Sales Director, Chicago

Outfront Media • Chicago, IL

2d • $200,000 - $230,000

About The Position

About OUTFRONT We are one of North America’s most innovative media companies. We leverage the power of creative excellence, unbeatable locations and smart audience data to change the game for advertisers. Our purpose as a company is to help people, places and businesses grow stronger. To do this, we make meaningful connections between brands and people when they are outside of their homes through one of the largest and most diverse sets of out-of-home assets including billboards, transit and mobile displays across the U.S. We connect diverse audiences across over 150 markets and conduct our business considering all our stakeholders, from clients and employees, to the communities where we operate. We are committed to creating a diverse and inclusive work environment that promotes the growth of our people. Come join our industry-leading team! What We Offer OUTFRONT offers a comprehensive benefits program including: Medical, Dental, Vision (including same and opposite-sex domestic partners) HSA and FSA plans, Family Benefits, Pet Benefits 401(k) Plan with an Employer Match Paid Time Off, Commuter Benefits, Educational Assistance Robust Diversity, Equity and Inclusion program including 7 Employee Resource Groups (ERGs) Overview 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.

Requirements

• 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

Responsibilities

• 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
• 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.
• 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

Benefits

• Medical, Dental, Vision (including same and opposite-sex domestic partners)
• HSA and FSA plans, Family Benefits, Pet Benefits
• 401(k) Plan with an Employer Match
• Paid Time Off, Commuter Benefits, Educational Assistance
• Robust Diversity, Equity and Inclusion program including 7 Employee Resource Groups (ERGs)

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed