Are people suited only to a particular company stage (e.g., zero-to-one vs scale), or can they grow with the company across stages?

TJ Parker · Jun 5, 2023

People cannot move seamlessly between different types of companies and jobs; you should optimize for what your personality is best suited to

Being both successful and happy in a huge company and also successful and happy in a startup is unlikely

Scope: a reversal of his prior belief

55:19 20VC: The Largest Venture Backed D2C Consumer Exit; PillPack: $0-$300M Revenues in 5 Years & The Biggest Lessons Scaling the B2B Business to $300M in 2.5 Years with TJ Parker, Co-Founder @ PillPack

Brian Halligan · Jan 15, 2024

He was not well suited to being CEO of a large company and was at his best scaling HubSpot from roughly 20 to 2,000 people, not from two people to 20 or from 2,000 to today's size

He likes being viscerally in touch with product, customers and a small team he knows personally, and dislikes the governance, enterprise risk management and legal work that dominate a big-company CEO's time

Scope: self-assessment

16:20 20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap | The Best Series A Investment in Venture History & What Makes Sequoia so Successful?

Brian Halligan · Jan 15, 2024

People really are suited to particular stages of company building, and a leadership team must turn over generations as the company scales

He assumed the terrific early HubSpot crew would still be there at today's scale, but HubSpot is on its third or fourth generation of leaders — not because the early people weren't good, but because they weren't interested in the next phase

Scope: he did not believe this when he started the company

18:28 20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap | The Best Series A Investment in Venture History & What Makes Sequoia so Successful?

Eléonore Crespo · May 9, 2025

People are genuinely suited to particular company stages, and someone who stops scaling with you was not necessarily a hiring mistake

Skill sets required at different stages are very different; that person did things at their stage no one else could have done, and the new stage demands a skill set they have never seen

25:01 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment

Kipp Bodnar · Sep 28, 2022

Team evaluation should start from the problem and principle layer — write down growth constraints, what needs doing, and what success looks like — and only then overlay the existing people against that.

Taking the people out of the equation first is what makes the assessment objective; then you can see whether each person has the skills, has a coachable gap, or needs to be replaced.

Scope: applies to the moment a leader switches into the 'general manager' hat

34:42 20Growth: Hubspot CMO Kipp Bodnar on Why the Best Marketers Think Like VCs | Why the Best Companies Do Not Start with Product Marketing | New Channels; When To Do, How Much To Spend, How To Test, When To Stop

Craig Courtemanche · Dec 4, 2023

Leaders should be assessed on whether they can take the company to its next level, not rewarded for having gotten it to where it is

He took Tobi's scaling principle to heart and reviews his leadership team critically against future requirements, telling people someone outside may be able to do the job and be someone they can learn from

Scope: acknowledges it is never easy

43:53 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

Chandra Narayanan · Mar 13, 2024 · hedged

People are not inherently destined for one company stage, but adaptability is set early: below roughly 27-30 anyone can be molded, while older people are much harder to change unless they built a growth mindset early

Beyond a certain age, working inside a certain type of company sets people in their ways and modes of thinking; those who developed a growth mindset early keep a nimble, flexible mind and can take on almost anything

55:57 Adaptability is set early via growth mindset not fixed by company stage

Will Quist · Sep 12, 2022

Organizations should be read through a special-forces vs infantry lens: founders are special forces, the leader does a thing the first time, the special-forces team manages times 2-10, and infantry who love process should be brought in for times 11 through 100

Special forces deliver extraordinary output against loose objectives but at dramatically different cost; building supply lines and repeatable process is a completely different skill set

30:28 Special forces personalities suit founding and early scaling while infantry personalities suit repeatable process phases

Fabien Pinckaers · Feb 12, 2025

People are not destined for particular company stages; smart people can evolve from zero-to-one through scale

Most of the people still working with him have been there since the beginning and the company grew from one to 5,000 people

40:34 Smart people can evolve across company stages rather than being stage locked

Kipp Bodnar · Sep 28, 2022

Judging whether someone has outgrown their stage is hard because a CMO (or founder) has to be both coach and general manager, and those roles conflict.

As coach you're in the trenches with people and have trust and loyalty; as GM you have to ask coldly whether you have what you need to win.

33:19 Coach and general manager roles conflict making stage fit judgment hard

Tom Blomfield · May 13, 2024

The trap of being good at early-stage company building is that success turns the company into a big company, and running a big company is miserable

What he loves — early stages, smart people, building, fast decisions, feeling the whole company move at pace — disappears at scale

47:21 Success forces a stage locked founder into running a big company they find miserable