Delivery Lead

About Aiwyn Who is Aiwyn and what do we do? Aiwyn is building the operating layer for accounting firms — automating the workflows that sit between client engagement and getting paid. Our platform spans Payments, Engagements, and Practice Management, and we're deploying it inside some of the most respected accounting firms in the country, including Big 4 and Top 25 firms. ABOUT THE ROLE The Delivery Lead is the Directly Responsible Individual for Aiwyn's most complex, high-stakes customer implementations. Where an Implementation Specialist owns a single-firm, defined-scope deployment, the IPM owns programs — rolling M&A playbooks, multi-phase enterprise rollouts, and multi-product deployments that span quarters and involve multiple internal teams and firm-side stakeholders simultaneously. This role sits at the center of Aiwyn's Advanced Implementation delivery model, leading a cross-functional trio alongside a Solutions Architect and Implementation Engineer. The IPM is accountable for the overall success of the program — scope, timeline, delivery quality, and customer confidence — while coordinating execution across every workstream. This is not a coordination role. It's an ownership role. The success or failure of the program lands here. WHAT YOU'LL OWN Program Ownership & Delivery Leadership Own the end-to-end success of complex, multi-product customer implementations. Develop and maintain comprehensive program plans that coordinate multiple workstreams, phases, and product deployments. Ensure all implementation activity stays on schedule, on scope, and aligned to delivery objectives. When something threatens the program, you see it first and act on it. Cross-Functional Leadership Lead the Advanced Implementation Delivery Trio — Solutions Architect and Implementation Engineer — driving alignment and accountability across each function without direct authority over the success of the project. Coordinate across Implementation, Product, Engineering, Customer Success, and Support to ensure nothing falls through the cracks between teams. Customer & Executive Engagement Serve as the primary delivery leader for enterprise customers throughout the implementation. Facilitate executive-level conversations on program progress, key decisions, and delivery strategy. Manage escalations with clarity and composure. Maintain customer confidence even when the program is under pressure. Scope & Risk Management Own scope integrity across the program — identify scope creep early, manage change control, and communicate tradeoffs to both the customer and internal leadership. Maintain a live risk register. Surface risks before they become fires and drive resolution with urgency. Solution Coordination Partner closely with the Solutions Architect to ensure the proposed solution is being executed as designed. Ensure the Implementation Engineer has what they need to execute technical workstreams on time. Identify misalignment between design and execution early and drive it to resolution. Workflow Solutioning & Product Expertise Serve as a product expert and trusted advisor to the customer throughout the implementation — not just a project coordinator. When a customer's existing workflows need to change to get the most out of Aiwyn, you lead that conversation. You understand the product deeply enough to guide firms on how it should be configured and used, translate their operational requirements into the right implementation approach, and push back constructively when a requested workflow runs counter to how the product is designed to work. Customers should leave every session with you having a clearer picture of both what they purchased and how to make it work for their firm. Ongoing Program Cadence Establish and own the operational rhythm of the program — weekly syncs, milestone reviews, status reporting, and executive readouts. Keep all stakeholders informed without creating meeting overhead that slows the team down. WHAT WE'RE LOOKING FOR You've mana