Big Fish, Small Pond: How Startups Can Partner with Giants

When a startup swims into enterprise waters, the rules change - and the current can turn fast. 

That’s why at Startup Boston Week, we sat down with four leaders who have lived the highs and lows of working with corporate giants: Justine Jordan, Head of Strategy at BeFree; Evan Grossman, CPO at Affineon; Shankar Krishnan, Product Leader at AWS; and Melissa Appel, fractional head of product who moderated the discussion. 

The full event video is embedded below if you’d like to watch the conversation start-to-finish, or keep reading for an overview.

The panel didn’t sugarcoat it: enterprise partnerships can change your trajectory, or consume your company whole.

Understand the Maze: Org Charts Don’t Show You the Power

Startups often assume a neat decision tree. Big companies run on overlapping interests, hidden roadblocks, and misunderstood processes.

Jordan admits her biggest lesson was learning to openly say: “I don’t know how this works here, can you walk me through your process?” People inside enterprises often don’t understand it either.

Krishnan broke down the usual path: business champion → finance → procurement → legal.

But he warned AI has reshuffled that: legal now walks into meetings first, asking how your model is trained and whether they’re exposed.

Grossman added a sharper angle: some “innovation leads” aren’t pursuing partnerships, they’re collecting knowledge. “You’re free education,” he said. If they can’t explain a budget, timeline, and who will actually use your product: walk.

Champions > Contracts: Find the Person Who Needs the Win

Partnerships succeed because one person inside the organization decides to care.

Jordan’s 10-year saga building an integration with Salesforce showed this clearly. At first, every team said no. But she finally found a product marketing leader who needed their specific value for the segment she owned. That changed everything: that person sold the idea internally to procurement and legal.

Why did others say no? Spiffs. Their sales reps were literally paid extra to sell the existing, inferior solution. Until incentives aligned, no amount of product quality mattered.

Grossman put it simply: “There aren’t a lot of organizations saying: ‘We want more startup products to sell.’” You must show that your champion’s life gets easier and their boss’ boss will notice.

Know When the Deal Is a Trap, Even from Famous Logos

Enterprise deals are not automatically good deals. They often ask for:

• Full IP ownership

• 1-off product forks

• Years of exclusivity

• Rev-share upside with no revenue guarantee

Grossman walked away from an enterprise deal after realizing three branches of the organization - investing arm, IT, and clinical teams - were fighting for different priorities. The only “win” they offered was their brand. That wasn’t enough.

Krishnan added another bright-red flag: Deals based on “net new spend,” innovation money with no budget owner. Those die quietly after years of effort.

The litmus test: Can they tell you clearly where the budget lives?

Customization Can Kill You, Unless You Make It Your Acceleration Engine

Every large customer believes their custom request is universal. It almost never is.

Jordan’s company once rebuilt their integration model (from white-label OEM to “bring-your-own-account”) because the old one was a blocker. But they only did it when they realized: every future partner would need it too.

Grossman shared the internal script he uses to avoid “forked” code: Explain how splitting versions will hurt their experience and cost them more later. When they understand the consequences, they’re usually willing to solve the real root problem instead.

The mantra from the stage:

Don’t build for One Big Customer. Build for the segment they represent.

Where Enterprise Partners Truly Level You Up

Startups often think the benefit is just the logo, but it’s actually the learning:

• Dropdown menus that break at 300 departments

• Time zone changes that duplicate medication schedules

• Localization that isn’t “just automatic”

• Data migrations that stall rollouts

• Support expectations that require 24/7 coverage

Grossman: “Scaling from a single-doc practice to a hospital is totally different.” These are the “hidden scalability taxes” you don’t see until a whale sits on your product.

Krishnan emphasized that enterprise usage teaches you the real needs of the user persona, insights you can reuse across the whole market.

Pricing Innovation: The AI Era Has Changed the Game

Krishnan noted that traditional seat-based pricing is fading fast. Large organizations now expect:

• Gain-share pricing (“we pay only when there’s measurable value”)

• Synthetic data demos to prove outcomes before purchase

• Rapid pilots instead of 18-month procurement timelines

Founders must be ready to defend (with math) how they impact the P&L.

And sometimes, as Melissa noted, you can charge implementation, support, or rollout fees, since enterprise expects and budgets for them.

The Psychology Behind All of This

The audience asked: Why do big companies fight innovation?

Because…budget = power.

Krishnan explained that when AI reduces headcount needs, execs fear their budgets (and teams) shrinking. Even if revenue increases somewhere else, their own performance is measured on what they control.

Jordan summed it up: “The CEO may care about innovation, but my bonus is based on this.” And those two things rarely align.

Final Takeaways

Partnerships with major enterprises are never quick, never simple and never just about technology. They hinge on:

1. Champions with political capital

2. Incentives you fully understand

3. Boundaries that protect your product roadmap

Above all, don’t pretend you know the maze: ask. It’s the fastest way through it.

The full event video is embedded above (or you can watch it directly on YouTube) to catch the complete Q&A and founder stories shared from the stage.