🌴 JobsLeisure.com

Where Work Meets Adventure

← Back to Leisure Jobs

Senior Enterprise Sales Executive Sales Home-based, Canada (ON)

Hospitality Full Benefits Career Growth
Company

Checkout Ltd

Location

remote, Canada

Posted

May 26, 2026

Start Your Adventure

Join our team and work where others vacation

Apply Now

About This Opportunity

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 Checkout.com in‑m...