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Senior Enterprise Sales Executive Sales Home-based

Remote / Online - Candidates ideally in
Delta, BC, Canada
Listing for: Checkout Ltd
Remote/Work from Home position
Listed on 2026-06-08
Job specializations:
  • Sales
    Business Development, B2B Sales
  • Business
    Business Development
Job Description & How to Apply Below
Position: Senior Enterprise Sales Executive Sales Home-based ON)

What you will do

  • 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 our local GTM playbook.
  • Represent  in‑market
    , helping to raise our profile, develop merchant relationships, and contribute insights to our global teams.
Core Competencies
  • Entrepreneurial Drive:
    Operate with urgency, persistence, and accountability—running territory like your own business.
  • Strategic Acumen:
    Highly analytical and data‑driven, building smart hypotheses, using insights to guide prioritisation, and leveraging 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 organised, strong at prioritising, and effective at managing large deal cycles with multiple moving parts.
  • Communication:
    Clear, compelling written and verbal communication skills.
What Makes This Role Unique
  • Founding market team:
    Shape the GTM motion, culture, and strategy for Canada from day one.
  • High‑impact market:
    Canada is a top strategic priority for  globally in 2026 and beyond.
  • Best‑in‑class product + new local acquiring capabilities:
    Sell a modern platform that already wins with sophisticated merchants—now enabled for true local performance in Canada.
  • Career‑defining opportunity:
    Outstanding performers will have significant room for advancement as the Canada organization scales.
Benefits
  • Hybrid working model offering flexibility, with three days per week in the office to support collaboration and connection.
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Position Requirements
10+ Years work experience
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