Looking to make the jump from VC to startup operator - advice?

Judith's profile thumbnail
I've seen this move made pretty often. Usually it's made by an angel or VC who makes an early investment in a start-up, provides more and more hands-on assistance, and then shifts into a C-level role at the startup. Is that what you're looking to do? Or do you have a burning new idea that you want to start? Because you have all the best connections for that also.
Hi Judith - thanks for your message. Yes, joining one of my portfolio companies is a possibility. If I can follow up with another question - what roles do you see ex-VCs typically stepping into and adding the most concrete value? From friends I've spoken with on the startup side, heading up strategy/ops if the company is still early (say <200 FTEs) would be most impactful.
Judith's profile thumbnail
I agree, I usually see it in the COO or VP Operations side, or GC, but I have seen the occasional person step into a VPE/CFO type role, and one step in as CEO when the original CEO/founder realized that he was not well matched to the CEO's 'public face & fundraising' role and preferred the visionary/CTO role. Depending on your personal background, you know what you are bringing to the table.This is generally about you and the startup finding a match, where they see your skill set as something that they are lacking that they need full-time onboard.
iynna's profile thumbnail
jessicali's profile thumbnail
Thank you, Iynna! I also wrote about my first quarter on the job here (still in draft phase so it is a word doc): https://docs.google.com/document/d/1D9JbIJbFJ_fVrqZueN0k8RxkiCtZ1DzhkVXGVuUveTw/edit and more on what I actually do in growth marketing (in case that is an area you are interested in): https://butwhatdoyouactuallydo.substack.com/p/but-what-do-you-actually-do-whatIf you are interested in staying connected to the startup/VC ecosystem after your transition, I would recommend: angel investing through groups like The Council mentoring at acceleratorsregular catch ups with your VC friends getting on advisory boards of startupsdoing more content part time roles with startups When I made the decision to switch, I focused on:Stage (wanted mid sized company)Sector (loved healthcare and wanted to be closer to it)Role (wanted to be in a relatively new department, in a revenue oriented role)Location (wanted to be on the East Coast)Culture (preferred a place where I knew someone internally/could vet the culture better) Hope this helps and feel free to reach out with any other questions!
Hi Jessica - thanks for putting together such thoughtful reflections; these are great and I'm sure they've been solid resources for your readers! I'll definitely take your points here into consideration. Nice to know we have similar approaches to networking and it seems to have worked well for you. Cheers
jessicali's profile thumbnail
So glad to hear and thank you for the read and note! Reach out any time if I can help in any way!
teresaman's profile thumbnail
Hey anon! Not sure if you're thinking of going back to engineering side of operator — if so, our Office Hour this week may be just the right place for you to ask any questions!
Hi Teresa. I probably won't go back into such a heavily-technical role, but I really appreciate the suggestion!
ChloeZZ's profile thumbnail
Hi,Good luck with your move! I recently moved from investing to an operator role and shared my thoughts here https://medium.com/@chloezzzzz/the-most-overlooked-investments-by-growth-stage-companies-lessons-from-an-investor-turned-operator-f9266048a4ff
CourtneyWebster's profile thumbnail
I loved this article! As someone who's been in a growth-stage company operator role, you were 100% on point.
chelseagoddard's profile thumbnail
Depends on a few things- Your interests- Why you are making the transition- Stage of startup- Relationship with startupI think the most successful transition I've seen is typically VC to Product Manager/Marketer
jessss's profile thumbnail
I’ve done this! I still haven’t gone back to VC, which is the end goal for me. I haven’t gone back because I had (and do have) too much fun being in an “operational” role. I thought VC was hard and a total grind - so I didn’t expect to bust my ass so hard working at a startup and actually building something - I think that’s the most rewarding part. I see a lot of Corp Dev, Biz Dev, Strategy & Product focused roles for those coming from VC. One role I’ll add if it’s interesting to you is leading a new product or a new segment of the business at that startup - acting as the GM of the “startup within a startup” it takes grit, financial acumen, strong leadership & one other important skill of a VC - the ability to do market research and know what to go after. I also see Chief of Staff from time to time. My one piece of advice work for a startup that you would invest in - be picky. And believe in the startup and what they’re building. That sounds obvious I guess but do the same kind of diligence you would do for an investment on where you want to work. DM if you want to chat more :)
Congrats on the successful transition! I'm excited to get back into building. Let me narrow some things down further, and I will very likely reach out to you soon. Really appreciate the offer. Thanks Jess.