Director, Software Sales – Upper Mid-Market

Versapay

Director of Software Sales leading strategy for Versapay to grow new bookings among upper mid-market clients while managing a high-performing team.

Posted 7/21/2026full-timeRemote • 🇨🇦 CanadaLead💰 CA$160,000 - CA$180,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive experience in leading SaaS Sales teams, negotiating high-value software agreements, and implementing effective sales strategies. Proven ability to build relationships with key decision makers and track sales performance through established KPIs.

Highest-signal resume keywords

SaaS Sales LeadershipNegotiation SkillsSales Methodology ImplementationKPI DevelopmentCross-Functional Collaboration

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Sales Strategy DevelopmentSales Process KnowledgePipeline ManagementBusiness Case DevelopmentPerformance Monitoring

Soft Skills

CoachingRelationship BuildingCommunicationProblem Solving

Industry Keywords

SaaSFintechPayments IndustryEnterprise SalesUpper Mid Market

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

🌐 Worldwide ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs ✉️ Email Alerts 👤 Account Versapay Website LinkedIn All Job Openings 201 - 500 employees Founded 2006 🤝 B2B 💳 Fintech ☁️ SaaS 💰 $4M Post-IPO Debt on 2019-11 B2B
Fintech
SaaS Versapay is a company offering a collaborative accounts receivable (AR) network designed for industry-leading AR automation and B2B payment solutions. The platform provides tools to automate AR tasks, manage cash applications, and facilitate B2B payments across channels, integrating with ERP systems like Microsoft Dynamics, NetSuite, and Sage Intacct. Versapay's solutions help teams collaborate effectively over the cloud, reducing manual processing and improving cash flow. The company focuses on simplifying the invoice-to-cash process using artificial intelligence, enhancing customer experience with easy-to-use portals, and offering comprehensive digital payment methods. Versapay also supports large-scale B2B transactions worldwide, promoting efficiency and environmental benefits through digital invoicing. Director, Software Sales – Upper Mid-Market Job not on LinkedIn 🔥 34 minutes ago 🇨🇦 Canada – Remote 💵 $160k - $180k / year ⏰ Full Time 🔴 Lead 🤑 Sales Apply Now Find Hiring Managers Customize resume + cover letter Report problem ☆ Save ☑️ Mark as applied ❌ Hide 📋 Description
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. 🎯 Requirements
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.
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