Director of Sales

The company has 600+ employees, operates almost entirely remote, and runs a flat, low-ego, performance-driven sales culture with low attrition.

The Role

The Director of Sales, SMB is a first-level, player-coach sales leader running a team of 7–10 quota-carrying Account Executives selling to small and mid-sized businesses across North America. The team carries roughly $2–3M in new ARR annually, with individual AE quotas of about $250–300K.

The team has historically benefited from strong inbound demand. This leader's mandate is to keep that engine running while building a real outbound motion, and to own the team number end to end. 

What You'll Do

• Lead, coach and hold accountable a team of 7–10 SMB Account Executives.


• Own the team's quarterly new-ARR number, including pipeline reviews and forecasting for a high-velocity sales cycle.


• Shift the team from a mostly inbound model toward consistent outbound prospecting, building the habits, cadences and accountability to make it stick.


• Make the hard people calls: develop reps who embrace the change and performance-manage those who don't.


• Stay hands-on as a player-coach — joining deals, running call reviews and modeling what good looks like.


• Partner with senior sales leadership as the broader North American sales organization scales.

What You Bring

• A track record leading a team of quota-carrying Account Executives (not SDR-only or partnerships leadership).


• Experience running SMB, commercial or inside sales teams with high-velocity deal cycles and AE quotas in the $250–300K range.


• Proven ability to build outbound discipline in a team accustomed to inbound leads.


• Comfort being a hands-on player-coach who is close to the deals.


• A stable career history and the humility to talk openly about what you've gotten wrong as a leader and what you learned.

Nice to Have

• Background selling EHS, compliance, safety, training or LMS software.


• Experience in a private-equity-backed company.


• Familiarity with a multi-product, land-and-expand sales model.


• Ambition to grow into a more senior sales leadership role over time.

Why This Role

• Earn from day one. You inherit an established, stable team, with a roughly 60-day supported ramp.


• Plans that work. Low sales attrition (about 12–15%), realistic quotas, uncapped comp with accelerators, and no disruptive annual plan overhauls.


• Room to grow. The company is actively expanding its North American sales leadership and organization.


• Culture. Flat, no-ego and performance-driven, with leadership that values candor and self-awareness.