Director of Sales

Director of Sales

Be the visionary who drives CareGuide's next wave of growth. At CareGuide, we help millions save billions on healthcare. The Director of Sales is a key growth driver, and we are looking for a trailblazer : visionary, competitive, goal oriented, and unafraid of challenge. If you thrive on building, pivoting, and scaling bold ideas into measurable impact, this is your next big stage. Reporting directly to the Chief Executive Officer (CEO), you will be at the forefront of CareGuide's expansion. You will drive new opportunities, forge bold partnerships, and shape go-to-market strategies in priority verticals. This role blends hands-on execution with strategic vision, delivering short-term wins while laying the foundation for long-term growth. By inspiring clients and industry leaders, you will position CareGuide as the trusted partner in our mission to help millions save billions on healthcare costs. You will design the engine, lead the charge, and motivate those around you while keeping your eyes fixed on outcomes. This is about starting something big, proving it works, and empowering your team to scale it while you move on to the next frontier.

All applicants must complete this screening to be considered :

Who you are :

• A visionary competitor. You are driven, persuasive, motivating, and relentless in pursuit of goals.
• A builder at heart. You enjoy designing systems, starting the process, and then empowering others to sustain and scale.
• Comfortable with variety and change. You pivot fast, thrive in ambiguity, and keep the mission in focus.
• 7 to 10+ years of progressive B2B sales experience, including leadership roles, with a proven track record of sourcing, negotiating, and closing complex, high-value deals in healthcare technology, HR / benefits technology (InsurTech or BenefitsTech), or related SaaS solutions.
• Strong executive presence. You know how to engage C-level leaders and win trust.
• Data-savvy and CRM-fluent (Zoho, HubSpot, etc.), able to combine analytics with gut instincts.
• Entrepreneurial, adaptable, and aligned with CareGuide's mission to revolutionize healthcare savings.

About us join a team that's making a real impact in healthcare :

At CareGuide, we are more than just a companywe are a team of problem-solvers and relationship-builders on a mission to make healthcare more affordable and accessible for millions. We take pride in fostering a supportive, collaborative environment where every team member is valued and has the opportunity to thrive both professionally and personally. We don't just talk about our values, we live them. Our culture is rooted in transparency, teamwork, and a commitment to excellence. Whether it's helping clients navigate complex healthcare costs or supporting each other in daily tasks, we believe strong relationships and well-structured processes lead to success. At CareGuide, we're not just changing healthcare costswe're changing lives.

What you will do :

Why CareGuide?

CareGuide is proud to be an equal opportunity employer. We do not discriminate based on race, color, national origin, gender identity or expression, sexual-orientation, religion, age, disability, veteran status, marital or family status, or any other legally protected status. All employment decisions are made with integrity, fairness, and respect.