Director, Customer Success Management- Remote

Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. As Director of Customer Success, you will lead a high-impact team focused on ensuring maximum value for Highspot’s Enterprise and Strategic customer segments.

Responsibilities:

• Ensure every customer experiences consistent, high-quality engagement throughout their lifecycle
• Partner with Sales, Renewals, and Services leadership to drive adoption, retention, and expansion across the customer base
• Model and coach a cohesive account team approach — ensuring CSMs, TAMs, Account Executives, and Renewal Managers operate as a unified team aligned on customer outcomes
• Provide executive sponsorship for strategic accounts and serve as a trusted advisor to C-level customer stakeholders
• Uphold one of the hallmarks of Highspot’s Customer Success team by developing and maintaining deep knowledge of our platform and its integrations within customer environments
• Ensure the CSM organization is equipped to provide best practices, training, and guidance that maximize customer value and adoption
• Champion product expertise as a differentiator, reinforcing credibility and trust with customers at every level
• Lead with a people-first mindset — genuinely investing in the development, wellbeing, and career growth of every member of your team
• Hire, coach, and develop top talent at every level of the CSM org, leading with high emotional intelligence and self-awareness
• Set and uphold high performance and engagement standards, balancing accountability with empathy
• Cultivate a culture that embodies Highspot’s guiding principles, especially 'Enjoy the Ride.'
• Lead a team in owning and exceeding a dedicated customer retention target for your assigned strategic portfolio
• Drive adoption of MEDDPICC sales methodology
• Ensure your CSMs run proactive renewal validation — confirming stakeholder alignment, surfacing risk, and documenting customer value — in close partnership with their Renewal Managers
• Maintain forecasting accuracy for renewals and expansion, providing reliable, data-driven insights to leadership
• Drive your CSMs to surface and qualify expansion opportunities in partnership with Account Executives who own the commercial relationship, stepping in to support key deals as needed
• Partner with Product leadership to channel customer insights into product strategy and innovation
• Work with Marketing and Sales to align on customer advocacy, referenceability, and expansion opportunities
• Collaborate with Operations and Analytics to ensure data-driven decision-making across the CSM function
• Build and inspire a segment-focused Customer Success team that sets the standard for excellence across Enterprise and Strategic accounts
• Implement scalable processes, tools, and metrics that drive efficiency, consistency, and predictable outcomes
• Develop the leadership bench within the CSM org, ensuring succession planning and long-term organizational strength

Requirements:

• 8+ years of experience leading high-performing teams in Customer Success, post-sales, or sales
• 6+ years of direct client management experience specifically tailored to Enterprise or Strategic segments
• Demonstrated ability to design, build, and scale global organizations and processes
• Track record of owning retention and growth metrics, including experience partnering with renewal and sales teams on commercial execution
• Experience building and modeling cohesive account team motions across CS, Sales, and Renewals
• Proven executive leadership and decision-making capabilities with strong operational rigor
• High emotional intelligence and a people-first leadership style — you lead with empathy, build trust quickly, and bring out the best in the people around you
• Strong communication and storytelling skills, with the ability to influence internal stakeholders and engage with C-level executives
• Deep familiarity with SaaS businesses, including metrics, challenges, and lifecycle dynamics
• Experience working cross-functionally with Product, Sales, Services, and Marketing to deliver seamless customer outcomes
• Familiarity with MEDDPICC or comparable sales methodologies and their application within a Customer Success context
• Successful history of hiring, developing, and retaining world-class talent across leadership and frontline roles
• Strong technical and product acumen, including experience with CRM platforms (Salesforce/Dynamics 365) and sales enablement technologies
• Entrepreneurial mindset, adaptable to change, with a focus on solutions and opportunities