Are candidates from large incumbent tech companies good hires for a startup?

Jackie Reses · Mar 31, 2023

Companies that are struggling rather than minting money are great places to recruit from, because their people are grittier and carry a chip on their shoulder

Her observation from running HR at Yahoo was that anyone who chose Yahoo had to work harder than people at higher-profile companies where 'gold falls from the sky'

14:59 20VC: The Secret to Negotiating; Making $50BN for Yahoo on Alibaba | Why Everything You Know About Hiring is Wrong; Domain Knowledge and Past Experience are Dangerous | The Next 10 Years for Fintech; Winners, Losers and Crypto with Jackie Reses, CEO @ Lea

Akin Babayigit · Jun 26, 2023

Hire for hunger, grit and bias for action rather than pedigree — experience at a shiny company or the best school should be treated with suspicion

Someone without the credentials will probably be hungrier; they want people who take initiative and ask for forgiveness rather than permission

Scope: not advocating pedigree be the sole disqualifier

54:52 20VC: Eight Pieces of Startup Advice that are BS: Why You Do Not Have to Love Your Space, It Is Ok To Do It For The Money, Focus Is Not Everything, Speed Is Not The Most Important Thing with Akin Babayigit, Co-Founder @ Tripledot Studios

Jack Zhang · May 27, 2025

Early hires should be selected on competency, curiosity, determination, resilience and belief in the vision rather than on prior big-company experience

Airwallex hired many experienced bankers from Citibank and SWIFT backgrounds who told the team they knew nothing; none of them worked out, and all had to be fired, slowing the company and generating bad press

Scope: drawn from the first four to five years of Airwallex

76:49 20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Jason James · Aug 29, 2025

Early-stage companies do not need proven, great-resume operators to get off the ground; competent, driven, ambitious, hardworking people are enough until you've earned the right to attract remarkable people

Experienced 40-plus founders can pull veteran talent, but new grads or dropouts don't need it and can get plenty far on drive and competence

Scope: experienced founders can attract veterans; young founders don't need to

22:50 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi

Alan Chang · Jan 5, 2026

You should hire back-end engineers without regard to their specific language experience, testing coding in a language of their choice plus system design, problem solving and culture fit

Scope: Fuse's back end is in Python yet Python knowledge is not required

29:51 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Andrew Dudum · Apr 4, 2026

When hiring, grit and having been through crisis matters more than fancy credentials from great tech companies

Disrupting an industry inevitably brings chaos, so you need a team used to being uncomfortable, staying calm and getting through it

Scope: specific to companies disrupting an industry

6:17 20VC: Hims & Hers: $4.3BN Market Cap on $2.3BN of Revenue: The Comeback | Why Being Public is 10x Better | The Death of the "Strategy" Hire | Why Performance Marketing is Worse than Brand Marketing with Andrew Dudum

Andrew Dudum · Apr 4, 2026

Hiring the credentialed 'big strategy person' who has seen more scale than you is a huge mistake founders should fight at all costs

It feels confidence-inducing as a founder but he has made that hire and always come back to people who love the mission, love to build, are tactically excellent at the function, and are gritty

Scope: based on his own hiring mistakes

7:56 20VC: Hims & Hers: $4.3BN Market Cap on $2.3BN of Revenue: The Comeback | Why Being Public is 10x Better | The Death of the "Strategy" Hire | Why Performance Marketing is Worse than Brand Marketing with Andrew Dudum

Matteo Franceschetti · Nov 20, 2023

Founders need to be very careful when hiring executives out of big companies

He made this mistake himself despite it being well known

40:26 20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep

Matteo Franceschetti · Nov 20, 2023

Executives from very large companies often can't operate at startup requirements — a startup needs people who will launch a product in two days to test it, and after two to five years in a big company that instinct is hard to reverse

Startups are pirates and big companies are the Navy; if a hire starts worrying about brand impact instead of taking risks to learn faster, they won't fit

40:46 20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep

Geoff Charles · Dec 6, 2023

Stage fit matters far more than category fit when hiring — take someone from a comparable-stage company over someone from your category.

People from larger companies are shocked by the lack of resources and aren't used to doing the work themselves, whereas scrappy operators have gotten their hands dirty; and the category itself isn't rocket science.

7:42 20VC: Ramp's Product Playbook: How To Hire Product Teams, How to Run Sprints, How to Increase Product Velocity, When and How to Go Multi-Product with Geoff Charles, VP Product @ Ramp

Mike Hudack · Sep 13, 2024

Operator angels should invest in people they believe in and should not assume strong managers or ICs from large companies will succeed going zero to one

58:40 20Product: What Facebook, Monzo and Deliveroo Do and Do Not Do To Build Great Products | How to Structure Product Teams For Success | Is Simple Always Better in Product and The Art vs Science of Product Design with Mike Hudack

Akshay Kothari · Sep 18, 2024

Hiring VPs and CXOs out of big tech firms into a small, lean company tends to fail; the leaders who succeed are builders

Big-company execs depend on machinery that doesn't exist at a lean startup, and in a crisis they reach for extra headcount or blame the systems instead of solving the problem themselves

Scope: specific to very small and lean companies like Notion

13:30 20VC: Notion's Founder on "Founder Mode": When it Works & When it Doesn't | Why The Way Startups Fundraise & Construct Boards is Broken | Raising at a $10BN Valuation in Peak Bubble Times and How Notion Has More Money Than Ever Before with Akshay Kothari

Johannes Reck · Jun 23, 2025

Series A to C stage companies need fundamentally different people than pre-IPO or public companies, and VCs often conflate the two phases

Early stage requires being in the weeds, shipping, and being opinionated while refining product market fit; later stage requires managing multiple teams, roadmaps and structure — different skill sets and typically different people

Scope: people effective at Netflix, Meta or Google often don't thrive at 30-50 person companies; the reverse also holds: early entrepreneurial hires often don't work out at IPO stage

34:55 20VC: The Wild Story Raising $450M From Masa and Softbank | Why My Biggest Mistakes Came From Listening to VCs | Why 100 VCs Turned Us Down | Why European Founders Are Tougher Than US Founders with Johannes Reck, GetYourGuide

Shreyas Doshi · Aug 3, 2022

The biggest mistake founders make hiring their first product leaders is overweighting background, resume, titles and prior companies while ignoring their own instinct about the candidate during the interview process

Founders who override that instinct end up regretting the choice six to twelve months later

42:06 20 Product: Shreyas Doshi on The Three Different Types of Product Leaders and How To Hire Them, The 6 Different Product Metrics You Need To Know and What Good is For Each of Them & Table Stakes Features vs Wow Features; What To Prioritise

Alex Bouaziz · Feb 1, 2023

Fit at a fast-scaling company is about life stage and honest expectation-setting: if a thousand-miles-per-hour lifestyle isn't what someone wants, they won't enjoy the ride and shouldn't join.

Everyone at the company is going at that pace, so a mismatch in desired lifestyle makes the experience miserable for the hire.

Scope: Says it's totally okay if that's not the life someone wants; 'Not in a bad way' — not a judgment on the person

15:08 20VC: From $57M in ARR to $297M in Just 12 Months; Why Speed of Execution is the Most Important Factor to Success, Hiring 2,000 People in 3 Years Remotely & Secondaries; Why, When and How Much To Take Out with Alex Bouaziz, Co-Founder & CEO @ Deel

Harry Stebbings · Dec 4, 2023

Founders frequently hire for brand-name pedigree assuming the person must be great, and the result is terrible

He has done it many times himself and sees many founders do it

41:40 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Mike Hudack · Sep 13, 2024

Founders' biggest mistake in building a product team is overriding their own gut in favour of impressive pedigree once the company starts growing

The founder is probably right about their own company — a Google director or VP won't necessarily do well at a 100-person company — and you need such deep trust in the person in that role that hiring while doubtful is a mistake

59:37 20Product: What Facebook, Monzo and Deliveroo Do and Do Not Do To Build Great Products | How to Structure Product Teams For Success | Is Simple Always Better in Product and The Art vs Science of Product Design with Mike Hudack

Craig Courtemanche · Dec 4, 2023

There are specific large tech companies you should not hire from, because you import their existing culture along with the person

If the culture in those companies is toxic, hiring from them brings that toxicity in

41:48 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Chris Degnan · Oct 10, 2025

Salespeople from Salesforce are the worst hires because they are order takers who don't know how to sell

Coming from a place where demand arrives to you means you never learn to qualify or drive a deal

56:50 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

Cliff Weitzman · May 9, 2026 · hedged

Hiring from Google is a bad bet because those candidates come from abundance, lack hunger, and carry habits that can infect your culture

Personal experience hiring from large organizations; Speechify's DNA is closer to Amazon's, and Google hires need to be coached out of bad habits

Scope: his personal experience; diamonds in the rough exist and should be hired

45:32 20VC: What I Learned from 100 of the Best CEOs in the World | What I Learned from Staying with Mr Beast for 3 Weeks | How We Will Spend More on Tokens than Salaries with Cliff Weitzman, Speechify

Harry Stebbings · Aug 10, 2022

The biggest hiring mistake founders make in growth is confusing the brand of the company someone worked at with that person's own capability

If you were on Google's or Facebook's growth team at the right time you were riding a gravy train anyway, and moving to a 10-person startup is a completely different job

Scope: about growth hires specifically

23:33 20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing @

Miki Kuusi · Nov 28, 2022

His biggest hiring mistakes were hiring for logos — chasing candidates who had worked at well-known companies rather than assessing actual capability

Impressive logos dazzle you because they are global services you've heard of, but equally fantastic people exist in companies nobody has heard of; what matters is that people are very capable, wherever they come from

32:25 20VC: Wolt CEO, Miki Kuusi on Leadership Lessons Scaling to a Reported $8.1BN Exit to Doordash, Building Teams not Families, The Difference Between Trust and Safety Within Companies, How To Use Compensation to Create Culture & Why You Should Not Be Lookin

Akin Babayigit · Jun 26, 2023

Their biggest hiring mistakes came from hiring for pedigree and seniority

Candidates from a known gaming company who look super senior and check out in due diligence often don't work out, because they arrive saying 'this is how we used to do things there' and the organizations are potentially very different

35:04 20VC: Eight Pieces of Startup Advice that are BS: Why You Do Not Have to Love Your Space, It Is Ok To Do It For The Money, Focus Is Not Everything, Speed Is Not The Most Important Thing with Akin Babayigit, Co-Founder @ Tripledot Studios

Zach Perret · Oct 16, 2024

The 'experience trap' — assuming anyone with 15–20 years in a field won't hustle — was a bad assumption; as a company matures into specialized domains, deeply experienced hires make a huge difference and you should filter for mindset rather than screen out experience.

The old rule came from seeing experienced hires who were jaded or unwilling to work hard, and from an era where hustle mattered more than expertise; now a twenty-year ML fraud engineer transforms the fraud product.

16:22 Experienced hires become valuable as company matures filter for mindset not tenure

Noah Desai Weiss · Jun 16, 2023

You learn far more from facing headwinds than from growth, and people who have only worked at large companies often never learn to manufacture momentum from scratch or turn a business around

When metrics keep rising you assume everything you do is brilliant; large-company tailwind and distribution hide whether your work actually works

5:44 Growth hides whether work is effective while headwinds teach real momentum generation

David Lieb · Sep 21, 2022

Founders should be careful hiring from large incumbents: some people there are genuinely great, but another set are there for career, paycheck or status and have never had to solve these problems themselves.

Big companies have a specialist expert for every problem, so individuals never have to own the whole problem themselves.

27:34 Some incumbent hires are excellent but a subset chase career status not problem ownership

Kieran Flanagan · Aug 10, 2022

An average marketer at a great company makes more money than a great marketer at an average company, and a great personal brand out-earns both

People at great companies can ride the gravy train to success, so founders must separate what the individual did from what the collective did

24:00 Compensation reflects company brand gravy train effect not individual marketing skill

Harry Stebbings · May 31, 2024

Investment bankers move at higher velocity than strategy consultants, and the slowest executors of all are VPs of product from large companies who have never founded and who raise very large early rounds

With three years of money in the bank, the urgency and speed simply aren't there

20:40 Vp product hires from large companies execute slowest especially when flush with large early raises