The Opportunity:As our Head of Customer Success, you will own Reevo's entire post-sales function and be accountable for customer activation, time-to-value, product usage/adoption, and retention. Your mandate is simple: ensure customers consistently realize the outcomes they bought Reevo for - and make that repeatable at scale.
You will directly lead and build the full post-sales org, including:
- Onboarding / Activation (Implementation)
- Customer Success Managers (CSMs)
- Technical Account Managers (TAMs)
- Customer Support
You will design the operating model, systems, and metrics that turn
implementation into durable adoption, adoption into
measurable business outcomes, and
outcomes into retention - while partnering closely with Sales / Account Management on renewals and expansion. Customer outcomes aren't a vibe, they are a measurable business function you will run end-to-end.
We care a lot about building a strong in-person culture, and we're very much in build mode. We expect the team to be in our SF office five days a week - that's important to how we operate and scale right now.
Who You Are:- You are a customer-obsessed business leader who is relentless about activation → adoption → outcomes → retention. You build teams and systems that make time-to-value predictable, product usage durable, and renewals boring.
- You bring deep operational judgment. You know how to scale post-sales organizations that balance structure and flexibility across segments, while holding a high bar for customer experience and execution quality.
- You think systemically and strategically, connecting product usage signals and customer outcomes to product direction, GTM execution, and long-term unit economics.
- You are an exceptional communicator and influencer- trusted by executives, product leaders, and customers to navigate complexity, drive alignment, and make high-quality decisions.
- You thrive in high-ambiguity environments, bringing clarity, momentum, and calm as the organization scales.
What You'll Do:- Own Customer Activation, Time-to-Value, Adoption, and Retention
- Define and drive the strategy for customer activation and time-to-value, ensuring every customer reaches meaningful "first value" quickly and reliably.
- Establish adoption and usage as leading indicators of customer health, retention, and expansion - then operationalize the playbooks to move those levers.
- Run and Scale the Post-Sales Organization
- Own the strategy, structure, and execution across Onboarding/Activation, CSM, TAMs, and Customer Support.
- Operate post-sales as a core business function with clear accountability for retention outcomes and customer value realization.
- Build Leaders and Talent Density
- Recruit, develop, and retain exceptional leaders and ICs across post-sales functions.
- Set a high bar for ownership and performance; build a leadership bench that scales with the company.
- Design the Customer Success Operating System
- Build the full CS machine: onboarding frameworks, success plans, outcome tracking, health scoring, executive engagement cadences, escalation protocols, renewal readiness, and QBR/EBR standards.
- Ensure a consistent, segment-aware customer experience - from the first week through renewal.
- Operationalize Product Usage Into Measurable Outcomes
- Define what "success" means by customer profile and translate it into measurable signals: activation milestones, key workflows adopted, time-to-value, engagement depth, and business outcomes.
- Create proactive risk detection and intervention motions using product signals + qualitative inputs.
- Own Retention and Renewal Readiness (and Partner on Expansion)
- Be directly accountable for retention; ensure customers recognize and realize Reevo's value and renew with confidence.
- Partner with Sales / Account Management on expansion by making adoption and customer outcomes the foundation for growth.
- Create Executive-Level Visibility
- Establish operating cadences (weekly/monthly/quarterly) that drive accountability and fast decision-making.
What You Bring:- 10+ years of experience in Customer Success, Implementation/Professional Services, Support, or Post-Sales Leadership within B2B SaaS or enterprise software
- Proven experience leading multi-function post-sales organizations, including Onboarding/Implementation and Support, and ideally technical post-sales roles (SA/TAM)
- Demonstrated success improving activation, time-to-value, adoption/usage, and retention through scalable systems and great teams
- Strong background in operating model design, process improvement, and leadership development
- Experience partnering closely with Sales, Product, and Engineering in high-growth environments
- Exceptional executive communication and stakeholder management skills
- High EQ, strong judgment, and a bias toward action
- Familiarity with AI-driven products and the ability to translate technical concepts into clear customer and executive narratives is a strong plus
- Startup or scale-up experience strongly preferred
What We Offer:- Compensation: A highly competitive base salary and bonus structure, and early-stage equity that aligns your success directly with the company's growth.
- Comprehensive Benefits: Competitive health, dental, and vision coverage, generous paid time off (PTO), and other valuable perks designed to support your well being.
- Growth & Development: Clearly defined career advancement paths, dedicated mentorship opportunities, and a strong commitment to investing in your continuous professional development and skill enhancement.
- Dynamic Culture: Join a collaborative, innovative, and fast-paced work environment where your direct contributions have a tangible and immediate impact on the product, the sales strategy, and the overall company trajectory.
