Customer Operations Lead

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 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 100+ leading health systems, pharmacies, and healthcare organizations across the country. If you’re excited to help shape the future of healthcare, we’d love to meet you. Apply now to join our growing team. About the Role We’re looking for a senior individual contributor to help our Customer Success team deliver measurable customer value and grow recurring revenue. You’ll improve how we bring customers from contract to activation, support their success over time, and secure renewals. You’ll use financial modeling and AI-driven processes to give the team better insight and help it act sooner. You’ll also directly manage a select group of key accounts, owning those relationships and customer outcomes. The account work will keep you close to the customer experience and inform the improvements you make across Customer Success.

What You’ll Do

• Improve how Customer Success activates contracted revenue and supports renewals by identifying patterns and risks across accounts, then helping Account Managers act on them.

• Manage key customer relationships, helping customers realize value, reach it sooner, and build a clear case for continued partnership.

• Build and evolve the activation model so Account Managers and leaders have a clear view of customer progress, commitments, and risks.

• Use financial modeling to understand activation timing, customer value, revenue risk, and the resources needed to deliver.

• Design and own AI-driven workflows that help the team work more effectively and consistently.

• Work across Sales, Finance, Product, Engineering, and Customer Success to improve the customer journey and resolve issues that affect outcomes.

You May Be a Fit If

• Significant experience managing complex customer accounts and improving how a Customer Success team operates.

• A track record of driving customer activation, retention, and measurable value.

• Strong financial modeling skills and the ability to turn analysis into sound decisions.

• Experience using AI to improve workflows that people adopt and trust.

• The ability to lead cross-functional work and influence outcomes without formal authority.

• Comfort moving between strategic account work, analysis, hands-on building, and ongoing operational ownership.

Why You'll Love Working Here

• 🚀 Mission-Driven, World-Class Team — Join an exceptional group of professionals aligned around a meaningful mission and committed to making an impact

• 📈 Opportunities for Growth — Strengthen your expertise through collaboration with experienced, high-performing leaders across the organization

• 🏢 Flexible Hybrid Work Environment — We're remote-first, with meaningful office presence in San Francisco and New York. R&D roles follow a hybrid model, with two days per week in our San Francisco office

Benefits & Perks

• 🏥 Healthcare Coverage — Full medical, dental, and vision insurance for you and participation for your family

• 💰 401(k) with Company Match — Plenful matches 50% of your first 3% contributed

• 📊 Equity — Every full-time employee shares in our success

• 🌴 Unlimited PTO — Take the time you need, when you need it

• 🍽️ Daily Lunch Stipend — $100/week to cover your midday meals

• 💪 Wellness Stipend — $100/month to support your health and well-being

• 🚇 Commuter Benefits — $100/month for SF and NYC-based employees

• 👶 Parental Leave — Paid leave to support growing families