Sales Leader, Enterprise

Accountabilities

• Own revenue outcomes for the Enterprise segment, ensuring accountability for performance, growth, and achievement of sales targets.

• Partner with senior Enterprise Account Executives through a collaborative team-selling approach to improve win rates on the organization's largest opportunities.

• Provide hands-on leadership throughout complex enterprise sales cycles, helping teams assess deal risks, navigate competitive replacement opportunities, and close strategic accounts.

• Build, hire, onboard, and scale a high-caliber team of Enterprise Account Executives in line with market demand and business priorities.

• Coach and develop sales professionals to generate their own pipeline and successfully close both tactical deals and larger strategic opportunities.

• Establish and reinforce a strong enterprise sales methodology, encouraging continuous learning, experimentation, and consistent execution.

• Build trusted relationships with customers and facilitate strategic, peer-level conversations between senior business leaders.

• Develop deep expertise in the product portfolio and the broader talent acquisition technology market, enabling the team to deliver informed, differentiated customer engagements.

• Drive alignment across Product, Marketing, Solutions Engineering, and Professional Services to strengthen enterprise acquisition and create a repeatable growth engine.

• Contribute significantly to go-to-market strategy, sales planning, and the continued development of the enterprise sales organization.

• Maintain an active role in deal strategy, pipeline management, and day-to-day sales operations rather than focusing exclusively on reporting and forecasting.

• Report to the Head of AMER Sales and collaborate with senior leadership on segment priorities and long-term growth.

Requirements:

• Demonstrated experience leading and scaling a team of SaaS Enterprise Account Executives in an organization that has grown beyond $100 million in annual recurring revenue.

• Track record of leading an enterprise sales team delivering at least $5 million in annual revenue.

• Experience helping win complex SaaS deals valued at $1 million or more with publicly traded companies.

• Proven ability to recruit, hire, onboard, and develop Enterprise Account Executives who can independently generate pipeline and close deals ranging from approximately $100,000 to $500,000 or more.

• Strong understanding of enterprise sales strategy and execution, including pipeline development, deal qualification, forecasting, negotiation, and competitive positioning.

• Experience successfully selling complex, multi-product SaaS platforms and winning competitive replacement or rip-and-replace sales opportunities.

• Ability to lead strategically while remaining directly involved in important deals and the daily operations of the sales team.

• Strong customer relationship skills, with the confidence to facilitate senior-level conversations and build long-term strategic partnerships.

• Ability to develop deep product and industry expertise and translate complex capabilities into practical customer value.

• Collaborative leadership style, with experience working across Product, Marketing, Solutions Engineering, and Professional Services.

• Strong sense of ownership, sound judgment, and principled decision-making, combined with clear and thoughtful communication.

• Growth mindset and willingness to learn, experiment, and adapt sales approaches as the product portfolio and market evolve.

• Nice to have: Experience selling to Talent Acquisition and/or People leaders, with an understanding of their priorities, challenges, and purchasing needs.

• Location: Candidates must be based in Canada and comfortable working remotely.

Benefits:

• Competitive compensation package of CA$352,000–CA$418,500, with a 50/50 base salary and commission split.

• Equity opportunities.

• Unlimited paid time off, with four weeks recommended annually.

• 10-year exercise window for stock options.

• Generous budget for equipment, software, and office furniture.

• Monthly education budget of $100, with additional learning expenses such as conferences potentially covered with manager approval.

• Fully remote working arrangement.

• Opportunity to lead a high-impact enterprise sales segment and help shape the growth of a multi-product SaaS platform.

• Professional development opportunities, with an emphasis on coaching, career progression, and continuous learning.