Customer Success Lead, Enterprise
Company shown to members 🔒 · Remote · US only
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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- Senior
- Where you can live
- US only
- Skills and tools
- salesforce, hubspot, customer success, onboarding, retention, upsell
- Job type
- Full-time
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Job details
- Where you can work
- United States
- Employment type
- Full-time
- Advertised pay
- Not stated by the employer
- Experience
- Senior
- Employer publication date
- 23 April 2026
- First recorded by Psst
- 12 October 2026
- Last checked at the source
- 10 November 2026
About the job
ABOUT the company
At the company, we are building the modern platform for medical record retrieval. Legacy record retrieval is notoriously slow and unreliable; our system uses AI to deliver decision-ready records much faster and more accurately.
Started just over a year and a half ago, our volume is doubling MoM with a clear path to category leadership. We support practices ranging from Plaintiff Law to Specialty Healthcare. We are a well-funded, rapidly growing team focused on growing 100x from where are today.
Our mission is to automate record retrieval, which will only be achieved through innovative engineering and relentless execution.
ABOUT THE ROLE
Enterprise law firms are our most complex and highest-value relationships. As our Enterprise Customer Success Lead, you'll own a portfolio of high volume firms, whatever shape they take — building deep relationships, driving adoption, and ensuring they realize measurable value from the company. You'll be the single point of accountability for account health, expansion, and executive engagement. You'll work closely with the Head of CX, operations, and product to translate customer feedback into real improvements.
WHAT YOU'LL OWN
- Own a portfolio of enterprise accounts starting post-sale, from building key relationships to maintaining account health
- Lead structured onboarding for new enterprise customers — platform training, first case submission, integration into firm workflows
- Conduct regular business reviews (QBRs) and executive check-ins to surface value, resolve friction, and identify growth opportunities
- Maintain documented account health status for every firm in your portfolio; flag at-risk accounts and lead recovery plans
- Own expansion within your book: upsell volume, additional practice areas, additional offices, and new service lines
- Be the customer's advocate internally — route feedback to product, operations, and leadership and close the loop with customers on outcomes
- Build and iterate on scalable playbooks for onboarding, QBRs, renewals, and escalations
- Collaborate with the Support Lead to ensure enterprise escalations are resolved quickly and with white-glove service
WHAT WE'RE LOOKING FOR
- 4–7 years of B2B Customer Success or Account Management experience, ideally in legal tech, healthcare tech, or a document/workflow SaaS
- Demonstrated track record managing enterprise accounts with strong NRR and expansion results
- Executive presence — comfortable running QBRs with partners and firm administrators
- Highly organized, process-oriented: you build playbooks, not just relationships
- Strong instincts for identifying expansion signals and converting them into revenue
- Experience with CRM / CS platforms (Salesforce, HubSpot, Gainsight, or equivalent)
- Comfortable in an early-stage environment — you can build structure without waiting to be told
SUCCESS METRICS
- Net Revenue Retention: Retain and grow ARR within your portfolio
- Onboarding Completion: 100% of enterprise customers complete structured onboarding within 2 weeks
- QBR Cadence: All enterprise accounts on a regular review schedule (quarterly minimum)
- Account Health Coverage: Every account has a documented health status; zero surprise churns
- Expansion Pipeline: Active expansion opportunities identified and progressed each quarter
The company · Customer Experience · Hiring 2026
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