Director of Business Development - Jobs in Toronto, Ontario, Canada, M4C

Job Description

StaffScheduleCare (SSC) is the leading provider of workforce management (WFM) software in the Canadian senior care industry. Their software simplifies scheduling, timekeeping, and compliance for long-term care (LTC) and hospital staff – improving workflows so caregivers can focus on what matters most: residents.With hundreds of facilities relying on them, high retention rates, and strong momentum, they are now expanding into the U.S. and investing in scaling our team and processes. Backed by growth capital and led by seasoned SaaS operators, SSC is a mission-driven, people-first company on a high-growth journey!About the RoleStaffScheduleCare is looking for a scrappy, full-cycle salesperson who is passionate about LTC and energized by fieldwork, relationships, and results. As the Director of Business Development, you’ll take ownership of new business generation, run the full sales cycle, and help grow the footprint across Canada (and early-stage U.S. markets). You’ll report directly to the Co-CEO and collaborate closely with and mentor Customer Success Managers.This is an individual contributor role with the potential to evolve into a player-coach leadership position as we grow the sales function.New Business Development (40%)

• Represent SSC at tradeshows and industry events (~1/month travel)
• Generate and qualify outbound leads through networking and targeted outreach
• Build and nurture relationships with decision-makers in senior care

Pipelineamp; Sales Process Management (30%)

• Manage discovery, qualification, and proposals
• Leverage HubSpot CRM to maintain momentum through the mid-funnel stages
• Partner with CSMs on technical demos and solution validation

Closingamp; Revenue Generation (30%)

• Lead negotiations and close deals ranging from $15K–$50K+
• Collaborate cross-functionally to ensure a seamless hand off post-sale
• Influence pricing and go-to-market strategies with leadership

RequirementsAbout You

• We’re looking for someone who thrives in fast-moving, high-responsibility roles and deeply understands the culture and nuance of long-term care.
• 3–7 years in B2B software or healthcare sales (SaaS or LTC experience preferred)
• Proven ability to generate leads, manage full sales cycles, and close deals
• Deep familiarity with selling into regulated, unionized, or healthcare environments
• Strong trade show and networking background; you enjoy working in the field
• Excellent communicator with a track record of building trust with diverse stakeholders
• Comfortable in a builder environment with minimal hand-holding
• Hunger to win and comfort with outbound, high-effort sales
• High EQ, grit, and humility – you know how to win business and build trust
• Discipline and structure – you value process, documentation, and follow-up
• A team mindset – ready to contribute to the growth story and mentor others along the way
• Must be located in the Greater Toronto Area
• Must be comfortable with travel to tradeshows and field work
• Bonus Experience
  • Background in nursing or direct LTC operations
  • Familiarity with workforce management software or platforms like PCC
  • Prior experience mentoring junior team members or supporting a growing sales org
  • Exposure to U.S. healthcare markets

BenefitsThe Extras that Matter:

• Join a Market Leader – Serving 450+ senior care homes with industry-leading retention
• Growth Opportunity – Help shape our U.S. go-to-market and future sales team
• People-First Culture – Collaborative, low-ego, mission-aligned environment
• Executive Access – Report directly to the Co-CEO and shape the sales playbook
• Strong Compensation Package
• Hybrid Flexibility – Work in-office, remote, and travel-based as needed
• Professional Development – Budget for education, conferences, and mentorship