Sales Leader, Enterprise - Americas

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

TA tools in the Enterprise represent a huge market opportunity, a $1B+ TAM, and 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 HCM market as customers realize value in a multitude of ways, and we are on track to do the same.

We are seeking an experienced Enterprise Sales Leader in North America to lead the segment and scale our Enterprise AE team - West (Mountain, Pacific, Central). There are three primary responsibilities that this sales leader will take on:

1. Own the revenue outcomes for the segment, with clear accountability for delivering results. Partner with the senior AEs in a team selling motion to maximize our win rates on the company's largest opportunities. Manage deal risks and help navigate the complexities of large-scale competitive replacement deals.

2. Build a high caliber team in lock step with market demand. In general we believe that smaller, high caliber teams can achieve remarkable results. Your Enterprise team will be an adept group of solution selling experts.

3. Establish a reputation for excellence by fostering alignment across Product, Marketing, Solutions Engineering & Professional Services creating a flywheel for future enterprise customer acquisition.

In this role, you’ll report to our Head of AMER Sales (Leigh Brown) and have significant impact in defining our go-to-market strategy and sales methodology. If we are even moderately successful relative to our ambition, we'll have an incredible growth story to tell in just a few years!

• 💼 You’ve led and scaled a team of SaaS Enterprise Account Executives delivering $5M/yr+ at a company that has scaled beyond $100M ARR

• 💰 You have helped win $1M+ SaaS deals with publicly traded companies, and can help your team see around corners on complex deals

• 🥇 You have a proven track record of hiring and onboarding Ent AEs who can create their own pipeline and close both more tactical ($100k) and strategic ($500k+) deals

• 📊 You have a strong mental model for enterprise sales execution. At the same time, you're a lifelong learner and are open to new ideas and experimentation.

• 🤝 You build trusted relationships with customers and confidently facilitate peer-to-peer conversations between senior leaders to deepen partnerships and elevate strategic engagements.

• 🤓 You become a product and industry expert. You connect the dots quickly. Customers and your team trust you to provide practical advice and relevant stories.

• ⚙️ You have successfully sold a complex multi-product platform and have won competitive rip-and-replace sales motions.

• You have sold to Talent and/or People leaders and are familiar with their pains and priorities

• You're a dashboard-and-forecast manager who doesn't like to get into the deals and daily operations

• You're not keen on learning our substantial product. "That's for SEs" isn't how we approach things here.

Our Philosophy

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

• We have clear expectations about what it means to be a 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 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 Recruiting 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 career journey in some detail to highlight your experience, achievements, and points of learning to understand how you've developed into the leader you are today.

3. Panel Presentation (1 hr) - We'll provide you with pipeline data and seek your perspective on the segment. You'll discuss your approach to hiring, coaching and sales execution.

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

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.