Advertising Sales Representative (Hybrid / Remote)
Location: Katonah, NY (Hybrid Remote — Servicing Northern Westchester County and surrounding area
Job Type: Contract / Flexible Part-Time (Minimum 15 hours/week high-impact activity)
Compensation: Commission-Based (Realistic target: $35,000 - $75,000/year based on performance/hustle)
Target Territory: Armonk, Bedford, Chappaqua, Katonah, Mount Kisco, Somers, Yorktown Heights, and surrounding towns, North Salem and Pound Ridge
About Us
Connect to Northern Westchester (Sonder Publishing) is a premium, rapidly expanding multimedia platform. We bridge the gap between high-end national magazine sophistication and passionate local journalism. With a highly coveted print reach of 27,000+ homes and businesses per issue, an active digital presence, and a cutting-edge custom video production suite, we don't just sell ad space we provide an elite marketing ecosystem that helps regional and local brands truly thrive.
About the Role
We are seeking an ambitious, self-motivated Advertising Sales Representative deep local roots to join our team.
This is a true "hunter" role designed for a seasoned sales professional who loves remote autonomy and wants to manage their own schedule. You will step into the field armed with a world-class multimedia toolkit: upscale print real estate, digital integrations, social media campaigns, and high-production sizzle reels. If you have a passion for community storytelling and the consultative grit to turn local business owners into long-term marketing partners, this is your canvas.
Key Responsibilities
- New Client Acquisition: Proactively source, pitch, and close new B2B advertising accounts through structured cold calling, regional networking, and localized relationship building.
- Consultative Multimedia Selling: Pivot away from transactional ad sales. You will act as a strategic marketing consultant, diagnosing business needs and pairing them with our print, digital, custom content, and video suites.
- Territory Mapping & Strategy: Analyze market potential across northern Westchester towns to stay ahead of local business trends, grand openings, and seasonal marketing shifts.
- Pipeline Management: Manage and report your sales cycle independently, keeping a clean internal CRM to track leads, touches, and closed contracts.
Candidate Qualities & Job Requirements
- Proven Track Record: Minimum of 5 years of successful experience in advertising sales, B2B media sales, or local print/digital ad space layout.
- Hyper-Local Territory Knowledge: You must currently reside in or near Westchester County, NY, with a deep personal understanding of the northern Westchester business landscape.
- Expert Closing Acumen: Exceptional active listening and negotiation skills, with a proven ability to handle objections and guide clients from a "no" to a consultative "yes."
- Tech-Forward Productivity: Highly proficient in Google Workspace. Bonus points if you comfortably leverage modern AI tools (like NotebookLM) to maximize your productivity, outreach copy, and research efficiency.
- Mobility & Autonomy: Must have reliable, independent transportation to meet with business owners face-to-face across the region. A disciplined, remote-work veteran mindset is mandatory.
What We Offer
- Uncapped Earning Potential: A straight-commission structure built to reward your direct work and closing volume without corporate ceilings.
- Unrivaled Sales Toolkit: It is incredibly easy to sell a product that looks this good. Our premium layout, strict editorial separation, and unique local video partnerships give you instant credibility at the door.
- Maximum Flexibility: Control your own calendar. This role is primarily remote, allowing you to seamlessly integrate your professional targets with your personal life.
Company Description
Connect To is a local media source mailing to over 27,000 homes & businesses throughout northern Westchester. We cover the towns of Armonk, Bedford Corners, Bedford Hills, Bedford Village, Chappaqua, Cross River, Goldens Bridge, Katonah, Mount Kisco, North Salem, Peekskill, Pleasantville, Pound Ridge, Purdys, Somers, South Salem, Waccabuc, Vista and Yorktown Heights.
Our goal is to connect you to everything that makes our region special. Considered a national publication on a local level, we tackle important topics, profile extraordinary people, and provide useful information on a range of topics. And we believe that if you live in our community, this magazine is for you.
When someone picks up Connect To to read just one page or one article, they find themselves reading much more. In fact, many read our magazine cover-to-cover. Even elementary school children love Connect To and send us fan mail.
Launched in May 2022, the print version of Connect To has already featured so many incredible people in our towns. We’ve introduced our readers to talented local teens, phenomenal artists, valuable experts, successful business owners and more. Off the pages, we’ve connected many residents with each other, helping them achieve their dreams.
Connect To is so much more than a local magazine—we’re a creative force that tells stories every way we can: print, online, social media, video, etc. We shine a light on the real people of our community—the creative, the inspirational, the thought-provoking, the colorful, the humorous, the sporty and the just-plain-weird folks who shape our towns’ souls.
We encourage you to say hello. We want to know you. We want to tell your story.