The $2,000 Ticket Paradox
Most sales leaders will tell you they optimize for efficiency. Colin Specter optimizes for presence. When Orum needed to lock down Ramp and court Rippling—two marquee accounts—Specter didn't schedule another Zoom. He took them to the World Series. The tickets ran about $2,000 each. The total bill, including dinner, hovered around $7,000 to $8,000. In a market where qualified appointments cost upwards of $1,000 online, the math is simple.
Specter has become the face of Orum the way Devin Reed was for Gong or Kyle Coleman for Clari. But his role transcends typical VP of Sales duties. He's an evangelist, a road warrior, and a believer in the counterintuitive idea that in an era of freemium SaaS and product-led growth, the highest win rates still demand flesh-and-blood relationship building. Remote selling works. On-site selling works better.
Our win rate goes up exponentially when we can get on site with the champions and with the users and potential customers on the stakeholders. It's outside of the back and forth emails, it's outside of the formal screen share Webex experience.
— Colin Specter
This isn't nostalgia for the Mad Men era of three-martini lunches. It's a calculated arbitrage: the cost of a few thousand dollars in travel and entertainment versus the lifetime value of a mid-market or enterprise contract. For accounts that matter, Specter is willing to partner with other vendors to share costs, book panel appearances around customer cities, or arrange happy hours in London the week before a big RFP closes. The strategy is deliberate, repeatable, and—crucially—measurable.
Selling a Commodity by Not Selling It
Orum is, at its core, a phone system. Specter will call it a "live conversation platform" or an "AI telephony solution," but he's refreshingly direct about the category: it's a commodity. He spent five years at Namely selling HR tech and payroll—another commodity. The playbook he's refined over a decade is built around a single insight: when you're selling something that competes with dozens of alternatives, you can't win on features alone. You win by reducing uncertainty.
At Namely, Specter sold with decks, discovery calls, and social proof. Prospects never touched the product until after they signed. The sales motion was pure persuasion—aligning on workflow, building a business case, convincing evaluators that Namely's mid-market focus beat Workday's enterprise bloat or Gusto's SMB simplicity. It worked. Namely went from zero to $70 million in five years. But Specter learned the limits of that model.
At Namely, I need to convince you, I need to align with you on your workflow, your personal win, and convince you I'm best suited to do it. Whereas at Orum, I can prove it to you before you even sign.
— Colin Specter
Orum flipped the script. Prospects can spin up a trial in minutes, plug in their sales team, and see live results before anyone talks pricing. This isn't product-led growth in the Slack or Figma sense—Orum still has a sales team—but it's trial-assisted selling. The difference is proof over promise. When a champion can show their VP of Sales real connection rates, real time saved, real pipeline generated during a two-week pilot, objections evaporate. The deal isn't hypothetical. It's empirical.
The Remote Evangelist Who Lives on Planes
Orum is a fully remote company. Specter has no office to go to. His "office" is Delta flights, hotel lobbies, and customer conference rooms. During the second half of 2024, he was in a new city nearly every week. He earned Delta Platinum Medallion status. He believes this was the breakout year for post-pandemic events, the first time sponsorship and attendance felt like pre-2020 levels.
The travel isn't mandated by his job description. It's driven by two forces: Specter's personality and Orum's go-to-market strategy. He thrives on in-person connection. As a remote employee with two young kids, he's negotiated a boundary: he's home for Friday night dinner, no exceptions. That leaves Monday night through Friday morning as his travel window, with a strong preference for Tuesday through Thursday to protect family time on the edges.
I'm very much a person that kind of thrives connecting with people whether it's in an office or out in the field and at events and customer offices. Getting that kind of itch scratched through the travel of getting on site with our customers and potential customers and partners.
— Colin Specter
Most of his time on the road splits between customer visits with account executives, partner dinners, and panel appearances. Twice a year, Orum brings the full revenue team—sales, customer success, solutions engineering—together for Revenue Kickoff (RKO). Outside those gatherings, Specter sees his team at events or during customer on-sites. He recently flew to London to visit clients and co-host a partner happy hour. The calculus is simple: for high-value accounts, physical presence increases win rate. For a VP of Sales who doubles as brand evangelist, that means saying yes to a lot of flights.
Bootstrapped Beginnings and the Mid-Market Sweet Spot
Orum didn't start as an SMB play. Five and a half years ago, when Specter and CEO Jason Specter (no relation, though the shared last name is a fun coincidence with the Bond franchise) began selling, they targeted pre-IPO, well-capitalized tech companies. The focus was surgical: HR tech, payroll, and cybersecurity. Early customers included CrowdStrike, Ultimate Software, and Zenefits. The strategy was informed by Orum's own constraints. As a bootstrapped company, they lacked the SOC 2, SOX compliance, and enterprise certifications required to sell into public companies. But they didn't want to grind through SMB volume, either.
You want to strike the balance of I need some velocity wins, some logos now to get momentum and excitement for our business, improve product market fit. But I don't want them to be too small to where it's not worth it. That balance we found was in the mid-market.
— Colin Specter
Mid-market buyers had just enough risk appetite to work with an early-stage vendor and just enough budget to make deals meaningful. The segment isn't as vast as SMB or as lucrative per deal as Fortune 500, but it's the Goldilocks zone for a Series B company building enterprise features without enterprise baggage. Over time, Orum's upmarket motion accelerated—partner happy hours, World Series outings, and panel circuits don't make sense for $5,000 annual contracts. But the mid-market foundation gave Orum the credibility and cash flow to invest in enterprise sales without overextending.
Product-Market Fit Is a Sales Team Aligned With What You Actually Built
Specter references Amit Bendov's famous framework: to build a billion-dollar company, you need a GTM team good enough to sell a weak product and a product team good enough that a weak GTM team can sell it. Orum, he believes, has both. But he adds a critical caveat: "Best ever product for who?" The biggest mistake startups make is building for mid-market and hiring enterprise sellers—or vice versa. At Namely, the team aspired to enterprise but found their product was purpose-built for mid-market. Once they accepted that and focused, growth exploded.
Orum has stayed disciplined. The product is built for SDR teams and inside sales. Specter experiments at the edges—account executives, RevOps, customer success—but the core persona and industry focus remain tight. He contrasts this with Rippling's "all things everywhere all at once" strategy, which works at scale but requires different resources. At Series B, hyperfocus wins. Orum sells to sales development teams at tech companies, and the product roadmap reflects that. The sales team isn't asked to stretch into markets the product can't serve well.
When you align your sales team with the market that your product is purpose-built for, that's the best of both worlds. That's where you have true market fit with the product that you've built.
— Colin Specter
Specter's belief is that great salespeople can sell almost anything, but sustainable growth requires matching seller skill to product strength. His Orum reps could sell Namely. His Namely reps could sell Orum. Both teams know how to compete in crowded categories, differentiate commodities, and build champions. But the reason Orum's win rate spikes when they get on-site isn't just sales skill—it's that the product delivers fast, visible proof in the hands of the buyer. The trial does half the work. The relationship closes it.