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Daniel Yanisse: Biggest Mistakes Founders Make in the Hiring Process | 20VC #903

Daniel Yanisse is the co-founder and CEO of Checkr, a leading HR technology company, currently valued at $5 billion. During the journey, Daniel has raised over $679M for Checkr from some of the best including Accel, Bond, Coatue, GV, Elad Gil and IVP to name a few. Prior to Checkr, Daniel was a software engineer and helped develop prototypes of the Mars Rover for NASA. Daniel has been recognized in Forbes “30 Under 30” and recently Checkr was recognized by Forbes as one of America’s best start-up employers. ------------------------------------------- Timestamps: 0:00 The Story of Checkr 2:36 How to delegate 5:38 What were your biggest mistakes hiring? 8:06 How to tell if FAANG candidate is ready for leadership 9:38 When is the right time to hire an experienced FAANG candidate? 10:48 How long to give new hires store you decide it isn’t working? 12:00 How to give effective feedback 13:45 What the right way to let someone go? 15:24 Team Building 17:27 CEO Coaches 22:20 Board Management 27:17 Did you have insecurities when you were young? 28:18 Have you ever gotten too confident? 29:35 Why were 2019-2020 so hard for you? 31:55 Do you worry about raising capital at such high valuations? 34:45 Mistakes founders make when fundraising 39:08 Best/Worst decisions you made for Checkr? 43:28 Biggest lessons learned on M&A 44:59 Quick Fire Round ------------------------------------------- In Today’s Episode You Will Learn: 1.) The Origins of Checkr: The $5BN Company How did Daniel come to co-found Checkr? What was the a-ha moment? How did Daniel’s experience with his prior company impact how he thought about building Checkr? What does Daniel know now that he wishes all first-time founders knew when they started? 2.) Hiring 101: What are the single biggest hiring mistakes Daniel made in the early days of Checkr? How does Daniel structure his interview process for new candidates today? How has it changed? How does Daniel test for ego and humility in the interview process? How does Daniel approach giving feedback today? How has it changed over time? What does Daniel believe is the right way to let someone go? How long does one give a team member who is not performing? 3.) Fundraising 101: How does Daniel advise founders going out to raise today in the challenging market conditions? What terms should founders optimize for? What terms should they not optimize for? What are the single biggest mistakes Daniel sees founders make when raising? What does Daniel wish he had done differently with Checkr’s raises? What was the hardest raise for Checkr? Why was it so hard? What was the outcome? 4.) Going into Enterprise: Why does Daniel believe they went into enterprise too soon? What was the result of this? How does Daniel advise founders on when is the right time to go into enterprise? What changes in both your company and your product when moving to enterprise? ------------------------------------------- #DanielYanisse #HarryStebbings #20VC

Daniel YanisseguestHarry Stebbingshost
Jul 1, 202249mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Founder Daniel Yanisse Reveals Hiring, Firing, and Boardroom Mistakes

  1. Checkr founder and CEO Daniel Yanisse walks through his journey from hacking in a living room to building a multi‑billion‑dollar API-first background check platform. He explains how he evolved as a leader, especially around delegation, executive hiring and firing, feedback, and team cohesion. Yanisse dives into common founder pitfalls in hiring big‑company executives too early, managing boards, fundraising at high valuations, and timing moves into enterprise markets. He also emphasizes the transformative role of CEO coaching, cultural fit in M&A, and the importance of humility, resilience, and staying close to customers.

IDEAS WORTH REMEMBERING

5 ideas

Treat delegation as a discipline you must force yourself to learn.

Founders often obsess over details and slow the company down; Yanisse only improved when he hired strong senior leaders, consciously let go of work, and redirected his focus to truly founder‑only tasks like vision, fundraising, and deep customer engagement.

Optimize executive hiring for humility and stage fit, not just logos.

He repeatedly hired impressive FAANG‑style executives who lacked humility or were too accustomed to operating at massive scale, making them poor fits for a messy, hands‑on startup environment; he now screens hard for ego and relevant stage experience.

Give frequent, balanced feedback and escalate clearly before firing.

Most founders avoid or delay hard feedback; Yanisse now starts with specific positives, then adds one focused area for improvement, and over months makes the importance of repeated issues explicit before deciding on a separation.

When firing, be direct but humane—and generous in the exit process.

He emphasizes that the decision itself should not be a surprise, and that crafting a positive departure message, providing strong severance, and actively helping with references preserves relationships and culture.

Invest intentionally in leadership team cohesion, especially in remote settings.

Daily standups with his exec team, informal iMessage group chats about life outside work, and regular in‑person dinners and home visits significantly increased trust, fun, and retention among leaders after years of exec churn.

WORDS WORTH SAVING

5 quotes

You only spend a few hours to evaluate someone and then you’re going to work with them for thousands of hours.

— Daniel Yanisse

Some of the best leaders are not the ones with the most amazing logos on their resume; they’re the hungry ones who still want their big success.

— Daniel Yanisse

It’s been the best thing in my life. I don’t know if I would have made it this far without a CEO coach.

— Daniel Yanisse

You want to be confident without losing humility and perspective.

— Daniel Yanisse

Any company is going to hit the wall at some point. That’s part of the journey, and you have to persevere through it and learn from it.

— Daniel Yanisse

Founding story of Checkr and early product insightDelegation and the changing role of the founder/CEOHiring, managing, and firing senior leaders and executivesLeadership development, CEO coaching, and self-awarenessBoard management, fundraising strategy, and valuation disciplineEnterprise go-to-market missteps and lessons learnedM&A strategy, cultural integration, and building cohesive leadership teams

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