Sales Leader

Location: Toronto, ON (Hybrid), travel required. Language: Strong written and verbal communication skills in English required. Duration: Permanent.

Background Check Requirement: Criminal Record Check required. About the Opportunity This is a unique opportunity to step into a senior commercial leadership role within a fast‑growing, digital‑first organization focused on transforming workforce transitions. You will play a pivotal role in redefining how employers support employees through change, offering modern, tech‑enabled outplacement solutions that deliver meaningful outcomes.

In this role, you will work closely with executive leadership, including the CEO, as well as cross‑functional teams across sales, marketing, product, and customer success. Your ability to build trusted relationships with senior HR leaders will directly impact how organizations navigate restructuring and career transitions, making a tangible difference for both businesses and individuals. What’s in it for You Join a forward‑thinking organization that values innovation, impact, and fresh perspectives.

You will have the opportunity to shape commercial strategy, influence product direction, and bring a differentiated solution to market. This is a workplace that empowers leaders to build, not maintain, offering high visibility, meaningful ownership, and the chance to work alongside a collaborative and driven leadership team. You will be part of a culture that values accountability, growth, and modern approaches to solving real workforce challenges.

Your Responsibilities You’ll own and drive revenue growth for the outplacement business, including pipeline development and achieving commercial targets. You’ll lead enterprise sales cycles end‑to‑end, from initial engagement through to negotiation and close. You’ll build and nurture relationships with senior HR leaders, positioning yourself as a trusted advisor.

You’ll shape market positioning by collaborating with sales and marketing to refine messaging and differentiate offerings. You’ll represent the organization at industry events and in key client conversations, strengthening brand presence. You’ll provide strategic oversight on program delivery, ensuring quality, scalability, and alignment with client needs.

Skills and Qualifications 8-10 years minimum of sales enterprise experience. Proven ability to build and manage executive‑level relationships and influence senior stakeholders. Strong track record of leading enterprise sales and achieving revenue targets.

Experience working with or implementing digital tools and platforms in HR or outplacement. Experience leading teams with a focus on performance, growth, and accountability. A consultative, solutions‑focused mindset with a proactive and results‑driven approach.

Note from the Hiring Manager “We’re looking for someone who truly understands this space and is ready to challenge how it’s always been done. If you’ve built strong relationships in the market and want to represent a solution you genuinely believe in, this is your opportunity to make a real impact.” Equal Employment Opportunity All qualified applicants will receive fair consideration for employment. We welcome individuals of all backgrounds, experiences, and identities including those who identify as women, members of racialized groups, Indigenous Peoples, persons with disabilities, and 2SLGBTQIA+ communities.

If you require an accommodation, please review our accessibility policy and reach out to our accessibility officer with any questions. #J-18808-Ljbffr