Conversation
Highlights

Nine Months of Selling to the Wrong Customers Taught DOSS More Than Any Playbook Could

Most GTM post-mortems are written after the win. This one starts in the middle of the mess.

Wiley Jones, Co-Founder and CEO of DOSS, spent roughly nine of his first 22 months in market selling to customers he now knows he should never have sold to. Each deal felt explainable in isolation — a champion who left, a budget that got pulled, a requirement that crept. That’s the trap. The structural mismatch underneath stayed invisible for months.

In a recent episode of Unicorn Builders, Wiley unpacks what it actually took to build a repeatable GTM motion for DOSS — an operations cloud combining procurement, inventory management, and order management for physical-products companies. The through-line isn’t about what he got right. It’s about how long it takes to see what’s wrong, and what happens when you finally act on it.

The ICP Diagnostic Nobody Teaches You

DOSS’s current ICP is specific: physical-products companies doing roughly $20M–$200M in revenue, complex enough to have outgrown spreadsheets, but not so complex they’re building rockets or running pharmaceutical supply chains. It took nearly two years to get there.

The early version was broader. Manufacturing companies were in. Different shapes and complexities of physical-products operations got a shot. And for a while, that felt like the right kind of optionality.

The problem with a wide ICP isn’t that you can’t close deals. It’s that the feedback signal is corrupted. When a deal goes sideways with a near-ICP customer, there’s always a proximate explanation. The structural mismatch underneath stays invisible because you keep finding reasons that sound true.

Wiley’s diagnostic wasn’t sophisticated. It was just honest. “Go look at the customers that have been slam dunk successes and be like, are they all the same? What is common about the ones that have been catastrophic failures? And then having the courage to be intellectually honest to then cull a large percentage of your pipeline.”

The manufacturing segment was the hardest cut — close enough to the real ICP to keep rationalizing, not repeatable enough to scale. The tell: “It wasn’t rinse and repeat enough for the stage we’re at as a business.” They cut it anyway. The decision wasn’t hard. Accumulating the information to justify it took most of those nine months.

The Ecosystem Conversation That Rewrote the Product Boundary

While working through the ICP problem, DOSS was also selling its own finance and accounting product alongside the core operations platform. Owning the full stack felt like a competitive advantage. Then a former public-company CEO — now at a top VC firm — looked at what DOSS was building and ended the debate in one sentence:

“If you don’t figure out how to play nicely with the ecosystem and coexist with the people who think you are competitive right now, you will get your face ripped off.”

Within a month, DOSS shut down first-party finance and accounting entirely and rebuilt around co-selling with established providers. “It has been transformative for the business.”

The product framing that emerged is now the core of how DOSS positions itself in market. “We think of DOSS as the donut and ERP as the entire system of the donut. And the donut hole is the general ledger. We just want to sell the ring around.” That boundary — what DOSS explicitly does not do — turned out to be as important as what it does. The co-sell strategy didn’t just remove a competitive threat. It made the product easier to buy by slotting into existing infrastructure rather than asking customers to rip it out.

What Founder-Led Sales Actually Costs You

For most of those 22 months, Wiley was running GTM himself. No process. No enablement. No tooling. Just him — functioning simultaneously as subject matter expert, solutions consultant, and sales engineer for every deal in the pipeline.

When DOSS brought in a sales leader, the diagnosis was swift. “Do you understand how hard this product is to sell?” Wiley said no. “Yeah, that’s the problem.”

The issue wasn’t rep quality. It was that the entire motion had been built around a single person’s context. No one else in the building could move a deal forward without Wiley in the room. That’s not a sales system — it’s a single point of failure dressed up as founder hustle.

The transition required something Wiley hadn’t anticipated. “The thing that comes after founder-led sales is unlearning all the stuff that worked in founder-led sales.” The instincts that make founders effective in early sales — deep product fluency, improvisation, the ability to carry a deal on personality — actively undermine the repeatable infrastructure you’re trying to build behind them. The post-transition role is narrower and harder to accept: executive alignment, top-of-deal vision selling, and closing when the moment calls for it. The pipeline doesn’t need the founder. It needs the system.

On the sales leader hire itself: Wiley’s framework was to talk to enough variants — the evangelist, the Rolodex hire, the process builder — before he could name what was actually missing. For DOSS, it was a systems thinker with domain expertise and the rigor to install process into an organization that had never had it. That clarity only came from eliminating the wrong fits. He used an executive search firm and has no regrets.

Field Marketing at the Conferences Your Customers Actually Attend

With the ICP tightened, the product boundary redrawn, and a sales leader in seat, the 2026 bet is field marketing — but not the kind that defaults to industry analyst events or software conferences.

DOSS goes to the vertical trade shows where their customers are already in growth mode: food and beverage, specialty retail, consumer goods. “We’re going to a coffee trade show. We’ll probably be the only software vendor there.”

The logic is precise. Customers aren’t thinking about their operations stack when a cold email lands. They are thinking about the future of their business when they’re at an industry event surrounded by peers making the same decisions they are. The aperture is open. DOSS shows up in those rooms not to sell, but to show what’s possible — and brings live customer stories to anchor the conversation. Verve Coffee, a DOSS customer and well-known Bay Area brand, is one of those stories. A recognized name in the room, talking about what they’ve built on the platform, carries more weight than any demo.

“How do we go to the places where our customers are paying attention and opening their minds to new ideas?” The answer, for DOSS, is to be the only software company in a room full of operators who are already thinking about growth. That’s a different conversation than the one you get at a SaaS conference — and a different kind of relationship.