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 prospects
Manage risks in complex competitive replacement deals
Build a high-caliber Enterprise AE team
Align Product, Marketing, Solutions Engineering, and Skilled 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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📌 Enterprise Sales Leader North America Toronto
🏢 Ashby
📍 Toronto