Head of Sales - Americas

About Ashby

• We’re building the next generation of enterprise software, starting with products that help talent leaders, recruiters, and managers unlock hiring excellence

• Raised our Series C in early 2024, and are growing ARR >100% YoY (and accelerating)

• Have thousands of amazing customers including OpenAI, Snowflake, Ramp, Deliveroo, Notion and Reddit

• Multiple products to win both land-and-expand and material new business deals

• Consistently strong SMB & MM segments and rapidly moving into the Enterprise with no signs of slowing down

• Implemented AI throughout the platform

• Known for our pace of innovation and advanced analytics

About this Role

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.

Our Philosophy

Here are a few key points that should give you an idea of what it is like to work with us:

• 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 TA 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 product 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 Enterprise 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 Jim Miller, our Head of People & Talent to discuss your fit for the role and address questions about our market and solution

2. Experience Deep Dive (1 hr) - You'll walk Mike 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

• 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.

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.