Sales Specialist (Chicago, Minnesota, Indiana)

About OUTFRONT

OUTFRONT (NYSE: OUT) is one of the largest and most trusted out-of-home media companies in the U.S., helping brands connect with audiences in the moments and environments that matter most. As OUTFRONT evolves, it's defining a new era of in-real-life (IRL) marketing, turning public spaces into platforms for creativity, connection, and cultural relevance. With a nationwide footprint across billboards, digital displays, transit systems, and other out-of-home formats, OUTFRONT turns creative into powerful real-world experiences. Its in-house agency, OUTFRONT STUDIOS, and award-winning innovation team, XLabs, deliver standout storytelling, supported by advanced technology and data tools that can drive measurable impact.

OUTFRONT Media is one of the world’s most innovative media companies. It combines the power of strategic real estate with innovative technology, data-driven insights, and creative excellence to connect brands with consumers in meaningful ways. With one of the largest and most diverse portfolios of billboards, transit, and mobile assets in the industry, OUTFRONT Media is fundamentally changing the way advertisers engage audiences on-the-go and the way advertisers think about reaching their customers.

OUTFRONT’s network of more than 500,000 canvases reaches seven out of ten Americans weekly, generating 14.1 billion impressions that not only introduce leading brands to a wide audience but also build lasting consumer connections and brand affinity. Advertisers can choose from digital and static options, representing both traditional billboard inventory and media in some of America’s busiest transit systems. From compact posters to larger-than-life spectaculars, OUTFRONT offers coverage in the top 50 U.S. markets sure to include the right asset to deliver brands’ messages to exactly the right audience

Their Purpose: They help people, places, and businesses grow stronger. At OUTFRONT, they’re in the business of growth. Growing their partners’ businesses, growing the places they touch, and growing their people.

Their Belief: They deliver the United States of Audiences. It is a nation of diverse demographics, lifestyles, and geographies. A patchwork of people with preferences for everything. They impact everyone with canvases that exist in the places that matter most and primed to bring brands to life.

Their Vision: To impact every American Daily.

Their Mission: Simple, short, and memorable, grounded by three letters: TLC. They leverage the power of technology, location, and creativity to deliver impactful and engaging interactions with audiences as they live their lives.

Their Brand Promise: Their iron-clad commitment to deliver impact where it matters. Their media network leverages the power of the largest canvases across America to grow brands and businesses by driving impact, engagement, fame, and trust across every touchpoint.

OUTFRONT. We get you America.

Your Role

OUTFRONT Media is seeking a highly motivated Sales Specialist to support and help scale our Central sales organization.
 

This role is designed as a formal Account Executive (AE) development track, with the expectation that high-performing individuals will be eligible for promotion to Account Executive within 12–36 months, based on demonstrated performance, sales competency development, and business need.
 

Over time, the role will evolve from sales support to active participation in client-facing selling activities, including prospecting, pitch development, and revenue ownership. The Sales Specialist will work closely with the Area VP and sales leadership to drive efficiency, contribute to revenue growth, and build the skills required to succeed as a quota-carrying seller.

Your Responsibilities
 

Sales Enablement & Coordination

• Partner with Account Executives to coordinate and develop proposals, RFP responses, and client-facing materials
• Support client research, prospecting efforts, and pre-sale strategy development
• Assist in building compelling media plans and sales narratives across OOH and digital solutions
• Provide day-to-day support to the Area VP and sales team, helping to prioritize activities that drive revenue
• Coordinate and support pipeline tracking, deal progression, and follow-ups to ensure opportunities are advancing through the sales cycle

Sales Operations & Administrative Support

• Manage internal documentation, reporting, and organization of sales materials and collateral
• Coordinate meetings, pipeline reviews, and team communications to ensure alignment and efficiency
• Support onboarding new hires and training logistics
• Maintain accuracy in CRM systems and assist with reporting and forecasting support

Client Exposure & Development

• Support preparation for client meetings and presentations, with opportunities to observe and gradually participate in client-facing interactions
• Assist Account Executives in client follow-ups and communication, building familiarity with client needs, relationships, and sales dynamics
   

Market & Revenue Growth Support

• Contribute to new business development efforts, including prospect research, account targeting, and outreach preparation
• Support strategic initiatives across key growth areas (e.g., digital, programmatic, transit, experiential) to drive revenue opportunities
• Analyze sales performance and pipeline data to identify trends, uncover opportunities, and inform go-to-market strategies
   

Professional Development (AE Track)

• Actively participate in sales training, client exposure, and pitch development
• Shadow Account Executives and gradually take on client-facing responsibilities
• Build foundational skills in prospecting, negotiation, and closing

What You Bring

• 2–5 years of experience in sales, sales support, or sales operations
• Demonstrated interest in building a long-term career in sales (AE path)
• Strong communication and collaboration skills, with the ability to work effectively across teams and stakeholders
• Analytical and detail-oriented mindset; comfortable working with data, reporting, and CRM systems (Salesforce a plus)
• Highly organized with the ability to manage multiple priorities and follow through on key initiatives in a fast-paced environment
• Proactive, growth-oriented mindset with a desire to take ownership and drive outcomes—not just support them
• Experience or exposure to media, advertising, or marketing sales preferred
• Proficiency with common workplace tools (e.g., Excel, PowerPoint, collaboration platforms)
• Bachelor’s degree preferred
   

What Success Looks Like

• The sales team operates with greater efficiency, visibility, and consistency
• The Sales Specialist begins to meaningfully contribute to pipeline growth and deal progression
• Sales processes are standardized and scalable across markets

The salary range for this role is $65,000-$70,000 per year. 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.

OUTFRONT Media is not responsible for any fees related to unsolicited resumes.

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.