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Director, Software Sales- Upper Mid-Market

VersapayCanadaFull-timeC$160,000 - C$180,000 per yearPosted Oct 21, 2026Closes Dec 20, 2026

Versapay has an opening for a Director, Software Sales- Upper Mid-Market as a remote role open to applicants in Canada. It is listed as a full-time, leadership position.

Written by Dev Global Jobs

DGJ summary of this job

Our own short read of this listing, built only from the facts it gives. The employer’s original text follows further down.

Versapay has an opening for a Director, Software Sales- Upper Mid-Market as a remote role open to applicants in Canada. It is listed as a full-time, leadership position.

Reading the advert, the employer asks for 7+ years of experience.

Skills and tools named in the text include Salesforce, sales, negotiation, B2B and SaaS.

The listing gives the pay as C$160,000 - C$180,000 per year.

Dev Global Jobs found this job on Himalayas on Oct 21, 2026; applications close on Dec 20, 2026.

Employer
Versapay
Location
Remote (Canada)
Job type
Full-time
Level (from the title)
leadership
Pay
C$160,000 - C$180,000 per year
Experience asked
7+ years
Found
Oct 21, 2026 on Himalayas
Closes
Dec 20, 2026
Employer text
764 words, about 3 min to read
Skills named in the advert
SalesforcesalesnegotiationB2BSaaS
Before you apply
  • Apply only on the official page (himalayas.app). Dev Global Jobs is not the employer and never asks for a fee.
  • Compare your own experience with the 7+ years the advert asks for, and show it clearly near the top of your CV.
  • Mirror the skills the advert names (Salesforce, sales, negotiation and B2B) in your CV where you really have them; applicant tracking systems look for these words.
  • Plan to apply before Dec 20, 2026.
  • Read the employer’s full text below (about 3 min) before you apply.
  • Build or check your CV with the free DGJ CV Builder.
Only on Dev Global Jobs

DGJ Insight

Our own data about this role and place, from official statistics and our live job index.

Updated Nov 1, 2026
Pay benchmark
Average wage, Canada
CAD 85,588 average / year

Source: OECD Average annual wages, 2025

Job description

About the role

Full text from the employer, as published on Himalayas, arranged into sections. Nothing added or removed.

01About Versapay 🚀

Versapay turns accounts receivable (AR) into a competitive advantage.Inefficient AR processes slow cash flow and stall growth. Versapay removes friction, unlocks working capital, and accelerates momentum, giving finance leaders the clarity and control they need to drive business forward. Versapay automates accounts receivable, removing barriers to collecting and reconciling B2B payments. Our solutions connect finance teams, customers, and business systems in one ecosystem to ensure cash flow clarity. With over 10,000 customers and 5M+ companies transacting on the platform, Versapay processes over 110M transactions and $257B annually.Think you might be the next Veep to join? Read on!!

02About the Role

As the Director of Software Sales - Upper Mid-Market, you will lead Versapay’s strategy to grow new bookings and revenue across $100M+ companies. You will build and scale a high-performing team of Software AEs, drive execution across Sales Development and strategic partner channels, and own the Upper Mid-Market team’s annual revenue target. Partnering closely with Sales, Marketing, Product, Finance, and Partner teams, you will translate market opportunity into repeatable sales motions, stronger partner leverage, and measurable revenue outcomes. This role requires deep fintech expertise, strong software sales leadership, and the ability to build strategic relationships that create value for customers, partners, and Versapay.

03What you'll do

  • Coach and executive sponsor a team of highly skilled and passionate 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 key performance indicators (KPIs) and operating mechanisms to continuously measure sales success and partnership effectiveness.
  • Monitor sales team performance and track progress toward achieving targets.
  • Provide regular reports and updates to senior management on sales activities and outcomes, including conversion rates, pipeline generated, and pipeline closed.
  • Collaborate cross-functionally with Sales Development, Sales Engineering, Product, Marketing, Sales Support, Underwriting, and Implementation teams.
  • Collaborate with the Product Development team to ensure product-market fit and confirm that integrations are working effectively for mutual clients.

04Required

  • 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 as part of the core buying persona, including Controllers, VPs of Finance, CFOs, CTOs, CIOs, and/or CAOs.
  • Experience implementing, reinforcing, and providing ongoing coaching using a proven sales methodology, with deep knowledge of the sales process from discovery through solutioning, ROI discussions, executive proposals, negotiation, closing, and implementation team handoffs.
  • Proven track record building relationships with key decision makers, moving opportunities forward, delivering results, and exceeding quota.
  • Experience working with and leading virtual teams across functions and geographies.
  • Experience creating operational rigour and identifying and replicating core KPIs.
  • Experience in the payments industry is a plus.
  • 05Preferred

  • Passion for sales and all things sales-related.
  • Excellent at building strong relationships and collaborating with others.
  • Ability to prioritize multiple projects, opportunities, and personalities across the deal cycle.
  • Problem-solving mentality: you leverage internal and/or external resources, resolve conflicts, and follow through with partners.
  • Naturally curious and confident, you ask thoughtful questions, listen, learn from conversations, and use those insights to evangelize how innovative fintech solutions can help partners and prospects on their path to digital transformation.
  • Very comfortable with Salesforce reporting and working with both structured and raw data to understand the business well enough to grow and exceed targets.
  • Well organized, you manage many moving pieces at once, often coordinating internal teams to bring the best Versapay can offer to clients.
  • Bias toward action: you love to dive in and get things done.
  • Comfortable working with people at any level in the organization, you nurture relationships as needed and become a trusted advisor.
  • Competitive attitude with experience crushing a sales quota; you love closing deals.
  • We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

    Originally posted on Himalayas

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