Head of Customer Success
About The Position
We’re seeking a data-driven, relationship-focused Head of Customer Success to lead our next phase of growth and customer retention. This leader will own the entire post-sales journey — onboarding, adoption, health monitoring, renewals, and expansion — and will be responsible for building a proactive and highly effective CS organization that protects and grows revenue. You’ll combine operational rigor with charismatic relationship-building, bringing best-in-class SaaS practices to anticipate churn risk early, implement adoption strategies that drive measurable ROI, and engage directly with executives at customer organizations to retain and expand partnerships. This is a senior leadership role for someone who thrives in high-growth startups and wants to build, not just manage, a world-class CS function.
Requirements
- SaaS CS Leadership: 7+ years in Customer Success within SaaS; at least 3+ years leading and scaling CS teams in a high-growth, startup environment.
- Retention & Expansion Expertise: Proven success building renewal and expansion playbooks, negotiating large and complex deals, and driving measurable NRR.
- Data-Driven Operator: Hands-on experience implementing and managing platforms like Planhat, Gainsight, or Totango to monitor health, predict churn, and trigger engagement.
- Strategic Adoption: Strong track record designing and executing adoption and success strategies that deliver measurable ROI and deepen product stickiness.
- Executive Presence: Highly personable, charismatic, and persuasive; able to build trust and influence decision-makers up to the C-suite.
- Team Builder & Mentor: Experience hiring, developing, and scaling high-performing CS organizations across SMB to Enterprise segments.
- High-Growth Startup Experience: Comfort with ambiguity, pace, and change; proven ability to build processes from the ground up.
- Analytical & Insight-Driven: Skilled at using data to inform strategy, drive accountability, and communicate impact to leadership and the board.
Responsibilities
- Build and oversee systems (Planhat or similar) to track adoption, engagement, and health scores.
- Identify churn risk early and deploy proactive playbooks to protect revenue and increase lifetime value.
- Develop and execute customer adoption frameworks that drive ROI, usage, and long-term stickiness.
- Partner with customers to embed Awarded AI into their workflows and strategic priorities.
- Serve as a trusted advisor and executive sponsor for key accounts.
- Negotiate renewals and expansions with a consultative, value-first approach.
- Build, lead, and inspire a multi-segment CS organization — SMB, Mid-Market, and Enterprise.
- Recruit, mentor, and retain top Customer Success Managers (CSMs); create career paths and a performance-driven, engaged culture.
- Design scalable onboarding, implementation, and success playbooks that drive efficiency and predictability.
- Create structured reporting and dashboards for CS metrics — retention, net revenue expansion, health scores — to guide decisions and inform leadership.
- Work closely with Sales, Marketing, and Product teams to ensure a seamless handoff from sale to onboarding, and to surface customer feedback that drives product strategy and roadmap.
Benefits
- Competitive executive salary plus performance-based incentives and stock options
- Comprehensive health plan for you and your family
- Flexible, remote-first work arrangements
- Significant leadership opportunity and direct impact on company trajectory
- Be a ground-floor leader at a rapidly scaling, VC-backed SaaS company
- Professional development and advancement opportunities
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What This Job Offers
Job Type
Full-time
Career Level
Executive
Education Level
No Education Listed
Number of Employees
51-100 employees
