Director of Sales

Our client is a private-equity-backed software company helping organizations keep their workforce safe, compliant and trained. Its platform spans environmental, health and safety (EHS) software, compliance training and workforce development, sold to thousands of businesses across North America.

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.