Director of Sales

We're building healthcare tech for a system that desperately needs it.

Each year, millions of Americans deal with confusing changes to their Medicare plans that impact their prescriptions, access to care, and pocketbooks. These aren’t just inconveniences – they are potentially life-altering changes that leave seniors medically and financially vulnerable.

Independent Medicare advisors play a crucial role in guiding seniors through this complexity and helping them find the right coverage for their needs. But their ability to be effective healthcare advocates has long been hamstrung by broken tools and outdated systems.

Spark is fixing that. We’re the fastest-growing Medicare platform in the country, combining AI , an industry-leading CRM , and client services to transform how 10,000+ brokers acquire, enroll, and support clients in their local communities.

Join a talent-dense team from Square, Ramp, Yext, Oscar, and Cedar — backed by Primary Ventures and Viewpoint Ventures — that is serious about building technology to expand access to quality healthcare. We offer remote work, sabbaticals, company retreats, and other generous benefits that earned us recognition as one of Inc. Magazine’s Best Workplaces of 2025

Healthcare is overdue for innovation. Let’s redefine what its future looks like — together.

About the Role

We're looking for a Director of Sales to lead and develop our national sales organization during an exciting stage of growth.

This is a hands-on leadership role for someone who loves building high-performing teams, coaching sellers, and winning alongside them. You'll lead a team of Account Executives while serving as a strategic partner across Revenue Operations, Customer Success, Account Management, and executive leadership to help us scale our go-to-market organization.

We're looking for a leader who enjoys being in customer conversations, helping shape deal strategy, coaching reps in real time, and creating the operational rigor that allows a fast-growing sales organization to thrive.

If you're energized by developing people, navigating complex customer relationships, and building the playbook for the next stage of company growth, we'd love to meet you.

What You'll Do

• Lead, coach, and develop a team of quota-carrying Account Executives, driving both performance and career growth.
• Build a culture of accountability, continuous coaching, and high execution.
• Partner with sellers throughout the sales cycle, providing deal strategy, executive support, and escalation assistance to help close strategic opportunities.
• Create consistency in pipeline management, forecasting, inspection, and overall sales execution.
• Own sales enablement, ensuring the team has the skills, messaging, and tools needed to succeed.
• Partner closely with Revenue Operations to improve processes, reporting, forecasting, and overall operational excellence.
• Collaborate with Marketing to strengthen top-of-funnel performance, improve lead quality and conversion, provide market feedback, and align on campaigns, messaging, and pipeline generation initiatives.
• Work cross-functionally with Account Management, Customer Success, and Onboarding to ensure smooth customer transitions and long-term customer success.
• Participate directly in customer meetings, executive presentations, product demonstrations, and key negotiations when needed.
• Help refine our sales methodology, onboarding, and coaching programs as we continue to scale.
• Bring customer feedback and market insights back to Product, Marketing, and leadership teams to influence company strategy.

What We're Looking For

• Experience leading and developing high-performing B2B sales teams, including direct management of quota-carrying Account Executives.
• Proven ability to coach sellers through complex opportunities and improve team performance through consistent feedback and development.
• Strong sales leadership fundamentals, including forecasting, pipeline management, deal inspection, and operational discipline.
• Executive presence and excellent communication skills with the ability to build credibility quickly with customers and internal stakeholders.
• Comfortable operating in a fast-moving, high-growth environment where priorities evolve and leaders are expected to be hands-on.
• Experience selling relationship-driven solutions into mid-market organizations.
• Ability to adapt communication and leadership style across a wide range of customer personalities and organizational dynamics.
• Willingness to travel as needed to support customers, the sales team, and company initiatives.

What Will Make You Successful

The ideal candidate is a player-coach who loves developing people as much as winning business. You're just as comfortable joining a customer call as you are delivering coaching after it. You know that great sales organizations are built through disciplined execution, strong relationships, and consistent coaching—not heroics.

You bring structure without bureaucracy, urgency without chaos, and a genuine passion for helping both customers and teammates succeed.

Why Join Us

You'll have the opportunity to shape the future of our sales organization at a pivotal stage of company growth. You'll work alongside experienced leaders, influence our go-to-market strategy, and play a meaningful role in building the team, processes, and culture that power our next phase of growth.

Our salary ranges are based on paying competitively for our company’s size and industry, and are one part of the total compensation package that also includes equity, benefits, and other opportunities at Spark. In accordance with New York City, Colorado, California, and other applicable laws, Spark is required to provide a reasonable estimate of the compensation range for this role. Individual pay decisions are ultimately based on a number of factors, including qualifications for the role, experience level, skillset, geography, and balancing internal equity. A reasonable estimate of the current salary range is listed below. We expect most candidates to fall in the middle of the range. We also believe that your personal needs and preferences should be taken into consideration, so we allow some choice between equity and cash.

Base Salary: $150,000 - $200,000 USD

OTE: $275,000 - $325,000 USD