What are the responsibilities and job description for the Regional Account Executive- Milwaukee Market position at Heritage Outdoor Media?
Milwaukee, WI | Hybrid
Reports to: Midwest Regional Account Manager
About Heritage
Heritage Outdoor Media builds premium billboard platforms and lasting client partnerships. We’re a people-first company with a growth mindset, strong family values, and a relentless focus on results. When our clients win, we win.
The Opportunity
We’re hiring a driven Regional Account Executive to grow local and regional, client-direct revenue across Heritage’s digital and static billboard portfolio in Milwaukee.
This role sits at the center of our growth strategy. Over the next two years, we plan to quadruple our Milwaukee footprint, creating real earning power and clear advancement for the right sales professional.
If you thrive on ownership, relationships, and closing, you’ll feel at home here.
What You’ll Do
- Build trusted relationships with Milwaukee business owners, marketers, and decision-makers
- Prospect new business through outbound calling, in-person outreach, networking, and community engagement
- Develop smart, custom billboard solutions aligned to client goals and budgets
- Own your pipeline from first conversation to close
- Collaborate with regional leadership on strategy, forecasting, and account growth
- Stay plugged into the Milwaukee market, competitive landscape, and new inventory
- Represent Heritage with professionalism and integrity in every interaction
Who You Are
- Self-motivated, competitive, and accountable
- Coachable and collaborative
- Comfortable with outbound sales and face-to-face prospecting
- Confident presenter and clear communicator
- Familiar with the Milwaukee market and local business community
- Media or billboard sales experience is a plus, not a requirement
- Proven sales performance matters more than industry background
Compensation & Benefits
- Competitive base salary plus uncapped commission
- Full benefits package
- Ongoing sales training and mentorship
- Clear path for growth as the market expands
Why Heritage
- Growth You Can Feel: A rapidly expanding Milwaukee footprint
- Real Ownership: Autonomy with support, not micromanagement
- Earning Power: Performance-driven upside tied to market growth
- Leadership Access: Direct mentorship from experienced operators
- Career Momentum: As we scale, you scale
Ready to make your mark in Milwaukee?
Apply now and help shape the future of Heritage Outdoor Media.