Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Josh Daiter — co-founder and CEO of InVintory — to examine what happens when a product-first founder takes the top seat. Daiter holds degrees in computer engineering, entrepreneurship, and artificial intelligence. He replaced over a million dollars in contractor costs by deploying AI to enrich a database of two million wines, with one human sommelier validating the output. That operational shift is what the transition from chief product officer to CEO made possible: not just building a better product, but restructuring how the company works at scale. Gow talked with Daiter about what product-first CEOs miss when they take the top seat, how to separate signal from noise in customer feedback, and where AI delivers real operational leverage versus a press release.
This episode is for CEOs who came up through product or engineering and are now wrestling with distribution, customer pivots, and how to use AI as operational leverage rather than a press release.
Key Takeaways
- Product-first founders who become CEO face a hard truth: a great product does not sell itself. Distribution is the other half of the business, and the CEO seat forces that reckoning.
- CEOs who treat every customer complaint as a roadmap item risk building for the noisiest voice in the room. The signal-to-noise discipline — survey data over one-off feedback — determines what actually moves the needle.
- Asking customers “why did you buy this?” reveals motivations that engineering teams never anticipate and that no product spec captures.
- AI replaced over a million dollars in contractor costs at InVintory by automating wine database research and duplicate detection, with a human validator remaining in the loop.
- When pivoting from B2C to B2B, buying behavior, product requirements, and willingness to pay all change. The only way to learn the difference is through direct customer conversation.
What Product-First CEOs Miss About Scaling
When Josh Daiter co-founded InVintory, his instinct was to build the best possible product and let it sell itself. That instinct helped InVintory gain traction. But the CEO seat showed him what the product seat hides.
“Stepping into the CEO role, I have to sort of look at the business more high level and think, well, you know what, we built this really great product, but distribution is the other half. Like we really got to ramp up our marketing and really, really dial into the unit economics of understanding how people are converting, how are we acquiring new customers? Sure, we’ve got a great product and we know that and we’ve known that for a few years now, but how are we going to get this in the hands of more wine collectors and really tap into the entire market?”
CEOs who come from product know how to build. The CEO seat demands they also learn how to distribute. Those are different skills, and the transition requires a deliberate mindset shift.
How CEOs Separate Signal from Noise in Customer Feedback
The foundation is surveys over individual complaints. One customer asking for a feature is not a roadmap item. It is a hypothesis worth testing.
“A one-off person telling you, you need to implement this into your product or you got to do this. Definitely take it with a grain of salt. Like I usually respond with, I hear you, we’ll take a look and then we’ll corroborate that with the average results from a survey. So that might be a positive signal to put that thing into some kind of product feedback survey, see how do other people feel about this?”
The survey often reveals the individual was an outlier. That matters because early-stage CEOs face a specific trap: building for the noisiest customer, not the largest market opportunity.
“You really got to understand like what’s that thing that’s gonna tip people over to be a paying customer or be a lost customer versus just, I’m just so passionate about your product, I’m giving you some criticism.”
The disciplined question is not “is this feedback valid?” It is “does acting on this feedback move us toward the market we want to win?”
What CEOs Learn When They Ask “Why Did You Buy This?”
InVintory’s pivot from B2C wine collectors to B2B restaurants surfaced a lesson that applies far beyond the wine industry. Most companies ask prospects why they did not buy. Few ask paying customers why they did.
Daiter made that ask — and got an answer he did not anticipate.
“We didn’t realize the use case that these particular restaurants were using InVintory for, because there’s so many competitors and they can go with something that does more, right? We had a very specific use case that they used InVintory for that we weren’t prepared to hear.”
The restaurants were not using InVintory for the monthly inventory management Daiter expected. They were using it so floor staff could find a bottle without interrupting the head sommelier.
Glenn Gow made the same observation from his own research experience: a large technology company discovered their customers were not buying for features or functions. They were buying because the software could be purchased on a credit card without a purchase order.
The why-did-you-buy question reveals the real job customers are hiring the product to do. That answer is rarely what the founding team expected. CEOs who ask it early enough can align their product roadmap and go-to-market motion to the actual use case rather than the assumed one.
How InVintory Uses AI to Do Work That Once Cost Over a Million Dollars
InVintory manages a database of two million wines. Each week, approximately 1,500 new wines are submitted by users. That volume of data enrichment and quality control was once handled by contractors — at a cost Daiter estimates exceeded one million dollars over time.
AI now handles most of that work.
“We actually go and have AI do research for us to say, hey, what is the region of this wine? What is the price, critic scores, the drink window, all of that, and it will do that for us. And then we have a SOM in-house that just check, check, check, check validates it. So there’s a human in the loop, but it’s really, really helped us become more efficient. Like we used to outsource all of this to like contractors to do this, which costs us, I want to say over a million dollars, like through this period. And we’ve been able to cut a lot of costs there and become a lot more efficient.”
AI also runs duplicate detection across the full database before a new submission is accepted, reducing the manual review burden further.
The model is not AI replacing human judgment. It is AI handling volume so the one human expert in the loop focuses only on validation. For a small team, that separation of tasks is the operational advantage that lets InVintory scale without scaling headcount at the same rate.
Daiter frames this as a structural advantage small companies have over large ones: “In bigger companies that are more, that are slower to adapt AI or are sort of like making hard pivots to try and implement AI, it’s kind of like shoving it down the company’s throat. But for us, like we’ve adopted it naturally with our small and nimble team.”
InVintory’s AI Sommelier, Vincent, and Where the Line Is
On the product side, InVintory built an AI sommelier named Vincent. Users can tell Vincent they are hosting ten people, set a budget between $200 and $500, describe the occasion, and Vincent will recommend three wines from the user’s existing collection.
The positioning is deliberate. Vincent is not a replacement for a human sommelier.
“Sommeliers definitely should not be intimidated by Vincent taking their jobs. And that’s absolutely not our intention either. We just want it to be a nice tool to help people.”
Some professional sommeliers have adopted Vincent as a filtering tool — give it fifty wines, narrow it to four, then apply their own palate and expertise. That positions AI as an input to human judgment rather than a substitute for it. That line matters for how any CEO introduces AI into a market where human expertise carries professional identity.
How CEOs Build Resilience Through Market Presence
InVintory shares daily customer feedback in a general Slack channel, and Daiter shares the full profit and loss statement with every employee each month. Both practices were in place before the company began its B2C-to-B2B pivot — and both kept the team anchored to outcomes that are not their own job title while the business model changed around them.
InVintory began as a project between Daiter and his father. The most lasting lesson from that partnership is not technical.
“Don’t let one piece of negative feedback or one bad month or a rejection from an investor get you down. The companies that are the most successful, believe it or not, are the ones that are in market the longest and that can just bear through the bad times and learn from them.”
That disposition — calm through crisis — shows up in how InVintory operates internally. The team shares daily customer feedback in a general Slack channel. Monthly, Daiter shares the profit and loss statement with the full team. Both practices connect employees to outcomes that are not their own job title.
“We love to be extremely transparent with our employees. So for example, we’ll reinforce their mission by — my wife does our customer support and she’ll often put in our general channel in Slack, like great feedback from customers every day — cause they email us every day and it’ll be like, I love this app so much. This just changed my life. Like people will literally say that. It makes our employees feel so good about what they’re doing.”
| Principle | What It Means in Practice | Named Evidence from This Interview |
| Distribution is the other half | Building a great product is necessary but not sufficient. The CEO seat requires owning acquisition, conversion, and unit economics. | InVintory had traction and a validated product when Daiter stepped into the CEO role — and immediately identified that acquisition and unit economics were the gap blocking scale, not the product itself |
| Survey over one-off feedback | Treat individual customer requests as hypotheses. Validate against the broader customer base before committing to roadmap changes. | InVintory uses surveys to corroborate or disprove individual feature requests; the survey discipline has prevented roadmap commits that would have built for outlier voices rather than the addressable market |
| Ask why they bought | The real use case is rarely the intended one. Asking paying customers what motivated their purchase reveals what to build next and how to position it. | Daiter discovered InVintory’s restaurant customers were using the platform for staff bottle lookup — not monthly inventory management — a use case the founding team had not anticipated and could not have derived from usage data alone |
| AI as volume handler, not decision maker | Use AI to absorb high-volume, repeatable tasks. Keep a human expert in the loop for validation. | InVintory replaced over a million dollars in contractor costs with AI-powered wine data enrichment and duplicate detection, maintaining accuracy with one in-house sommelier checking output — without adding headcount |
| Resilience through market presence | The companies that survive long enough to get to the right answer win. A bad month is data, not a verdict. | InVintory remained in market through the full B2C-to-B2B pivot without outside investor pressure, with operating continuity attributed to the daily customer feedback loop and monthly P&L transparency Daiter built into company culture from the start |
Quotes from This Episode
- “Distribution is the other half. Like we really got to ramp up our marketing and really, really dial into the unit economics of understanding how people are converting, how are we acquiring new customers?” — Josh Daiter, Co-Founder and CEO, InVintory
- “The companies that are the most successful, believe it or not, are the ones that are in market the longest and that can just bear through the bad times and learn from them.” — Josh Daiter, Co-Founder and CEO, InVintory
- “You really got to understand like what’s that thing that’s gonna tip people over to be a paying customer or be a lost customer versus just, I’m just so passionate about your product, I’m giving you some criticism.” — Josh Daiter, Co-Founder and CEO, InVintory
- “We actually go and have AI do research for us to say, hey, what is the region of this wine? What is the price, critic scores, the drink window, all of that, and it will do that for us. And then we have a SOM in-house that just check, check, check, check validates it. So there’s a human in the loop, but it’s really, really helped us become more efficient.” — Josh Daiter, Co-Founder and CEO, InVintory
- “We didn’t realize the use case that these particular restaurants were using InVintory for, because there’s so many competitors and they can go with something that does more, right? We had a very specific use case that they used InVintory for that we weren’t prepared to hear.” — Josh Daiter, Co-Founder and CEO, InVintory
Frequently Asked Questions
How does a CEO know whether they have a product problem or a scaling problem?
When churn and conversion rates track close to industry benchmarks, the product is likely working. Josh Daiter, CEO of InVintory, applies this rule: check the numbers against industry standards first, then layer in qualitative feedback from customers to determine whether criticism is broad or niche. Broad criticism across multiple channels points to a product gap. Niche criticism from power users often points to a segment the company may not want to serve.
When a CEO pivots from B2C to B2B, what changes most?
Buying behavior, product requirements, and price tolerance all shift. B2B buyers have fewer options in a given category but evaluate them more deeply. Josh Daiter, CEO of InVintory, found that the use case InVintory’s restaurant customers were actually solving for — staff bottle lookup without interrupting the sommelier — was not the use case InVintory built toward. That discovery came only through direct conversation with paying customers, asking why they bought rather than assuming they bought for the intended reason.
How should a small team use AI operationally without losing quality control?
Assign AI to tasks that involve high volume and clear rules — data enrichment, duplicate detection, categorization — and keep a human expert responsible for final validation. InVintory processes 1,500 new wine submissions per week using AI for research and duplicate matching, with one in-house sommelier checking the output. That structure replaced over a million dollars in contractor costs while maintaining accuracy. The human stays in the loop; AI handles the volume that would otherwise require a team.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first.If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
