Head of Customer Success- Remote

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 Head of Customer Success, you will lead Highspot’s Customer Success organization, shaping the vision, strategy, and execution that ensures our customers achieve maximum value from our platform. This high-impact, executive role spans all customer segments—from SMB to Strategic and Enterprise—owning the global CSM team and driving our post-sales engagement, adoption, and expansion strategy. You will be responsible for scaling and developing a world-class Customer Success organization, fostering strong customer partnerships, and ensuring our customers realize the full benefits of Highspot. You will work closely with leaders across Services, Sales, Renewals, Product, and Marketing to define and implement customer strategy, and you will serve as the executive voice of the customer, championing their success at the highest levels of the company.

What You’ll Do

Drive Customer Value & Growth

• Ensure every customer experiences a consistent, high-quality engagement throughout their lifecycle.
• Partner with Sales, Renewals, and Services leadership to drive adoption, retention, and expansion across the customer base.
• 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 for our team, reinforcing credibility and trust with customers at every level.

Foster a High-Performance Culture

• Hire, coach, and develop top talent at every level of the CSM org.
• 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.”

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, reference-ability, 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 Customer Success organization that sets the standard for excellence and drives outcomes across all segments.
• 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

• 12+ years of experience leading high-performing Customer Success or post-sales organizations in a SaaS environment, with proven success at scale.
• 7+ 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, growth, and customer satisfaction metrics across a large customer base.
• Proven executive leadership and decision-making capabilities with strong operational rigor.
• Strong communication and storytelling skills, with the ability to influence internal stakeholders and engage externally 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.
• Successful history of hiring, developing, and retaining world-class talent across leadership and frontline roles.
• Strong technical and product acumen, with the ability to translate customer needs into product strategy.
• Experience with enterprise SaaS technologies (CMS/DMS, CRM platforms such as Salesforce/Dynamics 365).
• Entrepreneurial mindset, adaptable to change, with a focus on solutions and opportunities.
• Proven track record of defining and optimizing customer success processes to drive scale and impact.

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
• 7
• 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
• #BI-Remote

Base salary range: $176,400 – $265,300. On Target Earnings (OTE) range: $252,000 – $379,000, 70.00% base/30.00% variable target OTE split. Employees are eligible to receive stock options and may also receive other forms of compensation.

The above represents total expected compensation for this role. Actual compensation will depend on various job-related factors, including, but not limited to, location, experience, and job qualifications.

Highspot also offers the following employee benefits for this position:

• 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

#LI-JB1

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.

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