Note: The job is a remote job and is open to candidates in USA. 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

Skills

• 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

Benefits

• Comprehensive medical, dental, vision, disability, and life benefits
• Health Savings Account (HSA) with employer contribution
• 401(k) Matching with immediate vesting on employer match
• Flexible PTO
• 8 paid holidays and 5 paid days for Annual Holiday Week
• Quarterly Recharge Fridays (paid days off for mental health recharge)
• 18 weeks paid parental leave
• Access to Coaches and Therapists through Modern Health
• 2 volunteer days per year
• Commuting benefits

Company Overview