Winning Enterprise Clients as a Seed Stage Company

Gabriel Matuschka
Fly Ventures
Published in
3 min readOct 28, 2020

A pillar of our investment strategy is to back seed stage startups serving large Enterprise clients, often eying ACVs of $50k to >$500k from the start.

This is anything but trivial. Hence, we spend a good amount of the first 18–24 months after our initial investment working on go-to-market (GTM) strategy with our portfolio companies.

Sarah @Greylock wrote a great piece on Startups Serving The Enterprise in 2018 covering many aspects from the risks of customization to the “desert of procurement”.

We further developed this working with founders over the past few years. Our shared goal is to win the first 3–10 high ACV clients in the life of a startup. A concept we have been referring to for a while now is:

Photo by Ryan Geller on Unsplash

The Magic Triangle of Enterprise Sales

To us this means you, as a founder, should try to engage with all three personas below in a client organization. Working with all of them in parallel positively impacts your success in engaging with everyone individually — and signing an Enterprise client.

A quick description of the personas and what drives them:

  1. Executive Sponsor
    Someone high up in the organization (C-level, VP or Department Head). You won’t be able to speak to her more than 1–2x / year. However, her buy-in will help you overcome organizational friction. Key goal: Find out which company wide OKR / goal you are explicitly addressing with your product. Make sure to adopt the exact wording used for this inside the client org.
  2. Line Manager / User(s) of your product
    The person(s) actually pushing the buttons of your product. If you can’t get their buy-in, even if you somehow manage to sell your offering once, adoption will be limited and the client will churn during the pilot phase. So delight them by helping them achieve their internal goals with your solution. Significantly contributing to a company wide OKR / goal can get the line manager a promotion — and he will love you for that.
  3. Innovation Department Representative
    Often dismissed as “has no say”, yet he is so helpful. His goal is to bring innovative solutions to the enterprise, i.e. he succeeds if you succeed (aka a rare friend in your GTM challenge). We have seen founders very wisely nurturing these relationships to the point of e.g. openly discussing the maximum price acceptable to the Line Manager / Exec Sponsor. However, make sure you are helped by the innovation department guy, not sponsored by him — as his budgets are non-permanent.

How to get to engaging with all of them

There are many different strategies for your best way in. It can be helpful to start with a warm intro to the Exec Sponsor. However, you better be ready for this with your product and — many seed stage companies are not.

Initially learning from Line Managers / Users, maybe being helped navigating the organization by the Innovation Department oftentimes is the more fruitful starting point in the early days. You also learn how to generate leads bottom-up and which communications channels work best for you. We have seen portfolio companies achieve >$500k ACVs company wide roll-outs that started with a very personalized cold outreach on LinkedIn.

If you are working on a product where the above GTM sounds like it’s a good fit, email me at gabriel@fly.vc Happy to speak even if you aren’t looking for funding yet.

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