Sales —> VC

Your better path is going to be (a) joining a venture-backed startup in a business role, (b) crushing it as an operator, (c) advising a couple earlier-stage startups on the key function that is your day job, and then (d) moving into venture.

Let's lay some context.

Venture roles are few and far between. The premier funds have lofty standards for who they want to hire. Look at the requirements listed for the junior partner role Ellen Pao was hired into at Kleiner before her discrimination suit: engineering undergrad, JD and MBA, and previous operating roles at technology companies. The younger, less-glitzy, but still notable funds (think Thrive, Spark, General Catalyst) are not as exacting but still enjoy the ability to be extremely discerning on who they add to their ranks. For this crop of funds, if it's an external hire it's almost universally an operator (not a banker, consultant, or PE guy moving to VC) or someone poached from another fund.

That means you need to either start your own business and scale it to the point you either exit or can hand over the reins to a non-founding CEO (this generally takes four years minimum) or join someone else's as a mid-senior or senior hire.

So, let's break the path down.

(a) If you've had success (as in an exit) as a lifestyle entrepreneur, it shouldn't be hard at all to get in touch with seed or Series A startups who've closed a proper venture round and explain how you're now interested in a more scalable, challenging business. Founders will love that. Sales is an especially hard thing to find qualified leaders in.

Live, breathe, consume, and digest everything that exists in the tech blogosphere on startup sales. First Round Review, Medium, etc. Know the difference between inside and outside sales, pure sales versus SDR roles. Know what sales ops is. Make yourself the go-to guy so that if someone gives you a shot, you can jump in and crush it.

Always get warm intros (read all the 'how to' posts on Medium about how and why this is important), always demonstrate value, don't treat these like the banking 'can I take you to coffee' pure volume play that college sophomores on this site follow, find a way to do work for free (again, read Medium for how smart people find ways to do free work for founders as a means of impressing them enough to win a job), and get in the door at an exciting company.

(b) If at the 9-month mark you can see that the company is not hockey-sticking to the point that you and the founders can comfortably identify that it's a winner (will be able to attract great talent, raise larger rounds of capital at a quicker interval between rounds), decide whether it's a thing that can be jumpstarted within another 6-month window or not. If it isn't, spend 3 months identifying the next startup you want to join and getting yourself in the door. (Make sure to hit that one-year cliff so you vest a portion of your equity.) If it is, spend the 6 months and reassess. If nothing changed for the better, find your next target. If things did change for the better, ask the founders for more responsibility.

The point is that you should be spending no more than 12-18 months at a startup if it isn't going to produce the operational track record you need to shine as a candidate for mid-senior venture roles. You need to be tied to at least one company that was a real win for all the investors involved and where your responsibility scaled regularly because your domain of coverage was critical to the business' success.

This may take two or three attempts, but as long as your filters are correct, your hit rate shouldn't be bad. You could literally pursue only YC companies, or trawl through the portfolio pages of funds like Andreessen, First Round, Lightspeed, Thrive, etc. to find who they funded and make them your targets.

(c) When you've gotten into a company where you were able to serve as a business lead while the company grew from 25-100 (and thus your team grew from 5-30 or whatever), you should start to look for opportunities to give back. Some people start angel investing; I think that's a waste of time unless you're patient enough to take the better part of a decade to move into venture. It takes so long for a company to move from angel stage to raised-three-institutional-rounds-and-everyone-can-consider-me-a-success.

What's more impactful is finding exciting early stage companies for whom your insight is immensely valuable (seriously, who doesn't want to know how to avoid the basic mistakes they don't even know about) and being an advisor. Don't hold more than two advisor roles at once. One of two things will suffer: either your performance at your day job or the value (clarity of insight, responsiveness, etc.) you offer as an advisor.

You can get equity grants out of it: often as high as 50 bps for seed companies. You can structure it however you like (there's a litany of free template contracts floating around from the tech-focused law firms like Cooley, Gunderson, etc.). It's often a commitment of X-hours per week for Y-period of months (usually 12).

The point here is that you're building a roster of people beyond the founders of the company you work at who can attest to the value of the insight you share.

(d) You now have much more of a well-rounded operator's profile where you look like someone who can add value to a portfolio of startups. Ideally you've developed relationships with the VCs who invested in the company(ies) you worked for, and beyond that, all the conference attending and networking events you went to (or better, hosted) as part of your process for identifying the startups to advise or candidates to recruit as direct reports to you at your day job company hopefully yielded some casual relationships with younger guys in venture who you then went on to develop a relationship with.

With this you can try to move in as a Principal (some firms call this VP; it's the role below partner). The most important thing to know about venture is that you can't brute force your way in like you can in banking (or arguably, even PE). It's not a numbers game. It's a quality of relationships thing, not quantity.

If you are a well-regarded person with a track record of performance at one or two fast-growing startups, a deep slate of people who can be solid on-list references and off-list references (this means when someone plugs your name in LinkedIn, sees 27 mutual connections, and asks them over quick phone calls what you're like, there isn't a glaring disparity between what the people on a reference list you provided and what people off of it say about you), and a proven mechanism for sourcing dealflow and talent, you are hire-able in venture.

Quick unsolicited pointers from what I can see about you.

(i) I would tighten up your presentation. I get that this is a free Internet forum, but the way you write comes across as slightly sloppy. You have typos, inconsistent formatting (e.g. spacing between in paragraphs), and grammatical errors -- it's all low-hanging fruit that someone with better attention to detail wouldn't let slip. You'd be surprised at how vigilantly people study your every move to see whether you're someone they're comfortable having represent or be associated with their brand.

(ii) Work on honing your story. If you ever tell someone in VC you "really enjoy the investing and analysis side of finance", they will mentally garbage-bin you. That's tragic, because not only did you close the door with them, but if your name comes up in conversation with someone else, they may shitcan you there as well. Even worse, if you do make it into the industry, when you encounter them at an event or even through a shared portfolio company, that impression you made still sticks.

Good luck.