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 maintaining 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.

About the role

As our first Canada-based Enterprise Account Executive, your primary mandate is net-new logo acquisition, with expansion of our existing Canadian accounts as a secondary focus. You will help build the Canadian sales playbook alongside the Managing Director, executing a relationship-led go-to-market strategy tailored to the Canadian market, building on your network and targeted prospecting, and partnering closely with our operations and compliance teams so clients are onboarded successfully and see sustained performance.

Where you'll work

• Remote within Canada. Greater Toronto Area preferred for customer proximity and industry events. Some travel expected.
• You must hold full working rights in Canada.

What you'll do

• Drive new business development primarily across banks, credit unions and lenders, with adjacent opportunities across BNPLs, telcos, utilities, insurers, subscription and D2C commerce, and mobility and POS marketplaces.
• Support expansion within our existing Canadian client base as a secondary priority, identifying cross-portfolio opportunities and deepening multi-stakeholder relationships.
• Build a high-quality pipeline using your existing network, targeted outreach, industry events, partnerships and inbound interest.
• Lead the full enterprise sales cycle: identifying opportunities, qualifying, positioning the solution, managing procurement, negotiating and closing.
• Collaborate with the Managing Director to execute territory plans and accelerate commercial traction in a longer-cycle, relationship-driven market.
• Work closely with our global delivery, compliance and operations teams to ensure smooth client onboarding and sustained performance.
• Develop strong, trusted relationships with senior decision-makers across credit, collections, risk, finance and operations.
• Provide accurate forecasting and timely reporting of pipeline, activities and progress in our CRM.
• Build expert knowledge of InDebted's products, compliance posture, competitive strengths and the Canadian regulatory landscape.

What you'll bring

• Five or more years of B2B sales experience, with a proven track record of generating new business in enterprise environments.
• Experience selling financial services, collections, fintech, SaaS or other complex solutions to senior decision-makers (C-level, Heads of Credit, Heads of Collections, Risk, Finance and similar).
• Demonstrated success operating in long-cycle enterprise sales with multiple stakeholders and rigorous procurement, security and vendor-risk processes.
• Ability to quickly learn the compliance, privacy and regulatory nuances of digital collections in Canada, including provincial collection agency licensing, PIPEDA and Quebec's Law 25.
• Exceptional communication and presentation skills, equally comfortable in executive-level conversations and hands-on solution selling.
• An entrepreneurial, self-directed approach, comfortable operating with autonomy, high ownership and clear accountability in a remote-first team.
• Fluency in English.

Nice to have

• Established relationships across Canadian banks, credit unions and lenders, or adjacent sectors such as telcos, utilities, BNPLs and large consumer brands.
• Fluency in French, a strong advantage given the Quebec market.

Why you'll love it here

• Genuine market ownership, as our first Enterprise Account Executive in Canada, with the mandate and resources to shape how we win here.
• Direct executive access, working closely with the Canada Managing Director and InDebted's global leadership team.
• Autonomy to own your territory strategy and execution, supported by global technology, operations and compliance capabilities.
• Uncapped earnings that scale directly with the business you close.
• The opportunity to shape the Canadian sales playbook that future hires will follow.

What success looks like

In your first 90 days, you will build a focused territory plan, develop strong knowledge of our product and market, and establish a qualified pipeline across priority Canadian accounts. During your first year, you will deliver against an agreed ramped revenue target, win net-new enterprise clients and identify meaningful expansion opportunities within existing accounts.