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.

What You'll Do

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.

Your Background

8+ years of experience in Customer Success, post-sales, or sales leadership in SaaS, with a focus on Enterprise or Strategic segments.
6+ years of direct client management experience with enterprise-level customers.
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.

This position is available either in-office or remote, as applicable, at the following locations:

Arizona - Remote
Arkansas - Remote
California - Remote
Connecticut - Remote
Florida - Remote
Georgia - Remote
Idaho - Remote
Illinois - Remote
Maryland - Remote
Massachusetts - Remote
Michigan - Remote
Minnesota - Remote
Missouri - Remote
Montana - Remote
Nevada - Remote
New Hampshire - Remote
New Jersey - Remote
New York - Remote
North Carolina - Remote
Ohio - Remote
Oregon - Remote
Pennsylvania - Remote
South Carolina - Remote
Tennessee - Remote
Texas - Remote
Utah - Remote
Virginia - Remote
Washington - Remote
Washington - Seattle
Washington, D.C. - Remote
Wisconsin - Remote

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

Equal Opportunity Statement

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of age, ancestry, citizenship, color, ethnicity, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or invisible disability status, political affiliation, veteran status, race, religion, or sexual orientation.

Did you read the requirements as a checklist and not tick every box? Don't rule yourself out! If this role resonates with you, hit the ‘apply’ button.