Sales Director, Chicago

Sales Director

The Sales Director supports the VP, Sales in managing day-to-day sales execution, with direct responsibility for a subset of the AE team. This role is focused on coaching and developing sellers, improving proposal quality, and driving AE performance. This leader will be a critical element of creating a high-performing sales team and driving accountability.

Sales team leadership:

• Lead a team of AEs with direct responsibility for their performance, quota attainment and professional development
• Provide hands-on coaching and deal support, joining client meetings, improving pitch quality, and upskilling reps in storytelling/outcome-based messaging
• Coach your team to position OUTFRONT as strategic partner to our clients, guiding them to deliver tailored solutions that utilize our full product portfolio (incl. transit and digital) and deliver measurable business outcomes
• Run weekly 1:1s and team stand-ups to monitor pipeline health, provide in-the-moment coaching, and reinforce a high-performance mindset
• Establish a performance-driven culture and drive accountability through a rigorous, data-driven operating rhythm that includes weekly pipeline reviews
• May take on market-specific or functional leadership roles (e.g., transit oversight, in-office culture champion)
• Act as an internal leader and point of continuity for AEs, especially during times of transition or change

Sales execution & support:

• Support the proposal process to ensure high-quality, client-relevant presentations and media plans
• Monitor pipeline activity, support in deal strategy, and ensure AE accountability across all funnel stages
• Act as the first line of escalation for client or internal issues, working cross-functionally to resolve quickly and protect revenue
• Partner closely with the VP Sales within the Market to contribute to strategy planning efforts
• Provide insights from the field to help shape sales strategy, including client feedback, market dynamics, and product needs.

Leadership development:

• Act as a key succession candidate for VP Sales roles by demonstrating strategic thinking, talent development, and business acumen
• Invest in your own leadership growth, participating in mentorship opportunities, and industry learning

Required Qualifications:

• 5+ years of commercial sales experience, with experience in OOH, digital and transit advertising and programmatic media
• 3+ years' experience coaching or managing sales talent, either formally or informally
• Strong understanding of the end-to-end sales process, from prospecting and proposal development to closing and retention
• Excellent interpersonal skills and ability to build trust quickly with both clients and team members
• Demonstrated ability to support others in client strategy, pitch quality, and deal execution and comfortable operating in a "coach" (vs. player-coach) capacity
• A growth mindset with the willingness to take on leadership stretch assignments, cross-functional initiatives, and team culture roles

The salary range for this role is $200,000-$230,000 per year. This role is also eligible for incentive compensation. Compensation is determined during our interview process by assessing a candidate's experience and skills relative to internal peers and market benchmarks evaluated for the scope and responsibilities of the position.

OUTFRONT Media Is An Equal Opportunity Employer. All applicants shall receive equal consideration without regard to race, color, religion, gender, marital status, gender identity or expression, sexual orientation, national origin, age, veteran status or disability.