AMP/Sinclair continues to expand its digital-first Entertainment and Lifestyle portfolio, anchored by emerging brands such as Amazing America and Criminally Obsessed. These brands sit within a broader, scaled media ecosystem under the AMP Enterprise Sales division, which includes:
- Tennis Channel, Tennis Channel 2, Tennis.com, PBTV
- Premium Sports Podcast Network
- Cousins (Vince Carter, Tracy McGrady)
- The Triple Option (Urban Meyer, Mark Ingram, Rob Stone)
- Unfiltered Soccer (Landon Donovan, Tim Howard)
- Post Moves (Candace Parker, Aliyah Boston)
- Throwbacks (Matt Leinart, Jerry Ferrara)
- And More….
- Sinclair’s national broadcast footprint (179 stations across linear and digital)
Role Overview
The Director of Sales (Entertainment) – Lifestyle / True Crime will serve as a key business leader and revenue driver within the AMP Enterprise Sales organization, working in close partnership with the VP of Sports & Entertainment Sales to lead go-to-market strategy and unlock new partnership opportunities across this rapidly growing vertical.
This role is responsible for identifying, developing, and closing strategic partnerships across both client-direct and agency channels, while collaborating cross-functionally with portfolio sellers to scale AMP’s entertainment and lifestyle brands in the marketplace.
Key Responsibilities:
- Lead revenue strategy and market positioning for Lifestyle & True Crime verticals
- Identify and secure high-value partnerships across brands, agencies, and emerging categories
- Develop integrated, multi-platform sales solutions leveraging AMP’s full portfolio (digital, audio, linear, and experiential)
- Partner with cross-portfolio sales teams to drive incremental revenue and share growth
- Translate audience behavior and content engagement into compelling commercial narratives
- Build long-term client relationships that extend beyond transactional media buys
- Collaborate with various AMP/Sinclair internal teams (marketing, operations, production, business development, programming, editorial, social) to identify, evolve, and create sales opportunities
Qualifications:
- Minimum 8+ years of experience in media/advertising (sales or agency), preferably in digital and/or content
- 2+ years of management (team or vertical experience)
- Proven track record of selling/executing integrated client partnerships and branded content partnerships
- Self-starter who approaches work in a collaborative way
- Passionate about Entertainment and Lifestyle media with the ability to create and bring creative ideas to client partners and internal teams
- Ability to be a consummate team player and a goal-oriented thinker
- Strong analytical and organizational qualities
- Excellent written and presentation skills
- Proficient in MS Office applications
Please note that this position is not eligible for visa sponsorship, including employer sponsorship for an H-1B visa, OPT-STEM employment, or related programs.
The base salary compensation range for this role is $150,000 to $200,000. In addition, this role may be eligible for a discretionary annual bonus, which would be awarded based on individual and company performance. Final compensation for this role will be determined by various factors such as a candidate’s relevant work experience, skills, certifications, and geographic location. Full time positions are eligible for benefits that include participation in a retirement plan, quarterly and annual incentive plan bonuses, life and disability insurance, health, dental and vision plans, flexible spending accounts, 15 paid vacation days, 2 paid personal days, 9 paid holidays, 40 hours of paid sick leave, parental leave, and employee stock purchase plan.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory


