VP, Small Business Sales

About Role:

The VP of Small Business Sales will lead Carrot’s SMB sales organization, owning strategy, execution, and team performance for a high-growth segment of the business. This is an opportunity to shape and scale a sales team within a rapidly growing health technology company with a mission to provide equitable fertility and family-forming care while helping employers manage healthcare costs.

Carrot’s sales team partners with fully insured and self-funded employers to design customized fertility and family-forming benefit programs. In this role, you will lead a team of SMB sales representatives, support strategic deal execution, and partner cross-functionally with Sales, Marketing, Product, Customer Success, and Revenue Operations to strengthen go-to-market strategy, improve sales effectiveness, and inform product and service priorities based on market feedback.

Key Responsibilities

• Develop and execute the SMB sales strategy to meet or exceed quarterly and annual revenue goals.
• Lead, coach, and develop a team of SMB sales representatives, fostering a culture of accountability, strong performance, and continuous improvement.
• Establish clear goals, operating rhythms, and performance expectations aligned to defined KPIs.
• Participate in key customer and prospect conversations, including executive-level discussions with HR, Benefits, Finance, and C-suite stakeholders.
• Accurately forecast revenue performance, pipeline health, and deal progression to the Chief Growth Officer and broader sales leadership team.
• Conduct regular 1:1s, pipeline reviews, deal strategy sessions, and team meetings to support rep development and business outcomes.
• Partner closely with Sales leadership, Revenue Operations, Marketing, and Customer Success to identify obstacles, improve processes, and share strategies and learnings.
• Provide market feedback to internal teams to help shape product priorities, service offerings, messaging, and value propositions.
• Build strong relationships with brokers, consultants, and other external partners that influence employer benefit decisions.

The Team

The VP of Small Business Sales will oversee a team of approximately 8–10 SMB sales representatives. This position reports to the Chief Growth Officer. This role will partner closely with the Chief Growth Officer and other Sales leaders to define performance goals, monitor progress, and develop strategies that support continued growth within the SMB segment.

Minimum Qualifications

• 8–10+ years of sales experience, including meaningful experience in sales leadership.
• Proven experience leading and developing high-performing sales teams.
• Experience selling multi-million-dollar contracts or leading teams responsible for complex revenue targets.
• Demonstrated success building, negotiating, and closing deals across multiple levels of an organization.
• Experience selling into HR, Benefits, People, Finance, and/or Healthcare leadership teams.
• Experience working with health benefits brokers, consultants, or channel partners.
• Comfort engaging with and selling to C-suite and senior executive stakeholders.
• Strong ability to forecast revenue, assess pipeline health, and use data to drive sales execution.
• Proven ability to partner cross-functionally to resolve business obstacles and improve go-to-market effectiveness.

Preferred Qualifications

• Experience selling employer-sponsored healthcare, benefits, fertility, family-forming, or digital health solutions.
• Experience scaling or transforming a sales segment within a high-growth company.
• Familiarity with both fully insured and self-funded employer benefit models.

Compensation:

Carrot offers a holistic Total Rewards package designed to support our employees in all aspects of their life inside and outside of work, including health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and a competitive compensation package. The starting base salary for this position will range from $185,000-$200,000. Actual compensation may vary from posted base salary depending on your confirmed job-related skills and experience.

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