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About the role

  • Enterprise Account Executive responsible for full-cycle sales at Alternative Payments, a fintech company revolutionizing payment systems for SMBs. Seeking a proactive builder focused on self-sourcing and closing deals.

Responsibilities

  • Own your pipeline end to end. Generate your own pipeline through outbound prospecting, targeted account research, referrals, and partnerships — you are entirely responsible for building the top of your funnel, not waiting for leads to be handed to you.
  • Run the full sales cycle from first outreach through discovery, demo, business case, negotiation, and close — with sole ownership of every deal in your book.
  • Build and execute strategic account plans for enterprise and upmarket targets, mapping multi-stakeholder buying committees and navigating complex procurement, security, and finance approval processes.
  • Serve as a trusted advisor to CFOs, finance leaders, and operations executives, translating Alternative Payments' platform into clear, quantified business value.
  • Collaborate with cross-functional teams — Marketing, Product, and Customer Success — to sharpen messaging, inform the roadmap, and ensure seamless handoffs after close.
  • Travel expectation: This role is expected to be on the road approximately 25% of the time.
  • Consistently hit and exceed quota, forecasting accurately and maintaining a clean, well-documented pipeline in our CRM.
  • Propose improvements and help establish the outbound playbooks, workflows, and best practices that will scale our enterprise motion as we grow.

Requirements

  • 5+ years of full-cycle B2B sales experience, with a track record of self-sourcing pipeline and closing complex, multi-stakeholder deals.
  • Demonstrated success carrying and exceeding a quota in an enterprise or upmarket segment (larger deal sizes, longer sales cycles, multiple decision-makers).
  • Strong outbound and prospecting skills — you are comfortable and effective building pipeline from scratch across email, phone, social, and in-person channels.
  • Proven experience selling a technical or financial software product, with the ability to lead value-based, ROI-driven conversations with senior finance and operations stakeholders.
  • Strong communication and executive presence to build credibility and drive alignment across teams, regions, and stakeholders.
  • A proactive, ownership mindset with the ability to operate independently, prioritize ruthlessly, and drive deals forward without hand-holding.

Benefits

  • Competitive salary tailored to your experience, skills, and expertise.
  • Equity opportunities so you can share in our growth and success.
  • Unlimited PTO and flexibility when you need it the most.
  • Yearly learning & development stipend to help you grow and do your best work.

Job type

Full Time

Experience level

Mid levelSenior

Salary

CA$150,000 per year

Degree requirement

Bachelor's Degree

Location requirements

HybridTorontoCanada

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