Director B2B Sales - Blair Health (US/ Canada - Remote)

Director of B2B Sales (US & Canada)Location: Remote (US or Canada)Reports to: CEO & Co-FounderCompensation: Competitive base + meaningful equityBlair 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.ApplyShare your resume with us at careers@blairhealth.ca — we’d love to meet you.