At MacPaw, we craft software that makes everyday tech life simpler, cleaner, and more enjoyable. From globally loved products like CleanMyMac and Setapp to emerging cybersecurity tools like ClearVPN and Moonlock, we are building a product ecosystem that reaches millions of people worldwide.
We believe humans and technology can reach their greatest potential together. By fusing high engineering standards, thoughtful design, and practical AI, we rethink how people interact with their devices and shape the daily tech routines of the future.
Working at MacPaw means owning outcomes, not just tasks. We build for global scale from day one, giving you the trust, freedom, and room to experiment.
In our team, we challenge ideas directly, support each other genuinely, and build software that makes a meaningful difference — both in the tech world and beyond.
We're looking for a Senior Product Manager to join the team behind Leebry, a B2B AI platform at an early, fast-moving stage of product development.
Leebry connects the tools enterprise teams already live in — Confluence, Slack, Jira, GitHub, Okta, and more — and turns them into a single intelligent layer that answers questions and automates repetitive IT requests: access provisioning, onboarding, offboarding, and the hundreds of small workflows that eat up IT teams' time every day.
As a Senior PM, you'll own the automations roadmap — the part of the product that makes Leebry act, not just answer. You'll drive it from early MVP to polished product, working closely with a small and sharp team of engineers and designers. The role is high-impact and deeply cross-functional: you'll spend as much time shaping engineering direction as you will talking to customers.
If you're excited to build AI automation that enterprise teams can actually trust with real workflows, we'd love to hear from you.
In this role, you will:
- Own the automations roadmap end-to-end: priorities, readiness, reliability, research, and growth trajectory.
- Run customer development — dig past surface-level requests to uncover real problems and turn them into clear, actionable use cases.
- Use AI tools and rapid prototyping to shrink the gap between idea and shipped feature — the faster you move, the more you get to build.
- Partner with design, analytics, and marketing to define user flows, copy, analytics events, and edge cases.
- Communicate decisions with exceptional clarity to engineering, design, and stakeholders — turning ambiguity into direction.
- Groom and maintain a fully understood backlog: initiatives, insights, tasks — aligned with engineering and design.
- Iterate rapidly based on market and customer signal, committing to decisions.
Skills you'll need to bring:
- 5+ years of hands-on experience shaping and shipping products.
- Proven ability to move fast: you can show concrete examples of compressing timelines, building MVPs, or unblocking engineering through better product clarity.
- Strong working knowledge of web products — you understand how front end and back end connect, and you can speak the language of engineers building complex systems.
- Deep, practical AI fluency — you use frontier models daily, have built something real with them, and understand how models differ, what their limitations are, and how to apply them in a product context.
- Data-driven decision-making: you find and use data to make decisions, source it yourself when none exists, and change course when evidence says you're wrong.
- A track record of taking products from zero to shipped — not just defining what to build, but making it happen.
- At least Upper-Intermediate (B2) English.
As a plus:
- Background in B2B SaaS or enterprise tooling.
- Experience in early-stage startup environments or as a founder.
- Familiarity with ITSM, IT automation, or agentic AI workflows.
What We Offer
Your well-being is always a priority
- We believe the health, satisfaction, and financial security of employees and their families are important not only to each individual’s well-being but also to achieving our organization’s overall objectives. We offer medical, vision, and dental insurance benefits.
Hybrid work model & flexible working hours
- We offer a hybrid work model, with at least three days a week on-site in our Boston office. You can choose a schedule that is comfortable for you. No one here tracks your clock in/out because MacPaw is built on trust and cooperation.
Space to grow both professionally and personally
- Whatever your dreams and aspirations are, we have you covered. Education opportunities to grow both hard and soft skills, annual development reviews, internal community.
Teams we are proud of
- We build honest, transparent, and reliable relationships within teams. Every Macpawian can improve processes and implement their ideas. We encourage open and constructive feedback and provide training for Macpawians on giving and receiving feedback.
Time-off policy that covers life’s needs
- At MacPaw, we genuinely understand the value of taking time to unwind and attend to your loved ones. That's why we provide our employees with a generous PTO benefit that can be utilized for multiple purposes.
We’re an equal opportunity employer. Here is a safe place for applicants of all backgrounds
- We are hiring talented humans. Meaning with all our variety of backgrounds and identities, including service members and veterans, women, members of the LGBTQIA+ community, individuals with disabilities, and other often underrepresented groups. MacPaw does not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.
