Head of Sales

Cavallo is looking for a leader who can build and operate the customer growth engine for our Microsoft Solutions business. We are not looking for a relationship manager. This role owns growth from existing customers. New logo acquisition is owned by the sales organization. Your mission is to maximize customer lifetime value through retention, adoption, expansion, advocacy, and customer success across the Microsoft Solutions Segment.

Microsoft Solutions sits at the center of two important opportunities for Cavallo. First, we have a large and loyal base of SalesPad customers that represents significant recurring revenue and expansion potential. Second, we are investing in the future through Business Central and other Microsoft-based solutions that require a modern, scalable customer growth motion.

You will lead our Customer Growth team and build the systems, playbooks, metrics, and operating disciplines that ensure customers achieve measurable business outcomes while Cavallo captures the full value of every customer relationship.

Success in this role means:

• Achieving world-class customer retention.
• Driving strong Net Revenue Retention through expansion and adoption.
• Building a repeatable customer growth playbook that scales with the Microsoft Solutions business.
• Creating deep alignment between customer outcomes, revenue growth, and profitability.
• Establishing customer growth as a competitive advantage for the Microsoft Solutions segment.

• Own Customer Lifetime Value: Own retention, expansion, adoption, and customer advocacy across the Microsoft Solutions customer base. Drive Net Revenue Retention and customer health outcomes. Build account planning and expansion disciplines, and create visibility into churn risks and growth opportunities.
• Build the Customer Growth Function: Develop the operating model for Customer Growth. Create scalable customer success, renewal, and expansion playbooks. Establish customer health scoring and growth metrics, and build the processes and systems needed to support future growth.
• Lead the Team: Recruit, develop, and lead a high-performing Customer Growth organization. Establish clear accountability, performance standards, and coaching rhythms while fostering a culture of ownership, urgency, and customer value creation.
• Partner Across the Business: Work closely with Sales, Professional Services, Product, and Marketing. Ensure customers achieve measurable business outcomes. Drive customer feedback into product and service improvements, and identify opportunities for Business Central adoption and broader solution expansion.
• Drive Operational Excellence: Partner with RevOps to ensure accurate customer reporting and forecasting. Implement customer health dashboards and performance reporting, and create disciplined renewal, expansion, and account review processes.

• 7+ years in Customer Success, Account Management, Revenue Growth, or related leadership roles.
• Experience managing and growing significant recurring revenue portfolios.
• Demonstrated success improving retention and Net Revenue Retention.
• Experience building teams, processes, and scalable operating models.
• Experience in B2B SaaS, ERP, distribution technology, or related markets.
• You think like an owner, not a service provider.
• You understand that customer success and commercial success are inseparable.
• You are highly analytical and data-driven.
• You build systems, not dependencies.
• You thrive in environments undergoing transformation.
• You are willing to lead from the front when needed.

• Month 1: Assess customer portfolio, team capabilities, and current operating model. Identify retention risks, expansion opportunities, and process gaps.
• Month 2: Implement customer health frameworks and account planning disciplines. Establish operating cadence and performance metrics.
• Month 3: Deliver a 12-month Customer Growth strategy for Microsoft Solutions. Present retention, expansion, and NRR improvement roadmap. Demonstrate measurable progress in customer visibility and growth execution.

• Shape and own the future of a high-growth, high-impact product portfolio.
• Operate at startup speed with established resources-the best of both worlds.
• Be part of an elite team of technologists, business leaders, and disruptors.