Senior Program Manager, Commercial Strategy

Squarespace is looking for a Senior Program Manager to support the Commercial Strategy team’s mission to accelerate revenue growth by ensuring the team performs at its best with efficiency. Your responsibilities will include ensuring clear project/program planning, transparent progress tracking, risk mitigation, team process improvements, and efficient and scalable delivery. You will help connect the dots across people and projects, and proactively surface opportunities to go beyond the status quo. The Commercial Strategy team accelerates revenue growth data-driven strategies that optimize pricing, product monetization, and profitability. We drive alignment across the company to ensure successful execution of various initiatives, partnering with product, business, and engineering teams. You will report to the Director of Commercial Strategy and work hybrid from our NYC office 2-3 days per week. You’ll Get To… Project/Program Management Build and maintain clear project plans covering scope, milestones, owners, risks, dependencies, and issue tracking. Break down silos, surface conflicting priorities, and ensure coordinated execution, including simultaneous launches across multiple product areas. Track and communicate project status to stakeholders; own recurring executive-level communications and leadership agenda updates. Use AI tools to synthesize meeting outputs and draft communications at pace. Facilitate cross-functional collaboration across Product, Engineering, Analytics, UXR, Tax, Legal, and Finance. Manage A/B test pipeline sequencing across concurrent experiments, tracking interdependencies and flagging downstream schedule impacts. Team Operations & Processes Design and implement sustainable processes and playbooks for collaborative, transparent execution, incorporating AI-assisted workflows where they improve speed or quality. Identify bottlenecks and inefficiencies in team workflows and drive solutions, including evaluating and piloting AI tools that could meaningfully reduce manual effort. Manage the team’s operating rhythm: project lifecycles, planning cycles, goal-setting, team rituals, and leadership updates. Hold teams accountable for commitments and remove blockers. Establish regular reviews of key pricing levers including foreign currencies, discounts, and optimization opportunities. Create and maintain a source of truth for pricing and packaging decisions; drive knowledge-sharing best practices, including AI-assisted documentation to make institutional knowledge more accessible. Who We're Looking For 5+ years of program or project management experience, driving cross-functional initiatives with stakeholders from diverse disciplines; preference for experience in a SaaS or software environment. Strong knowledge of the product development lifecycle; familiarity with Agile, Scrum, and Waterfall methodologies. Experience with A/B testing methodologies; working knowledge of statistical and financial analysis and qualitative/quantitative research. Track record of bringing structure and predictability to a fast-paced environment with ease in context-switching. Ability to influence without authority across functions and levels; exceptional communication and stakeholder management skills. Proficiency in Jira, Google Workspace, Excel, Looker, Amplitude, and Statsig (or equivalent A/B testing platforms). Comfortable using AI tools (e.g. Claude, ChatGPT, Gemini) regularly to research, draft, and synthesize; demonstrated ability to evaluate and apply them critically. Interest in software products, business strategy, pricing models, and competitive landscape. Experience shipping products globally with an understanding of localization and internationalization is a plus. Direct experience with online checkout, billing, payment processors, or pricing strategy is preferred. Benefits & Perks A choice between medical plans with an option for 100% covered premiums Fertility and adoption benefits Access to supplemental insurance p…