OverviewAs a Business Development Representative, you will sell premium digital out-of-home advertising on an iconic large-format screen in the heart of Times Square, sold as full-year advertising runs. You will prospect and pitch directly to the C‑suite — CEOs and CMOs — at U.S. brands of roughly $20 million or more in revenue across tourism boards, hotels, travel, food and beverage, and Fortune 500 companies. This is a 100% new business development role: you will self‑source your own lead lists every day using AI‑assisted prospecting tools and cold‑call directly into senior executives — no warm leads or supplied lists are provided. The territory is the entire United States, with no geographic boundaries or assigned accounts. This is an expansion hire with multiple openings, reporting to the VP of Sales. The base salary is $70,000 CAD, plus uncapped commissions.Compensation & Benefits$70,000 CAD base salary, plus uncapped commissions paid monthlyYear 1 OTE: approximately $100,000 – $210,000 CAD, depending on deals closedYear 2 OTE: increases with tenure and deal volume as you build experience and a stronger pipelineTop performers have historically earned approximately $340,000 CADUncapped commission with no ceiling on earnings — you keep 100% of the commission on every deal you originate, even though the VP of Sales leads the closeCompany‑paid health benefits plus a health benefit allowanceEmployee recognition, gifts, and rewards programFurther‑education reimbursementCompany social events and bonus trips10 vacation days, 5 sick days, and 5 personal daysFive U.S. holidays plus paid time off between Christmas and New Year'sNew external sales‑training program being introducedThe Company & CultureOur client was founded approximately 20 years ago and is a privately owned, family‑founded company now operating under new ownership and a new CEO. They are a profitable scale‑up, having grown through a macro‑driven downturn and now reinvesting in larger offices, senior leadership, and a sales‑team expansion. The company has roughly 19 employees, scaling to about 24 with this hire, and a sales team of 10 reps scaling to 14. They are headquartered in Oakville, Ontario, Canada.Our client sells premium digital out‑of‑home advertising on an iconic large‑format screen at the corner of 42nd and Broadway in Times Square. Brands buy a full‑year run, sold directly to senior executives. Their customers span tourism boards, hotels, travel, food and beverage, and Fortune 500 brands. Clients include Samsonite, Live Nation, Hard Rock Cafe, Cadillac, Iceland Air, Nassau Tourism, and Parlux.The culture is family‑like, people‑first, and high‑energy. It is a structured, nurturing environment with a young, hungry sales floor — an old‑school sales culture where a closed deal still earns a champagne toast on the floor. The company operates under a positive, supportive culture, and employees report a high level of satisfaction.Office Location & Sales TerritoryHead office: Oakville, Ontario, CanadaWork arrangement: Hybrid — 3 days per week in office (Monday, Thursday, Friday) and 2 days remote (Tuesday, Wednesday)Ideal candidate location: GTA West, within roughly 45 minutes of the Oakville office, given the 3‑day in‑office requirementSales territory:



National United States — no geographic boundaries or assigned accounts. Reps self‑source nationally; once a prospect is qualified it is protected through the sales cycleHours: Monday to Friday, 8:00 a.M. – 4:00 p.M., 40 hours per week, aligned to U.S. business hours. No mandatory evenings or weekendsOvernight travel: None (0%) — the role is fully phone‑ and office‑basedExperience, Background & Education Requirements1–5 years of sales experience — demonstrated cold‑calling ability matters more than years in the roleHigh‑volume, phone‑based B2B outbound experience, with genuine comfort cold‑calling and holding the attention of C‑suite executives (CEO / CMO)Media or advertising sales background preferred but not required — out‑of‑home / billboard / transit, radio, TV, digital media, magazine / publication, or event / sponsorship sales. The product will be taughtStrong door‑to‑door / B2C canvassers who have moved into B2B are also a fit — the grit that motion builds is valuedMust be able to self‑source leads using AI‑assisted prospecting tools and build your own listsStability: more than 3 roles in the past 9 years is a concern for this roleNot a fit: pure SaaS / transactional / one‑call‑close backgrounds, low‑activity or order‑taker mentalities, and anyone unwilling to cold‑call the C‑suiteEducation: high school minimum; a degree is not requiredNo driver's licence or vehicle requiredTechnical SkillsMicrosoft Teams — BasicMicrosoft Word — BasicAI‑assisted prospecting and list‑building tools (e.G., Claude, ChatGPT, Lusha) — comfort requiredNo CRM experience required — the company does not currently use a CRMThe Product / Service / SolutionFull‑year advertising runs on a premium large‑format digital screen at the corner of 42nd and Broadway in Times SquarePremium placement near the Ruby Red Steps, with the Current Year's Eve ball‑drop as a backdropYear‑round exposure across every premium holiday — New Year's, Christmas, Black Friday, and Thanksgiving — with no blackouts and no holiday premiumSocial amplification of the on‑screen placementProspective Customers / Industry Focus / Decision MakersU.S. companies at roughly $20 million or more in annual revenueIndustries: tourism boards, hotels, travel, food and beverage, and Fortune 500 brandsDecision‑makers: the C‑suite — CEOs and CMOs — reached directly on direct‑dial numbersGeography: the United States, nationalSales Cycle / Order Value / Account SizeA standard deal is a full‑year advertising package, valued at approximately $300,000 per annual runThis is a long‑term branding sale to the C‑suite — a considered, executive‑level decision rather than a transactional one‑call closeThe BDR's portion of the cycle is hook, pitch, and send media kit; once a customizedmediakit goes out,



the VP of Sales takes over follow‑up and the closeCompetitive AdvantagesThe annual run is the core differentiator — competitors sell one‑week‑to‑one‑month, high‑share‑of‑voice campaigns, while our client keeps a brand on screen for a full yearEvery premium holiday is included with no blackouts and no holiday premiumAn iconic, high‑traffic location in the heart of Times SquareThe New Year's Eve ball‑drop backdrop — and in 2026, America's 250th anniversary brings a second NYE ball dropCustomized media kits produced by an in‑house production team20 years in business, profitable, and reinvesting in growthTypical Day & Duties100% New Business DevelopmentOn a typical day you will self‑source daily lead lists using AI‑assisted prospecting tools, place a high volume of outbound cold calls directly to the C‑suite, open with a tailored hook to earn the conversation, pitch the Times Square talking points, and — on interest — trigger a customized media kit. You will then sit in on post‑kit follow‑up calls and negotiations led by the VP of Sales to build objection‑handling and full‑cycle skills toward an Account Executive path.Leads100% self‑sourced and self‑prospected — you build your own daily lead lists using AI‑assisted prospecting tools0% warm or supplied leads, with the rare exception of an occasional trending social‑media lead pushed out internallyThis is a pure cold‑prospecting, hunting role measured on activity, media kits sent, and deals closedOvernight TravelNone (0%) — the role is fully phone‑ and office‑based. No vehicle or driver's licence is requiredSupport & TrainingFull product training on the Times Square offering is provided — media or advertising experience is not requiredCoaching from the VP of Sales, an 18‑year Times Square media‑sales veteran who takes over follow‑up and the close and develops reps toward a full‑cycle Account Executive roleYou will sit in on post‑kit follow‑up calls and negotiations to build objection‑handling and full‑cycle competencyA new external sales‑training program is being introducedYou will begin self‑sourcing and cold‑calling early in onboarding, with the goal of being productive ahead of the Q3/Q4 peak seasonWhy You Should ApplyUncapped, monthly commission with no ceiling — top performers have historically earned approximately $340,000 CAD, and you keep 100% of the commission even though the VP of Sales closes the dealSell a genuinely one‑of‑a‑kind product — an iconic Times Square placement with a real differentiator (a full‑year run with no blackouts) that opens doors at the C‑suiteA clear Business Development Representative to Account Executive career path — learn the full sales cycle alongside an 18‑year media‑sales veteranA profitable, growing, 20‑year company investing in its expansion, with a positive, people‑first, high‑energy cultureNo travel, no driver's licence, and no CRM administration — your focus stays on selling, within a structured and supportive environmentEqual Opportunity EmployerJust Sales Jobs and our clients are equal chance employers. We do not discriminate. All candidates are evaluated solely on performance merit and organizational fit.#J-18808-Ljbffr

📌 Business Development Representative - Time Square Billboard Advertising - C$70,000 A Year (Winnipeg)
🏢 Just Sales Jobs
📍 Winnipeg