VP, Strategic Account Sales

The Role: 

The Vice President, Strategic Account Sales is a senior sales leadership role responsible for leading and scaling Carrot’s Strategic and National Account Executive team while driving revenue growth with some of the most complex and influential employers in the market. This role sits at the intersection of revenue strategy, team leadership, and executive partnership—selling customized fertility and family-forming benefit solutions to both fully insured and self-funded employers.

As a key member of the Sales leadership team, this leader will directly manage a team of 6–10 Strategic and National Account Executives, partner closely with the Chief Growth Officer, and play an active role in shaping Carrot’s go-to-market strategy. The VP will personally engage in high-impact deals, selling to C-suite and senior HR, Benefits, and People leaders, while also collaborating cross-functionally to inform product roadmap priorities and sharpen Carrot’s value proposition in the market.

Key Responsibilities:

Revenue Strategy & Execution

• Develop and execute a revenue strategy aligned to defined KPIs to meet and exceed quarterly and annual sales targets.
• Accurately forecast revenue performance, pipeline health, and deal risk to Sales leadership.
• Actively participate in complex, high-value strategic and national account deals, engaging executive-level stakeholders through close.

Team Leadership & Performance

• Lead, coach, and develop a team of 6+ National and Strategic Account Executives, fostering a culture of accountability, high performance, and continuous improvement.
• Conduct regular 1:1s, deal reviews, pipeline inspections, and performance coaching to drive consistent execution.
• Champion disciplined Salesforce hygiene to ensure data integrity, forecast accuracy, and visibility into pipeline health, deal risk, and revenue trends.
• Lead team meetings focused on strategy, skill development, and knowledge sharing across the broader Sales organization.

Cross-Functional Partnership

• Partner closely with Sales leadership to identify and remove obstacles, share best practices, and continuously improve sales effectiveness.
• Collaborate with Product, Marketing, Client Success, and Partnerships teams to provide market feedback, influence product and service innovation, and strengthen key value propositions.
• Serve as a senior voice of the customer, translating employer and consultant insights into actionable business inputs.

Leadership Capabilities

• Strategic & Commercial Acumen: Ability to think holistically about market dynamics, enterprise buying behaviors, and long-term revenue growth while driving near-term execution.
• Executive Presence: Credibility and confidence engaging with C-suite leaders, brokers, and consultants in complex, high-stakes sales cycles.
• People Leadership: Proven ability to attract, develop, and retain top sales talent; sets clear expectations and coaches to high performance.
• Data-Driven Decision Making: Uses metrics, forecasts, and pipeline insights to inform strategy, prioritize resources, and manage risk.
• Cross-Functional Influence: Builds trust and alignment across teams, balancing revenue goals with product, client, and operational considerations.
• Change Leadership: Comfortable leading through growth, ambiguity, and evolving sales motions in a fast-scaling health technology environment.

Minimum Qualifications:

• 8+ years of experience in sales leadership roles, with direct responsibility for managing enterprise or strategic Account Executives
• Demonstrated success leading sales teams responsible for multi-million-dollar contract values and long, complex sales cycles
• Proven track record of building, negotiating, and closing enterprise-level deals across multiple stakeholder levels
• Experience selling into HR, Benefits, People, and/or Healthcare organizations
• Strong experience working with health brokers and consultants
• High comfort level selling to and influencing C-suite and senior executive stakeholders

Preferred Qualifications:

• Experience in health technology, benefits, or healthcare services environments
• Track record of significantly increasing team revenue year over year
• Established relationships with senior HR, Benefits, and broker/consultant networks
• Experience scaling and maturing sales teams in high-growth organizations

 

Compensation: 

Carrot offers a holistic Total Rewards package designed to support our employees in all aspects of their lives 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 $190,000-$200,000. Actual compensation may vary from the posted base salary depending on your confirmed job-related skills and experience.

 

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