Head of Mid Market Sales

Ashby

. Lead the high-performing Mid-Market sales team in AMER .

Posted 11/9/2026full-timeRemote • United States, CanadaLead💰 $320,000 - $407,500 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading high-performing sales teams within a high-growth SaaS environment, focusing on talent acquisition, pipeline generation, and strategic go-to-market execution to drive significant revenue growth.

Highest-signal resume keywords

Second-Line Sales Leadership ExperienceHigh-Growth SaaS ManagementPipeline Generation PracticesSales Strategy DevelopmentPerformance Management Decision-Making

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Strategy DevelopmentPipeline GenerationPerformance ManagementTalent AcquisitionRevenue Growth Execution

Soft Skills

CoachingCollaborationChange Management

Industry Keywords

Mid-Market SalesGo-To-Market StrategyAccount ExecutivesServiceable Addressable MarketCompetitive Rip-and-Replace Deals

About the role

Key responsibilities & impact

Lead the high-performing Mid-Market sales team in AMER
Initially oversee three managers, growing to four in Q2
Hire, lead, coach, and develop North American sales managers and Account Executives
Own regional revenue and business results
Execute the sales plan across all segments
Foster programs that ensure high-caliber execution
Partner with Revenue Operations and Marketing to expand Ashby’s Serviceable Addressable Market
Define go-to-market strategies supporting growth toward $200M+ ARR in 2027
Build a team-based sales motion for high-impact deals
Develop talent acquisition subject-matter expertise and differentiated buyer experiences
Participate in the four-round interview process, including a practical business and pipeline analysis exercise

Requirements

What you’ll need

Second-line sales leadership experience at a high-growth SaaS company scaled past $100M in ARR
Proven track record of hiring high-performing Managers and Account Executives
Experience making timely performance management decisions
Experience managing a Mid-Market sales-led go-to-market motion for companies with 100–1000 FTE
Expertise in modern pipeline generation practices and sustainable pipeline coverage programs
Ability to collaborate internally and drive change initiatives
Ability to evaluate business health and identify impactful performance opportunities
Experience developing sales strategies for multi-product platforms and competitive rip-and-replace deals
Experience managing managers at a high-growth SaaS business
Experience managing Account Executives delivering $XXM/yr+ of ARR contribution at a growth-stage SaaS company

Benefits

Comp & perks

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 equipment, software, and office furniture budget
$100/month education budget
More expensive education items such as conferences covered with manager approval
Competitive compensation and meaningful upside
Remote-first work environment
Coaching and career development opportunities