Commercial Enablement Innovation Lead

Overview: The Commercial Enablement Innovation Lead is a newly created role on the Commercial Effectiveness team with a clear mandate: rebuild and own Omada’s Business Case as an AI-native, scalable solution, then extend that innovation mindset into other high-value commercial workflows. This is an individual contributor role reporting directly to the Senior Director, Commercial Effectiveness. The right candidate brings advanced professional experience, strong analytical and systems thinking, and the ability to solve complex, cross-functional problems with creativity and sound judgment. This person will operate at the intersection of commercial operations, analytics, sales, and customer success. Responsibilities: Business Case Strategy and Ownership Rebuild Omada's Business Case from scratch as a flexible, AI-native solution Own ongoing maintenance, QA, and evolution post-launch, ensuring the tool stays accurate and field-ready Partner with Finance, RevOps/Forecasting, PMM, and Sales to align inputs, pricing logic, ROI methodology, and Salesforce integration Establish governance that reduces single-threaded ownership AI-Driven Enablement Innovation Lead AI Enablement for the Commercial organization helping our Commercial team leverage tools for maximum impact. Identify, prototype, and scale AI-enabled workflows that improve commercial productivity —projects could include items such as AI-driven prospecting, automated presentation generation, and AI-assisted content creation Apply prompt engineering and generative AI to build repeatable workflows, content templates, and decision-support tools for the field Evaluate emerging AI and enablement technologies and operationalize capabilities that meaningfully improve seller effectiveness Experience & Qualifications: 5+ years in sales enablement, commercial operations, revenue operations, or a related GTM function — with a track record of building or redesigning complex sales tools or models in a B2B environment Advanced data and modeling skills — Excel and/or Google Sheets fluency, assumptions-based modeling, and the ability to translate data into clear business recommendations; experience with Salesforce and commercial enablement systems a strong plus Hands-on AI and prompt engineering experience — demonstrated ability to build workflows, iterate on outputs, and create repeatable AI-native solutions using tools such as ChatGPT, Claude, Perplexity, or similar platforms Cross-functional project leadership — proven ability to drive complex, multi-stakeholder work to completion without formal authority; strong communicator who adapts messaging to both technical and executive audiences Commercial instincts — deep understanding of how AEs and commercial teams operate, what makes a tool get adopted, and how enablement connects to revenue outcomes Benefits: Competitive salary with generous annual cash bonus Equity grants Remote first work from home culture Flexible Time Off to help you rest, recharge, and connect with loved ones Generous parental leave Health, dental, and vision insurance (and above market employer contributions) 401k retirement savings plan Lifestyle Spending Account (LSA) Mental Health Support Solutions ...and more! It takes a village to change health care. As we build together toward our mission, we strive to embody the following values in our day-to-day work. We hope these hold meaning for you as well as you consider Omada! Cultivate Trust. We listen closely and we operate with kindness. We provide respectful and candid feedback to each other. Seek Context. We ask to understand and we build connections. We do our research up front to move faster down the road. Act Boldly. We innovate daily to solve problems, improve processes, and find new opportunities for our members and customers. Deliver Results. We reward impact above output. We set a high bar, we’re not afraid to fail, and we take pride in our work. Succeed Together. We prioritize Omada’s progress above team or in