Director of Sales

The Role

As Director of Sales, you'll lead a regional team of Enterprise and Mid-Market Account Executives. You'll own new business results for your region, from pipeline generation and forecasting through hiring, coaching, and closing.

This is a player-coach role. You'll build and develop a high-performing team, partner with the CRO on territory and quota planning, and stay close to the deal: leading executive conversations, guiding complex multi-stakeholder sales cycles, and helping customers through AI security, privacy, and procurement reviews. You'll report to the CRO and work closely with Marketing, Partnerships, Solutions Engineering, and Customer Experience to build a repeatable, scalable sales motion.

What You'll Do

• Lead and develop the AE team. Run 1:1s, pipeline reviews, and deal strategy. Coach to each seller's specific gap, whether that's multi-threading, executive presence, or closing.
• Own the number and the forecast. You're accountable for new-logo bookings. Set territories and quotas with the CRO, enforce MEDDPICC-level rigor, and deliver a forecast leadership can plan around.
• Hire and ramp great sellers. Define the profile, run the loop, and get new AEs productive quickly in a complex domain.
• Build the playbook. Codify the discovery, positioning, and close plans that win, then improve them every quarter.
• Get into the deals that matter. Join executive meetings with CHROs and CFOs, and step into strategic negotiations when it moves the deal forward. You'll also set clear co-sell rules with our broker and consultant partners.
• Lead with AI. Our sellers use Claude, Granola, and similar tools daily. You'll use them yourself and spread the workflows that work across the team.

What We're Looking For

• 10+ years in B2B SaaS sales, including a track record personally closing $150K+ enterprise deals into HR, Benefits, or Finance buyers
• 3+ years leading enterprise AEs, with a team that consistently hit its number
• Experience leading a new-category sale where buyers have to be educated before they buy
• A record of hiring and developing enterprise sellers into top performers
• Disciplined pipeline and forecast management (MEDDPICC or equivalent)
• Daily, hands-on use of AI in your own work and in how you run a team
• Experience selling enterprise AI, ideally into HR and Total Rewards buyers
• A hands-on leader who thrives at startup pace: you set the tempo, travel to key deals, and can run a deal end to end alongside your reps
• Technical fluency to handle first-line questions on GDPR, the EU AI Act, AI diligence, infosec, and data privacy, and to demo the platform yourself
• Experience personally negotiating enterprise contracts, including terms like limitation of liability and data privacy

Nice to Have

• Experience selling benefits, HR tech, or healthcare to self-funded employers
• Relationships across the broker and consultant ecosystem (Mercer, Aon, WTW, Lockton, OneDigital, Howden, Segal Benz)
• Experience scaling a sales team at an early-stage company where you built the playbook

Our four values aren't aspirational. They translate into concrete operating tenets that shape how we make decisions every day.

Beat Yesterday. We re-evaluate our own toolkit every quarter, because the workflows that made you effective three months ago may already be outdated. We act on 70% of the information rather than waiting for certainty. We timebox, execute, and iterate, getting work in front of real people quickly instead of polishing in isolation. And we own our output regardless of how we produced it. AI can get you 80% of the way there. Everything that goes out with your name on it is your responsibility to review, refine, and stand behind.

Embrace Type 2 Fun. We take on hard problems and find meaning in the work, even when it's uncomfortable. We assume good intent and follow up directly rather than venting in side channels. We celebrate wins loudly and specifically, naming the actual behavior so the whole team learns what great looks like. We are on by default, because we owe it to each other and to our customers to be available beyond what a regular corporate job would demand. And we do unscalable things today that build scalable advantages tomorrow: every hand-built account play and late-night proposal turnaround earns us the right to scale later.

Stay Hungry, Stay Curious. We expect everyone to be the expert on AI in their function before anyone asks them to be. The landscape changes weekly. When you learn something, teach it. Learn enough about adjacent functions to ask good questions. Ask the question you think is too basic, because in complex domains like benefits, the cost of a wrong assumption can be a lost account. And remember: curiosity without urgency is a hobby. Learning has to translate into action on a timeline that matches the opportunity.

Act Like an Owner. We say the uncomfortable thing early, raising missed commitments or quality gaps directly with the person within 48 hours. We surface problems when they're small, not the week they become a crisis. Customer-facing work gets priority, always. And we close the loop every time, because over-communication is a feature at our stage, not a bug.