Conversation
Highlights

How Campfire Turned Category Frustration Into a Founder’s Edge

There’s a specific kind of frustration that only comes from knowing exactly what a product should do — and watching it fail to do it, year after year.

John Glasgow lived that frustration for over a decade. As a corporate finance leader at Adobe, then as CFO at Invoice2Go through its $625 million acquisition, he was the end customer of the enterprise accounting software that runs financial operations at scaling tech companies. The same software. The same limitations. The same workarounds.

“I saw in a QPANE that there’s very outdated technology,” he said in a recent episode of BUILDERS. So after Invoice2Go was acquired, he applied to Y Combinator to build the ERP he always wished he’d had. That company is Campfire — the AI-native ERP for growing tech companies, now used by companies like Replit and Posthog.

What makes John’s GTM story worth studying isn’t the founding insight. It’s what he did in the two years between starting and finding product-market fit — and why the specific decisions made in that window are harder to replicate than they look.

The Cold Outreach Signal That Mattered More Than Any Warm Intro

John started YC with a newborn at home and three months until demo day. He got to paying customers within 30 days — with a product he describes as rudimentary. The channel wasn’t his finance network. It was cold LinkedIn outreach to strangers.

One message led to a prospect who described his financial reporting situation as so bad that he offered to meet weekly for an hour — no equity, no compensation — purely to help build something better.

That response is the actual signal worth examining. Not the willingness to meet. The willingness to invest recurring time with zero upside. In a category like accounting software — where John notes buyers are “probably a bit more risk averse given the sensitivity of the data” — that level of unsolicited commitment from a stranger is a stronger PMF indicator than any paid pilot or signed LOI.

It also reveals something about why cold outreach outperformed his network in this specific case. A warm contact signs up to be supportive. A stranger with no social obligation, in a risk-averse category, investing serious time to fix a problem — that’s a category in genuine pain.

The Objection Flip Most Founders Never Try

John watches founders repeatedly accept a prospect’s condition — “once you ship X, we’ll sign” — as a reason to keep building without commitment. His counter is simple and underused: flip it.

“If that was true, then why don’t you sign up now as a customer? As soon as this feature is done it’ll turn to a contract.”

The reason this works isn’t psychological pressure. It’s information. A prospect who won’t commit to a contingent contract wasn’t going to buy when the feature shipped either. The condition was a deflection, not a requirement. Pushing on it surfaces that truth early — before you’ve spent months building to a deal that was never real.

The broader principle John ties to this: “As opposed to longing for tomorrow, learn to live for today.” He applies it beyond sales — to hiring decisions, to waiting for a bigger funding round to add credibility, to holding off on content until the brand feels more established. The compounding cost of waiting is underestimated at every stage.

What Two Years as the Sole AE Actually Buys You

From June 2023 through May 2025, John was Campfire’s only AE and its only solution consultant — running demos himself in a category that traditionally separates those roles. This is worth dwelling on because the instinct at Series A is usually to hire sales fast and step back. John did the opposite and views the two years of friction as structural, not incidental.

“What that allowed me to do those first two years is remain incredibly close to the product feedback,” he said. When you’re the only PM, AE, and SE simultaneously, every lost deal, every demo objection, and every onboarding friction point feeds directly into what gets built next. That translation layer between customer pain and product decisions is nearly impossible to reconstruct once you’ve introduced organizational distance.

His recommendation is unambiguous: “Even with all of the AI technology in the world, still get to Series A with founder-led sales if it’s a sales-led business.” The qualifier matters — this is specific to sales-led motions. But in those contexts, the opportunity cost of handing off too early is a product that drifts from what the market actually needs.

Why the First AE Came From Oracle, Not a Startup

When the time came to hire, John ignored the standard advice. He didn’t look for someone with a fast-growth startup pedigree. He hired from Oracle.

The reasoning is category-specific and worth unpacking. There were no startups with meaningful depth in enterprise accounting software. The competitive landscape was dominated by incumbents — NetSuite, Sage Intacct — that had been around for 25-30 years. In that context, the person best equipped to sell against the incumbent was someone who had just left it.

“They were also able to sell against the incumbent because they came from the incumbent,” John said. The hire arrived with institutional knowledge of the competitor’s weaknesses, credibility with buyers who recognized the background, and enough entrepreneurial instinct to operate without infrastructure. Their calendar was full from day one without formal onboarding.

Since then, Campfire has hired 14 more AEs with more varied backgrounds. The incumbent-first logic was specific to the moment — a category with no startup analog, a risk-averse buyer, and a competitor whose own former employees were the most effective weapon against it.

Brand Credibility as a Conversion Rate Decision

Campfire’s fifth employee was a head of marketing — now VP — hired at seed stage. John is explicit about why: in a category where buyers are handing over their board reporting, investor reporting, and tax compliance infrastructure, the appearance of a scrappy early-stage company is a sales liability.

“We have to build trust with the customer as a system of record,” he said. The brand investment — visual identity, website quality, a dedicated recording studio built for daily content production — wasn’t a vanity decision. It was a calculated response to the trust threshold required to close deals in this category.

The content operation that studio enabled has compounded significantly. Today, 80% of Campfire’s customers are inbound. John posts daily on LinkedIn, structured around roughly five content pillars — internal AI adoption, customer stories, company milestones, founder journey, and category insights. He records voice notes walking to his car after CFO dinners. He doesn’t batch-write on Sundays.

The format works because it matches how he actually thinks. That alignment between format and cognitive style is what makes a content cadence sustainable — and what most founders miss when they try to copy someone else’s posting rhythm without copying the underlying structure.

One signal that the content is working beyond pipeline: a CFO referenced six specific posts in their first meeting as though they were colleagues. That’s the asymmetric relationship that consistent content builds — the prospect feels like they know you before you’ve spoken a word.

The Org Design Decision Most Founders Get Wrong

John leads a 30-person sales team today and still considers himself the de facto CRO at Campfire. His framework for how founders should think about the sales leadership transition is specific: founder-led → founder running the sales org → 90-day co-ownership with a future sales leader before any hard handoff.

“Founder-led sales to founder-led head of sales would be my strong recommendation,” he said. His reference point for why total handoff is a mistake: even at Adobe, the CEO was present in major deal meetings. The instinct to step back entirely after hiring an AE or a sales leader is a founder solving for their own comfort — not for revenue.

The through-line across all of it is simpler than the individual decisions suggest: every choice John made — staying as the sole seller, hiring from the incumbent, bringing in marketing at employee five, building a studio, staying close to sales post-Series A — was a bet on remaining closer to the customer than his category typically allowed. In a market where the incumbents had grown distant from their users over 30 years, that proximity was the actual competitive advantage.