Health & Benefits - AI Bot Optimization Specialist (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.
Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.
Join us on our journey as we work together to take on the complex and the everyday--turning collective effort into life-changing impact that enriches lives and helps build a better future. Learn more at inspirafinancial.com.
We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday). This requirement does not apply to support specialist positions.
Don't meet every single requirement? That's okay. At Inspira Financial, we know growth comes from people who are willing to learn, challenge themselves, and aim higher. We value individuals who lead with heart, cultivate trust, and collaborate to win together. If you're energized by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, Inspira Financial could be the right next step in your journey. We look forward to receiving your application.
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
The AI Bot Optimization Specialist owns the ongoing performance, testing, and refinement of Inspira's virtual agent experience. This role analyzes conversation-level and aggregate performance data, runs structured tests ahead of and following changes, and tunes the AI Bot configuration and conversational flows to improve resolution rate, deflection, and customer satisfaction. The Bot Optimization Specialist works in close partnership with the Content Specialist(s), translating performance data into prioritized content and configuration fixes, and shares accountability for the digital experience's overall self-service effectiveness.

• Own day-to-day performance monitoring, testing, and refinement of Inspira AI bot, including, but not limited to, Fin Voice where applicable, targeting resolution rate, deflection, and CSAT goals.
• Conduct weekly review of conversation transcripts, escalations, and handoffs to identify knowledge gaps, mis-routed intents, and breakdowns in bot understanding.
• Design and execute structured test scenarios, including regression and A/B testing of flows and prompts, prior to and following knowledge base or configuration changes.
• Tune AI bot's retrieval configuration, intents, and conversational flows based on performance data and testing outcomes.
• Partner with the Content Specialist to translate identified knowledge gaps into prioritized content tickets, and validate that published fixes resolve the underlying issue.
• Monitor and test configuration changes affecting AI bot's suggestions for human agents.
• Maintain a bot performance dashboard covering resolution rate, deflection rate, CSAT, and escalation volume, reporting trends to leadership on a monthly cadence.
• Lead root-cause analysis for significant bot performance dips or recurring failure patterns, driving remediation with the Content Specialist and platform/IT support as needed.
• Monitor AI Insights, including CX Score, Topics Explorer, and Trends reports, to identify emerging customer topics not yet covered by the bot.
• Make light, time-sensitive content corrections directly, such as typo fixes or quick clarifications, to resolve an active bot failure, coordinating promptly with the Content Specialist to formalize the change.
• Support new bot use case rollouts, including test plan development and go-live monitoring for new flows or digital agent capabilities.
• Stay current on AI platform updates and features, evaluating applicability to Inspira's use case.
• Perform other duties as assigned.

Preferred Qualifications
Education & Experience:

• 2+ years of experience in conversational AI or chatbot optimization, digital customer experience analytics, or CX systems administration; experience with Intercom Fin or a comparable AI virtual agent platform strongly preferred.
• Experience with contact center or digital CX performance metrics, including resolution rate, deflection rate, CSAT, and NPS, required.
• Familiarity with prompt engineering, RAG-based retrieval systems, or conversational flow design preferred.
• Experience with A/B testing, structured QA, or data-driven experimentation in a customer-facing digital tool preferred.
• Bachelor's degree in Business, CX, Data Analytics, Computer Science, or a related field preferred; equivalent experience considered.

Skills & Abilities:

• Strong analytical skills; able to interpret conversation-level and aggregate performance data to identify patterns and root causes.
• Detail-oriented and methodical approach to testing; able to design and execute structured test plans before deploying changes into a live customer-facing environment.
• Working understanding of how knowledge base content quality drives bot performance; able to translate bot failures into clear, actionable content or configuration requests.
• Comfortable partnering across content, platform administration, and compliance functions to resolve performance issues.
• Effective communicator; able to present bot performance trends and recommendations to non-technical leadership audiences.
• Comfortable operating in a fast-paced, iterative environment with frequent testing cycles and evolving platform capabilities.
• Demonstrates the highest degree of honesty, integrity, and ethical conduct in all professional activities.

Compensation & Benefits
$36.00/hr-$40.00/hr