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Enterprise Sales Leader North America

Job in Calgary, Alberta, T1W 0K6, Canada
Listing for: Ashby
Full Time position
Listed on 2026-11-02
Job specializations:
  • Sales
    VP of Sales
  • Management
Salary/Wage Range or Industry Benchmark: 447000 CAD Yearly CAD 447000.00 YEAR
Job Description & How to Apply Below

Lead Enterprise sales at Ashby across North America, combining team leadership with complex SaaS deal execution in a remote-first organization.

As Enterprise Sales Leader, you will lead the West segment across Mountain, Pacific, and Central regions. You will scale an Enterprise Account Executive team while shaping go-to-market strategy and sales methodology. The role focuses on talent software consolidation, competitive replacement, and large enterprise opportunities.

Key Responsibilities:
  • Own revenue outcomes and accountability for the Enterprise segment
  • Partner with senior AEs on largest opportunities
  • Manage risks in complex competitive replacement deals
  • Build a high-caliber Enterprise AE team
  • Align Product, Marketing, Solutions Engineering, and Professional Services
Requirements:
  • Led SaaS Enterprise AE teams delivering $5M annually
  • Experience at companies exceeding $100M ARR
  • Helped win $1M-plus SaaS deals with public companies
  • Hired and onboarded Enterprise Account Executives
  • Sold complex multi-product platforms competitively

Bring enterprise sales leadership, coaching, and complex deal expertise to Ashby's expanding talent platform across North America.

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