Senior Product Manager - Acuity Payments & Mobile

At Squarespace, we empower product teams to solve meaningful customer and business problems. Millions of entrepreneurs across 200+ countries rely on our platform to build their online presence, monetize their work, and manage their operations.

As a Senior Product Manager on the Acuity Scheduling team, you will lead product management across Acuity's payments ecosystem and mobile surfaces. Acuity Scheduling helps service-based SMBs manage booking, client relationships, and revenue collection end-to-end. In this high-growth role, you will own the long-term strategy to expand how and where service business owners collect revenue—building high-converting web and mobile checkout experiences, default payment setups, partner integrations, and in-person POS capabilities that make on-platform collection the natural choice for merchants.

Key Responsibilities

• Payments & Mobile Vision: Own the multi-quarter strategy and roadmap for payments, transaction flows, and mobile surfaces across Acuity Scheduling on web, iOS, and Android platforms.
• Gross Payment Volume (GPV) Growth: Balance build, partner, buy, and deprecation decisions to accelerate revenue growth, platform adoption, and payment processing volumes.
• Evidence-Based Discovery: Conduct rigorous problem discovery grounded in quantitative financial data, user research, competitive benchmarking, and merchant interviews before committing to major engineering investments.
• Checkout UX & Integrations: Drive intuitive payment integrations and seamless checkout UX across web booking flows, mobile apps, and emerging customer booking channels.
• External Strategic Partnerships: Partner with external payment gateways, financial institutions, and point-of-sale (POS) vendors to unlock novel revenue opportunities for service businesses.
• Cross-Functional Go-To-Market: Collaborate closely with Marketing on product launches, Customer Operations on merchant support workflows, and Analytics to track engagement metrics and unit economics.
• Metrics & Executive Alignment: Own core performance indicators for the payments business area, framing clear strategic narratives and prioritization frameworks for executive stakeholders.

Requirements

Product Management & Fintech Depth

• 6–8+ years of progressive product management experience in SaaS or consumer software platforms, with a track record of driving measurable commercial outcomes.
• Fintech & Payments Expertise: Deep hands-on experience with digital payments, financial infrastructure, third-party payment gateway integrations, transaction processing, and checkout conversion optimization.
• Mobile Product Leadership: Proven experience leading mobile app development across both iOS and Android ecosystems.
• Data & Financial Rigor: Exceptional data and financial analysis skills with demonstrated expertise in market opportunity sizing, unit economic modeling, and hypothesis testing.
• High Technical Fluency: Comfortable partnering with engineering leads on complex financial data models, backend webhooks, API schemas, and multi-sided platform architectures.
• Problem-First Mindset: Demonstrated ability to thoroughly define problem spaces and validate user demand before jumping to solution design.

Preferred Qualifications

• Direct experience with in-person payments, hardware-adjacent products, or POS (Point-of-Sale) software integrations.
• Domain expertise with SMB operational software, online booking platforms, appointment scheduling, or client management tools.
• Experience managing multi-currency checkout or international payment methods.

Total Rewards & Benefits

• Compensation & Equity: Base cash compensation of $153,500 – $247,000 USD + stock option grants in Squarespace.
• Healthcare & Family Planning: Choice of comprehensive medical plans (including options with 100% covered premiums), fertility/adoption benefits, and 12 weeks of paid parental leave.
• Workplace Perks: Dog-friendly NYC HQ with free daily lunch, snacks, private rooftop access, pretax commuter benefits, and bi-annual Hack Weeks.
• Wellness & Growth: Headspace subscription, global Employee Assistance Program (EAP), retirement benefits with employer match, flexible paid time off, and education tuition reimbursement.