Media Sales Professional - Insurance

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.