How to break into Venture – A Sales Playbook

I’ve frequently been asked about my path to working at a venture fund by other enthusiasts trying to break in. My story is not a traditional one, and I’m sharing it to encourage you to think differently, to think like a salesperson.

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I don’t have an MBA. I never worked in Investment Banking or M&A. I didn’t have any startup operating experience. I am the child of derivatives trading and brokerage, turned vendor sales, turned VC, and now, turned entrepreneur.

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What I do have is a ton of curiosity, tenacity, and mad relationship building skills. I’m resourceful, organized, and I am great at reading people. It turns out, that is half of what early-stage investing is. These are also the essential ingredients for a great salesperson.

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And if you really think about it…venture is sales. It’s about accelerating revenue, outsized returns, and relationships.

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So here is my story and a sales playbook to break into the illusive venture inner circle, which I encourage you to improvise on.

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#1 – Know Your Customer. It all starts with research. Get to know the people, the terminology, and the trends. Be super curious, resourceful, and organized.

#2 – Be solution oriented and value add. Be insanely helpful, a super connector, and a self-made solution database. I believe it’s true in sales, venture, and in life, that you win by being intentional and other-focused.  

#3 – Be an expert. Develop a subject matter expertise and a network around it. You can go vertical or horizontal. Most people go vertical by focusing on an industry like healthcare or crypto, but you can also go horizontal with things like sales, marketing, talent, or future of work. Horizontal expertise is valuable across every industry.

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Let’s break that down further…

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Do your homework

When I ‘got my break’, I was working in vendor sales…selling HR and benefits of all things. Not sexy at all, but, 100% necessary for every business. I was fascinated by venture and knew I wanted to focus on selling into VC and their portfolio to be close to the action. I studied the early-stage market like a hawk. I subscribed to every Crunchbase and Innovation subscription I could find, I googled ‘most active investors in the Midwest’, I followed all the top funds on Twitter and subscribed to all their newsletters and blogs. I knew the names and the news.

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I also studied the industry terminology. Every time I’d read or hear a term that I didn’t know like pre-money valuation, pro rata rights etc.…I’d Google it. The internet is a beautiful thing and there is a ton of amazing content out there. When you talk the talk, you build credibility and trust. When I was in vendor sales, I remember going to lunch with Tamim at OCA Ventures, and bringing up ‘deal flow’. He looked at me surprised and said, ”I never expected you to say deal flow before I did”. Hot tip: join an angel syndicate like Vitalize Angels for accelerated access to education and information.

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Next, I built a bench of people who could solve any fund or founders’ problem. I figured out which service providers were already considered their trusted advisors, and I made friends with them. To do this, I figured out which CPAs, lawyers, insurance brokers etc. had a venture go-to-market strategy and respect. Again, Google is wonderful, but this can also be accomplished by focusing on the logos that are sponsoring venture capital summits, events, and organizations. I became the go-to people and resource database and connector.

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Be helpful

I also believe success in sales and venture, is highly correlated to TRUST (know the people and the things) and TIMING. If you want to get timing right, you need to be top of mind for all the people in your target’s orbit. Consistency and creativity are key. You want to be like a drip campaign, right when you’re out of mind, then you’re back again. But there is an art here too. Don’t just flood people. Find reasons to keep in touch creatively and intentionally. Being other-focused is also critical. If you are just giving to get something back – everyone knows and it’s not cute.

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Tactical things can you do to help a venture fund -

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Subject Matter Expertise

Again, you can go vertical or horizontal here. There are a lot of generalist funds out there that can benefit immensely from specific industry expertise during diligence, or industry connections to support a portfolio company. And every fund needs core functional expertise in sales, marketing, and talent, but not every fund can afford to build out a robust platform team. Venture is about making money, and you need the best people, resources and pipeline to do that. Leverage (or build) your industry or functional knowledge and network. Particularly, if you work at a larger company or enterprise, then you have exclusive access to a massive internal network that can help funds and founders obtain information and influence.

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Investor Introductions

Venture investing is an inherently collaborative game. Oftentimes, one fund doesn’t fill out the whole round and they certainly don’t fill out the entirety (if any) of the subsequent rounds. VCs like to meet other VCs. Be an investor match maker.

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Deal Flow

If you’ve done your research and built a network, then you know who does what and who knows who. Start using this as leverage to build deep relationships with founders. Founders need a lot of help. They need capital, service providers, advice, and even informal therapy. If you build relationships with founders, and add value for them, you can start to become the broker between founders and VCs. When you’re the broker, you are adding value to both sides at the same time. Efficient value-add – my favorite. Focus on quality over quantity, people will notice. Added bonus, a founder may even offer you a formal advisory role.

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Fundraising

If you have personal or professional ties to potential limited partners…that is huge. By limited partners, I mean anyone who has the financial means to invest in a venture fund (a high-net-worth individual, family office, an institutional investor, etc.) Even if your introduction doesn’t materialize into a check, it’s still A++ for effort and you’ll make an impression.

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Sponsorship

If you’re currently working at a larger enterprise, you’ve likely got access to a significant budget too. Put together a business case to sponsor an upcoming VC or founder event (a happy hour, dinner, Summit etc.). If you can’t get the budget approved internally, see if you can get one of your other service provider friends to pitch in. Another win-win you can create.

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Phew....

That all might sound like a lot…and it is. But if that scares you, venture probably isn’t the career for you. Working at a fund is 110 mph every day. And even if you are a top performer, it’s a challenge to keep up with the volume and depth of knowledge required, particularly in the ever-changing world we live in. And a lot of funds are doing it all with a very lean team. Your help, in any way, really is impactful.  

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If you read this with a smile on your face and can’t wait to piece together the Rubik’s cube that is early-stage investing, then hopefully this helps you think about less traditional and creative ways to make an entrance.

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Personally, I loved working in venture, but I love being an operator more. I’m fortunate to have the best of both worlds now as a full-time entrepreneur and a part-time member of the investment community. As a side hustle, I am a Venture Partner at Forum and an active angel investor. Yet another nontraditional venture path for you to consider!  

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With love for all things sales and venture –

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Jess

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