Head of Sales – Americas

The incumbents are legacy players. We are displacing a collection of tools (ATS, Sourcing & CRM, Scheduling, Analytics, Offers & Approvals) with a consolidated talent suite. This is a proven playbook that Workday used to win the Enterprise HCM market as customers realize value in a multitude of ways.

We are seeking a senior B2B SaaS sales leader, to lead and scale our high performing Americas sales team. This second-line leadership role has responsibility across all three of our business segments (SMB, MM & ENT). The selected candidate will lead a team that today consists of three segment-based managers and their direct reports. The plan for 2025 is to double ARR again, and to grow the sales team in lock-step with capacity needs.

This strategic leadership role reports directly to our VP of Sales (Mike Clapson). There are three primary responsibilities that this senior sales leader will take on:

1. Build an Amazing Team. Hire, lead, coach, and develop the North American sales team including Managers and Account Executives.
2. Execute on the Sales Plan. Be accountable for the region’s revenue and results. Foster programs that ensure high-caliber execution across all segments.
3. 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.

You will have a significant impact in defining our go-to-market strategies and allocating resources to help us achieve our ambitious growth plans. You can read more about our Sales Team here.

If we are even moderately successful, we’ll have an incredible growth story to tell in just a few years!

You could be a great fit if:

• 💼 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

You shouldn’t apply if:

• 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.