Vice President of Sales, Labor & Trust

About the role

The Vice President of Sales, Labor & Trust will join Carrum's growing sales team, supporting the company's expansion efforts. This role focuses on driving new bookings and revenue growth by selling Carrum Health services to labor unions, multiemployer health funds, and Taft-Hartley trusts.

Responsibilities

• Execute Carrum’s market strategy to drive revenue opportunities with labor unions, multi-employer health funds, and Taft-Hartley trusts.
• Lead the sales process by identifying, engaging, scoping and executing sales opportunities with sophisticated buyers.
• Build and develop relationships with targeted brokers and consultants to build pipeline.
• Establish communication strategies for sharing market feedback with the company.
• Establish mechanisms to effectively manage and report on the sales pipeline.
• Collaborate with the Chief Commercial Officer to reflect the company’s vision for growth and expansion into an effective business plan.
• Manage effective communication of the Carrum value proposition, product features and partnership expectations with both prospects and clients.
• Strong execution of phone/web/in-person meetings, follow-through, contracting and transition to the requisite implementation teams.

Requirements

• Experience: Proven success with 10+ years of B2B healthcare or benefits sales experience, ideally with a focus on the labor, union, or public-sector markets.
• Domain Expertise: Deep familiarity with union benefit structures, including health and welfare funds and their specific governance and procurement processes.
• Communication: Exceptional verbal and written communication, presentation, and negotiation skills, with the ability to influence C-level and trustee stakeholders.
• Analytical Abilities: Strong business acumen and data analytics skills to build business cases, analyze performance, and articulate value-added solutions.
• Self-Motivation: A proactive, self-directed, and results-oriented mindset with the ability to work independently and manage a large territory.
• Travel: Ability to travel nationally as required to meet clients and attend industry events (approx. 50%).
• Licensing: Must possess or be eligible to obtain necessary general health insurance licenses within a specified timeframe (e.g., 90 days of hire).
• Experience selling health technologies, medical insurance, employee benefits, SaaS or consulting solutions in the employer market, targeting all levels of organizations with a focus on CFO, HR or benefits professionals.
• Demonstrated ability in developing and successfully carrying out sales and marketing strategy (e.g., customer segmentation, sales process and organization design, and performance management).
• Proficiency in all aspects of the sales process including: performing initial outreach, developing relationships, negotiating and closing contracts and managing ongoing relationships.
• Outstanding customer focus and professionalism to clarify and validate client needs on an ongoing basis.
• Entrepreneurial and resourceful — As an early member of a startup, we need people who can find creative ways to make a big impact quickly and without much direction.
• Experience handling deadlines, keeping many balls in the air, and prioritizing work in a fast-paced, dynamic environment.
• Passion for collaborating cross-functionally with sales, operations, client success, data, and product teams to ideate, complete projects, and drive impactful results.

Qualifications

• Experience: Proven success with 10+ years of B2B healthcare or benefits sales experience, ideally with a focus on the labor, union, or public-sector markets.
• Domain Expertise: Deep familiarity with union benefit structures, including health and welfare funds and their specific governance and procurement processes.
• Communication: Exceptional verbal and written communication, presentation, and negotiation skills, with the ability to influence C-level and trustee stakeholders.
• Analytical Abilities: Strong business acumen and data analytics skills to build business cases, analyze performance, and articulate value-added solutions.
• Self-Motivation: A proactive, self-directed, and results-oriented mindset with the ability to work independently and manage a large territory.
• Travel: Ability to travel nationally as required to meet clients and attend industry events (approx. 50%).
• Licensing: Must possess or be eligible to obtain necessary general health insurance licenses within a specified timeframe (e.g., 90 days of hire).
• Experience selling health technologies, medical insurance, employee benefits, SaaS or consulting solutions in the employer market, targeting all levels of organizations with a focus on CFO, HR or benefits professionals.
• Demonstrated ability in developing and successfully carrying out sales and marketing strategy (e.g., customer segmentation, sales process and organization design, and performance management).
• Proficiency in all aspects of the sales process including: performing initial outreach, developing relationships, negotiating and closing contracts and managing ongoing relationships.
• Outstanding customer focus and professionalism to clarify and validate client needs on an ongoing basis.
• Entrepreneurial and resourceful — As an early member of a startup, we need people who can find creative ways to make a big impact quickly and without much direction.
• Experience handling deadlines, keeping many balls in the air, and prioritizing work in a fast-paced, dynamic environment.
• Passion for collaborating cross-functionally with sales, operations, client success, data, and product teams to ideate, complete projects, and drive impactful results.

Skills

• Proven success with 10+ years of B2B healthcare or benefits sales experience, ideally with a focus on the labor, union, or public-sector markets.
• Deep familiarity with union benefit structures, including health and welfare funds and their specific governance and procurement processes.
• Exceptional verbal and written communication, presentation, and negotiation skills, with the ability to influence C-level and trustee stakeholders.
• Strong business acumen and data analytics skills to build business cases, analyze performance, and articulate value-added solutions.
• A proactive, self-directed, and results-oriented mindset with the ability to work independently and manage a large territory.
• Ability to travel nationally as required to meet clients and attend industry events (approx. 50%).
• Licensing: Must possess or be eligible to obtain necessary general health insurance licenses within a specified timeframe (e.g., 90 days of hire).
• Experience selling health technologies, medical insurance, employee benefits, SaaS or consulting solutions in the employer market, targeting all levels of organizations with a focus on CFO, HR or benefits professionals.
• Demonstrated ability in developing and successfully carrying out sales and marketing strategy (e.g., customer segmentation, sales process and organization design, and performance management).
• Proficiency in all aspects of the sales process including: performing initial outreach, developing relationships, negotiating and closing contracts and managing ongoing relationships.
• Outstanding customer focus and professionalism to clarify and validate client needs on an ongoing basis.
• Ability to find creative ways to make a big impact quickly and without much direction.
• Experience handling deadlines, keeping many balls in the air, and prioritizing work in a fast-paced, dynamic environment.
• Passion for collaborating cross-functionally with sales, operations, client success, data, and product teams to ideate, complete projects, and drive impactful results.

Benefits

• Stock option plan
• Flexible schedules and remote work
• Chicago and San Francisco offices available
• Self-managed vacation days, within reason
• Paid parental leave
• Health, vision, and dental insurance
• 401K retirement plan

Pay

The salary range for this role is $180,000- $200,000, depending on geography and level of experience, plus equity and variable compensation.

Schedule

National travel as required.