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.

We have 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 are rapidly extending from a best-in-class recruiting product toward a multi-product platform, expanding upmarket, into new industries, and internationally. We have established a remote-first, high-performing sales organization that rewards learning and accountability, uses data to set achievable quotas, and rewards sustained impact with competitive compensation and meaningful upside.

About the Role

TA tools in the Enterprise represent a huge market opportunity ($1B+ TAM), and incumbents are legacy players. We are displacing a collection of tools (ATS, Sourcing & CRM, Scheduling, Analytics, Offers & Approvals) with a consolidated talent suite.

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).

Key Responsibilities

• Own Revenue Outcomes: Drive segment revenue with clear accountability. Partner with senior AEs in a team selling motion to maximize win rates on large opportunities, manage deal risks, and navigate complex competitive replacement deals.
• Build a High-Caliber Team: Scale an adept group of solution-selling experts in lockstep with market demand.
• Establish Excellence: Foster alignment across Product, Marketing, Solutions Engineering, and Professional Services to create a flywheel for future enterprise customer acquisition.

You will report to our Head of AMER Sales and have significant impact in defining our go-to-market strategy and sales methodology.

Qualifications

• Led and scaled a team of SaaS Enterprise Account Executives delivering $5M+/year at a company scaled beyond $100M ARR.
• Helped win $1M+ SaaS deals with publicly traded companies and navigated complex deal structures.
• Proven track record of hiring and onboarding Enterprise AEs who create their own pipeline and close both tactical ($100k) and strategic ($500k+) deals.
• Strong mental model for enterprise sales execution paired with an open mind toward experimentation.
• Proven ability to build trusted customer relationships and facilitate peer-to-peer conversations between senior leaders.
• Deep product and industry curiosity with the ability to connect dots quickly for customers and team members.
• Successfully sold a complex multi-product platform and won competitive rip-and-replace motions.

Bonus

• Experience selling directly to Talent and/or People leaders and familiarity with their priorities and pain points.

You Might Not Be a Fit If

• You prefer high-level dashboard monitoring over getting into deal dynamics and daily operations.
• You are reluctant to dive deep into learning the product details.

Our Philosophy

• We maintain clear expectations for leadership and foster a team-based sales motion.
• We develop deep subject matter expertise to provide a differentiated buyer experience.
• We invest heavily in engineering and product quality to ensure a strong competitive advantage.

Interview Process

1. Intro Call (30 min): Screening with Recruiting to discuss role fit, market context, and Ashby's solution.
2. Experience Deep Dive (1 hr): Walk through career history, achievements, and leadership development with the Head of AMER Sales.
3. Panel Presentation (1 hr): Analyze sample segment data and present your approach to hiring, coaching, and execution.
4. Final Round (2.5 hrs): Four focused conversations with cross-functional leaders.

Benefits & Perks

• Competitive salary, commission, and equity.
• 10-year exercise window for stock options.
• Unlimited PTO (four weeks per year recommended).
• Budget for home office furniture, hardware, and software.
• $100/month education budget (with additional coverage for conferences upon manager approval).