Director of League Sales (Midwest)
Overtime
Sales & Business Development
Chicago, IL, USA
USD 150k-150k / year + Equity
Posted on Oct 9, 2025
Director of League Sales (Midwest)
This role is built for a proven revenue leader with a history of securing multi-year, multi-million dollar partnerships with major brands, often including category exclusivities. As Director of League Sales, you will drive the commercial growth of Overtime’s flagship league properties (OTE, OT Select, OT7, OTX, OT Nationals) while playing a key role in achieving the broader League Sales team’s annual revenue objectives.
We are looking for an individual who can evangelize the Overtime narrative with key decision makers across both the brand and agency landscape. You will lead negotiations, navigate complex deal structures, and deliver fully integrated partnerships that live across the Overtime universe (content, events, athletes, and social). Your focus will be on developing long-term, high-value relationships that embed partners into Overtime’s culture and IP, creating category-defining activations that drive measurable business impact for brands.
Key Responsibilities:
- Own aggressive annual revenue targets for assigned league property(ies) while driving impact toward the overall League Sales goal
- Lead complex, multi-year deal negotiations with major brands, delivering seven- and eight-figure partnerships with category exclusivities where possible
- Develop bespoke partnership strategies tailored to brand objectives, leveraging Overtime’s full ecosystem across live events, media, athletes, and social platforms
- Collaborate cross functionally with sales counterparts, marketing, creative, and operations teams to design world-class activations that deliver measurable ROI
- Cultivate and expand relationships with senior brand and agency leaders, positioning Overtime as a must-buy partner in relevant categories
- Actively integrate assigned league property into multi-league and portfolio-wide deals to maximize revenue opportunities
- Maintain a robust pipeline of high-value prospects, ensuring consistent deal flow and predictable revenue delivery
- Serve as the face of your assigned league in market, representing Overtime at industry events, major activations, and key partner meetings
Qualifications:
- 7+ years of experience in sports sponsorship or brand partnerships, with a history of selling multi-year, multi-million dollar deals to Fortune 500 brands
- Proven success securing category exclusivities and building long-term, strategic brand relationships
- Deep network within high-value categories such as CPG, QSR, Auto, Financial Services, and Telco
- Strong negotiation skills, with the ability to navigate complex legal and financial deal terms
- Exceptional strategic thinking, creativity, and ability to translate brand goals into high-impact partnership programs
- Comfortable operating in a high-growth, entrepreneurial environment with ambitious revenue targets
Overtime expects the base salary for this role to start at a range of 150K+ in addition to a sales incentive plan, medical benefits, and stock options in the company.