Head of Mid Market Sales

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 my 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. This strategic leadership role reports directly to our Head of AMER Sales (Leigh Brown). 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 through a focus on new verticals and products.

You will have a significant impact in defining our go-to-market strategies 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 $100M+ high growth SaaS company

• 🥇 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. Your team trusts you to provide practical advice and consultation to 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.

Our Philosophy

Here are a few key points that should give you an idea of what it is like to be a Sales Leader at Ashby:

• 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 at the end of the day, 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. Please read more about our operating principles here.

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. You’ll have opportunities to ask questions of our team throughout.

The interview process for this role is four rounds in the following order:

1. Intro Call (30 min) - You'll meet with Steph Fish, our TA Manager for Sales, to discuss your fit for the role and address questions about our market and solution

2. Experience Deep Dive (1 hr) - You'll walk Leigh through your leadership experience in some detail to highlight your achievements, and points of learning.

3. Panel Presentation (1 hr) - We'll provide you with Ashby data and seek your perspective on the business and focus areas. You'll discuss your approach to leadership, hiring and developing managers and sales execution.

4. Final Round (2.5 hrs) - You'll have a set of four interviews with a range of cross-functional leaders

Benefits

• You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible.

• You get to sell a product that our prospects & customers are truly excited about.

• 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. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅

• Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.

• 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

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.