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.