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

Deann93·Jan 04, 2021

Posted in:Advice

Hi Elpha community,I've been working in portfolio management and investment for an early-stage VC for about four years. I'm grateful for the learning opportunities and network that the role has granted me, but I feel it's time to move on as I crave the hands-on roll-up-your-sleeves many-hats environment that a startup would offer. I should mention I previously made the jump from operator (engineer) to VC where I was responsible for technical design, large-scale project management, team leadership, so I do come with operational experience, but it's not a muscle I've flexed recently. **Has anyone else made a similar transition? Given my immediate work history, what advice would you share as to what to attributes to highlight during the interview process, how to ramp up in the first six months in the role, etc.?**I welcome any thoughts. Thank you!

Judith·Jan 04, 2021

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.

Deann93·Jan 05, 2021

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·Jan 05, 2021

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·Jan 04, 2021

The amazing @jessicali did it a few months ago and wrote about it https://jessli.medium.com/im-leaving-vc-this-is-what-i-didn-t-expect-to-learn-3e83ece49c50

jessicali·Jan 04, 2021

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!

Deann93·Jan 05, 2021

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·Jan 05, 2021

So glad to hear and thank you for the read and note! Reach out any time if I can help in any way!

teresaman·Jan 05, 2021

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!

Deann93·Jan 05, 2021

Hi Teresa. I probably won't go back into such a heavily-technical role, but I really appreciate the suggestion!

ChloeZZ·Jan 05, 2021

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·Jan 06, 2021

I loved this article! As someone who's been in a growth-stage company operator role, you were 100% on point.

chelseagoddard·Jan 06, 2021

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·Jan 06, 2021

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 :)

Deann93·Jan 08, 2021

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.