About the Role

Inbound has carried this business. We booked over 400 demos last month without anyone sourcing a single one. That's a good problem, and it's also the reason this role exists - the accounts worth winning next are not going to raise their hand, and the category is being decided right now.

We're hiring a VP of Sales to build the outbound motion, move the business upmarket, and grow the team that does both. Today it's three to five reps running a high-velocity transactional motion against inbound. Where we're going is different: larger commercial and mid-market deals in the $50K-$100K range, with a CTO or CIO in the room, real discovery, proof of value, an implementation plan, and security and migration review.

That's not a bigger version of the same sale. It's a different one, and building it is the job.

This role reports directly to our CEO.

What You'll Do

Build the outbound motion from the ground up. This is greenfield: you'll decide which accounts matter, how we reach them, and how the territory is designed. The companies deciding this category won't come inbound, and there's urgency to get in front of them now.

Move the business upmarket. The companies coming inbound started as seed and Series A. The last few months have brought larger commercial and mid-market accounts, and that trend is the strategy. You'll build the motion that wins them: discovery, proof of value, implementation planning, and the security and migration review that comes with a technical buyer.

Build and lead the team. The current reps run velocity. The next cohort looks different - more senior, able to source their own pipeline and win head-to-head deals upmarket. You'll define that bar, hire against it, and lead both groups without breaking the motion that already works.

Be the GTM thought partner. ICP, segmentation, positioning, packaging, and headcount allocation are all still being worked out, and all of them move again as we go upmarket. You'll shape those calls with the founders, Product Marketing, and the Head of GTM rather than receive them.

Own the number and the forecast. Set quota, build the capacity model, and forecast accurately enough that the company can plan against it.

Build the sales process. Stages, qualification, deal reviews, forecasting cadence, and the CRM discipline itself. We build a CRM - how we run our own process is a product input.

Who You Are

You've built an outbound motion from nothing. Not optimized one, not managed an SDR team that already existed. You've picked the accounts, written the sequences, and proved a channel worked before you staffed it. Tell us what the first version looked like and what you learned that changed it.

You've moved a company upmarket. You've taken a business from small deals to larger ones, and you can describe what actually had to change - the rep profile, the sales process, the proof points, the security review, the deal desk. This is the single most relevant thing on your resume if you have it.

You can sell to a technical buyer. CTOs and CIOs, security review, migration planning. You've been in those rooms yourself, recently enough that you'd be credible in one next week.

You've hired senior reps who source their own pipeline, and they worked out. You can describe your bar, and you can describe a hire that didn't work and what you missed.

You've run both motions at once. Velocity and upmarket in the same org, without letting the second cannibalize the first.

You're commercially fluent. Segmentation, quota modeling, capacity planning, and headcount allocation are things you've owned rather than inherited.

You operate at early-stage pace. You'd rather run the deal today than schedule a process review about it.

You're AI-native. You use these tools to run your own work, and you can sell a product whose value depends on customers trusting it with their email and calendar.

Nice to have

• You've sold a CRM, a GTM tool, or another product bought by sales leaders and RevOps.
• Founding AE or first sales hire somewhere in your background.
• You've navigated a pricing model transition - seats to usage, or similar. We're making that move.
• You've built a sales team on top of a self-serve or product-led motion, not just outbound.
• You've been the first sales leader at a company that went from single-digit to meaningful revenue in under two years.

Benefits & Perks

• Competitive salary
• Meaningful early equity
• Health insurance (medical, dental, vision)
• 3 weeks of PTO
• 11 paid company holidays + we enjoy a winter holiday break
• 3 months of paid family leave
• Wednesdays work from home
• Regular team dinners, events, offsites, and retreats
• 401k plan
• Other perks include: commuter and lunch stipend