Head of Mid Market Sales, Americas - Ashby

About Ashby

Sales at Ashby is a unique opportunity to sell a product customers genuinely love during an AI-fueled market expansion. Over 5,000 companies rely on Ashby including Shopify, Snowflake, OpenAI, Bolt, and Notion, and our business is durably growing faster than 100% year-over-year. We’re well funded, and on a path to profitability. That's exceptionally rare for a company at our scale, and puts us in the top 10% of benchmarks.

We have, in just a few years, replaced incumbents Greenhouse and Lever more than 500 times each, clear evidence of strong product-market fit and a meaningful opportunity to help modern teams move beyond legacy recruiting software. Ashby replaces 3-5 tools in a consolidation & efficiency play that’s equally loved by recruiters and CFOs. We’re known as a clear AI-leader in the recruiting space.

And the market opportunity is growing. We are rapidly extending from a best-in-class recruiting product toward a multi-product platform, expanding upmarket, into new industries, and internationally. For sales reps, that means a large market full of legacy tools, and a product portfolio that creates room for both new business and expansion. This is a chance to participate in how a category-defining company wins in its next phase of growth.

We are equally intentional about how we build the business. We have established a remote-first, high-performing sales organization that rewards learning and accountability. We use data to set achievable quotas, and reward sustained impact with competitive compensation and meaningful upside. We prioritize coaching and career development, with AEs advancing to Enterprise & Leadership roles in just a few years — 38% of the team who have been here more than a year have been promoted or taken on a new role!

You will work with people who care about craft, customer outcomes, and winning together—without sacrificing the trust, autonomy, and balance required to do your best work over the long term. Don’t just take our word for it, see what the team has to say about working here.

About this Role

To scale Ashby into the hundreds of millions of ARR, we are seeking a senior B2B SaaS sales leader to lead our high performing Mid-Market sales team in AMER. The start date of this role will be Q1. This is currently a second-line leadership role, initially overseeing a team of three managers growing to four in Q2. The plan for 2027 is to grow Mid Market net ARR by 80%.

This strategic leadership role reports directly to our Head of AMER Sales. 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 $200M+ in ARR in 2027.

You will have a significant impact in defining our go-to-market strategies to help us achieve our ambitious growth plans.

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 a Mid-Market sales-led go-to-market motion (100-1000 FTE).
• You are well versed in modern pipeline generation practices and programs that ensure sustainable pipeline coverage for substantial YoY growth.
• You’re an expert collaborator who builds relationships internally and can drive change initiatives forward to improve overall operations.
• You connect the dots quickly. You can evaluate the health of the business and hone in on the most impactful areas to drive performance and bend the growth curve.
• 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 forecasting and extracting information from your direct reports rather than actively driving performance.

Our Philosophy

• We're highly collaborative and we believe in a team-based sales motion to maximize our win rates on high impact deals.
• We believe in developing subject matter expertise (not just on our product but also the talent acquisition space broadly) which allows us to provide a differentiated buyer experience.
• We continue to make material investments in engineering and product because we know having the best products makes winning new customers easier.

We value a strong sense of ownership, principled thinking over decades of experience, and thoughtful & clear communication both internally and with customers.

Interview Process

Our interview process is designed so you can showcase your achievements and points of learning and apply those to a practical exercise. We'll provide you with sample customer calls and pipeline data so you can develop a well-informed perspective on our product and the Mid Market segment.

1. Intro Call (30 min) - Meet with our TA Manager for Sales to discuss fit and address questions about our market and solution.
2. Experience Deep Dive (1 hr) - Walk through your leadership experience in detail to highlight achievements and learnings.
3. Panel Presentation (1 hr) - Review Ashby data, share your perspective on the business, and discuss your approach to leadership, manager development, and execution.
4. Final Round (2.5 hrs) - Four interviews with a range of cross-functional leaders.

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 (expanding to other countries as situations arise).
• Generous equipment, software, and office furniture budget.
• $100/month education budget with more expensive items (like conferences) covered with manager approval.
• High-autonomy, remote-first environment focused on sustainable long-term work.