Head of Sales

Summary

Join Ashby, a rapidly growing B2B SaaS company, as a senior sales leader to lead and scale our high-performing Americas sales team. This second-line leadership role oversees three business segments (SMB, MM, and Enterprise) and involves building a strong team, executing the sales plan, and unlocking new opportunities. The goal is to double ARR in 2025 and reach $100M+ ARR by 2027. You will play a key role in defining go-to-market strategies and resource allocation. This is a high-impact role with significant growth potential in a dynamic and innovative company.

Requirements

• You’ve been a second line sales leader at a high growth SaaS company, that has scaled past $100M in ARR
• You have a proven track record of hiring high performing Managers and AEs who quickly move the needle. You’re also comfortable making timely performance management decisions
• You have managed both high velocity SMB and consultative Enterprise go-to-market motions and are equally comfortable problem solving in both arenas
• You are well versed in modern pipeline generation practices and programs that ensure sustainable pipeline coverage for substantial YoY growth
• You have helped win $1M+ deals with publicly traded companies and are confident acting as an executive sponsor on such opportunities
• You’re an expert collaborator who builds relationships internally and can drive change initiatives forward to improve overall operations
• You connect the dots quickly. Your team trusts you to provide practical advice and consultation to help navigate challenging or complex issues
• You are adept at developing sales strategies for multi-product platforms and competitive rip-and-replace deals

Responsibilities

• Build an Amazing Team. Hire, lead, coach, and develop the North American sales team including Managers and Account Executives
• Execute on the Sales Plan. Be accountable for the region’s revenue and results. Foster programs that ensure high-caliber execution across all segments
• Unlock new Opportunities. Partner with peers in Revenue Operations and Marketing, to expand Ashby’s Serviceable Addressable Market to clear a path to $100M+ in ARR in 2027

Preferred Qualifications

• You haven’t managed managers at a high growth SaaS business
• Your primary focus is the forecast and extracting information from your direct reports. At Ashby, your job is to bend the curve, not just report the numbers

Benefits

• A product that our prospects & customers are truly excited about
• Competitive salary, commission and equity
• 10-year exercise window for stock options . You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable
• Unlimited PTO with four weeks recommended per year
• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!
• $100/month education budget with more expensive items (like conferences) covered with manager approval