OUTFRONT Media · 20 hours ago
Sales Director, Chicago
Chicago, IL
Full-time
Onsite
Lead/Staff, Director/Executive
$200K/yr - $230K/yr
5+ years expOUTFRONT Media is one of North America’s most innovative media companies, seeking a Sales Director to support the VP of Sales in managing day-to-day sales execution. This role involves coaching and developing sellers, improving proposal quality, and driving AE performance to create a high-performing sales team.
AdvertisingBrand MarketingNewsOutdoor AdvertisingReal EstateSports
Responsibilities
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
Qualification
Required
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
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)
Company
OUTFRONT Media
Visual Displays and Marketing Solutions It is a sub-organization of CBS Corporation.
1001-5000 employees
Funding
Current Stage
Public CompanyTotal Funding
$1.85BKey Investors
Wells FargoProvidence Equity Partners
2025-09-24Post Ipo Debt· $1B
2023-11-07Post Ipo Debt· $450M
2020-04-16Post Ipo Equity· $400M
Leadership Team
Matthew Siegel
Chief Financial Officer
Sean Andersen
Vice President Interactive Services
Recent News
2026-01-16
2025-12-08
Company data provided by crunchbase