Is It You or Your Product? The Truth About Product-Market Fit | Collin Stewart - 2039

Product-market fit isn't a yes or no question, and treating it like one is what trips up most founders and sales leaders. That's the core idea Collin Stewart, co-founder and CEO of Predictable Revenue and host of the Predictable Revenue Podcast, brought to this episode, and it reshaped how I think about why some go-to-market motions take off and others stall no matter how hard the team works.

Product-Market Fit Isn't Binary, It Has Strength

• Most founders treat product-market fit as something you either have or don't, which makes the conversation almost impossible, because any founder with paying customers can point to that as proof they already have it.
• Instead, Collin described product-market fit as existing on a scale, from barely there to overwhelming, which means two companies can both have "a product in market" while one sells at a fraction of the speed of the other.
• That distinction matters because it shifts the question from a debate over whether fit exists to a real conversation about how strong that fit is and what would make it stronger.

The Uber Eats Story That Proved the Point

• Collin shared that his old cold email agency normally booked around ten meetings a month for a client using the same process and the same team.
• When a former client joined Uber to launch what's now Uber Eats and asked Collin's team to run the exact same playbook, that single campaign of a thousand outreach emails booked 327 meetings in one month.
• The rep running the campaign hadn't changed and the process hadn't changed, so Collin concluded product-market fit acts as a multiplier on go-to-market effort, and Uber's fit was roughly 33 times stronger than anything else his team had worked on.

Strengthening Fit Starts With Customer Development Interviews

• The fastest way to raise the strength of your product-market fit is to run structured customer development interviews with your pipeline, your existing customers, and people in adjacent markets.
• The key question to ask is what problem you'd solve for them if you could solve anything, then follow it with two scoring questions: how satisfied are they with how they currently solve it, and how important is solving it to them.
• The sweet spot is a problem that scores high on importance and low on satisfaction, because a painful, unsolved, high-stakes problem is what founders should build around, not a nice-to-have improvement.

Why Working Harder Without Direction Backfires

• Collin compared weak product-market fit to riding a tricycle with the brakes clamped down, where grinding out more calls and more outreach just burns energy without covering more ground.
• He said the instinct to just work harder is the wrong move, because a founder who pauses to fix the product and the direction first will out-pace a founder who never stops to check if they're racing toward the right finish line.
• For sales leaders specifically, Collin's advice is to track whether a consistent process with consistent inputs is producing results that are out of line with a rep's past performance, because that gap is the signal that the product, not the person, needs the fix.

How to Build a Case When the Founder Isn't Convinced

• If a founder isn't open to hearing that product-market fit is weak, a sales leader should still go run customer development interviews across five or six verticals on their own. Because that data builds the case no argument alone can win.
• He stressed that every customer development call should end with booking the next call while you're still on the phone, since the entire feedback loop breaks down without that habit and waiting to follow up later multiplies the work.
• Collin kept a sticky note on his monitor that read "don't forget to book the meeting" for years, because that one small discipline is what turns a single interview into a repeatable feedback loop with a prospect.

What to Do About Outbound When Fit Is Still Weak

• The first move when fit is weak is to keep sending customer development interview requests instead of sales pitches, because the goal at that stage is learning, not closing.
• He walks prospects through a loop that moves from a discovery interview, to feedback on a paper prototype, to feedback on an MVP, to the question of what it would take for them to pay, and finally what it would take for them to refer three friends.
• Collin was direct that this only works if you book the next touchpoint before the call ends, because without that step you lose the momentum and have to restart the relationship cold every time.

Leadership Advice, Books, and Quotes

Collin Stewart recommends The Terrifying Art of Finding Customers, his book on connecting customer development to sales. Which he describes as part how-to guide and part honest account of the mistakes he made building his own companies.

Resources

• Connect with Collin Stewart on LinkedIn.
• Learn more about Predictable Revenue, the company Collin co-founded and leads as CEO.
• Check out Predictable.ai, Collin's newer tool for running plays like customer development and social listening; it's in beta, and interested listeners can email Collin at his first name at predictablerevenue.com for details.
• Subscribe to Collin's newsletter at foundersed.co for more on the book and his other projects.
• Grab a copy of The Terrifying Art of Finding Customers.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

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Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.