Thoughtful AI

Engineering Manager

• 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.

Senior Engineering Manager, Applications

Executive Assistant

• Own and manage all aspects of the CPO’s calendar—ensuring meetings are strategically scheduled and time is aligned with top priorities.
• Proactively manage and coordinate meetings, events, and internal touchpoints with CPO’s direct reports and other key stakeholders.
• Provide scheduling and logistical support (meetings, travel, briefings) to CPO’s department leads as needed—high-leverage assistance that helps the whole org run more smoothly.
• Coordinate complex travel planning and itineraries across time zones.
• Prepare and organize materials for key meetings (e.g., agendas, briefing docs, notes).
• Monitor the CPO's inbox, identifying areas that need action and supporting the CPO by proactively using discretion to handle action items, clearly communicating what's been completed and what still needs attention, then blocking his time to ensure nothing gets missed.
• Maintain discretion and handle confidential information with care and professionalism.
• Serve as a dependable liaison between the CPO’s office and internal teams.

Recruitment

• Manage end-to-end recruitment for our sales, marketing, partnerships, and customer success departments.
• Partner closely with commercial leaders to refine hiring processes and identify key profiles needed to accelerate revenue growth.
• Immerse yourself in our go-to-market strategy to deeply understand how our teams operate, what skills are required, and what talent profiles drive success.
• Build sourcing strategies to attract top-performing sales and GTM professionals, including outbound prospecting, lead generation, and market mapping.
• Actively network with potential candidates at industry events, sales conferences, and professional communities.
• Craft compelling job descriptions tailored to the nuances of competitive sales and marketing roles.
• Conduct structured interviews and assessments to evaluate candidates across sales performance metrics, market expertise, and cultural alignment.
• Champion a strong candidate experience that reflects the energy and professionalism of our go-to-market teams.

Business and Sales Recruiter

Technical Recruiter

• End-to-end recruitment for our product and engineering departments
• Collaborate closely with engineering hiring teams to streamline our hiring process and to attract and filter top-tier talent
• Immerse yourself within our engineering teams to garner a deep understanding of our operations, technology, and talent requirements
• Strategize and implement plans for sourcing diverse talent (outbound strategy, lead generation, face-to-face meetings)
• Network with potential candidates at industry conferences, local tech gatherings, and university recruitment drives
• Craft detailed and engaging job descriptions and conduct prescreening procedures to evaluate the suitability of applicants
• Interview candidates employing a mix of methods (structured interviews, technical assessments, and behavioral questions)
• Identify, attract, and close top technical talent to scale Thoughtful AI's healthcare RCM platform

Business Development Rep

• Opportunity: As a member of the Thoughtful Sales team, your role is pivotal in driving new business within the healthcare sector. We\'re seeking a candidate who not only delivers exceptional results but does so with a seamless, professional, and polished execution—a standard reminiscent of the world\'s most elite sales teams. This role is tailor-made for an individual who thrives under pressure, embraces challenges, and consistently achieves outstanding results through a combination of relentless commitment, disciplined execution, and a level of finesse that sets a new industry standard. • At this juncture, you are not just a product evangelist but an orchestrator of the sales process, seamlessly integrating with our delivery and engineering teams while enriching our marketing efforts with invaluable customer insights. Your dedication to enhancing the customer experience transcends the sales department; you are a true customer advocate, orchestrating, coordinating, and collaborating across multiple departments to deliver an unparalleled white-glove customer experience. • Learn more about our Warrior culture. • Targeted Business Development: Be the architect of success, discerning and strategically penetrating high-value healthcare accounts, with the ability to use your intuitive judgement and expert know-how to orchestrate and direct multiple stakeholders through complex, multi-process, and multi-variable sales cycles, leading them to triumphant conclusions. • Sales Excellence: Exhibit unparalleled negotiation skills, adeptly navigating multifaceted deal intricacies, and exceeding ambitious multi-million dollar annual sales quotas. • C-suite Partner: Forge deep relationships with sophisticated healthcare C-suite executives, offering consultative insights, possessing knowledge of healthcare invoicing processes, and positioning Thoughtful\'s solutions as pivotal to their operational success. • Operational Guru: Leverage CRM tools with surgical precision, maintaining precise records of client interactions, ensuring flawless execution of sales strategies. • Land and Expand: Cultivate your portfolio of healthcare providers, commencing with initial engagements in the RCM department and progressively expanding to HR, IT, and F&amp;A. • Apprenticeship Model: Develop your AI sales craft through immersive on-the-job training and an unwavering commitment to the process. • Delivery Excellence: Partner with our world-class Program Management and Customer Success teams, guaranteeing the timely delivery of contracted outcomes with unparalleled value.

Senior Engineering Manager, Applications

Executive Assistant

Business and Sales Recruiter

Technical Recruiter

Regional Vice President (RVP), Director of Business Development