Senior Director Of Sales

Description:

Playfly Sports, a leading full-service sports marketing and media company, is seeking a Director/Senior Director of Sales (Paragon Properties) to lead strategic sponsorship and partnership initiatives across a portfolio of elite high school content and events produced by Paragon Marketing Group.

This role is designed for a highly experienced sales leader capable of driving multi-year sponsorship deals, leveraging a strong network, and utilizing consultative sales techniques to generate significant revenue growth. The position offers a hybrid work environment in Chicago, IL, or Los Angeles, CA, with opportunities for national engagement.

Key Responsibilities

• Drive new and incremental revenue to meet sales targets through strategic sponsorship and partnership sales.

• Cultivate and manage relationships with brands, media, and sponsorship agencies to enhance property visibility and secure multi-year deals.

• Sell across multiple platforms, including events, television media, digital sponsorship, and on-site activations.

• Develop and execute go-to-market strategies, create customized sales packages, and deliver client presentations.

• Maintain accurate pipeline reporting, revenue tracking, and sales documentation.

• Collaborate with internal teams (Creative, Activation, Insights) to design bespoke partnership solutions.

• Represent the company at industry events, networking functions, and client-facing opportunities.

Qualifications

• Bachelor’s degree required (Sports Media, Communications, Marketing, or related fields preferred).

• Minimum 10 years of sales/marketing experience with 6–8+ years in sponsorship sales or business development.

• Proven success in College/High School multimedia rights, team sponsorship, or sports arena sales.

• Strong communication, negotiation, and presentation skills.

• Experience with CRM systems and revenue generation tools preferred.

• Strategic thinker with deep understanding of sports sponsorship sales across various channels.

Compensation & Benefits

• Salary range: $130,000–$180,000 annually (approx. $10,833–$15,000 monthly).

• Actual compensation varies based on skills, experience, certifications, and location.

Attributes for Success

• Strategic and results-driven mindset with a proven track record of revenue generation.

• Ability to build strong, high-level client relationships.

• Skilled in consultative selling, negotiation, and long-term partnership development.

• Comfortable working in a collaborative and cross-functional environment.