Director of Sales,Union Labor and Trusts Job Chicago area,Illinois USA,Sales

Accountabilities

- Drive new business development:
Manage established prospects through the full sales cycle, from initial engagement and qualification to contract negotiation and closing.
- Generate and convert opportunities:
Leverage marketing campaigns, demand generation initiatives, and strategic outreach to build a robust pipeline and acquire new clients.
- Grow revenue:
Secure new customer agreements and identify opportunities to expand existing relationships in the union, labor, and trust markets.
- Build strategic partnerships:
Collaborate with Customer Success and health plan teams to identify expansion opportunities and increase customer value.
- Strengthen channel relationships:
Engage and educate administrative services-only (ASO) partners, benefits consultants, and other intermediaries to support territory growth and improve sales conversion.
- Develop market presence:
Represent the organization at union events, trustee summits, and industry conferences to increase brand awareness, build relationships, and generate qualified leads.
- Manage territory strategy:
Partner with sales development representatives to develop territory plans, prioritize prospects, and execute a structured business development strategy.
- Build stakeholder trust:
Establish and maintain strong relationships with union trustees, fund administrators, consultants, and other key decision-makers.
- Collaborate cross-functionally:
Share customer and prospect feedback with Marketing, Product, Operations, and other teams to improve sales effectiveness and support commercial growth.
- Execute an effective onboarding plan:
Build internal relationships, master the organization's value proposition, begin engaging prospects, and establish a clear business plan during the first 90 days.
- Use technology strategically:
Apply AI tools and data-driven approaches to improve sales productivity, streamline workflows, and strengthen pipeline management.

Requirements

- Professional experience:
At least 7 years of experience selling innovative healthcare solutions to union, labor, and trust organizations across the United States.
- Proven sales performance: A consistent, quantifiable track record of meeting or exceeding individual sales targets and closing new business within the relevant market.
- Industry expertise:
Strong understanding of union benefit structures, trustee governance processes, and the decision-making dynamics of labor organizations and benefit trusts.
- Relationship management:
Demonstrated ability to establish and maintain trusted relationships with union trustees, fund administrators, benefits consultants, and other senior stakeholders.
- Full-cycle sales capabilities:
Experience managing consultative sales processes from lead generation and qualification through negotiation, contracting, and closing.
- Pipeline and territory management:
Ability to proactively manage opportunities, prioritize prospects, develop territory strategies, and maintain accurate sales forecasts.
- Communication and presentation:
Excellent verbal, written, and presentation skills, with the ability to communicate complex healthcare solutions clearly and persuasively to decision-makers.
- Cross-functional collaboration:

Experience partnering with Marketing, Product, Customer Success, Operations, and other internal teams to maintain sales momentum and deliver business results.
- Industry representation:
Willingness and ability to attend relevant union, labor, trustee, and industry events to develop relationships and generate opportunities.
- Technology and adaptability: A proactive approach to using AI tools and other technologies to improve efficiency, combined with the ability to thrive in a fast-paced, evolving startup environment.
- Mission…

Director of Sales, Union Labor and Trusts