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.

Benefits

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

Complex Sales Management

Navigating 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

Solution & Value Positioning

Design tailored payment solutions aligned with client business models

Build and present ROI-driven business cases to senior leadershipAddress technical integration requirements in partnership with engineering

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

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

OTT Financial Group is committed to fostering an inclusive and accessible setting 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.

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📌 Key Account Manager (Ontario)
🏢 OTT Financial Group
📍 Ontario