Who is Aiwyn and what do we do?

Aiwyn is transforming the way accounting firms manage the entire revenue lifecycle. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology—and we’re doing it with world-class people, processes, and product.

Role Overview

We’re looking for a Program Manager to join our Services team. You will lead customers and implementation managers through implementation programs, onboarding and adoption of Aiwyn’s platform, ensuring projects are delivered on time, within scope, and with high customer satisfaction. You’ll manage a portfolio of multiple client projects (assigned to Implementation Managers), coordinate across Product, Engineering, and Customer Success, and play a hands-on role in shaping how implementations scale as we grow. This is a customer-facing role with direct visibility into leadership and real influence on client outcomes.

What will your day-to-day responsibilities look like?

Lead the programmatic structure for multiple customer implementation projects, from project kickoff to go-live, ensuring each customer achieves a smooth and successful deployment.
Own high-level project planning and execution, managing scope, milestones, and deliverables while keeping all stakeholders informed with clear, timely communication.
Collaborate with internal teams—from Sales to Customer Success to Product—to ensure seamless handoffs and alignment on client outcomes.
Facilitate change management strategies, working with client leadership to prepare, train, and engage their teams to maximize long-term value.
Proactively identify and mitigate risks, addressing challenges swiftly to maintain project momentum and client confidence.
Monitor and report on project progress, providing customers and leadership with transparent performance updates and success metrics.
Championing the client implementation experience, ensuring every interaction reflects Aiwyn’s commitment to partnership, innovation, and measurable impact.
Drive continuous improvement by contributing to the refinement of playbooks, processes, and tools that make implementations more scalable and efficient.

The ideal candidate candidate for this role:

3+ years of program management, consulting, or implementation experience in SaaS or technology services (or equivalent client-facing experience).
Strong organizational and communication skills; comfortable managing multiple projects at once.
Demonstrated ability to lead customer-facing projects and deliver measurable outcomes.
Experience working with cross-functional teams in dynamic environments.
PMP, CSM, or similar certification is helpful but not required.
Bachelor’s degree or equivalent work experience.

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.
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