Promising AI Finance Start up Or Stay Put at my UMM

Hi, I reached out and was invited to interview at one of those new finance AI startups (Hebbia AI, Rogo, etc). I currently make all in ~$415k at my UMM, and not yet feeling the burnout or intention to leave asap. I assume I will get shoved out and will not make VP. 

I have the potential to just coast and collect $400k+ for 2 more years. Should I instead take the hot AI startup? Thoughts? 

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As someone who recently left a MM fund as an associate, I’ll give you my biased 2 cents

1. IMO rogo, hebbia and even to some extent Harvey (to a lesser degree) I think are structurally challenged by the foundational models inevitably encroaching on their “bespoke / verticalized” value prop. Open to criticism but anecdotally my PE shop went all in on ChatGPT + Claude and the underlying logic is just they do everything and eventually will have the PE finance specific workflows integrated as well. I just can’t organically think of a situation where I’d seek out rogo or hebbia vs use Claude? Pulling comps, analyzing CIMs, mapping a data room, analyzing lender term sheets, pulling together IC decks - pretty much across the board I think the trajectory and use case optionality of the foundational models is superior. Maybe the MF assos / VPs have a different take here.

2. There are some interesting seed and series A AI bookkeeping and accounting software companies I’ve seen like Kick and Rillet which are actually trying to solve the general ledger reconciliation layer, beneath quickbooks. IMO that’s actually a really difficult, moaty and worthwhile problem in the broader professional F&A services space.

3. There are also interesting AI rollup / Holdcos like Thrive Holdings, the NMC healthcare rollup and the general catalyst backed rollups I think are more downside capped (and upside capped) but have interesting services multiple rerating stories you can potentially believe in based on the sub-vertical thesis.

Unless you really believe in a long-term differentiation / moat story vs the foundational models I think it’s a non-starter to leave PE given how saturated every AI adjacent startup and strategy has become, the abundance of capital and the lack of true barriers to entry in software. If you cant even get comfort that the foundational models won’t release an update that destroys your startup, I don’t know how someone could stomach all the other factors that make joining a startup from PE unpalatable.

 

I really, really appreciate the detailed write up. Thank you so much. Mind if I ask you one question im debating? I just landed an exit at a corporate the title is "Strategy Associate" and the pay all in is $355k. Hours are quoted 9pm-7pm. I think this is an anomaly offer right and I should take it? Aren't most roles that are Ex IB ex PE juniors like $180-$250k all in? 

 

speaking from experiences in my network, but I can attest that anything beyond $250k USD for Strategy Associate is an anomaly. Earning high salary in industry is a double-edged sword; if you don't produce, have good politcal standing, or if the business suffers, your name may be drawn come layoff season. 

My view of things - others can chime in if they've heard or seen differently.

 

Analyst 1 in IB - Cov

I really, really appreciate the detailed write up. Thank you so much. Mind if I ask you one question im debating? I just landed an exit at a corporate the title is "Strategy Associate" and the pay all in is $355k. Hours are quoted 9pm-7pm. I think this is an anomaly offer right and I should take it? Aren't most roles that are Ex IB ex PE juniors like $180-$250k all in? 

Can you please message me? I’m looking for a strategy role like this and would appreciate any guidance on finding these roles.

 

I'm pretty sure this says less about whether a verticalized solution is the right answer and more about hebbia and rogo being BAD vertical solutions....

If I saw a vertical solution that was MEANINGFULLY better than claude/gemini, it would change my mind completely. 

I also think from a business perspective you are completely missing the point - foundational models are not going to go verticalize every sector. They will do some lazy "Claude for Finance" type things, which are garbage. 

If you think models are going to magically get enough better to just "do an LBO" right from chatgpt, you just dont understand LLMs very well and their fundamental limitations....

 

Curious on your framing of Harvey (I haven’t used it), is there anything specific about it that reduces the vertical encroachment relative to the other guys? Or is your point regarding proprietary data/confidentiality issues

 

Yeah so if you see my thoughts below on accounting, legal falls into the same framework to me. Agentic workflows are more attractive the more deterministic and rules based they are, and less vice versa. On that alone, I see more value on the Harvey side, even though law is more judgement and open to interpretation than accounting, it’s still less than PE Imo.

 

I left to do 3.

The reason I think accounting is a much harder and moatier problem to solve from an LLM perspective is because, in theory, accounting is a rules based job. An extremely complex one with lots of edge cases, but a rules based job with deterministic answers. In the short run, this is in theory a more attractive problem set in my opinion for an AI wrapper startup to tackle, and add substantial value on top of the foundational models that is much harder for them to encroach on. If you can capture all those edge cases reliably, and truly automate the workflow, that’s a multi hundred billion dollar TAM and workflow (eg, everyone wants to be the quick books killer)

The job of a PE associate is also rules based, but largely comprised of synthesis tasks that involve some judgement and non-deterministic answers. In that case, copilot use case is inherently favored -> foundational models are cheaper, 80/20 a specialized solution, and more flexible / customizable.

 

Unless the startup has real revenue, a clear path to profitability, and you're getting meaningful equity, stay at the UMM. The optionality from a name-brand PE fund on your resume is worth more than most people realize — it opens every door for the next 10 years. AI startups are exciting but 95% of them won't exist in 3 years. You can always leave PE for a startup later, but going back to a UMM after leaving for a failed startup is nearly impossible. If you're genuinely passionate about AI in finance, build on the side while keeping your seat. The best time to take startup risk is when you have a safety net, not after you've burned your bridges.

Buy-side finance | Building institutional-grade models & AI tools
 

I really, really appreciate the detailed write up. Thank you so much. Mind if I ask you one question im debating? I just landed an exit at a corporate the title is "Strategy Associate" and the pay all in is $355k. Hours are quoted 9pm-7pm. I think this is an anomaly offer right and I should take it? Aren't most roles that are Ex IB ex PE juniors like $180-$250k all in? 

 

$355K all-in at a corporate for 9-7 hours is a strong offer — don't overthink the title. You're right that most ex-IB PE juniors land $180-250K, but those are fund roles with carry upside and worse hours. At $355K with work-life balance, your effective hourly rate is probably higher than most Associate seats. The question is whether you want optionality (stay in PE/fund track) or quality of life now. If you don't plan to go back to a fund, take the corporate role and don't look back.

Buy-side finance | Building institutional-grade models & AI tools
 

I really, really appreciate the detailed write up. Thank you so much. Mind if I ask you one question im debating? I just landed an exit at a corporate the title is "Strategy Associate" and the pay all in is $355k. Hours are quoted 9pm-7pm. I think this is an anomaly offer right and I should take it? Aren't most roles that are Ex IB ex PE juniors like $180-$250k all in? 

 

Do you have a sense of why they're offering more than street?  Digging into this can uncover a lot.

For example if it's because the role is more important to them than the analagous role is to other companies (leaner team, more responsibility, strong team that values each person as essential) then that would be a good reason for the high pay and indicate a role that can be a long-term win.

But there can be bad reasons for high pay too.  Maybe the company has a lot of turnover and needs to offer more to attract candidates.  Maybe the hours are way worse than advertised.  Just examples. 

Point is, find out what's going on with the high offer. Linkedin is surprisingly useful for finding ex employees and talking to them.

 

most AI startup moats will probably be obsolete in like 2-3 years (and that’s being generous), so there isn’t much long-term upside there

ask yourself why a company would pay for some external AI when they could just hire a team to build exactly what they need in-house 

Claude is also launching AIs almost weekly killing hundreds of AI startups before they even launch lol

incentives trumph ethics
 

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incentives trumph ethics
 

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