Head of Customer Success

About the Role

We’re looking for a Head of Customer Success to drive retention, expansion, and the entire post-sales journey. You’ll build the function from the ground up — crafting onboarding, advocacy, and feedback loops that turn customers into long-term partners and product co-creators.

What You’ll Do

• Build and scale the Success org: Establish playbooks, metrics, and reporting from scratch. Own NRR, GRR, churn, and expansion outcomes.

• Engineer the customer journey: Design enterprise onboarding, define health scoring, and reduce time-to-value across accounts.

• Lead relationships at the highest level: Manage renewals and executive alignment across large, complex healthcare systems.

• Close the feedback loop: Turn customer insights into clear product priorities and influence roadmap direction.

• Instrument success: Develop dashboards in Salesforce or Gainsight to forecast retention and growth trends.

What You Bring

• 5+ years leading Customer Success or post-sales teams for a technical SaaS or API-driven product.

• Direct ownership of $10–50M+ ARR with strong performance in NRR, GRR, churn, and upsell metrics.

• Proven record of building scalable playbooks, segmentation frameworks, and health scoring models.

• Experience managing enterprise relationships — especially with C-suite and clinical leaders.

• Cross-functional operator fluent in the languages of Product, Sales, and Engineering.

Bonus Points

• Founder or early-stage builder experience (0→1 team creation).

• Background in healthcare, life sciences, or other regulated industries (HIPAA familiarity a plus).

• Hands-on Gainsight or Salesforce admin/reporting expertise.

First 30 Days

• Audit current accounts, renewals, risk areas, and expansion pipeline.

• Deliver the first Success playbook covering onboarding, QBRs, escalations, and renewals.

• Define the product feedback system, decision rights, and SLAs between CS and Product.

90-Day OKRs

• Achieve ≥120% NRR and ≥95% GRR.

• Cut median time-to-value by 30%; reach 100% health score coverage.

• Secure ≥90% on-time renewals and executive sponsorship for top 50 accounts.

Who You Are

• Relentlessly resourceful and outcomes-driven.

• Unafraid to challenge leadership to protect customer value and delivery standards.

• Thrives amid ambiguity, speed, and startup-level intensity.