VP, Commercial Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop and implement a long-term account acquisition strategy for the designated region/vertical.

• Generate a sales pipeline through direct outreach, partnerships with brokers/consultants, and identifying market triggers.

• Oversee enterprise sales processes spanning 12 months or more, from initial engagement to contract finalization.

• Facilitate collaboration among 5–10 stakeholders, including C-suite executives, HR, finance, and clinical teams.

• Foster relationships with benefits consultants, brokers, and industry thought leaders.

• Conduct structured discovery sessions to identify employer challenges and translate clinical results into financial return on investment (ROI).

• Craft deal structures that address budgetary and timing challenges.

• Ensure Salesforce CRM is maintained accurately and deliver monthly/quarterly revenue forecasts.

• Produce detailed deal documentation for cross-functional implementation.

• Offer market insights to product, marketing, and leadership teams.

• Collaborate with Operations, Finance, Legal, and Client Services to define implementation requirements, success KPIs, and account strategies.

• Develop business cases for CFOs, CHROs, and benefits teams.

• Guarantee successful client onboarding.

⛳️ Requirements

• A minimum of 5 years of B2B sales experience with a proven record of meeting quotas in complex, long-cycle environments.

• At least 10 years of direct selling experience to HR/benefits decision-makers in enterprise accounts (1,000+ employees preferred).

• Demonstrable success in closing multiple deals with annual contract values exceeding $500K.

• Direct experience in one or more of the following areas: healthcare/benefits sales, insurance/broker channel sales, or HR technology sales.

• Proven proficiency in CRM systems (Salesforce or equivalent) with a strong emphasis on documentation and forecast accuracy.

• Experience managing sales cycles of 12 months or longer, including seasonal buying trends and navigating complex procurement processes.

• Willingness to travel approximately 50% of the time.

• Authorization to work in the United States.

🏝️ Benefits

• Medical / Dental / Vision insurance.

• Flexible Spending Account.

• Health Savings Account with matching contributions.

• Company-paid Short-Term Disability (STD), Long-Term Disability (LTD), Accidental Death and Dismemberment (AD&D), and Life insurance.

• Paid Family Leave.

• 401K plan with matching contributions.

• Paid Time Off.

• Eligibility for variable compensation.

• Entrepreneurial freedom and ownership.

• Opportunity to make a mission-driven impact.

• Strategic influence over product, positioning, and go-to-market strategies.