Director of Customer Success Management, Highspot
$205-295k
OTE
$143.5-206.5k
BASE
More information about location
AI-powered go-to-market platform
Be an early applicant
AI-powered go-to-market platform
1001+ employees
Be an early applicant
$205-295k
OTE
$143.5-206.5k
BASE
More information about location
1001+ employees
Company mission
To enable the impossible for GTM teams everywhere.
Role
Who you are
- 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
What the job involves
- 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
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.
The company has continued to expand and develop over the years, entering into the Canadian market and launching several innovations in sales enablement technology. Its latest release is its agentic AI to help sales teams more precisely target prospects and win more deals
Steph
Company Specialist at Welcome to the Jungle
Insights
-9% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Jan 2022
$248m
SERIES F
Feb 2021
$200m
SERIES E
Total funding: $644.9m
Company benefits
- Generous PTO
- Free, Immersive Learning Courses
- Flexible Transportation Options
- Equity For Everyone
- Medical, dental, and vision benefits
- Flexible work and holiday schedules
- Work from home opportunities
- Modern Health and Wellness Program
- 401K Retirement Plan
Company HQ
Seattle Waterfront, Seattle, WA
Leadership
Robert Wahbe
(CEO & Co-founder)Former Corporate Vice President of the Server and Tools Division at Microsoft
Oliver Sharp
(Chief Solution Architect & Co-founder)Former General Manager of Strategy, Server and Tools Division at Microsoft
David Wortendyke
(CTO & Co-founder)Former Partner Architect at Windows Azure for over 20 years
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