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Director, Software Sales- Upper Mid-Market

Versapay· Sales – UMM Sales
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Hybrid (Canada)$160k - $180k + bonusRegular Full-TimePosted 3mo ago

About the role

Direct leadership role driving new bookings and revenue for Versapay’s Upper Mid-Market segment (targeting $100M+ companies). Build and scale a high-performing Software AEs team, manage Sales Development and partner channels, and own the annual revenue target. Collaborate with Marketing, Product, Finance, and Partners to translate market opportunity into repeatable sales motions and measurable revenue outcomes.

Responsibilities

  • Coach and executive sponsor a team of Software Sales AEs responsible for closing multi-threaded deals referred by SDRs, FVARs, and Strategic Partner Sales Teams to maximize sales.
  • Deploy best-in-class sales strategies and processes and co-create and execute the blueprint for the team’s success.
  • Act as the primary point of contact for Software prospects’ inquiries, concerns, and escalations.
  • Negotiate high-value software agreements and terms to ensure favorable outcomes for both customers and Versapay.
  • Maintain a deep understanding of the pains we solve and how to build a business case for change with prospects.
  • Collaborate with Marketing and Partner teams to leverage partner relationships, meet bookings targets, and develop joint marketing initiatives, co-selling opportunities, and co-development projects.
  • Establish KPIs and operating mechanisms to measure sales success and partnership effectiveness.
  • Monitor sales team performance and track progress toward targets.
  • Provide regular reports to senior management on sales activities and outcomes (conversion rates, pipeline generated, pipeline closed).
  • Collaborate cross-functionally with Sales Development, Sales Engineering, Product, Marketing, Sales Support, Underwriting, and Implementation teams.
  • Collaborate with Product Development to ensure product-market fit and effective mutual-client integrations.

Qualifications

  • 7+ years of experience working for a fast-paced SaaS or Fintech company.
  • 5+ years of experience leading a SaaS Sales team.
  • 3+ years of experience leading an Upper Mid Market or Enterprise team.
  • 5+ years of experience negotiating directly with Finance leaders (Controllers, VPs of Finance, CFOs, CTOs, CIOs, CAOs).
  • Experience implementing and coaching using a proven sales methodology with end-to-end sales process.
  • Proven track record building relationships with key decision makers, moving opportunities forward, exceeding quota.
  • Experience working with and leading virtual teams across geographies.
  • Experience creating operational rigor and replicating core KPIs.
  • Experience in the payments industry is a plus.

Skills

Required:SaaS sales leadershipNegotiation with finance leadersSales process methodology
Last updated Oct 21, 2026. Interested? Apply on the company site.

About Versapay

Accounts receivable automation platform

Versapay’s unified accounts receivable automation platform simplifies the invoice-to-cash process by automating invoicing, facilitating B2B payments, and streamlining cash application with AI.

accounts receivableautomationB2B paymentsinvoice-to-cashAI
Company profileWebsite

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