You’re a high‑performing B2B media seller who wants bigger accounts, a faster trajectory, and a genuinely modern sales environment. At Key Media, you’ll sell into a market‑leading Insurance media portfolio, own Tier 1 relationships, and use cutting‑edge AI tools to accelerate both performance and earnings.

Role: Media Sales Professional – Insurance (B2B Digital Media)
Location: Flexible / hybrid | OTE: CAD $180k–$200k (uncapped)

What you’ll be doing

You’ll join a team of consultative, high‑performing sellers in our Insurance vertical, with clear ownership and support:

Sales motion & impact

• Own and grow a portfolio of existing Tier 1 insurance accounts, with direct responsibility for revenue growth and renewals
• Develop multi‑stakeholder relationships (carriers, brokers, service providers, tech vendors, agencies) and act as a trusted commercial partner
• Drive pipeline growth and revenue across our digital insurance brands via display, branded content, sponsorships and lead‑gen solutions
• Spot and convert new business opportunities within the broader insurance ecosystem to expand your portfolio
• Introduce innovative, data‑driven solutions and ad‑tech opportunities to deepen client engagement and share of wallet

How we sell (culture, pace, support)

• Join a collaborative, performance‑driven team that shares playbooks, insights and wins
• Work closely with marketing, editorial and design to build campaigns that actually solve insurance client problems
• Operate with realistic KPIs, transparent expectations and full visibility of your pipeline and performance
• Benefit from structured onboarding and ongoing coaching focused on consultative, account‑led enterprise sales

The tools & enablement

You’ll sell with a modern, AI‑enabled stack, not spreadsheets:

• Enterprise‑grade CRM to manage pipeline and key accounts
• Competitor analysis tools and market intel to sharpen your proposals
• Cutting‑edge AI to support prospecting, email drafting, meeting review and day‑to‑day productivity – freeing you to focus on high‑value conversations

What success looks like

• First 6 months: you’re fully ramped on our insurance brands and audience, running a healthy qualified pipeline, building strong relationships with key Tier 1 accounts, and hitting agreed ramp‑up targets
• 12 months+: you’re consistently meeting or exceeding revenue targets, demonstrating clear growth across Tier 1 accounts, and are recognised internally as a go‑to person in the Insurance vertical

Who will thrive in this role

You’re likely a strong fit if you:

• Have 3+ years’ proven B2B media or advertising sales experience
• Can demonstrate managing and growing Tier 1 / enterprise accounts, ideally in insurance or broader financial services
• Are motivated by ownership, accountability and seeing your numbers grow
• Bring strong client‑facing and negotiation skills, with a consultative, solutions‑led approach
• Are comfortable with KPIs, pipeline discipline and a fast‑moving commercial environment
• Are curious, coachable and excited to leverage AI and modern tools to level up your selling

This probably isn’t for you if you prefer purely reactive / inbound sales or are uncomfortable with visibility around performance.

What’s in it for you

• OTE CAD $180k–$200k, uncapped, with competitive base, commission on booked deals and accelerator models for top performers
• Ownership of high‑value insurance accounts within a global, market‑leading B2B media business
• A clear path to bigger strategic accounts, leadership opportunities, or broader vertical responsibility
• Flexible hybrid working, paid volunteer leave, extra annual leave accrual for tenure, and recognition programs (awards, vouchers, travel incentives)

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.

If you’re ready to accelerate your sales career, grow Tier 1 insurance accounts and sell across world‑class B2B insurance brands, we’d love to talk.

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, please contact us at [email protected].

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.