OTT Pay is part of the OTT Financial Group, which is a fully funded, established fintech leader delivering streamlined financial payment solutions. We are a results-driven organization aggressively scaling our mobile-first platform, which spans acquiring, card issuing, cross-border payments, loyalty solutions, and our rapidly evolving SuperApp ecosystem.
We are seeking an experienced Key Account Manager to drive enterprise-level growth within Canada’s restaurant, retail, and multi-location service sectors. This is not a high-volume transactional sales role. You will focus on winning and expanding large enterprise accounts, each representing significant annual transaction volume and long-term strategic value.
The ideal candidate thrives in complex sales environments, manages multi-stakeholder buying processes, and builds trusted advisor relationships with senior executives.
What’s in it for you:
- Base Salary $90K + Commissions
- Extended Health, Dental, and Vision Benefits
- Life and Disability Insurance
- Performance Bonus
- Vacation Leave
- Learning and Professional Development Support
- A chance to work in a dynamic, collaborative, progressive and high performing team
- Community involvement through the annual Terry Fox Run
- Tremendous opportunities for Growth and Development
Key Responsibilities
- Enterprise Account Acquisition
• Identify, target, and win multi-location and enterprise-level clients
• Conduct strategic account research and develop executive outreach plans
• Manage long, complex sales cycles (3–12+ months)
• Achieve 12-20 new enterprise wins annually
2. Complex Sales Management
• Navigate multi-stakeholder environments (Finance, IT, Operations, Procurement)
• Lead RFP responses, proposal development, and contract negotiations
• Coordinate internal technical, legal, and product teams to advance deals
3. Solution & Value Positioning
• Design tailored payment solutions aligned with client business models
• Build and present ROI-driven business cases to senior leadership
• Address technical integration requirements in partnership with engineering
4. Account Growth & Retention
• Serve as a long-term strategic advisor post-sale
• Conduct regular business reviews and identify expansion opportunities
• Drive upsell, cross-sell, and footprint growth while maintaining strong retention
5. Strategic Contribution
• Gather competitive and market insights from enterprise clients
• Provide structured feedback to leadership and product teams
• Support development of vertical and enterprise growth strategies
Skills & Competencies
• Strong executive-level communication and presentation skills
• High commercial acumen and financial literacy (ROI, TCO, EBITDA understanding)
• Strategic thinker with consultative selling approach
• Strong stakeholder mapping and influence management
• Excellent organizational and pipeline management skills
• Strong negotiation and commercial acumen
• Excellent relationship-building and communication skills
• Ability to engage executive and technical stakeholders
• Self-starter with an entrepreneurial mindset
Preferred Qualifications
• Existing network within Canadian POS or ISV ecosystems
• Experience building a partner program from early stage
• Background in restaurant, retail, or SaaS verticals
Inclusivity Statement
OTT Financial Group is committed to fostering an inclusive and accessible environment where all employees feel valued and respected. We are committed to providing reasonable accommodation, if required, and will work with you to meet your need.
OTT Financial Group Toronto, Ontario, CAN Office
1123 Leslie Street, Toronto, Ontario, Canada, M3C 2K5
OTT Financial Group Markham, Ontario, CAN Office
96 Steelcase Rd W, Markham, ON, Canada, L3R 3J9
OTT Financial Group North York, Ontario, CAN Office
5140 Yonge Street, Suite 510, North York, Ontario, Canada, M2N 6L7
