The RoleAs 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
What We OfferThe OTE for this role is
$350,000-$400,000. Where you land in that range depends on your experience, your skills, and how well your background fits what the role needs.
We also offer:
- Equity: Stock options, so you share in what we're building
- Health coverage: Medical, dental, and vision, with employee premiums covered by Avante
- Unlimited PTO: Take the time you need to rest and recharge, plus paid company holidays
- Retirement: 401(k)
- Commuter benefit: $150/month toward transit or parking
