Digital Media Account Executive & Community Lead

Village Media International; Oshkosh (WI); Hybrid; USD 59,000 - 72,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Paid time off

Professional development

Job summary

Village Media is hiring an in-market Account Executive & Community Lead in Wisconsin. You’ll split time between outbound B2B sales and community engagement, driving revenue with digital advertising packages and sponsorships.

Base salary is $65,000 with a $12,000 year-one guaranteed draw and uncapped tiered commissions, targeting $85,000–$115,000+ first year. The role requires relocation to or residence in Appleton, Fond du Lac, Oshkosh, or Sheboygan and daily local travel.

Qualifications

• 2+ years of outbound B2B sales experience (digital advertising or media sales preferred).
• Proven prospecting, cold-calling, needs-analysis and closing track record.
• Excellent verbal, written, and presentation skills.
• Familiarity with Northeastern/East-Central Wisconsin business ecosystem.

Responsibilities

• Prospect, cold-call, and close local business accounts across the territory.
• Present digital advertising, sponsorships, content packages, and directory listings.
• Build a robust sales pipeline to meet and exceed quarterly quotas.
• Represent Village Media at local chamber meetings and community events.

Skills

Outbound B2B sales

Prospecting

Cold calling

Needs analyses

Closing deals

Verbal communication

Written communication

Presentation skills

Community engagement

Job description

Location: Appleton, Fond du Lac, Oshkosh, or Sheboygan, WI (Local Hybrid / In-Market Field Sales). Position Type: Full-Time. Compensation: $65,000 base salary + uncapped tiered commission + $12,000 year-one guarantee. Target On-Target Earnings (OTE): $85,000 – $115,000+ (Year 1).

About Village Media & Our Wisconsin Launch

At Village Media, we build digital town squares that combine trusted local journalism with vibrant community platforms. Following the launch of AppletonToday.com, we are expanding across East-Central Wisconsin to bring dedicated local coverage and business growth tools to Appleton, Fond du Lac, Oshkosh, and Sheboygan.

Why Join Us? (The Compensation Package)

• Guaranteed base salary: $65,000 per year.
• Year-one commission draw: $1,000 per month ($12,000 annual guaranteed draw), ensuring a minimum year-one compensation floor of $77,000.
• Uncapped Tiered Commission Structure:
  • 6% on gross advertising sales up to $250,000
  • 10% accelerator on sales between $250,000 and $400,000
  • 12% top-tier accelerator on all annual sales above $400,000
• Comprehensive Benefits: Health, dental, vision, paid time off, and continuous professional development.

Position Summary & Key Responsibilities

As our in-market Account Executive & Community Lead, you will spend roughly 70% of your time driving outbound sales and 30% representing Village Media in the local community. Technical ad setup, design, and routine campaign fulfillment are supported by our centralized ad operations team, allowing you to focus on building relationships and closing revenue.

Outbound B2B Media Sales (70%)

• Prospect, cold-call, and consult with local small-to-medium businesses, corporate leaders, and non-profits across the territory.
• Present tailored digital advertising, newsletter sponsorships, content marketing, and directory listing packages.
• Build and maintain a robust sales pipeline to achieve and exceed quarterly revenue quotas.

Community Ambassadorship & Engagement (30%)

• Serve as the local face of Village Media at chamber of commerce meetings, business mixers, and community gatherings.
• Coordinate civic programs such as "Community Builder Awards" and "Random Acts of Kindness" to support local residents.
• Cultivate long-term client relationships to drive account renewals and regional partnership opportunities.

Work Arrangement & Territory Requirements

• Local Field Sales Structure: Flexible hybrid setup requiring daily in-territory travel for client visits and local networking events.
• Residency Requirement: Candidates must currently reside in (or be willing to relocate to) the target market territory (Appleton, Fond du Lac, Oshkosh, or Sheboygan).
• Logistics: Valid driver’s license and reliable personal vehicle required.

Qualifications

• Experience: 2+ years of successful outbound B2B sales experience (digital advertising, media sales, print/radio sales, or SaaS preferred).
• Sales Capabilities: Proven track record of prospecting, cold calling, conducting needs analyses, and closing new business.
• Communication: Exceptional verbal, written, and presentation skills.
• Community Connection: Familiarity with the business ecosystem and civic culture of Northeastern/East-Central Wisconsin.

The Kind of People We're Looking For

Village Media is beyond a traditional media company. We're a community impact organization. Our purpose is to help communities become stronger by keeping people informed, connected, and engaged.

That means we look for people who genuinely care about the places they serve.

We need teammates who are curious, collaborative, adaptable, and energized by solving problems. You’ll fit right in if you take initiative, embrace change, and are always willing to step outside your job description to help the team or the community succeed.

We're building something ambitious in the digital media space, so we value:

• Humility over ego
• Optimism over cynicism
• Ownership over 'that’s not my job'

We move quickly, support one another, and believe meaningful work comes from people who care deeply about both their colleagues and their neighbors. If you're excited by the opportunity to make a real difference where people live, you'll thrive here.

At Village Media, aptitude matters. Attitude matters more.

About Village Media

Village Media is a leading digital media company dedicated to strengthening local communities through trusted journalism, technology, and civic engagement. Headquartered in Sault Ste. Marie, Ontario, Village Media operates a growing network of local news publications and community platforms across Canada and the United States.

We are an equal opportunity employer. We value a diverse workforce and an inclusive culture. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability or veteran status. We are committed to providing a working environment that honors the unique backgrounds and perspectives of every team member.