Director, Software Sales- Upper Mid-Market

Canada
Remote
Posted Jul 20, 2026
1 position

$160,000–$180,000 / year

Opens an external site

Employment type: Full-time
Experience level: Lead · 10+ years
Posting language: English
Working hours: 40 hours per week

Job summary

Lead the strategy to grow new bookings and revenue for companies with $100M+ revenue by scaling a high-performing team of Software AEs. Collaborate cross-functionally to translate market opportunities into repeatable sales motions and manage high-value software agreements.

Job details

About Versapay 🚀 Versapay is the platform that rewires AR by removing barriers from collecting and reconciling B2B payments, providing end-to-end cash flow clarity and ensuring businesses can manage working capital on their terms. By closing the loop for finance teams and their business systems, customers, and payment activity into a single intelligent ecosystem, Versapay transforms money matters into a data-driven advantage. With 10,000 customers and 5M+ companies transacting, Versapay facilitates 110M+ transactions and processes $300B+ in payments volume annually. Think you might be the next Veep to join? Read on!! About 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. \n What 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. What you'll bring to the team: Required * 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. Preferred * 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. \n $160,000 - $180,000 a year OTE ranges from $ 270,000 to $300,000 CAD \n #LI-Remote 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.

What you’ll do

Requirements

Requires 7+ years of SaaS/Fintech experience, including 5+ years leading sales teams and 3+ years managing Upper Mid-Market or Enterprise segments. Must have a proven track record of negotiating with finance leaders (CFOs, Controllers) and implementing proven sales methodologies.