Labor & Trust Sales Director

We are seeking a Labor & Trust Sales Director to lead growth in the labor and Taft-Hartley fund market. This is a full-cycle sales role responsible for driving new business with trustees, benefits managers, and union leadership—bringing innovative, high-quality mental health solutions to working families nationwide. This person will play a pivotal role in expanding Spring Health’s reach in the labor segment, building strong partnerships that align with the mission and values of organized labor. This is a full time, fully remote position, reporting to our VP Public Sector. Anticipated travel of 30% to headquarters and for prospect meetings.

What you’ll be doing: 

• Manage the entire sales cycle for Labor & Trust opportunities, from pipeline generation through contract close.
• Partner with BDRs, Strategic Alliances, and channel partners to source and close new opportunities, while building your own relationships across unions, Taft-Hartley funds, and consultants that serve this business.
• Lead consultative sales conversations with trustees and benefits managers—uncovering needs, aligning on outcomes, and tailoring Spring Health’s value proposition. 
• Deliver compelling presentations, demos, proposals, and ROI analyses that clearly articulate the benefits for trustees, union members and their families.
• Collaborate with internal teams (CS and Implementation, specifically) to ensure product-market alignment and share insights from the labor segment that inform our go-to-market strategy.
• Build business cases and contracts that support the unique governance, funding, and decision-making processes of labor and trust clients.
• Represent Spring Health at labor conferences, trustee summits, and industry events (travel ~30%).
• Consistently meet and exceed sales targets by focusing on strategic, high-value accounts.

What success looks like in this role:

• Achieving and exceeding sales quota in the Labor & Trust segment.
• Building trusted, long-term relationships with union leadership, trustees, and consultants.
• Elevating Spring Health’s visibility and credibility as a partner to organized labor.

What we expect from you:

• 8+ years of Enterprise sales experience with a strong track record of quota attainment, including at least 5 years selling benefits, healthcare, or SaaS solutions to labor & trust, union, or Taft-Hartley clients
• Deep understanding of union benefit structures, trust governance, and decision-making processes.
• Proven track record of closing 6-figure+ enterprise deals and consistently achieving quota.
• Exceptional relationship-building, communication, and negotiation skills.
• Entrepreneurial mindset—self-starter who thrives in a fast-paced, mission-driven environment.
• Empathy and emotional intelligence; ability to engage with diverse stakeholders across industries and union structures.
• Passion for transforming mental health care for working people and their families.
• Willingness to travel up to 30% for client meetings and events.

The target base salary range for this position is $180,000 - $200,000, and is part of a competitive total rewards package including stock options and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay. 

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals. 
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub,  which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.