Head of Mid Market Sales

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Lead a high-performing Mid-Market sales team within the AMER region.

• Initially manage three team leaders, expanding to four by Q2.

• Recruit, mentor, guide, and develop North American sales managers and Account Executives.

• Take ownership of regional revenue and business outcomes.

• Implement the sales strategy across all market segments.

• Cultivate initiatives that guarantee exceptional execution.

• Collaborate with Revenue Operations and Marketing to broaden Ashby’s Serviceable Addressable Market.

• Establish go-to-market strategies aimed at achieving over $200M in ARR by 2027.

• Create a collaborative sales approach for high-impact transactions.

• Develop expertise in talent acquisition and deliver distinctive buyer experiences.

• Engage in the four-round interview process, which includes a practical business and pipeline analysis task.

⛳️ Requirements

• Experience in second-line sales leadership within a high-growth SaaS organization that has surpassed $100M in ARR.

• Demonstrated success in recruiting high-achieving Managers and Account Executives.

• Proven experience in making timely performance management decisions.

• Experience in managing a Mid-Market sales-led go-to-market strategy for companies with 100–1000 FTEs.

• Proficiency in modern pipeline generation techniques and sustainable pipeline coverage initiatives.

• Capability to collaborate internally and spearhead change initiatives.

• Skills in evaluating business health and identifying significant performance improvement opportunities.

• Experience in formulating sales strategies for multi-product platforms and competitive rip-and-replace engagements.

• Background in managing managers within a high-growth SaaS environment.

• History of overseeing Account Executives contributing $XXM/year or more in ARR at a growth-stage SaaS company.

🏝️ Benefits

• Ten-year exercise period for stock options.

• Unlimited PTO with a recommended four weeks off each year.

• Twelve weeks of fully paid family leave available in the US.

• Generous budget for equipment, software, and office furnishings.

• $100 monthly budget for educational purposes.

• More costly educational opportunities, such as conferences, covered with manager approval.

• Competitive salary with significant earning potential.

• Remote-first working environment.

• Opportunities for coaching and career development.