What Foreign Founders Get Wrong About North America · Howard Steinberg, HScott Tech Advisors

What we talked about.

Sunny Ray talks with Howard Steinberg of HScott Tech Advisors, a fractional sales and partnerships professional with multiple decades of experience. Howard explains that the most common mistake foreign founders make in North America is assuming one size fits all, along with overpromising what a product can do. He describes how his mathematical background shapes his approach, blending data with gut feeling, and why partnerships should start with a crawl before a sprint and stay a win-win. Howard looks back on his years at Ask Jeeves, where he joined in 2004, and on the Interactive Corp mobile team during the arrival of the app store. He shares how mentors shaped his career and how a handshake deal with a San Francisco founder that never materialized pushed him into independent work in 2010. The conversation also covers telling a product problem from a distribution problem, what makes a big partner say yes, how he tracks partnership health through rapport and regular check-ins, and what the first month with a new client looks like. He closes by sharing how to reach him.

Howard Steinberg explains why foreign founders stumble in North America and how to build partnerships that stay a win-win.

The questions, and the answers.

What is the first mistake you see foreign founders make when approaching North America?

I see founders assume one size fits all, and I see a lot of overpromising. Not every product can do everything, and that's okay. The Canadian, US and Mexican markets may not look like an Eastern European market. Begin interacting, qualify your opportunities, and make sure there's a win-win before you commit to a strategic partnership.

What does a math brain see in a deal that a salesperson might miss?

I rely on the way my brain works, which is analytical. I love having data behind me, but I marry it with gut feeling. Partnerships don't have to start at full speed either. Take an intentional crawl before you walk or sprint, because nobody wants a deal that benefits one side 90 percent and the other 10.

What did you believe about search at Ask Jeeves that turned out to be wrong?

Ask was founded in 1996 as a natural language search engine, where you asked a question and got an answer. Google changed behavior, since people just typed keywords and wanted answers fast. Ask was maybe ahead of its time, but Google's algorithm was relevant and quick, so trust was built. Ask never had that cachet.

What made you go independent in 2010?

It wasn't my plan. A San Francisco founder gave me a handshake agreement to bring me on full-time after fundraising, but that startup never came to be. Meanwhile, a VC contact pointed me to a portfolio company needing help. I realized a few clients could keep me busy, meeting new people, and I love being externally facing.

How do you tell whether a founder has a product problem or a distribution problem?

There's no better way than talking with people. Once you get targets on the calendar, they'll tell you whether the product fits. Even friendly conversations help. Run a de facto focus group. If you built something for financial services and have three friends in that industry, ask each for 15 minutes and listen to what they say.

What actually makes a big partner say yes?

Ask early what a win looks like for them. Tell them what you're looking for, then ask what they're looking for. It could be access to common customers, a pure revenue play, or something else. A lot of effort goes into forging a partnership, so you want it bearing fruit over many years, not ending after one quarter.

What do you track in partnerships that others ignore?

It's more of a feeling than data, and it's CRM-related. How often are we interacting, and what rapport do we have? I like a standing monthly call to check numbers and an annual or biannual meeting on the partnership's health. When things go wrong, we should have a frank conversation and fix it so it stays a win-win.

Who calls HScott Tech Advisors, and what does the first month look like?

Technology companies of various flavors call me. I'm not writing code. I'm an experienced sales and partnerships professional, doing strategic business development and straight sales. Month one is pipeline work: I share my network of influencers, decision makers and connectors, reach out, find second-degree contacts, and use cold outreach like email, LinkedIn, Apollo or calls if needed.