Join Our Mission to Revolutionize Healthcare

Thoughtful is pioneering a new approach to automation for all healthcare providers! Our AI-powered Revenue Cycle Automation platform enables the healthcare industry to automate and improve its core business operations.

We're looking for an Exceptional Sr. Manager of Engineering for our Applications team.

As the Senior Manager of Applications at Thoughtful AI, you’ll lead the engineering organization responsible for building the applications that bring our AI Agents to life for customers across the healthcare ecosystem. This role sits at the intersection of technology, design, and impact - ensuring the products we ship are not only powerful but intuitive, elegant, and transformative for the people who use them.

You’ll own the vision and execution for Thoughtful’s customer-facing applications and supporting services, from frontend experiences to backend systems, ensuring world-class usability, reliability, and developer experience. You’ll lead a team that transforms complex healthcare workflows into beautifully simple interfaces and robust backend systems, enabling customers to see and feel the power of automation every day.

This is an ideal role for a hands-on technical leader who thrives in high-growth environments, believes in engineering-led decision-making, and can bridge the gap between deep technical work and clear business impact.

Learn more about our Warrior culture.

Key Responsibilities

• Lead and grow the Applications Engineering team to 12+ Senior and Staff-level ICs spanning frontend, backend, and DevEx disciplines.
• Define and drive the vision and roadmap for Thoughtful’s applications, ensuring scalable, performant, and delightful user experiences.
• Partner with Design and Product to deliver polished, intuitive, and high-velocity customer-facing interfaces.
• Foster a Developer Experience culture that accelerates innovation through better tooling, automation, and feedback loops.
• Oversee backend systems that power our UIs, ensuring stability, maintainability, and security.
• Communicate complex technical concepts clearly to non-technical stakeholders - including customers, executives, and partners.
• Occasionally demo Thoughtful’s applications to customers and prospects, showcasing the product and technology vision.
• Develop clear success metrics and operational dashboards that connect engineering execution to business outcomes.
• Ensure strong collaboration across Product, Design, and Platform teams to balance feature velocity with reliability and user experience.
• Maintain a culture of ownership, energy, and craftsmanship in every part of the application stack.

What Success Looks Like

• A high-performing team that builds, owns, and iterates on user-facing applications with speed and confidence.
• Customer-facing UIs that set the industry standard for usability and design in healthcare automation.
• Engineering decisions guided by clear business outcomes and measurable impact.
• A team that moves fast but doesn’t break trust - balancing innovation with quality and reliability.
• Developers across Thoughtful benefit from strong DevEx and internal tooling, enabling high-velocity product iteration.
• Customers, internal stakeholders, and the team all feel inspired by your communication, clarity, and leadership.

Minimum Qualifications

• 10+ years of experience in software engineering, with at least 4+ years in senior technical leadership roles.
• Proven success leading large application teams (10+ engineers) and retaining high-performing talent.
• Deep experience building and scaling customer-facing applications and supporting backends.
• Strong understanding of UX principles and how they intersect with engineering decisions.
• Demonstrated excellence in Developer Experience (DevEx) and tooling.
• Proven ability to communicate complex technical ideas to non-technical audiences.
• Track record of partnering effectively with Product and Design to deliver impactful, user-centered solutions.
• Strong architectural judgment with a focus on pragmatic scalability and maintainability.

Bonus Points

• Experience with data lakehouse architectures (e.g., Athena, Glue, Parquet) or analytical systems.
• Previous experience building internal developer platforms or DevEx frameworks.
• Background in healthcare, regulated environments, or B2B SaaS.

Cultural Traits

• Passionate about improving the healthcare system through technology and automation.
• Thrives in a fast-paced, mission-driven environment - understands this is not a 9-to-5 role.
• Believes in engineering-led decision making and empowering ICs with ownership.
• Demonstrates authenticity, energy, and the ability to build rapport quickly.
• Brings contagious enthusiasm that inspires and excites the team to deliver their best work.

Why Thoughtful?

• Competitive compensation
• Equity participation: Employee Stock Options.
• Health benefits: Comprehensive medical, dental, and vision insurance.
• Time off: Generous leave policies and paid company holidays.