AI Deployment Strategist

About the AI Deployment Strategist Upperline is seeking a highly motivated individual to join our Business Operations & Strategy team and lead enterprise AI deployment. You will partner with the executive leadership team and other leaders at Upperline to plan, manage, and execute the incorporation of AI into every part of our operating structure. The right candidate is equal parts operator, strategist, and builder. You ask 'why do we do it this way?' before you ask 'how do we make this faster.' You're not afraid to challenge entrenched workflows. You’re the kind of person who gets energy from ambiguity, moves quickly without sacrificing judgment, and can context‑switch between tactical execution and big‑picture thinking. You’re comfortable navigating unstructured problems, and you have a bias toward action – even when the path isn’t fully mapped. This role reports to the SVP of Strategy & Analytics. This is a remote position with flexibility for travel as needed. What You’ll Do Executive Partnership, Communication, & Influence Build multi‑year enterprise AI roadmap with the SVP Strategy & Analytics, CEO, and COO. Skillfully lead large‑scale or high‑impact meetings and workshops, including the preparation of materials, driving decision‑making, and identifying concrete outcomes and next steps. Strategic Program Leadership & Execution Own the implementation of AI products and solutions across every Upperline department. Partner with department leaders and engineering team to execute highest‑impact incorporation of AI into that department’s workflows. Plan the work and work the plan – assign workstreams to team members and self that reflect skills and development needs while meeting company needs and timelines. Demonstrate leadership and the ability to influence by initiating partnerships that promote organizational objectives and change. Lead training sessions to ensure that the new solutions meet the department’s needs and have meaningful impact on the operations. Drive sustained department activation of AI including sustained usage and demonstrable business value. Leverage Complex Data to Drive Analytical Insights & Problem Solving Immerse yourself in the most critical workflows for each department to understand how work actually gets done. Stitch together data from different sources to identify opportunities and recommendations to improve the business. Break down complex problems into discrete tasks to scope projects into a defined set of tasks, responsibilities, and timelines and lead project execution. Assess the performance of pilots and quickly end or modify them if they aren’t delivering the expected results. Qualifications of the AI Deployment Strategist 3-6+ years of experience in a role focused on problem solving and leveraging artificial intelligence (management consulting with AI focus, operations at a growth‑stage company, deployment role in software company, basically any role where you just had to figure it out and get stuff done). Healthcare experience is not required. We are looking for an elite problem solver who can apply that skillset to healthcare. Strong technical depth across coding, agents, and APIs, with a practical understanding of how AI systems are built, evaluated, and operated in production. Strong ability to connect technical features and capabilities to concrete business outcomes such as productivity, efficiency, cost reduction, and revenue impact. Self‑driven and relentlessly proactive. You are constantly moving towards the next thing to make Upperline better and manage your to‑do list accordingly. Robust analytical skills and proven ability to be creative, resourceful, and relentless in solving complex problems with data and insights. Experienced in stakeholder management, with strong proficiency in managing tasks and timelines across multiple teams to meet targets. Strong interpersonal skills; ability to collaborate productively with a diverse group of cross‑functional partners and build trust with leaders. Excellent communication skills – verbal, written, and presentation. Highly adaptable and can pivot on the fly. Strong bias towards action and takes responsibility for achieving outcomes. Highly organized and ability to build scalable processes. High standard for work product, and ability to drive organization towards excellence. You stay current on a fast‑moving landscape not because it's your job but because you can't help it. Competitive benefit options include comprehensive medical, dental and vision plans, 401K (matching), PTO and parental leave. Compensation Compensation is commensurate to compensation for similar positions in the region and based on prior training and experience. Job Type: Full‑time Equal Opportunity Employer This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor. #J-18808-Ljbffr Upperline Health Inc