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.

What You'll Do

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

Who We're Looking For

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

Nice to Have

Experience with in-person payments, POS integrations, or hardware-adjacent product work

Familiarity with scheduling, booking, or operational tools for SMBs

Benefits & Perks

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

Cash Compensation Range: $153,500 - $247,000 USD

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.

About Squarespace

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.

Our Commitment

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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