Healthcare Sales Engineer

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 90+ leading health systems 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

Plenful is seeking a dynamic and customer driven Healthcare Sales Engineer to lead solution discovery, technical validation, and value storytelling across our enterprise sales motion. You will partner closely with Sales, Product, and Engineering to shape deal strategy, deliver compelling demonstrations, and guide customers from evaluation through go live Your work will directly impact pipeline conversion, deal velocity, and long-term customer success within a fast-growing healthcare technology company. Leading by example, you will champion Plenful’s Operating Principles—Speed, Customer First, Great People = Greater Outcomes, and Do the Right Thing—while fostering a collaborative, high-performance, and execution-focused go-to-market culture.

What You’ll Do

• Lead solution discovery and needs assessment across active sales cycles to align customer priorities with Plenful’s capabilities

• Partner with Sales to co-own deal strategy, shaping value narratives and competitive positioning for complex and enterprise opportunities

• Design and deliver tailored product demos and workflow walkthroughs that clearly communicate business impact and ROI

• Act as a trusted advisor on pharmacy operations, intake automation, prior authorization, and 340B workflows to guide buying decisions

• Support pilots and proof-of-concepts to validate business outcomes and accelerate stakeholder confidence

• Capture and translate customer insights into actionable feedback for Product, Marketing, and Sales enablement

• Establish Plenful as the Vendor of Choice by building executive trust, demonstrating value, and driving consensus across buyer groups

You May Be a Fit If

• Deep healthcare domain expertise, with 340B experience or strong working knowledge as a key differentiator

• Background in Solutions Consulting, Sales Engineering, Implementation Consulting, or Healthcare Operations

• Proven experience selling or supporting enterprise healthcare software, ideally within:

  • Health systems

  • Pharmacy operations

  • Prior Authorization

  • Benefits Investigation

  • 340B programs

• Demonstrated ability to lead discovery, challenge assumptions, and articulate clear business ROI

• Comfort operating in a startup or early-stage environment, with high ownership, ambiguity, and rapid iteration

• Strong executive presence with pharmacy leaders, compliance teams, and operational stakeholders, driving trust and decision alignment

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