started and we moved mostly to remote, we started doing daily standups. So we have a 30 minute daily standup with my leadership team every single morning, every day with each other.”
Yanisse: Behavior change is nearly impossible without a coach or therapist
“I think no one can improve on their own. It's almost impossible. Even if you're very self-aware, you need a friend to improve, whether it's like a therapist in life or a coach at, or in a professional setting, I do think you need others to help you. Otherwise …”
Yanisse: Hiring an executive coach is the best investment a CEO can make
“So I absolutely recommend it to any CEO. I mean, unless you are a CEO and you feel like you're doing amazing and there's nothing you can improve on which I would be skeptical for any founder or CEO. I think it's the best investment you can make.”
Yanisse: Saying you lack time for a CEO coach is nonsense
“Many people tell me that they don't have the time to spend time with a CEO, with a coach. I think that's BS because having a coach helps you better prioritize your time be more effective as a leader.”
Stebbings: Three- to four-hour board meetings are egregious and wasteful
“I don't know why boards are three or four hours. I'm really sorry. I find this egregious. It's a waste of your time. It's a waste of other people's important time.”
Yanisse: Most board meetings fail to add value and create excess burden
“Many board meetings, it's not adding value. It's actually, you know, Creating more burden and work for the leadership team and the CEO.”
Yanisse: Accel's Rich Wong is exceptional at coaching first-time founders
“Rich Wong from Excel is amazing. So he is really founder friendly really good at coaching, you know, first time founders and helping without imposing any vision or strategy, just helping the founders grow and learn.”
Yanisse: Checkr suffered 2019 headwinds when gig economy clients went public
“2019, you know, was starting to get some business headwinds because we grew very fast in the gig economy and with tech customers and those companies like, you know, Uber, DoorDash and others went public at those days and then started to suffer themselves. So t…”
Yanisse: Checkr renegotiated Series C terms after missing revenue targets
“I think it was our Series C hardest. I mean, overall we've been lucky. I've had really fast, easy fundraisers because the business has been performing well and we have a good team. But the Series C was one of the hardest because we got the term sheet for the S…”
Yanisse: Late-stage investors judge startups like public companies
“As you start to get very late stage and raising money from, you know, New York investors and mutual funds, they're going to be a bit closer to judging you like public investments. And so the accuracy and the forecast and those things are becoming more importan…”
Yanisse: Expanding Checkr into enterprise too early was his worst decision
“The worst decision for sure was to go too early into the enterprise. So after we had really good traction in the gig economy with tech companies, we decided, I read crossing the chasm. And so I decided, okay, let's expand to enterprise customers. And that was …”
Yanisse: 'Accelerate' provides the best framework to measure engineering performance
“It's called Accelerate. It's a book about engineering and DevOps, but it's very readable by any non-technical people. And that's the first book that gave me the answer on how to measure engineering in a tech company, because that's actually one of the hardest …”
Yanisse: Early NFT applications are a waste of top engineering talent
“All of the smart engineers are working on like, you know, million dollar NFTs to sell, which I, and I love web three and NFTs, and I think it's the coolest technology in opportunity in the world. It's just the early applications are a little bit underwhelming.”