Head of Enterprise Customer Success

📋 Description

• • Champion Net Retention, take full accountability across the enterprise portfolio, delivering regular strategic performance updates to executive leadership.
• • Drive account growth, actively identify and capture organic expansion opportunities within our existing customer base to maximize account value, moving well beyond simple account preservation.
• • Master the pilot conversion motion, design and manage a seamless pilot conversion motion, ensuring our partners who begin their engagements by piloting our products successfully convert into long-term partnerships for scale.
• • Meet customer needs. Plan capacity, hire and retain talent, and invest in the team's skills and culture as the segment grows.
• • Partner with Sales on a single commercial and implementation plan, so every enterprise customer is set up to succeed from the moment the contract is signed, not after something goes wrong.
• • Run a clear Account Plan and QBR cadence with every enterprise account, so nothing is being managed from memory.
• • Build and mentor talent, forecast organisational capacity, recruit top-tier Customer Success Managers, and cultivate a high-performance culture focused on continuous skill development to match our growth trajectory.
• • Bridge the Product Loop, translate frontline enterprise feedback and operational data into clear, actionable insights for our Product and Engineering teams to directly influence the product roadmap.
• • Collaborate with Support on a clean handoff for every account, and keep a live view of account health once it lands there.
• • The role requires 8+ years in customer success or account management, including 3+ years leading a CSM team inside a high-growth B2B SaaS company.
• • A track record of owning enterprise accounts (large, complex, multi-stakeholder), not a portfolio of small logos.
• • Experience building CS programs, playbooks, or segmentation from scratch, not just running an existing one.
• • Fluency in SaaS retention metrics (NRR, GRR, expansion) and comfort with CS or CRM tooling such as Gainsight, Totango, ChurnZero, or Salesforce.
• • Executive communication skills. You can hold a room with a practitioner and a room with a C-suite equally well.
• • Experience in healthcare, health-tech, or another regulated industry is a strong plus, not a requirement.
• • Nice to have: Experience with public health systems or government procurement, experience scaling a customer success function across multiple regions, clinical or EHR domain knowledge.
• • We take care of you. We offer a $1,000 annual learning and development budget, a $150/month health and wellness allowance, a $500 home office budget, 26 weeks paid primary parental leave and 18 weeks paid secondary parental leave, fertility support up to $10,000, four weeks of work from anywhere per year, and serious equity.
• • What success looks like: 30 days - mapped the current enterprise journey end to end with clear internal and customer-facing documentation, 60 days - the team has a documented Account Plan and QBR playbook and a real operating cadence, 90 days - you've presented a capacity and scaling plan to leadership, and enterprise customers can feel the difference in how consistently they're supported.
• • How we show up: Build for the next decade, not next quarter. Our targets are outrageous on purpose. The world's health doesn't have the luxury of incrementalism. Lead, don't wait. We treat tomorrow's problems today. Sometimes we build what's needed before it's wanted, and we're fine with that. Follow the evidence. Trust the patient. We pursue truth relentlessly. But when the subjective and objective disagree, we treat the patient, not the numbers. Ego is a comorbidity we can't afford. Own the outcome. Everyone here carries the company. Raise problems with solutions, solve them end-to-end, and never be a bystander. Ship, measure, go again. A button today, a workflow tomorrow. More iterations beat better planning. We're precise at pace, not reckless. Live in clinicians' reality. Not the ideal workflow, the twenty-patients-before-lunch actual one. We build for exhausted humans, and we'd better be decent ones while we do it.
• • Why Heidi? You’ll join a team focused on real-world impact over imaginary valuations and glossy PR. We live and breathe the challenges of modern health systems, and are laser-focused on exacting the change we’d like to see. We’re medicos, engineers, builders, and designers who’ve felt the moral and practical toll of what non-care feels like. True A-players progress extremely fast here. The nature of the scale-up game is demanding, but we value sustainable performance and mental health. You're trusted to perform, and you set your schedule. We operate on outcomes > inputs, not process theatre. We all take the bins out, metaphorically and literally.