Enterprise Account Executive (Canada) at InDebted

About InDebted in Canada

InDebted is a global leader in digital debt collection, helping some of the world's most innovative enterprises deliver a better collections experience for their customers. Our compliance-led, digital-first approach lets clients recover more while protecting their brand and keeping strong customer relationships. InDebted has proven success across the US, UK, Australia and New Zealand. Canada is one of our fastest-growing regions, with revenue growing 79 per cent year over year in FY26.

What sets us apart: our outreach is personalized and data-driven rather than one-size-fits-all, and we treat customers as people, not adversaries. Our collections fees are fully performance-based: clients pay a share of what we collect, with no flat fees. That model aligns our incentives directly with the outcomes we deliver for clients.

About the role

As our first Canada-based Enterprise Account Executive, you'll win enterprise accounts and grow them into long-term relationships. We focus on a defined universe of strategically important Canadian organizations that carry consumer debt on their own balance sheets: major banks, card issuers, lenders, BNPLs and telcos.

Deals typically move from a first conversation to a 90-day pilot. Go-live usually takes two to three weeks, and the pilot shows results month over month before a full MSA is negotiated. On large enterprise deals, you lead the relationship with support from our global leadership, product and operations teams. On mid-market deals, you run the process yourself from start to finish.

Where you'll work

• Remote within Canada, with regular in-person client meetings and travel. We strongly prefer the Greater Toronto Area, close to most major Canadian financial institutions.
• You must hold full working rights in Canada.

What you'll do

• Originate new business with banks, card issuers, credit unions and lenders. You'll also work with adjacent sectors including BNPLs, telcos, utilities, insurers, subscription and direct-to-consumer businesses, and mobility and point-of-sale marketplaces.
• Build pipeline through your own research and outreach, your network, industry events and partnerships.
• Run the full sales cycle: prospecting, discovery, scoping and running the pilot, then procurement, legal review and contracting.
• Grow the accounts you win. Stay close to each client after go-live, deepen executive relationships and expand into new portfolios and products.
• Build relationships with senior decision-makers across credit, collections, risk, finance and operations, and sustain them over years.
• Partner with the Managing Director on territory planning and with our global compliance and operations teams to ensure clients onboard smoothly and continue performing.
• Keep pipeline and forecasts accurate in our CRM.
• Learn our product, compliance approach and the Canadian regulatory landscape in depth.

What you'll bring

• Five or more years of B2B sales experience, with a demonstrated track record of originating and closing your own new business.
• Experience selling into large, complex organizations with multiple stakeholders and formal procurement, security and vendor-risk processes.
• The ability to earn the trust of senior executives and keep it over multiple years.
• Persistence and resilience through long sales cycles.
• Commercial judgment and self-direction. You're comfortable setting your own priorities in a remote-first team where the playbook is still being written.
• Coachability and curiosity. You don't need collections experience; we'll teach you the industry and the Canadian regulatory environment.
• Confidence using AI tools in your daily work.
• Clear, persuasive communication, and fluency in English.

Nice to have

• Experience selling into banks, credit unions, lenders, fintechs or other complex regulated enterprises.
• Fluency in French, which is valuable in the Quebec market.

We care more about how you sell than where you've sold. Some of our best-performing AEs worldwide came from events and distribution sales.

Why you'll love it here

• The chance to shape the Canadian sales playbook that future hires will follow.
• Direct access to the Canada Managing Director and InDebted's global leadership team.
• Uncapped commission tied to the revenue your clients generate.

What success looks like

In your first six months, we'll measure success by the quality of your pipeline, not by revenue. We'll look for meaningful opportunities and real progress into priority enterprise accounts, with pilots under way and a territory plan you own. By the end of year one, success will mean converting pilots into signed MSAs and beginning to grow the accounts you've won.