Overview

As 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% recent 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 monthly
- Year 1 OTE: approximately $100,000 – $210,000 CAD, depending on deals closed
- Year 2 OTE: increases with tenure and deal volume as you build experience and a stronger pipeline
- Top performers have historically earned approximately $340,000 CAD
- Uncapped 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 close
- Company‑paid health advantages plus a health benefit allowance
- Employee recognition, gifts, and rewards program
- Further‑education reimbursement
- Company social events and bonus trips
- 10 vacation days, 5 sick days, and 5 personal days
- Five U.S. holidays plus paid time off between Christmas and New Year's
- New external sales‑training program being introduced

The Company & Culture

Our 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 Territory

- Head office: Oakville, Ontario, Canada
- Work 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 requirement
- Sales 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 cycle
- Hours: 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 weekends
- Overnight travel: None (0%) — the role is fully phone‑ and office‑based

Experience, Background & Education Requirements

- 1–5 years of sales experience — demonstrated cold‑calling ability matters more than years in the role
- High‑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 taught
- Strong door‑to‑door / B2C canvassers who have moved into B2B are also a fit — the grit that motion builds is valued
- Must be able to self‑source leads using AI‑assisted prospecting tools and build your own lists
- Stability: more than 3 roles in the past 9 years is a concern for this role
- Not a fit: pure SaaS / transactional / one‑call‑close backgrounds, low‑activity or order‑taker mentalities, and anyone unwilling to cold‑call the C‑suite
- Education: high school minimum; a degree is not required
- No driver's licence or vehicle required

Technical Skills

- Microsoft Teams — Basic
- Microsoft Word — Basic
- AI‑assisted prospecting and list‑building tools (e.g., Claude, ChatGPT, Lusha) — comfort required
- No CRM experience required — the company does not currently use a CRM

The Product / Service / Solution

- Full‑year advertising runs on a premium large‑format digital screen at the corner of 42nd and Broadway in Times Square
- Premium placement near the Ruby Red Steps, with the New Year's Eve ball‑drop as a backdrop
- Year‑round exposure across every premium holiday — Current Year's, Christmas, Black Friday, and Thanksgiving — with no blackouts and no holiday premium
- Social amplification of the on‑screen placement

Prospective Customers / Industry Focus / Decision Makers

- U.S. companies at roughly $20 million or more in annual revenue
- Industries: tourism boards, hotels, travel, food and beverage, and Fortune 500 brands
- Decision‑makers: the C‑suite — CEOs and CMOs — reached directly on direct‑dial numbers
- Geography: the United States, national

Sales Cycle / Order Value / Account Size

- A standard deal is a full‑year advertising package, valued at approximately $300,000 per annual run
- This is a long‑term branding sale to the C‑suite — a considered, executive‑level decision rather than a transactional one‑call close
- The BDR's portion of the cycle is hook, pitch, and send media kit; once a customized media kit goes out,



the VP of Sales takes over follow‑up and the close

Competitive Advantages

- The 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 year
- Every premium holiday is included with no blackouts and no holiday premium
- An iconic, high‑traffic location in the heart of Times Square
- The New Year's Eve ball‑drop backdrop — and in 2026, America's 250th anniversary brings a second NYE ball drop
- Customized media kits produced by an in‑house production team
- 20 years in business, profitable, and reinvesting in growth

Typical Day & Duties

- 100% New Business Development

On 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.

Leads

- 100% self‑sourced and self‑prospected — you build your own daily lead lists using AI‑assisted prospecting tools
- 0% warm or supplied leads, with the rare exception of an occasional trending social‑media lead pushed out internally
- This is a pure cold‑prospecting, hunting role measured on activity, media kits sent, and deals closed

Overnight Travel

- None (0%) — the role is fully phone‑ and office‑based. No vehicle or driver's licence is required

Support & Training

- Full product training on the Times Square offering is provided — media or advertising experience is not required
- Coaching 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 role
- You will sit in on post‑kit follow‑up calls and negotiations to build objection‑handling and full‑cycle competency
- A new external sales‑training program is being introduced
- You will begin self‑sourcing and cold‑calling early in onboarding, with the goal of being productive ahead of the Q3/Q4 peak season

Why You Should Apply

- Uncapped, 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 deal
- Sell 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‑suite
- A clear Business Development Representative to Account Executive career path — learn the full sales cycle alongside an 18‑year media‑sales veteran
- A profitable, growing, 20‑year company investing in its expansion, with a positive, people‑first, high‑energy culture
- No travel, no driver's licence, and no CRM administration — your focus stays on selling, within a structured and supportive environment

Equal Opportunity Employer

Just Sales Jobs and our clients are equal opportunity employers. We do not discriminate. All candidates are evaluated solely on performance merit and organizational fit.

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📌 Business Development Representative - Time Square Billboard Advertising (Oakville)
🏢 Just Sales Jobs
📍 Oakville