Head of Customer Success & Experience

San Francisco Bay Area · Hybrid · Full-time · Reports to CEO

About Base

Base is building the AI Customer Growth Platform for modern B2B companies.

We help companies orchestrate customer engagement across the post-sale lifecycle—from onboarding and adoption to expansion, advocacy, and retention—through one unified platform.

We are a growing startup serving sophisticated enterprise Marketing, Customer Success, and GTM organizations that are rethinking how they operate in the age of AI. We are doing the same internally.

The role

We’re looking for a hands-on Head of Customer Success & Experience to lead and redesign an AI-first, value-obsessed, and AINS CS org.  You will own onboarding, implementation, adoption, customer health, ongoing success, PS, support, advocacy, and overall customer experience.

This is not a traditional CS leadership role centered on managing managers and maintaining an established playbook. You will work directly with strategic customers, coach the team through real account challenges, improve our operating model, and partner closely with Product and Engineering to eliminate customer friction.

Over the next 12 months, we expect the organization to include approximately 6–7 people across Customer Success, FDEs, onboarding, and support. Your goal is to build an exceptionally effective customer organization, not simply a larger one.

What you’ll own

• Customer onboarding, implementation, and time-to-value.
• Product adoption, measurable outcomes, and ongoing value realization.
• Identify growth potential – upsell, cross-sell, and expansion
• Customer segmentation and the appropriate engagement model for each segment.
• Customer health, risk identification, and early churn intervention.
• The day-to-day strategic relationship with customers.
• Customer Success, onboarding, and support team performance.
• Strategic, complex, and at-risk customer situations.
• Customer education, enablement, communications, and advocacy.
• Executive relationships and alignment around business outcomes.
• Customer coverage, team capacity, productivity, and operating cadence.
• Customer data, systems, automation, and AI-enabled workflows.
• Strong feedback loops among customers, Product, Engineering, Revenue, and Marketing.

How Customer Success partners with the Revenue/Sales Organization

• Customer Success and Revenue will operate as peer organizations with shared visibility and clear accountability.
• Customer Success owns customer outcomes and the ongoing value relationship. Revenue owns every commercial transaction, including pricing, proposals, negotiation, contracts, renewals, upsell, cross-sell, and expansion close.
• Together, the teams will maintain shared account plans, identify risks and opportunities early, and ensure customers buy the right solution, achieve value, renew, and expand at the right time.
• CSMs will contribute to customer health and growth signals, but they will not be expected to become quota-carrying salespeople.

Build an AI-native customer organization

A central part of this role is redesigning how customer work gets done-not simply adding AI tools to a traditional CS model.

You will determine:

• Which customer needs require human expertise and relationships.
• Which experiences should be delivered through product, automation, or AI agents.
• How onboarding can become faster, more personalized, and more scalable.
• How product usage, conversations, support activity, and sentiment can identify risks earlier.
• Which repetitive activities should be automated or eliminated.
• How each team member can support more customers while improving their experience.

We want practical transformation: better customer outcomes, fewer manual processes, earlier insights, and materially higher productivity per person.

What success looks like

Within your first several weeks, you will develop a clear understanding of our customers, product, team, and customer journey.

By the end of your first year, we expect:

• Significantly faster onboarding.
• Stronger adoption and measurable value realization.
• Earlier identification of customer risk.
• Clear customer segmentation and engagement models.
• Stronger executive relationships and customer advocacy.
• Effective partnership with Revenue.
• Better visibility into customer health and outcomes.
• Higher productivity and customer coverage per team member.
• Meaningfully more customer work is handled through product, automation, and AI.

You’ll define and align with leadership regarding KPI’s by months, quarters and full year.

What we’re looking for

You are likely a strong fit if you:

• Have built or materially improved Customer Success in a B2B SaaS company at a similar stage.
• Have led onboarding, adoption, customer health, retention, or support motions.
• Are exceptional directly with customers and still enjoy customer-facing work.
• Can engage credibly with day-to-day users and senior executives.
• Understand how to connect product adoption to measurable business outcomes.
• Have personally led complex, strategic, or at-risk customer situations.
• Have hired, coached, and developed customer-facing teams.
• Understand segmentation, capacity, productivity, and cost-to-serve.
• Think systematically about customer health rather than relying only on CSM sentiment.
• Have strong product instincts and can translate customer patterns into actionable feedback.
• Know how to partner with Revenue without turning CSMs into salespeople.
• Have used AI, automation, or product-led workflows to improve customer outcomes and efficiency.
• Are comfortable operating without multiple management layers or a large support organization.

Your mission will be to build an AI-native customer organization that helps customers achieve measurable value, creates experiences they want to advocate for, and provides the foundation for durable retention and growth.

This role is not

• A role primarily focused on managing managers.
• An Account Management or renewal-closing role.
• A model in which every customer receives the same level of human engagement.
• A function measured primarily by meetings, QBRs, or activity.
• A mandate to scale by continually adding CSM headcount.
• A mature, fully defined system to maintain.

This is a senior leadership role, but it is intentionally hands-on.