Sales at Ashby is a unique opportunity to sell a product customers genuinely love during an AI-fueled market expansion. 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. And the market opportunity is growing. 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. 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. 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. 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:



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. Build a high caliber team in lock step with market demand. Establish a reputation for excellence by fostering alignment across Product, Marketing, Solutions Engineering & Skilled 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. 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. You build trusted relationships with customers and confidently facilitate peer-to-peer conversations between senior leaders to deepen partnerships and elevate strategic engagements. 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. Bonus ~ We're highly collaborative and we believe in a team-based sales motion to maximize our win rates on high impact deals 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. 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. Intro Call (30 min)
- You'll meet with Recruiting to discuss your fit for the role and address questions about our market and solution. 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. A product that our prospects & customers are truly excited about ~ Competitive salary, commission and equity. ~Generous equipment, software, and office furniture budget. 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. 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.

📌 Sales Lead (Winnipeg)
🏢 Ashby
📍 Winnipeg