Executive Hiring

topic on 7 shows · 17 statements across 11 episodes

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17 statements about Executive Hiring, every show

Windley: Character, not competence, is the differentiator in executive hiring
“When you're hiring executives at one of these big companies, someone's going to be competent at all the things you need, right? You're hiring a CMO, you're hiring a chief technical, you're hiring a sales leader. They're going to be good at what they do. And th…”
David Windley Nov 25, 2025 ▶ 28:01 He Built a Mutual Fund Out of 200 Recruiting Clients and Hit $50M
IN DEPTH Insight
De Milliano: 80% of executive hiring success comes from pre-interview introspection
“And I actually think 80% of the work In hiring a great leader, who's a great fit for you, is figuring out that piece of it. Like, not even doing the interviewing, it's the, like, doing the introspection of whether this person is a good fit.”
Eeke de Milliano Mar 6, 2025 ▶ 6:10 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
IN DEPTH Assertion Not checkable as stated
De Milliano: Executive hiring decisions fail 50% of the time within 18 months
“And then at the end, a couple of them will have seemed interesting and like they'll have to make some sort of agonizing decision and like still 50% of the time they fail in their decision after a year or 18 months.”
Eeke de Milliano Mar 6, 2025 ▶ 7:18 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
IN DEPTH Insight
De Milliano: Only define executive hire success for years one and two
“I think you have to sort of be pretty concrete with yourself on exactly like what success looks like in year one and what success looks like in year two. Nothing past that because you have no idea what your company is going to look like past that.”
Eeke de Milliano Mar 6, 2025 ▶ 23:12 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
IN DEPTH Insight
De Milliano: Executive hiring decisions must never be made by committee
“I don't think any important decisions like this can be made by committee. Like they should, I mean, they should use input from all the folks who, you know, were part of the interview process, but ultimately the founder has to decide or the hiring manager.”
Eeke de Milliano Mar 6, 2025 ▶ 29:31 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
IN DEPTH Insight
De Milliano: Executive hires stretching up succeed more than those stepping down
“I think you're way more likely to be successful when someone is stretching up into the role because they're going to have a chip on their shoulder. And like, you really want them to prove themselves or they want to prove themselves.”
Eeke de Milliano Mar 6, 2025 ▶ 32:33 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
IN DEPTH Insight
De Milliano: Purely successful resumes make it hard to judge executive impact
“The folks who have only been at companies that have themselves done well, it's just really hard to be able to distinguish whether the company did well because of the founder or because of the leader, sorry, or the leader did well because of the company.”
Eeke de Milliano Mar 6, 2025 ▶ 44:57 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Stripe)
SAASTR Insight
Lemkin: Redact Prestigious Employer Logos From Resumes To Avoid Bad Hires
“If you fall in love with someone in any part because of that logo, literally, if you want, this is just for fun, print it out. If you can find a printer, take a black marker and black out the LinkedIn and for fun, hand around and say, would you still hire them…”
Jason Lemkin Jul 5, 2024 ▶ 43:40 Top 10 Go To Market Mistakes Founders Make Again … and Again with SaaStr’s Jason Lemkin
IN DEPTH Insight
Foster: Hiring senior executives willing to do tactical work is game-changing
“But if you can find somebody who has all the executive skill sets, who is willing to join your company and able to roll their sleeves up and do the job, that is a game changing hiring.”
Wade Foster Oct 5, 2023 ▶ 41:38 Contrarian takes on growth, hiring, and fundraising | Wade Foster (Co-founder & CEO at Zapier)
Lieberman: First-time leaders should assume they are mediocre due to blind spots
“Anytime you're doing something net new, you can assume that you're going to be mediocre at it because you have a lot of blind spots. And so, like, the first time you're a CEO, the first time you're a manager, the first time you do any job, the first time you h…”
Alex Lieberman Sep 4, 2023 ▶ 14:21 The Difference Between Demand and Product Market Fit
Internal benchmarking causes founders to hire 2x instead of 10x executives
“The more you use a reference point from your own business, the more you open yourself to possibly making the mistake of hiring someone who maybe is one or two X better versus the 10 to 15 X better because you don't truly have an understanding of what really se…”
Alex Lieberman Sep 4, 2023 ▶ 17:15 The Difference Between Demand and Product Market Fit
IN DEPTH Insight
Drumright: Asking leaders for their fallback skill reveals hidden hiring needs
“Your entire team disappears overnight. What's the skill set you hang your hat on? Because I think it tells you as a hiring manager or as like a cross-functional person interviewing, what is their killer skill set? And it also tells you, especially as a hiring …”
Anique Drumright Aug 3, 2023 ▶ 33:34 Lessons from Loom on product strategy and organizational leadership | Anique Drumright (COO at Loom)
a16z Insight
Ghodsi: An executive hiring mistake costs two years of progress
“I say mistakes take between a year and a half to two years. Takes you six months. Jury's out. Is this, do we really need, nobody wants to Fired someone within six months of hiring someone, right? So you've taken six months, then you need to have this conversat…”
Ali Ghodsi Jun 14, 2023 ▶ 38:16 Ben Horowitz on Executive Firing (and Hiring)
SAASTR Insight
Mehta: Parting with an executive at 15 months is worse than at 90 days
“Like, it's easy for somebody to join a company and leave, like, 90 days later. It's really hard if somebody leaves, like, a year and three months later after joining, because they've already put their imprints on the team, they've hired new people, they've reo…”
Nick Mehta Apr 26, 2023 ▶ 12:59 Gainsight CEO Nick Mehta: My Top 10 Mistakes In 10 Years (LIVE SaaStr Workshop Wednesday)
Ipsen: Non-transactional courtship builds stronger executive rapport than formal interviews
“You'll find that the founder and that leader will build a different level of rapport and trust by not going through a formal interview process and having it feel transactional, and then with that, magic can happen, and you can land incredible people.”
Lauren Ipsen Nov 3, 2022 ▶ 25:09 Lessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, GC)
SAASTR Insight
Delatorre: Executive growth slope matters more than absolute scale when hiring
“Slope matters more than scale, and so when you're hiring thinking, oh, I want to get to a hundred million, I need someone who has overseen a hundred million. Well, if they oversaw something that went from 80 to a 120, they might not be very good at building, a…”
Carlos Delatorre Jan 27, 2022 ▶ 44:31 Scaling Your Startup 10x From $20M to $200M with Sapphire, Lightspeed, TripActions, and 6Sense
20VC Insight
Horowitz: Consensus hiring policies for executive roles are destructive
“A lot of times you'll see rules in early stage companies where, okay, everybody's got to vote thumbs up in order for us to hire this person, or everybody's got to score them eight out of 10 or better or whatever. But with an executive, that kind of policy can …”
Ben Horowitz Oct 28, 2019 ▶ 18:41 20VC: a16z's Ben Horowitz on How To Create An Environment of Trust with Founders, How and Why Creating Shocking Rules Is So Impactful To Culture & What The Samurai, Shaka Senghor and Toussaint Teach Us About Company Culture Building

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