Delivery Lead

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 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.

Qualifications 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 Why Aiwyn The firms we serve — including some of the largest accounting organizations in the country — trust Aiwyn with some of their most consequential operational changes. As an Implementation Program Manager, you'll be the person they trust to make those changes land. You'll have real ownership, high visibility, and the opportunity to shape how Aiwyn delivers at enterprise scale as the company continues to grow.

Benefits and

Perks The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience. Other

benefits include: 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 Our Values: Relentless by Design Owners not Renters Trust at the Core Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances. Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa

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