Head of Mid Market Sales, Americas

Ashby • ,

2d • $320,000 - $407,500 • Remote

About The Position

Ashby is seeking a senior B2B SaaS sales leader to lead its high-performing Mid-Market sales team in the Americas as the company scales. This is a second-line leadership role, initially overseeing three managers and expected to grow to four managers in Q2. The plan for 2027 is to grow Mid-Market net ARR by 80%. The role reports directly to the Head of AMER Sales and is expected to start in Q1.

The leader will build and develop the North American sales team, including managers and account executives; own regional revenue and results while fostering programs for strong execution across segments; and work with Revenue Operations and Marketing peers to expand Ashby’s serviceable addressable market and support its growth plans. The role will also help define go-to-market strategies and improve business performance.

Requirements

• Experience as a second-line sales leader at a high-growth SaaS company that has scaled past $100M in ARR.
• A proven track record of hiring high-performing Managers and Account Executives who quickly make an impact.
• Comfort making timely performance-management decisions.
• Experience managing a Mid-Market, sales-led go-to-market motion serving companies with 100–1,000 FTE.
• Knowledge of modern pipeline-generation practices and programs that provide sustainable pipeline coverage for substantial year-over-year growth.
• Ability to collaborate, build internal relationships, and drive change initiatives that improve operations.
• Ability to assess business health, identify high-impact performance opportunities, and provide practical advice on complex or challenging issues.
• Ability to develop sales strategies for multi-product platforms and competitive rip-and-replace deals.

Responsibilities

• Hire, lead, coach, and develop the North American sales team, including Managers and Account Executives.
• Be accountable for the region’s revenue and results.
• Foster programs that ensure high-caliber execution across all segments.
• Partner with peers in Revenue Operations and Marketing to expand Ashby’s Serviceable Addressable Market and support a path to $200M+ in ARR in 2027.
• Help define go-to-market strategies to achieve Ashby’s growth plans.

Benefits

• 10-year exercise window for stock options.
• Unlimited PTO, with four weeks recommended per year.
• Twelve weeks of fully paid family leave in the US.
• Generous budget for equipment, software, and office furniture.
• $100 per month education budget, with more expensive items such as conferences covered with manager approval.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed