Senior Product Manager, Acuity Scheduling, Payments

At Squarespace, we empower product teams to solve meaningful customer and business problems. We're looking for a Senior Product Manager to join the Acuity Scheduling team, leading product management across Acuity's payments and mobile surfaces for one of Squarespace's core scheduling products.

Acuity Scheduling helps service businesses run their operations end-to-end: booking, client management, and getting paid. Payments is central to that value proposition, and it's one of Acuity's most significant growth opportunities. This role owns the strategy and execution for expanding how and where Acuity sellers collect revenue, building the payment experiences, defaults, and integrations that make on-platform collection the obvious choice across web, mobile, and emerging booking channels.

This is a hybrid role, requiring 1–3 days a week in our New York City office. You will report to the Product Director on the Acuity Scheduling team.

• Own the long-term strategy and roadmap for payments, transactions, and mobile on Acuity
• Lead rigorous problem discovery, deeply understanding customer, business, and market dynamics before pursuing major investments
• Develop evidence-based problem statements grounded in user research, competitive analysis, and financial data
• Define target segments, primary use cases, and expansion opportunities across web, mobile, and in-person payment contexts
• Balance partner, build, buy, and deprecate decisions to accelerate GPV growth and customer impact
• Drive payment integrations and checkout UX across Acuity's web and mobile surfaces
• Leverage relationships with external partners to address areas of opportunity where Acuity can serve customers in a distinctive way
• Partner with marketing to launch new products, with customer operations to develop excellent merchant support, and with analytics to monitor engagement and evaluate success
• Own the key metrics for your business area, explain trends, and build shared understanding across teams and stakeholders
• Create alignment across stakeholders through clear narratives, documentation, and prioritization frameworks

• 6–8+ years of product management experience in SaaS or consumer software, with a track record of shipping products that drive measurable business outcomes
• Deep experience with payments, fintech, or transaction products, including third-party integrations, checkout UX, and payment infrastructure
• Experience leading mobile product development across iOS and Android surfaces
• Strong data and financial analysis skills, with experience sizing opportunities and validating demand
• High technical fluency; comfortable partnering on complex workflows, data models, and platform integrations
• Proven ability to define the right problem before designing solutions, resistant to premature solutioning
• Excellent communication and interpersonal skills, with demonstrated ability to align cross-functional teams around business goals
• Customer-obsessed, with a history of conducting research, customer interviews, and usability testing to inform decisions
• Comfortable challenging default approaches when they conflict with user or commercial outcomes
• Experience with in-person payments, POS integrations, or hardware-adjacent product work
• Familiarity with scheduling, booking, or operational tools for SMBs

• A choice between medical plans with an option for 100% covered premiums 
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• 12 weeks paid parental leave and family care leave
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 7 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

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