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Director of Sales & Partnerships

Director of Sales & Partnerships

The Glide GroupChicago, IL, US
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Base pay range

$150,000.00 / yr - $175,000.00 / yr

About Our Client

Our client is a venture-backed technology company transforming the way organizations support employees during critical career transitions. Their innovative platform leverages AI to deliver meaningful cost savings for employers while providing individuals with access to essential benefits and resources. With strong early traction and a rapidly expanding market opportunity, they are building a category-defining solution at the intersection of HR, benefits, and technology.

The Opportunity

Our client is seeking a highly experienced Director of Sales & Partnerships to lead revenue growth and strategic relationships in the HR and benefits space. This is a foundational leadership role reporting directly to the CEO. You’ll play a key part in shaping go-to-market strategy, building partnerships with brokers and enterprise HR leaders, and driving adoption in an emerging market with very little competition.

This position is ideal for a self-starter with deep industry relationships who thrives in dynamic, high-growth environments and wants the opportunity to influence strategy at the executive level.

What You’ll Do

  • Own the full sales cycle from prospecting to close, with a focus on enterprise clients and benefit broker partnerships.
  • Build, strengthen, and expand relationships with benefit brokers, channel partners, and enterprise decision-makers.
  • Build and refine sales processes, playbooks, and performance metrics to establish a scalable, high-performing sales function.
  • Develop and execute partnership strategies to open new channels and accelerate growth.
  • Collaborate with leadership, marketing, and product to refine sales messaging, create targeted campaigns, and influence roadmap priorities.
  • Represent the company at industry events, conferences, and client meetings as a key ambassador of the brand.
  • Provide strategic insights on market trends, client feedback, and partnership opportunities to guide executive decision-making.
  • Maintain a disciplined approach to pipeline management, forecasting, and CRM hygiene.
  • Contribute to the scaling of a high-performing sales organization, helping define best practices and processes as the team grows.

Who You Are

  • 8+ years of B2B sales or partnerships experience in HR tech, employee benefits, healthcare, insurance, payroll, or related sectors.
  • Established network of benefit brokers, consultants, or enterprise HR / Finance decision-makers.
  • Demonstrated success closing complex enterprise deals and managing long sales cycles.
  • Proven ability to build and manage strategic partnerships that drive revenue growth.
  • Strong executive presence and comfort presenting to C-level audiences.
  • Skilled in virtual selling, solution-based consultative sales, and navigating multiple stakeholders.
  • Entrepreneurial mindset with the ability to thrive in a fast-paced, early-stage environment with minimal structure.
  • Highly organized, proactive, and motivated to deliver results while helping build something new.
  • Competitive base salary with uncapped commission
  • Remote flexibility
  • High visibility role reporting directly to the CEO
  • Opportunity to make an outsized impact in an emerging market with strong ROI and minimal competition

    • Travel Requirement : ~25–30% for customer meetings, conferences, and events.

    Employment details

  • Seniority level : Not Applicable
  • Employment type : Full-time
  • Job function : Business Development, Sales, and Human Resources
  • Industries : Technology, Information and Media, Health and Human Services, and Insurance and Employee Benefit Funds

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    Director Of Sales • Chicago, IL, US