Head of Customer Success, Highspot
$252-379k
OTE
$176.4-265.3k
BASE
70.00% base/30.00% variable target OTE split. Employees are eligible to receive stock options and may also receive other forms of compensation
More information about location
Sales enablement platform
Open for applications
Sales enablement platform
501-1000 employees
Open for applications
$252-379k
OTE
$176.4-265.3k
BASE
70.00% base/30.00% variable target OTE split. Employees are eligible to receive stock options and may also receive other forms of compensation
More information about location
501-1000 employees
Company mission
To empower companies to elevate customer conversations that drive strategic growth.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
- 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.”
- 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
- 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
Our take
Highspot is an AI-driven sales enablement platform that enhances sales team performance globally. It offers intelligent content management, training, contextual guidance, and customer engagement in a unified platform. This integration, supported by actionable analytics, helps companies turn strategic plans into effective sales.
Highspot's annual recurring revenue has grown over tenfold in recent years, highlighting the importance of sales enablement in improving sales team performance. The company's innovation and customer satisfaction have led to record new customer acquisitions and revenue growth, with clients like Hootsuite, Twitter, Siemens, and Nestle.
Despite a 10% workforce reduction following its expansion into Canada, Highspot continues to innovate. The Spring ’24 release expands generative AI capabilities, providing personalised, just-in-time coaching and content personalisation at scale. Highspot Discover showcases these innovations, reinforcing Highspot's leadership in sales enablement.
Steph
Company Specialist at Welcome to the Jungle
Insights
-9% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Jan 2022
$248m
SERIES F
Feb 2021
$200m
SERIES E
Total funding: $642.6m
Company benefits
- Generous PTO
- Free, Immersive Learning Courses
- Flexible Transportation Options
- Equity For Everyone
- Medical, dental, and vision benefits
- Flexible work and holiday schedules
- Competitive compensation
- Work from home opportunities
- Modern Health and Wellness Program
- 401K Retirement Plan
Leadership
Robert Wahbe
(CEO)Former Corporate Vice President of the Server and Tools Division at Microsoft
Oliver Sharp
(Chief Solution Architect)Former General Manager of Strategy, Server and Tools Division at Microsoft
David Wortendyke
(CPO)Former Partner Architect at Windows Azure for over 20 years
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