aiwyn - Delivery Lead

• 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 • 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