Director, Customer Success Management- Remote

About this role

About Highspot
Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. On a mission to transform the way millions of people work with sales enablement, Highspot is committed to building breakthrough software with a spark of magic. We believe a great place to work is about more than the work – it’s about what the company stands for, and how it authentically represents its values in the real world. To this end, we have put intentional focus on creating equitable workspaces for each of our employees. Our goal is to create a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change, with the ability to transform themselves, their workplace, and their world.

About the Role
As Director of Customer Success, you will lead a high-impact team of Customer Success Managers focused on Highspot’s Enterprise and Strategic customer segments. You will drive execution and strategic account management to ensure our largest customers achieve maximum value from our platform. This role owns the post-sales engagement, adoption, and expansion strategy for a significant portfolio, acting as a key leader in scaling team performance and fostering deep customer partnerships. You will ensure your CSMs partner effectively with Renewal Managers and Account Executives to drive renewal readiness and commercial outcomes — modeling and coaching the cohesive account team approach that drives the best results for customers, and stepping in to support when needed. Above all, you bring a people-first mindset — leading with high emotional intelligence, investing deeply in your team’s growth, and building the kind of trust that drives both employee and customer outcomes. You will work with leaders across Sales, Services, and Product to align on customer outcomes and serve as a senior voice of the customer, ensuring their success and long-term growth.

Drive Customer Value & Growth

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.

Cultivate Deep Product Expertise

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.

Foster a High-Performance Culture

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.”

Drive Commercial Impact & Retention

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.

Collaborate Cross-Functionally

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.

Lead & Scale the Organization

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. 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…