Sales Director, Chicago

About OUTFRONTWe 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 is to help people, places and businesses grow stronger by making meaningful connections between brands and people when they are outside 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 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.
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)
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.
What You’ll Do

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 a strategic partner to 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
Required Qualifications

5+ years of commercial sales experience, with experience in OOH, digital and transit advertising and programmatic media
3+ years of 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
Compensation

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. Please note that the foregoing compensation information is a good‑faith assessment associated with this position only and is provided pursuant to the Illinois Salary Transparency Law.
Equal Opportunity Employment Statement

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. Please refer to the OUTFRONT Media affirmative action policy statement.

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