Director, Software Sales- Upper Mid-Market

Versapay

27d • CA$160,000 - CA$180,000 • Remote

About The Position

Versapay is seeking a Director of Software Sales for the Upper Mid-Market to lead the strategy for growing new bookings and revenue within companies over $100M. This role involves building and scaling a team of Software Account Executives (AEs), driving execution through Sales Development and strategic partner channels, and owning the annual revenue target for the Upper Mid-Market team. The position requires close collaboration with Sales, Marketing, Product, Finance, and Partner teams to translate market opportunities into repeatable sales motions, enhance partner leverage, and achieve measurable revenue outcomes. Success in this role demands deep fintech expertise, strong software sales leadership, and the ability to cultivate strategic relationships that benefit customers, partners, and Versapay.

Requirements

• 7+ years of experience in 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, reinforcing, and coaching using a proven sales methodology, with deep knowledge of the sales process from discovery through implementation team handoffs.
• Proven track record of 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 rigor and identifying and replicating core KPIs.
• Comfortable with Salesforce reporting and working with data to understand the business and exceed targets.
• Well organized, managing multiple moving pieces and coordinating internal teams.
• Comfortable working with people at any level in the organization, nurturing relationships and becoming a trusted advisor.
• Competitive attitude with experience crushing a sales quota.

Nice To Haves

• Experience in the payments industry.
• 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: leveraging resources, resolving conflicts, and following through with partners.
• Naturally curious and confident, asking thoughtful questions, listening, learning, and using insights to evangelize fintech solutions.
• Bias toward action: diving in and getting things done.

Responsibilities

• Coach and provide executive sponsorship for a team of Software Sales AEs focused on closing multi-threaded deals from SDRs, FVARs, and Strategic Partner Sales Teams.
• Implement best-in-class sales strategies and processes, and co-create the team's success blueprint.
• Serve as the primary contact for Software prospect 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 customer pain points and effectively build business cases for change.
• 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 measure sales success and partnership effectiveness.
• Monitor sales team performance and track progress towards 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.
• Work with the Product Development team to ensure product-market fit and effective integrations for mutual clients.

Benefits

• OTE ranges from $270,000 to $300,000 CAD
• Equal opportunity employer
• Diversity valued
• No discrimination on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed