Vice President, Customer Success

Summary

Join ConnectWise as the Vice President of Customer Success, leading a global team to drive adoption, retention, expansion, and advocacy across the SMB customer base. You will be responsible for building and scaling digital customer success programs for high-volume SMB customers, while also leading a high-touch, white-glove success team for strategic accounts. This role requires a deep expertise in customer success, a passion for innovation, and the ability to lead and inspire large, distributed global teams.

Requirements

• Exceptional leadership and customer service skills
• Ability to effectively communicate complex problems and information that is understandable to colleagues cross-functionally
• Willingness to work in a team environment
• Strong organizational skills to give the team direction
• Professional presence suitable for interaction in meetings, in-person, or via email, as well as at internal and external facing events
• Excellent presentation and communication skills
• Demonstrated ability to lead and inspire large, distributed global teams
• Excellent communication, strategic thinking, and executive presence
• Passion for customer success and delivering best-in-class experiences
• Strong desire to innovate and be curious
• Bachelor’s degree in related field or equivalent business experience
• 10+ years of experience in Customer Success, with 5+ years in senior leadership roles
• Proven experience supporting SMB customers at scale through digital success models in a SaaS model
• Track record of building and optimizing white-glove high-touch programs for enterprise clients

Responsibilities

• Sets goals and objectives for multiple teams for the achievement of operational results
• Functions as the SME of the Customer Success team and provides updates and communication to Executive Leadership
• Manages experienced professional and management level colleagues
• Develop plans and talent required to optimize the execution of the Customer Success team’s strategies
• Manages, mentors, and coaches to develop a world-class customer success organization
• Coordinates cross-functional communication to align initiatives and strategies to drive efficiency
• Develop and execute a comprehensive customer success strategy that aligns with company goals and drives customer retention, renewals, growth, and satisfaction
• Define and lead segmentation strategies across SMB, mid-market, and enterprise customers, with tailored engagement models for each
• Build and scale a digital-led customer success motion that includes automation, in-product guidance, customer journeys, and tech-touch campaigns for the SMB segment
• Leverage tools like Gainsight and Salesforce to deliver scalable and data-driven customer success experiences while partnering with Marketing and our Learning teams
• Oversee the high-touch success team responsible for onboarding, training, strategic guidance, and relationship management for key Strategic accounts
• Ensure high levels of NRR, CSAT, and customer advocacy in this segment
• Foster a culture of accountability, customer-centricity, and continuous improvement
• Cultivate a culture space that focuses on career development
• Own the end-to-end customer journey — from onboarding and adoption to renewal and advocacy
• Partner cross-functionally with Sales, Services, Product, Marketing, and Support to create seamless and valuable customer experience
• Help evolve KPIs and dashboards to track customer health, engagement, and team performance
• Regularly report on customer outcomes, churn/retention trends, and success impact to the executive team – must be data driven

Benefits

• Onsite/Hybrid/Remote depending on location
• 30-40% travel may be required (regional and international)