Director B2B Sales

2 weeks ago

Toronto Montreal Calgary Vancouver Edmonton Old Toronto Ottawa Mississauga Quebec Winnipeg Halifax Saskatoon Burnaby Hamilton Surrey Victoria London Halton Hills Regina Markham Brampton Vaughan Kelowna Laval Southwestern Ontario R, Canada Blair Health Full time

Compensation: Competitive base + meaningful equity Blair Health is one of North America’s fastest-growing women’s health platforms, already trusted by leading employers. We’re redefining how women access midlife healthcare by closing specialist gaps through a clinically validated, AI-enabled model, and we’re scaling fast. We’re looking for a Director of B2B Sales to be our first on-the-ground sales hire—someone who can take our early momentum and 5x it. This is a true hunter role: you thrive on opening doors, building relationships quickly, and closing enterprise deals. You bring discipline, drive, and the ability to operate in a high-velocity startup environment. What You’ll Do Own and run the full B2B sales cycle across enterprise employers, brokers, and consultants in the US and Canada. Take Blair’s early sales playbook and supercharge it—iterating, scaling, and building repeatable motions. Generate and qualify pipeline, build relationships quickly, and close high-value contracts with HR and Benefits leaders. Build and maintain a strong network with brokers, consultants, and employer groups; act as a super-connector for Blair Health. Execute outbound campaigns and events to drive awareness and accelerate penetration into target segments. Partner closely with the CEO for major accounts, enterprise negotiations, and strategic opportunities. Provide tight product feedback to product and clinical teams to improve positioning and feature prioritization. Track metrics rigorously, including forecasting, CRM hygiene, weekly reporting, and sales performance dashboards. Help shape the long-term commercial strategy as we expand across North America. You Are A hunter at heart—competitive, persistent, resourceful, and energized by closing deals. A natural relationship builder who can connect with HR, Benefits teams, brokers, and executive leaders with ease. A strong communicator—clear, confident, and comfortable presenting Blair’s mission and value proposition. Outgoing and highly social, with an ability to build credibility quickly. Fast-paced, with a bias to action and comfort working in ambiguity. Product-savvy, capable of translating customer needs into actionable product feedback. Someone who wants to join an early-stage rocket ship and materially shape its future. What You Bring 4–6+ years of enterprise B2B sales experience (HR tech, benefits, digital health, healthcare, or SaaS preferred). Proven track record of closing mid-market and enterprise deals. Experience selling to benefits leaders, people teams, or brokers. Strong outbound capability and comfort driving pipeline from scratch. Experience in a startup or high-growth environment is a strong plus. Deep interest in women’s health, healthcare innovation, or mission-driven companies. Why Blair Health Be part of a category-defining women’s health platform solving one of the biggest unmet needs in healthcare. Work directly with the CEO and clinical founders; your work directly impacts revenue, scale, and strategy. Competitive equity and compensation. Join a team that moves fast, builds boldly, and cares deeply about improving care for millions of women. Help shape the commercial foundation of a company already working with leading employers across North America. Apply Share your resume with us at careers@blairhealth.ca — we’d love to meet you. Seniority level: Mid-Senior level Employment type: Full-time Job function: Sales and Business Development Industries: Technology, Information and Internet #J-18808-Ljbffr

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