Posted Sep 15, 2026

Director, Software Sales – Upper Mid-Market

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Job Description: • Lead Versapay’s strategy to grow new bookings and revenue across $100M+ companies. • Build and scale a high-performing team of Software AEs. • Drive execution across Sales Development and strategic partner channels. • Own the Upper Mid-Market team’s annual revenue target. • Partner closely with Sales, Marketing, Product, Finance, and Partner teams. • Translate market opportunity into repeatable sales motions, stronger partner leverage, and measurable revenue outcomes. • Negotiate high-value software agreements and terms to ensure favorable outcomes for both customers and Versapay. 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. • Experience in the payments industry is a plus. Benefits: • Health insurance • Retirement plans • Flexible work arrangements • Professional development • Bonuses