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Stay Ai


Stay Ai Navigates a Successful Series A

Stay Ai, a subscription enablement platform for ecommerce companies, raised $5.4 million in venture funding from multiple investors in early 2023. Later in the year, when it came time to raise a Series A, the company turned to one of those investors — York IE — for help navigating the process.

Josh Rombach, Stay Ai’s director of finance and operations, discusses the benefits of collaborating with York IE’s Corporate Strategy and Financial Planning and Analysis and Investments teams:

How did York IE help Stay Ai’s fundraising planning?

We’re a rapidly growing business with a rapidly growing team, where everybody’s wearing quite a few hats. Having York IE’s support on all things finance freed up our cofounders’ time to really focus on the fundraising process itself: networking, pitching, etc.

On the tactical side, they helped us prepare our financial model and think through the projections we were making going into that raise. We talked through questions like, “What’s the right way to think about a rev build?” and “How do we build out our go-to-market team in light of the projections we’re putting together?”

What challenges did you face, and how did you overcome them?

We opened up our fundraising shortly after Silicon Valley Bank collapsed, unfortunately. That sparked a pronounced change in terms of what venture investors were looking for.

York IE helped us establish the financial infrastructure that a rapidly growing company needs to scale successfully in this environment. And we crafted a story around capital efficiency to align with the huge shift happening in the market.

Having York IE to tag in on the actual execution work while we were dealing with the other aspects of the fundraise, and having them behind the scenes to help sanity check and craft our story, was hugely helpful.

What were the results of this work?

Your story is always evolving, but it certainly felt like ours resonated very well at that moment in time. We ended up raising a Series A led by Telescope Partners, bringing our total funds raised to $15.1 million. Things really could not have played out any better for us.

It’s rare to come across funds that are set up in a way to really add strategic value, but York IE does — and now Telescope as well. They represent the next generation of venture investors that have in-house resources and share the playbook for success. Enabling founding teams to find a correct path more quickly — particularly in this environment that’s focused on capital efficiency — is just an enormous benefit.

Fundraising can be stressful, but having established a prior relationship with York IE enabled some shorthand as we were going through the process. Working with people who are super sharp and exciting to chat with is an amazing spot to be in.

We were all able to respectfully push and challenge each other, and ultimately that led us to land in a better spot than we would have otherwise.

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