Deployment Strategist

As a Deployment Strategist at Thoughtful AI, you'll be at the heart of transforming how healthcare organizations operate, driving real-world impact through our advanced AI Agents. You will harness your skills in data analysis, customer discovery, and project management to deeply understand customer needs, crafting aggressive and high-impact product roadmaps that prioritize and amplify customer value.

In this role, you'll have the agility of a small, empowered team and the tools to turn vision into reality. You’ll work closely with cross-functional teams of engineers, PM’s, and customer success to ensure that our AI Agents deliver the goods, enhancing efficiency and patient outcomes across healthcare environments.

As a domain expert, you’ll lead the roadmap and execution of specific Thoughtful AI products, championing their implementation across diverse healthcare clients. Your blend of technical and strategic expertise will position you as a vital partner in helping customers unlock their operational potential and achieve never-before-seen results. 

Learn more about our Warrior culture.

• Lead Problem Discovery: Deeply investigate and define customer challenges, gathering insights to inform the strategic direction of AI Agent deployment
• Drive Data-Driven Decision Making: Use data analysis and customer research to prioritize product features and improvements, ensuring each roadmap decision aligns with customer needs and operational goals
• Exemplify Impeccable Project Management: Drive seamless project execution through meticulous planning, clear communication, and proactive issue resolution, ensuring timely delivery of high-impact initiatives aligned with customer and business objectives
• Serve as the Voice of Truth: Act as a trusted advisor to stakeholders, transparently communicating insights and findings about any current technical limitations or challenges encountered
• Evaluate Business Impact: Assess how different technical approaches influence business outcomes, supporting data-backed prioritization of product roadmaps
• Optimize Discovery and Delivery Processes: Collaborate on developing efficient processes and playbooks that streamline problem discovery and roadmap planning to ensure high-quality, scalable deployments
• Inform Product Design with Data Insights: Collaborate with the product and platform engineering teams, using findings from customer discovery to shape the design of products that align with emerging needs
• Lead Cross-Functional Collaboration: Guide and mentor a cross-functional team, including program managers and engineers, to ensure effective problem exploration and alignment across product initiatives

• Bachelor’s Degree in Computer Science, Math, or related discipline required, or eight years of equivalent work experience
• 5+ years of experience in program management, ideally with a focus on data science, machine learning / AI, search, or related technologies
• Experience in external customer-facing environment is essential
• The ability to think creatively to solve problems with a straightforward approach.
• Exceptional written and verbal communication skills with a talent for the precise articulation of hypotheses and outcomes
• Ruthless prioritization skills
• An entrepreneurial mindset and determination to do whatever it takes to achieve your mission

• Having worked in high-stakes projects with executive visibility and scrutiny 
• You have a strong background in technical program management, ideally coming from a data-heavy or healthcare technology company
• Experience with Python, AI, automation, RPA, OCR, IaaS, PaaS, DevOps, and product engineering
• The ideal candidate will have demonstrated the ability to work collaboratively across the organization, possess strong technical and leadership skills, and have experience building and fostering strong working relationships.
• Experience influencing without direct authority at senior levels of internal and external organizations, as well as strong people and negotiation skills

• Market-leading base salary and bonus
• Employee stock options
• Medical, dental, and vision insurance for you and your dependents
• We expect you to unwind and disconnect for three weeks per year while still getting paid