Vice President of Sales, Labor & Trust

Reporting to the Head of Sales, the Vice President of Sales, Labor & Trust will be joining our growing sales team, supporting our expansion efforts. A Taft-Hartley Sales Representative in digital healthcare is a specialized sales role responsible for driving new bookings and revenue growth by selling Carrum Health services to labor unions, multiemployer health funds, and Taft-Hartley trusts. This position requires a deep understanding of the unique governance, funding, and decision-making processes of these organizations, along with strong consultative selling skills. Your proven track record of  growing revenue-generating opportunities and client expansion in the labor & trust market will be invaluable to our key growth goals. As a pivotal member of the team, you’ll collaborate internally, as well as engage strategically, with external stakeholders to acquire new clients.

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

You’re excited about this opportunity because you will...

• 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

Key Responsibilities

• Sales Cycle Management: Own and manage the entire sales cycle within the labor and trust segment, from prospecting and pipeline generation to contract negotiation and closing deals.
• Relationship Building: Establish and maintain trusted relationships with key stakeholders, including union trustees, fund administrators, and benefits consultants.
• Strategic Planning: Develop and execute targeted go-to-market and client retention strategies tailored to the specific needs of the labor market.
• Consultative Selling: Lead consultative sales conversations to uncover needs, align on outcomes, and clearly articulate the value proposition and ROI of digital health solutions to trustees, union members, and their families.
• Product Expertise: Maintain in-depth knowledge of the company's digital health product portfolio, industry trends, healthcare economics, and cost containment strategies.
• Collaboration: Partner effectively with internal teams (general managers/ clinical,  marketing, legal, customer success) to ensure tailored proposals that meet compliance and member needs.
• Industry Representation: Represent the company at labor conferences, trustee summits, and industry forums to build brand awareness and generate pipeline opportunities.
• Documentation and Reporting: Utilize CRM software (Salesforce) to document sales activities, manage pipelines, and report on progress. 

We’re excited about you because...

• 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%).
• Bonus: 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.