VP of Sales

You'll set the strategy, coach future leaders, and personally influence high-value deals—all while partnering cross-functionally to deliver exceptional results.

ThrivePass is a rapidly growing tech company dedicated to innovating the world of employee benefits. Leveraging SaaS technology with traditional & progressive benefits - wellbeing initiatives, pre-tax, benefit enrollment and learning & development - ThrivePass is focused on revolutionizing the employee experience. To that end, we use technology to foster employee wellbeing from on-boarding to off-boarding.

Who We Are

At ThrivePass, we're on a mission to help employees and businesses Thrive—because benefits should be more than just checkboxes. Through personalized benefits technology, data-driven insights, and meaningful experiences, we empower companies to support their teams in ways that truly matter.

We don't just talk about culture—we build it. Everything we do is rooted in our CARE values:

• Courageous – We embrace new challenges and fresh ideas.
• Authentic – We show up as our true selves and value transparency.
• Resourceful – We find creative solutions and make things happen.
• Excellent – We hold ourselves accountable and take pride in our work.

At ThrivePass, performance isn't just about hitting goals—it's about how you show up. We invest in our employees' growth and encourage bold thinking, collaboration, and continuous learning. Join us in shaping the future of employee benefits

What You'll Do

As VP of Sales, you will lead ThrivePass' revenue engine by driving strategic growth, building a high-performing team, and ensuring flawless execution of our sales model. Your mission is to combine visionary leadership with hands-on selling, fostering a culture of accountability, collaboration, and innovation. You'll set the strategy, coach future leaders, and personally influence high-value deals—all while partnering cross-functionally to deliver exceptional results.

You will:

• Bring fresh ideas to the table—we're all about innovation and continuous improvement.
• Ensure successful execution of the sales model to meet or exceed bookings and revenue goals.
• Develop and implement strategic plans, setting leading indicators, KPIs, and team goals.
• Accurately forecast bookings and participate in forecast calls, pressure-testing assumptions.
• Lead and coach the sales team through regular 1:1s, providing executive-level guidance and grooming future leaders.
• Step in on high-value deals as needed, acting as a trusted advisor and closer.
• Build strong cross-functional partnerships with Marketing, Product, Customer Success, and Finance.
• Maintain a player-coach mentality—roll up your sleeves to sell ThrivePass's product suite while building a world-class team.
• Drive adoption of sales methodologies and processes to improve conversion rates and scalability.

What You Bring

We're looking for someone who's not just checking boxes but truly excited to make an impact. Here's what helps you shine in this role:

• A drive to innovate in employee benefits and make complex processes feel effortless.
• Strategic leadership combined with hands-on execution.
• Ability to inspire, coach, and develop high-performing teams.
• Deep understanding of enterprise sales cycles and benefit solutions.
• Strong analytical and forecasting skills.
• Collaborative mindset with proven success in cross-functional initiatives.

Must Haves

• 10+ years of experience in GTM benefit and software sales.
• 3+ years in a senior sales leadership role.
• Experience in Enterprise Software, B2B Sales, and SaaS.
• Proven ability to operate a 90-day+ sales cycle at scale.
• Track record of implementing sales methodologies and processes.
• Strong sales funnel management experience.

Nice to Have

• Experience with benefit brokers (strongly preferred).
• Background in creating unique sales motions and improving conversion rates.
• Familiarity with complex pricing strategies and contract negotiations.
• Exposure to high-growth environments and scaling teams.

Why You'll Love Working Here

• On target annual earnings: $350,000 - $450,000
• A culture that values courageousness, authenticity, resourcefulness, and excellence (we don't just say it—we live it).
• Opportunities to grow, learn, and level up your skills.
• A team that genuinely enjoys working together and celebrating wins.
• Competitive benefits package because we believe in walking the talk when it comes to employee well-being.
• An inclusive and welcoming environment for all. ThrivePass is committed to fostering a workplace where everyone feels valued and respected. We do not and shall not discriminate based on race, color, religion (creed), gender, gender expression, age, national origin (ancestry), disability, marital status, sexual orientation, or military status in any of our activities or operations.

Join Us

If this role sounds like your next great adventure, we'd love to hear from you. Apply today and let's build something amazing together

$350,000 - $450,000 per year