Senior Enterprise Sales Executive at Checkout.com

Ontario, Canada

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Fintech, PaymentsIndustries

Requirements

Entrepreneurial Drive: Operate with urgency, persistence, and accountability—running territory like own business
Strategic Acumen: Highly analytical and data-driven; build smart hypotheses, use insights to guide prioritization, and leverage new technologies (including AI) to accelerate performance
Deal Leadership: Strong executive presence and comfort leading complex, multistakeholder Enterprise deals with C-suite engagement
Learning Mindset: Actively seek feedback, iterate quickly, and adapt strategy based on results and evolving conditions
Relationship Building: Exceptional ability to build trust with senior merchant stakeholders and nurture long-term partnerships
Operational Excellence: Highly organized, strong at prioritizing, and effective at managing large pipelines

Responsibilities

Strategically prospect and plan within a defined territory of high-value Enterprise accounts—leveraging market intelligence, networks, and disciplined outbound execution to build a robust pipeline
Engage consultatively with merchant leaders, deeply understanding their payments, risk, and operational challenges to propose tailored, high-impact solutions
Act as deal captain: coordinate cross-functional resources (performance, solutions engineering, risk, legal), build quantitative business cases, and drive opportunities forward with clear, strategic leadership
Lead complex negotiations, manage objections, and consistently bring high-value, multi-product deals to closure
Operate with ownership: track and analyze performance metrics, continuously refine strategy, and help shape local GTM playbook
Represent Checkout.com in-market, helping to raise profile, develop merchant relationships, and contribute insights to global teams

Skills

Enterprise Sales

Fintech

Payments

Go-to-Market

Sales Strategy

Merchant Acquisition

Account Management

Checkout.com

High-performance payments platform for enterprises

About Checkout.com

Checkout.com provides a payments platform that helps businesses process payments, send payouts, and manage card programs. The platform is designed for large enterprises and growing businesses, allowing them to handle high volumes of transactions quickly and reliably. It integrates with clients' existing systems and offers a range of payment services, generating revenue through transaction fees and subscriptions. Unlike many competitors, Checkout.com focuses on providing a comprehensive, cloud-based solution that supports the financial operations of its clients across the globe. The goal of Checkout.com is to streamline payment processes and enhance the payment experience for both businesses and their customers.

London, United KingdomHeadquarters

2012Year Founded

$1,780.1MTotal Funding

SERIES_DCompany Stage

Fintech, Financial ServicesIndustries

1,001-5,000Employees

Benefits

Work-life balance - Flexible working and plenty of time off to unwind. We’ll even give you your birthday off.

Recognition - Peer recognition program and quarterly Hero Awards. We celebrate success together.

Career development - Tailored career development and learning pathways. We’ll help you unlock your potential.

Celebrating diversity - Internal community groups and cultural events. We celebrate our differences.

Staying healthy - A global wellness programme and private health insurance. We support your wellbeing.

Security for the future - Comprehensive plans for you and your loved ones. We’ll take care of you.

Giving back - Employee-led community outreach, payroll giving and a volunteering day. We care about your causes.

Risks

Checkout.com faces increased competition from emerging fintech startups.

Economic instability in the UK and EU may impact Checkout.com's revenue.

Regulatory scrutiny on data privacy could increase compliance costs.

Differentiation

Checkout.com offers payments in over 150 currencies with in-country acquiring.

The platform integrates fraud filters and reporting through a single API.

Checkout.com supports major international cards and local payment methods.

Upsides

Checkout.com is expanding in Japan, enhancing its global presence.

The partnership with Zing increases digital payment methods and product growth.

Checkout.com launched Octopus for online payments, a first for global PSPs.

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