Thoughtful AI is a trailblazing Series A startup on a mission to redefine the B2B landscape through pioneering AI solutions. With a culture that fosters innovation and excellence, we’re making waves in the massive healthcare industry, continuously pushing the envelope of what’s possible. We’re seeking an elite Technical Recruiter, a tenacious individual who mirrors our pursuit of world-class standards and relentless drive.

Our ecosystem thrives on resilience, ambition, and the ceaseless pursuit of innovation. If you are passionate about making an impact and excel in high-intensity, high-reward environments, Thoughtful AI could be your next arena.

About Thoughtful AI

We are Thoughtful AI — pioneering a new approach to automation for all healthcare providers! Our Fully-Human Capable AI Agents operate within existing healthcare RCM tech stacks to accomplish key tasks currently performed by human employees. The Thoughtful platform combines state-of-the-art technology, including Robotic Process Automation, Optical Character Recognition, Natural Language Processing, and Large Language Models that function in unison to create unparalleled results for RCM departments.

About the Role

We are looking for a highly organized, detail-oriented, and proactive Operations Analyst to drive operational excellence and ensure seamless day-to-day business functions. This role is perfect for someone who thrives in a high-growth, fast-paced environment, enjoys optimizing workflows, and loves tackling challenges across IT, HR, finance, and vendor management.

You’ll play a critical role in enhancing efficiency, ensuring compliance, and supporting company-wide initiatives—from process optimization to onboarding, insurance/taxes, office maintenance, and event coordination. Reporting directly to the Head of Business Operations, you will be a key partner in shaping how our organization scales.

Key Responsibilities

Operational Efficiency & Process Optimization

• Gather and analyze data related to business operations, workflows, resource usage, and performance metrics.
• Identify inefficiencies and propose process improvements to enhance productivity and reduce costs.
• Develop and implement new workflows, tools, and strategies to address operational challenges.
• Track and report on operational metrics to provide actionable insights to leadership.

Administrative & Compliance Support

• Assist with gathering and organizing documentation for insurance, taxes, and compliance-related items.
• Support onboarding and offboarding by preparing materials, managing documentation, and ensuring smooth transitions.
• Maintain and improve administrative systems and processes to streamline company operations.
• Serve as a liaison between departments to facilitate smooth communication and cooperation.

Office & Vendor Management

• Oversee office maintenance, ensuring everything runs smoothly for in-person and remote employees.
• Manage relationships with vendors and service providers, negotiating contracts and ensuring cost efficiency.

Events & Offsites

• Plan and execute company events and offsites, coordinating logistics, venues, vendors, and schedules.
• Assist with internal/external communications and team coordination for key events.

Problem Solving & Decision Support

• Identify and troubleshoot operational issues in real-time, implementing quick and effective solutions.
• Provide data-driven recommendations to leadership for strategic decision-making.

What Makes This Role Insanely Exciting

• Revolutionize Operations – This isn’t just about managing day-to-day tasks; you’ll have the opportunity to reshape and optimize how we work.
• Work with Visionary Leaders – Collaborate with entrepreneurs and dynamic leaders who are pushing the boundaries of success.
• Transformational Impact – Influence every aspect of the company— HR, Accounting, Compliance, Vendor Management, and beyond.
• No Two Days Alike – One day, you’ll be refining IT systems; the next, you’ll be enhancing HR policies, ensuring financial accuracy, or organizing an epic company offsite.

What You Need to Bring to the Table

• 5+ years of experience in operations, office management, or a similar role in a fast-paced, high-growth environment.
• Proven experience managing compliance, vendors, HR, IT support, and operational workflows.
• Ability to handle complex projects while balancing competing priorities and driving operational efficiency.
• Organizational Genius – You thrive in dynamic environments, creating systems out of chaos and juggling multiple priorities without missing a beat.
• Problem-Solver – You tackle challenges head-on, delivering creative solutions that drive results.
• Tech-Savvy – Proficiency with Google Workspace, HR platforms, and Notion.
• Strong Communication Skills – You’ll be working with vendors, leadership, and teams across the company, so clear and concise communication is key.

Minimum Qualifications

• Bachelor’s degree from a top-tier university required
• 3+ years experience at a top-tier management consulting firm (MBB, Big 4) or investment banking preferred
• Demonstrated track record of leading operational improvements in high-growth environments
• Project management certification (PMP, CAPM, or equivalent) preferred
• Experience with financial modeling and data analysis tools
• Strong understanding of startup operations and scaling challenges

Why Join Us?

• A high-impact role where your work directly improves operational efficiency and company success.
• Opportunity to be part of a fast-growing, AI-driven company.
• Collaborative, fast-paced environment with room for career growth.
• Competitive compensation and benefits.
• A culture built on our Warrior Manifesto.

If you’re a strategic thinker, problem solver, and operational powerhouse, we’d love to hear from you! Apply now.