HYGTN #1 with Sean Crafts: How Blind Forecasts Nearly Broke a $100M SaaS Company
Broke a $100M SaaS Company
How Misaligned Planning and Blind Forecasts Nearly Broke a $100M SaaS Company, and What They Did About It
In B2B SaaS, we’re all chasing “the number.” But what happens when no one can explain where that number came from in the first place?
In the launch episode of How’d You Get That Number?, Outset CEO Daren Lauda sits down with Sean Crafts — co-founder of Mavenlink and now operating partner at HLX to unpack one of the most painful, valuable growth lessons of his career: when your revenue target is a fantasy, no amount of hustle can save you.
The Setup: $19M Raise, 300% Growth Target
It was 2015. Sean’s company had just closed a $19M Series B. The board, full of optimism, handed down a top-line bookings goal: 300% year-over-year growth.
Sean had just enough data and GTM experience to know something wasn’t right.
“I knew it wasn’t going to work,” he said. “We had no enterprise pipeline, limited mid-market traction, and a brand new segment strategy. But we couldn’t find a common way to show why.”
The board saw sales attainment and pipeline. Sean saw funnel math, conversion lags, and unrealistic ramp timelines. And no one was looking at it the same way.
The Fallout: A 35% Miss and a Lot of Hired-Too-Early CSMs
Despite throwing every resource at the target — hiring reps, juicing SMB leads, even overinvesting in customer success headcount in anticipation — the team missed bookings by 35%.
“It was brutal,” Sean admits. “We had dozens of CSMs hired and trained for customers who hadn’t closed. Everyone felt like a failure.”
But they learned. Six months later, the business hit the original run rate. Just delayed. The problem wasn’t the target. It was the timing, and the disconnect between Sales, Marketing, Finance, and Product about what was realistically achievable when.
The Shift: “Let’s All Agree on Reality First”
Instead of blaming each other, the executive team rebuilt its process. The first step: one shared view of reality.
“We called it “alignment with reality.” Every two weeks, every function would come together to say: ‘Where are we today? What’s changed? What’s still true?’” said Sean.
Marketing started mapping the top-of-funnel by channel. Sales stopped hiding behind aggregate quota math. Finance got visibility into lead-to-booking timing. Product flagged roadmap delays early. And the entire ELT moved from finger-pointing to scenario planning.
The Takeaway: “That Number Is Infinitely Knowable”
The biggest surprise? How few companies actually know what their number should be if nothing changes.
Sean now works with startups and scale-ups through HLX, helping them build one integrated GTM and financial model, a foundation to forecast from reality, not fiction.
“Forecasting is not just a Sales or Finance problem. It’s a company problem,” he says. “And it starts with everyone aligning on what’s real, right now.”
Your Move, SaaS Leaders
Ask yourself (and your ELT):
- Do we agree on what’s true, right now, across the funnel?
- Can we model forward-looking outcomes from today’s performance?
- Are our targets grounded in actual capacity, or just spreadsheet fantasy?
- Are Sales, Marketing, Product, and Finance planning together?
If the answer is “sort of” or “not really,” you’re not alone. But you’re also flying blind.
Listen to the full episode of How’d You Get That Number? Featuring Sean Crafts.
Want your team to stop asking, “Where the hell did that number come from?”
Outset helps B2B SaaS companies build one unified plan across Finance, Sales, and Marketing, so you can forecast with confidence and grow with clarity.
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