Director, Technical Customer Success

About Plenful Plenful is on a mission to transform healthcare operations from the inside out. Fresh off our $50M Series B and backed by Notable Capital, Bessemer Venture Partners, TQ Ventures, Susa/Kivu Ventures, and other leading investors, we’re building the category-defining AI workflow automation platform that healthcare teams rely on to operate smarter, faster, and more efficiently. Our technology empowers healthcare operators across hospital and health systems, pharmacies and payors to eliminate manual work, reduce administrative burden, and improve compliance, all while unlocking critical revenue to fund programs for their in-need patient populations. Built by healthcare operators for healthcare operators, Plenful is driven by a deep understanding of the challenges facing today’s care teams. We’re passionate about equipping healthcare workers with world-class tools that deliver real, measurable impact, and we’re proud to serve 60+ leading health systems across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Join our growing team! What you’ll do Lead and scale our Technical Customer Success team as a true player-coach, balancing hands-on technical leadership with people development Accelerate time to value by designing scalable implementation playbooks and refining onboarding processes that evolve as we achieve our significant growth goals Own technical escalations, diving deep into SQL and Python-based issues when needed, to quickly unblock your team and ensure successful customer outcomes Forge powerful feedback loops with Product and Engineering to surface customer-driven insights, shaping feature prioritization, and driving constant product improvement Partner with Account Management and Sales teams to ensure seamless delivery of value, identify expansion opportunities, and drive exceptional customer satisfaction Measure success and lead by metrics. Own key KPIs, including time to value and technical issue resolution time; continuously assess and optimize team performance What we’re looking for Experience 8+ years in Solutions Engineering, Implementation, Technical Account Management, or a related field 4+ years in management roles scaling a technical, customer-facing organization (ideally in a SaaS or healthcare tech environment) A proven player-coach—someone who can both lead, manage, and hire effectively, and also step in to help solve challenging technical issues Strong people management and team-building experience, with a track record of sustaining high team performance and morale in a fast-growing startup Demonstrated ability to track, interpret, and act on KPIs to continuously improve customer outcomes Ability to explain complex technical problems in concise communication to both technical and non-technical stakeholders Experience in the healthcare industry (familiarity with data quality management, prior authorizations, benefits verification, etc.) Technical skills Proficient in SQL Experience in working with APIs and/or FHIR integrations (JSON, HL7, XML, etc.) [Nice to Have] Familiarity with code (Python, YAML, etc.) Additional skills Excellent verbal and written communication skills Strong problem-solving skills, ability to articulate unstructured problems effectively and with a customer-focused approach to addressing client needs and resolving issues Ability to serve as a senior technical point of escalation, representing Plenful externally on technical matters and ensuring clear, credible communication with customers during escalations or complex implementations Ability to work collaboratively across functions, including Sales and Account Management, to ensure a seamless customer experience Highly organized, able to manage multiple accounts, and prioritize tasks independently Miscellaneous A genuine interest in healthcare and making the industry more efficient Excitement to see and learn the company-building process firsthand alongside dedicated, hardworking, fun-loving team member A bias toward action and enjoyment working in a dynamic, fast-moving environment Plenful perks Great benefits include unlimited PTO, health insurance, meal stipend, health & wellness stipend, team offsites, 401K matching, and stock options. Opportunities to further develop and refine your partnership acumen by partnering with our seasoned leaders Originally posted on Himalayas