Director, Software Sales – Upper Mid-Market

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead and mentor a team of dedicated Software Sales Account Executives (AEs) tasked with finalizing multi-threaded deals referred by Sales Development Representatives (SDRs), Field Account Representatives (FVARs), and Strategic Partner Sales Teams to optimize sales performance.

• Implement top-notch sales strategies and processes while co-developing and executing the framework for the team’s success.

• Serve as the main point of contact for inquiries, concerns, and escalations from Software prospects.

• Negotiate high-stakes software contracts and terms to achieve beneficial outcomes for both clients and Versapay.

• Maintain an in-depth understanding of the challenges we address and how to construct a compelling business case for change with prospects.

• Work closely with Marketing and Partner teams to capitalize on partner relationships, reach booking targets, and create joint marketing efforts, co-selling opportunities, and collaborative development projects.

• Set key performance indicators (KPIs) and operational frameworks to consistently evaluate sales success and partnership efficiency.

• Track sales team performance and monitor progress towards reaching targets.

• Provide regular updates and reports to senior management on sales activities and results, including conversion rates, pipeline generation, and pipeline closure.

• Collaborate across departments with Sales Development, Sales Engineering, Product, Marketing, Sales Support, Underwriting, and Implementation teams.

• Work with the Product Development team to ensure the product aligns with market needs and verify that integrations function effectively for shared clients.

⛳️ Requirements

• Over 7 years of experience in a dynamic SaaS or Fintech environment.

• More than 5 years of experience leading a SaaS Sales team.

• At least 3 years of experience managing an Upper Mid Market or Enterprise team.

• More than 5 years of experience negotiating with Finance leaders as part of the primary buying group, including Controllers, VPs of Finance, CFOs, CTOs, CIOs, and/or CAOs.

• Proven experience in applying, reinforcing, and providing ongoing coaching with a recognized sales methodology, possessing a thorough understanding of the sales process from discovery through solution development, ROI discussions, executive proposals, negotiation, closing, and handoffs to implementation teams.

• A successful history of building relationships with key decision-makers, advancing opportunities, delivering results, and surpassing quotas.

• Experience in managing and leading virtual teams across various functions and locations.

• Background in establishing operational rigor and identifying and replicating essential KPIs.

• Experience within the payments sector is advantageous.

🏝️ Benefits

• Competitive salary with performance-based bonuses.

• Comprehensive health and wellness benefits.

• Opportunities for professional development and growth.

• Flexible work arrangements.

• Engaging work environment with a collaborative culture.