As a Business Development Representative, you will sell premium digital advertising on an iconic large-format screen in the heart of Times Square to senior executives at U.S. brands. You will cold‑call directly into the C‑suite — CEOs and CMOs — at companies of roughly $20M or more in revenue across tourism, hotels, travel, food and beverage, and Fortune 500 brands. This is a 100% new business development role: you self‑source your own lead lists every day using AI‑assisted prospecting tools — no warm leads or lists are provided. Your territory is the entire United States, prospected by phone from the Oakville head office on a hybrid schedule. These are multiple new openings on an expanding outbound team, reporting to the VP of Sales. The base salary is $70,000 CAD, plus uncapped commission.

Compensation & Benefits

$70,000 CAD base salary, plus uncapped commission

Year 1 OTE: approximately $100,000 – $210,000 CAD, depending on deals closed

Year 2 OTE: increases with tenure and pipeline as you build experience

Top‑performer OTE: approximately $340,000 CAD

Uncapped commission, paid monthly on every closed deal — you keep your full commission even though the VP of Sales runs the final close

Company‑paid health benefits plus a health benefit allowance

Employee recognition, gifts, and rewards

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 held, family‑founded company now operating under new ownership and a new CEO. The team is roughly 19 people company‑wide and is actively scaling. Based in Oakville, Ontario, the company sells premium digital advertising on an iconic large‑format screen in the heart of Times Square — brands buy a full‑year run, sold directly to senior executives.

The culture is family‑like, people‑first, and high‑energy, with a young, hungry sales floor and an old‑school sales spirit — a closed deal still earns a champagne toast on the floor. The company has been through a significant leadership change and now operates under a positive, nurturing, and structured culture. Brands that have run on the screen include Samsonite, Live Nation, Hard Rock Cafe, Cadillac, Iceland Air, Nassau Tourism, and Parlux.

Office Location & Sales Territory

Head office: Oakville, Ontario

Work arrangement: Hybrid — 3 days in office (Monday, Thursday, Friday) and 2 days remote (Tuesday, Wednesday)

Sales territory: National United States — no geographic boundaries or assigned accounts; reps self‑source nationally and qualified prospects are protected through the sales cycle

Ideal candidate location: GTA West, within commuting distance of Oakville (roughly 45 minutes), given the 3‑day in‑office requirement

Working hours: 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 — the role is fully phone‑ and office‑based

No driver’s licence or vehicle required

Experience, Background & Education Requirements

1–5 years of sales experience — time on the phone matters more than years of tenure

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 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 their own lists

Education: high school minimum; a degree is not a factor

No CRM experience required

Not a fit: pure SaaS / transactional or one‑call‑close backgrounds; low‑activity or order‑taker profiles; candidates unwilling to cold‑call the C‑suite.

Technical Skills

Microsoft Teams — Basic

Microsoft Word — Basic

AI‑assisted prospecting and list‑building tools — comfort required (e.g., AI research assistants, Lusha)

No CRM experience required — there is no CRM in use

The Product / Service / Solution

Premium digital advertising on an iconic large‑format screen in the heart of Times Square

Full‑year advertising runs — a brand stays on the screen for a full year, including every premium holiday with no blackouts and no holiday premium

Customized media kits produced in‑house for interested brands

Prospective Customers / Industry Focus / Decision Maker(s)

U.S. brands of roughly $20M or more in revenue

Verticals: tourism boards, hotels, travel, food and beverage, and Fortune 500 brands

Customers are located nationwide across the United States

Decision‑makers: the C‑suite — CEO and CMO — reached directly

Sales Cycle / Order Value / Account Size

Each deal is a full‑year advertising commitment — a high‑value annual contract

The motion is fast at the BDR stage: open with a tailored hook, deliver the pitch, and trigger a customized media kit

Once a media kit goes out, the VP of Sales takes over follow‑up and the close; the rep shadows the close to build full‑cycle skills

Competitive Advantages

The only full‑year run in the market — competitors sell one‑week to one‑month, high‑share‑of‑voice campaigns, while this product keeps a brand on the screen for a full year

Every premium holiday included (New Year’s, Christmas,



Black Friday, Thanksgiving) with no blackouts and no holiday premium

Iconic, high‑traffic Times Square location with a New Year’s Eve ball‑drop backdrop and social amplification

A long‑term branding position sold direct to the C‑suite — not a short‑term performance buy

An established roster of recognizable national and global brands

Typical Day & Duties

100% New Business Development

On a typical day you will self‑source a fresh lead list using AI‑assisted prospecting tools, cold‑call directly into the C‑suite at U.S. brands, deliver a tailored hook and the Times Square pitch, and — when an executive is interested — trigger a customized media kit and hand the opportunity to the VP of Sales. You will also sit in on post‑kit follow‑up calls to build full‑cycle skills.

Leads

100% self‑sourced and self‑prospected through daily cold outreach — you build your own lists

0% warm or supplied leads, with the rare exception of an occasional trending social‑media lead pushed out by the VP’s executive assistant

Lead sources: AI‑assisted prospecting and list‑building tools; you continuously research industries, brands, and trending social moments to identify timely prospects

High daily outbound talk time and call volume are core expectations of the role

Overnight Travel
None — 0%. The role is fully phone‑ and office‑based; no vehicle or licence is required.

Support & Training

Full product training on the Times Square offering — media or advertising experience is not required

Hands‑on coaching from the VP of Sales, an 18‑year Times Square media‑sales veteran who closes the deals and coaches reps toward the Account Executive path

You 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

A clear Business Development Representative to Account Executive career path for strong performers

Why You Should Apply

Uncapped monthly commission with a real six‑figure earnings story — you keep your full commission even though the VP of Sales runs the close, and top performers earn well into the six figures

A truly iconic product — a full‑year run on an iconic Times Square screen, an exciting and easy product to pitch to the C‑suite

A clear path from BDR to full‑cycle Account Executive, with mentorship from an 18‑year media‑sales veteran

A people‑first, high‑energy culture that celebrates wins and invests in its reps

A timely tailwind — Q3/Q4 is peak season and America’s 250th anniversary drives a second New Year’s Eve ball drop in Times Square in 2026

No vehicle, no licence, and no overnight travel — a phone‑based role on a hybrid schedule close to home

Equal Chance Employer
Just 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 (BDR) – Time Square Digital Billboard Advertising Sales (Ontario)
🏢 Just Sales Jobs
📍 Ontario