Delivery Lead

Aiwyn

7d • Remote

About The Position

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.

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.

Requirements

• You've managed complex, multi-workstream implementations before — the kind where the org chart on the customer side has multiple layers, the technical environment has real constraints, and slipping a milestone has downstream consequences you have to manage carefully. You know the difference between running a project and running a program, and you operate naturally at the program level.
• You lead through influence. You don't have direct authority over the Solutions Architect or Implementation Engineer, but you set the pace, hold the standard, and create the conditions for the trio to do their best work. People follow your lead because you're organized, decisive, and clear — not because of your title.
• You're an exceptional communicator. Executive-level customers trust you because you tell them the truth, you don't spin, and you always know where the program stands. Internally, your updates are crisp, your asks are specific, and your escalations come with a point of view on how to resolve them.
• You're structured but not rigid. Programs at Aiwyn don't always go according to plan — product gaps, customer readiness issues, and technical surprises are part of the reality. You know how to adjust without losing control of the program, and you're comfortable making judgment calls in ambiguous situations.
• You understand the technical layer well enough to hold the implementation engineer accountable and to have credible conversations with EPD when something needs to be escalated. You don't need to build an ETL flow, but you need to understand why one is taking longer than planned and whether that's acceptable.
• 6+ years in implementation, program management, or professional services delivery at a SaaS or enterprise software company
• Proven experience managing multi-phase, multi-stakeholder implementation programs — not just individual projects
• Strong track record of executive-level customer communication and relationship management in a delivery context
• Experience coordinating cross-functional delivery teams without direct management authority
• Familiarity with technical implementation concepts — data migration, system configuration, integration architecture — sufficient to hold technical workstreams accountable

Nice To Haves

• PMP, PgMP, or equivalent program management certification is a plus, not a requirement
• Prior experience in accounting technology, fintech, ERP, or practice management software is a meaningful differentiator

Responsibilities

• 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.

Benefits

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
• Remote -work-from-anywhere culture
• Flexible PTO
• World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
• Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
• 401(k) matching

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1-10 employees