Sales Representative Position Available In Middlesex, Massachusetts

Sales Representative Wayland Post Wayland, MA • Hybrid work Advertising & Sponsorship Sales Representative (Full-Time) –

The Wayland Post Location:

Wayland, Massachusetts Organization:

the Wayland Post (local nonprofit newspaper) Overview The Wayland Post is looking for an energetic, relationship-driven Advertising & Sponsorship Sales Representative to grow the local businesses and community partners that power our journalism. You will sell and manage print, digital, newsletter, podcast, and event sponsorships that connect Wayland merchants and organizations with our engaged readership. If you thrive on meeting goals, forging new relationships, and helping small businesses succeed, we want to hear from you. Key Responsibilities Revenue Generation Meet or exceed monthly and annual revenue targets by selling display ads, classifieds, digital banners, newsletter placements, and event sponsorships. Prospecting & Lead Pipeline Identify and qualify new local and regional advertisers through cold calls, drop-ins, networking events, and community referrals. Maintain an active, balanced pipeline in our CRM. Client Relationship Management Serve as primary point of contact for advertisers—understand marketing goals, recommend packages, create proposals, negotiate, close deals, and ensure timely payment. Campaign Planning & Execution Collaborate with design and editorial teams to develop creative assets and sponsorship integrations. Monitor campaign performance, provide mid-flight optimizations, and deliver post-campaign reports. Community & Event Sponsorships Package and sell sponsorship opportunities tied to Wayland Post events (candidate forums, community fairs, fundraising drives). Secure in-kind partnerships as needed. Market Intelligence Track competitive media, pricing trends, and local business openings/closings. Provide feedback to leadership on new products, pricing adjustments, and advertiser needs. Collaboration & Reporting Work closely with the publisher, finance, and editorial teams to forecast revenue, update sales dashboards, and ensure ads meet ethical and legal standards.

Required Qualifications Sales Experience:

3-5 years in advertising, media, or B2B sales with a proven record of meeting revenue goals.

Communication Skills:

Persuasive verbal and written communicator comfortable pitching over the phone, in person, and by email.

Local Knowledge:

Familiarity with Wayland/MetroWest business community—or ability to learn it quickly—and genuine enthusiasm for supporting local commerce.

Tech Savvy:

Proficiency with CRM software (HubSpot, Salesforce, or similar), Microsoft Office/Google Workspace, and basic digital-ad metrics (impressions, CTR, open rates).

Organization:

Excellent time-management, pipeline discipline, and follow-through; able to juggle multiple proposals and deadlines simultaneously.

Driver’s License:

Reliable transportation for on-site client visits and community networking events. Preferred Qualifications Experience selling integrated print + digital advertising packages or nonprofit sponsorships. Understanding of small-business marketing needs and ability to craft ROI-focused proposals. Familiarity with Adobe Creative Cloud or Canva for quick ad mock-ups. Existing relationships in Wayland, Sudbury, Weston, Natick, or surrounding towns. Additional language skills helpful for reaching diverse business owners. Ideal Candidate Profile You are outgoing, goal-oriented, and thrive on helping local businesses grow. Targets motivate you, but integrity guides you—you never oversell and always honor commitments. You enjoy walking Main Street, hearing merchants’ stories, and translating their needs into effective campaigns. You’re equally comfortable chatting at a chamber mixer or analyzing click-through numbers in a spreadsheet. Above all, you believe robust local journalism and vibrant local commerce go hand-in-hand, and you’re excited to champion both at The Wayland Post. Compensation includes base salary plus competitive commission, health-care stipend, paid time off, and mileage reimbursement. Flexible hybrid schedule with regular in-person client visits around Wayland and neighboring towns.

To Apply:

Send a résumé and a brief cover letter outlining your relevant sales successes to info@waylandpost.org with “Advertising Sales – [Your Name]” in the subject line. Applications reviewed on a rolling basis until the position is filled.

Job Types:

Full-time, Part-time, Contract Pay:

$20.00 – $30.00 per hour Expected hours: 10 – 40 per week

Benefits:

Flexible schedule

Compensation Package:

Uncapped commission

Schedule:

Monday to Friday No nights No weekends

Education:

Bachelor’s (Preferred)

Experience:

B2B sales: 3 years (Preferred)

Location:

Wayland, MA (Preferred)

Work Location:

Remote