Junior Field Sales Representative (B2B Partnerships)

Location: Toronto, ON (hybrid – mix of remote work, in‑office collaboration and in‑person outreach in downtown Toronto)

Experience level: Early career / 1–2 years in sales, partnerships, sponsorships or other customer‑facing roles

Employment type: Full-time or part-time

About Key Media

Key Media is a global, independent media company connecting niche professional and affluent audiences with the brands that want to reach them. Through market‑leading publications, events and digital platforms, we help businesses engage high‑net‑worth and premium consumer segments across multiple markets.

We are growing our commercial team in Toronto and are looking for an ambitious early‑career sales/partnerships professional who enjoys being out in the field talking to local businesses.

The role

This is a barter‑focused B2B sales role working with small and medium‑sized businesses across downtown Toronto. You’ll spend part of your week out in the field (door‑to‑door) visiting local businesses, and part of your week on the phone and email, building partnerships across all Key Media brands.

Instead of pure cash sales, you’ll use Key Media’s business data, event opportunities and media assets to structure value‑exchange / service‑for‑advertising deals that benefit both sides.

It’s a great fit for someone early in their sales career who is confident, proactive and comfortable spending time walking between businesses in downtown Toronto as part of their working week.

What you’ll be doing

Local business outreach (door‑to‑door and phone)

• Visit small businesses in downtown Toronto to introduce Key Media and explain our barter partnership model
• Run high‑volume outbound calls to targeted B2B barter prospects
• Follow up with tailored, persuasive emails to nurture and convert leads
• Build and manage a pipeline of potential partners across luxury, lifestyle, financial, professional services and premium local brands

Partnership pitching & deal structure

• Pitch cross‑brand barter partnerships (services/products in exchange for advertising, content and data‑driven exposure)
• Use Key Media’s audience insights, media inventory and event offerings to craft compelling partnership proposals
• Negotiate clear, mutually beneficial value‑exchange deals aligned with partner and Key Media objectives

Internal collaboration & execution

• Work closely with sales, marketing, events and editorial teams to ensure deals are deliverable and on‑brand
• Coordinate internally to activate campaigns across digital, print, events and content channels
• Track performance of partnerships and contribute ideas to optimise and grow them over time

What you’ll need to succeed

• 1–2 years of sales‑related or customer‑facing experience – e.g. B2B/B2C sales, partnerships, sponsorships, media sales, retail, hospitality or similar
• Toronto‑based with easy access to downtown, and comfortable spending time in the field visiting local businesses
• Comfortable spending extended periods on your feet and walking between businesses in a downtown environment as part of your working week (reasonable accommodations can be discussed where needed)
• Confident communicator – strong in‑person, phone and email skills; consultative, professional and persuasive
• Comfortable with outbound activity – you enjoy making calls, knocking on doors, following up and driving your own pipeline
• Organised and proactive – able to manage high call and email volumes, keep accurate records and follow through
• Results‑focused – motivated by targets and commercial outcomes
• Media/events or premium/affluent‑segment knowledge is a strong plus, but not essential

What we offer

• Opportunity to work across multiple leading media brands with premium, high‑value audiences
• A hybrid working environment combining flexibility, in‑office collaboration and in‑person field work in downtown Toronto
• Competitive starting salary and commission scheme (OTE $70–80k CAD)
• Training and support from experienced sales and media professionals
• Clear performance targets and the chance to directly impact revenue and growth
• A collaborative, entrepreneurial culture where new ideas and initiative are encouraged
• Health and Dental benefits
• Travel Orange – the chance to work from anywhere in the world for up to 12 weeks of the year

About Key Media

Key Media is a global business media company with leading B2B brands across insurance, finance, legal, HR and more, with offices in Sydney, Toronto, Auckland, Manila, Denver, London and Singapore. We connect business leaders with the insight, connections and recognition they need to thrive.

Vacancy status

This posting is for an existing vacancy that we are actively recruiting to fill.

Use of artificial intelligence in hiring

We use automated tools / artificial intelligence to help with note‑taking during interviews. All decisions on candidate progression and hiring are made by human reviewers.

Inclusion, equity & accessibility

We are committed to employment equity and an inclusive, barrier‑free selection process. We welcome applications from all qualified candidates, including members of visible minorities, Indigenous peoples, persons with disabilities, women, and persons of any sexual orientation or gender identity/expression. If you require accommodation during any stage of the recruitment process or to perform any aspect of the role, please contact us at alix.thompson@keymedia.com and we will work with you to support your needs.

Application updates

Candidates who interview for this role will receive an update on their application status no later than 45 days after their last interview, and in most cases much sooner.