Enterprise Operations Lead, Applied AI & Transformation

About Take Command Take Command is a start-up on a mission to improve the healthcare system, starting with health insurance. Pragmatically speaking, we help employers reimburse employees for individual insurance instead of offering a traditional one-size-fits-all group plan. We believe this model can empower employees (when they have the right support) to be savvy healthcare consumers and have a transformative impact on the entire healthcare system. Let’s be honest—health insurance is usually a confusing, frustrating, and even emotional experience for people. We want to fix that with a new model, great technology, and a superior user experience. We have made a great start, but we need your help to fully realize our long-term vision. Department: Enterprise Operations Employment Type: Full-time Location: United States / remote or hybrid based on company policy Salary Range: $75,000–$120,000 base salary, depending on experience, skills, location, and internal equity About Take Command Take Command is helping employers deliver better health benefits through Individual Coverage Health Reimbursement Arrangements, or ICHRAs. We are building practical, customer-centered technology and services that make health benefits easier to understand, easier to administer, and more useful for employers, employees, brokers, and partners. About the Role Take Command is looking for an Applied AI Specialist to help us apply AI in practical, measurable ways across our business. This role will start with primary ownership of Intercom Fin — improving how it supports customers today and exploring how it can support more advanced experiences in the future. This is a great opportunity for someone who is curious about AI, understands customer or member support workflows, and enjoys turning messy operational problems into clear, scalable solutions. You do not need to be an AI engineer to be successful in this role. We are looking for someone who can learn quickly, think analytically, write clearly, collaborate across teams, and develop deeper technical skills over time. Fin will be the anchor responsibility, but the role is broader than one tool. You will help evaluate where AI can improve customer care, client experience, member experience, internal workflows, and decision support. For example, this role may help explore whether AI could guide clients or members toward the best-fit health plan when supported by the right data, knowledge, rules, and compliance guardrails. What You’ll Do Own day-to-day performance, quality, and improvement of Intercom Fin. Monitor Fin metrics such as resolution rate, escalation rate, customer satisfaction, conversation quality, and recurring failure patterns. Review unresolved or escalated conversations to identify root causes and improvement opportunities. Improve Fin knowledge sources, instructions, workflows, routing, escalation logic, and guardrails. Partner with CX, Product, Compliance, Operations, Sales, Marketing, and technical teams to ensure AI-powered experiences are accurate, helpful, compliant, and aligned to business goals. Identify content, process, configuration, or data gaps that prevent AI tools from delivering a great user experience. Support internal pilots and beta tests for expanded AI use cases, including experiences beyond traditional customer support. Help define requirements, success metrics, test plans, rollout steps, and feedback loops for AI-enabled workflows. Evaluate when Intercom Fin is the right solution and when another tool, workflow, automation, or process change may be a better fit. Document learnings, risks, decisions, and recommendations so AI improvements can scale responsibly. What We’re Looking For Experience in customer support, customer experience, operations, business analysis, knowledge management, systems, or a related role. Strong problem-solving skills and the ability to investigate ambiguous issues, identify patterns, and separate symptoms from root causes. Clear writing and communication skills, especially the ability to explain complex topics in plain language. Comfort working with support conversations, feedback, metrics, spreadsheets, dashboards, or other qualitative and quantitative data. Strong judgment around customer experience, accuracy, risk, escalation, and when an AI tool should not answer. Curiosity about AI tools and willingness to learn prompt writing, tool configuration, testing methods, and light technical concepts. Ability to work cross-functionally with business, operations, compliance, product, and technical partners. Ownership mindset: you are comfortable finding problems, proposing solutions, testing improvements, and measuring whether they worked. Preferred Experience Hands-on experience with Intercom , Intercom Fin , or another AI chatbot / AI agent platform. Experience configuring, monitoring, testing, or improving Fin (or similar) responses, help center content, macros, workflows, or support automations. Experience in CX operations, help center management, support QA, business operations, or business analyst work. Experience with health insurance, benefits administration, ICHRA, open enrollment, or another regulated customer-facing environment. Comfort with reporting tools, spreadsheets, dashboards, workflow automation, CRM/support platforms, or systems administration. Familiarity with prompts, AI agents, APIs, SQL, structured data, or knowledge-base architecture. What Success Looks Like Fin becomes more accurate, useful, trusted, and measurable over time. Customers, members, clients, and internal teams get faster, clearer answers with appropriate human escalation when needed. Recurring support issues are identified and addressed through better content, configuration, workflows, data, or process changes. New AI use cases are tested responsibly before launch, with clear success metrics and compliance guardrails. Take Command develops a stronger operating model for applying AI to real business problems. Why This Role Matters AI is becoming an important part of how Take Command serves customers, members, clients, brokers, and internal teams. This role will help make sure our AI tools are not just exciting technology, but useful, accurate, measurable, and aligned to real human needs. If you are a strong operator, analyst, or customer experience professional who wants to grow into applied AI, this is an opportunity to help shape that capability from the ground up. Working at Take Command We’re excited to build a team and culture that reflects our values! We offer competitive pay and health benefits to share with this position. A generously funded ICHRA for medical, dental, and vision premiums and medical expenses. You get to use our own product and we think that’s so exciting and rare! Unlimited personal vacation in addition to regular company holidays. 401(k): 90-day eligibility for 4% match that vests over 4 years with a one year cliff! We have two beautiful offices in Richardson, Texas (City Line) and Austin, Texas. The kitchen is well-stocked and we've designed the space to have lots of different areas to work--lounge on the couch, stand near your colleague at a kiosk desk or hole up in one of our phone rooms! Competitive parental leave for new parents. Up to two paid days of Paw-ternity leave. We recognize that pets are family too - and supporting life outside of work (including four-legged members) matters! ClassPass corporate membership with access to over 73,000 fitness and wellness options. Flexible on where you work – we believe in the power of connecting with intention! While we hope to see you around the office on a regular basis, you also have the ability to work from home some when you need to get focus work done. More About Us We secured our Series B funding in 2023 and are thrilled to be able to expand our team. Despite being a small startup in a land of health insurance giants, we’re the recognized industry leader for what we do (health insurance reimbursements) and passionate about bringing it to market because we know we can help fix a broken system and improve our clients’ wellbeing and health outcomes. We’ve been featured in The New York Times , The Wall Street Journal , The Dallas Morning News , and other national healthcare publications and are excited about our growth opportunities. Take Command knows diversity and inclusion among our teammates is integral to our company’s success and growth. Our vision is to recruit, develop, and retain the best team from a diverse candidate pool. This has mostly been about us, but we’d love to hear from you--we can’t wait to hear your story! *Take Command is an equal opportunity employer! We celebrate diversity and are committed to creating an inclusive environment for all employees.