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.

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.

• 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.

• 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 1700 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 customer base but we also strive for 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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What We Do

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. At Squarespace we celebrate creative possibility. With a culture rooted in curiosity Squarespace aims to provide its employees with the support to turn possibility into reality – learning from challenges and celebrating progress. At Squarespace we root for customer and employee success uplifting them with the tools needed to achieve their goals while also applauding what makes them unique and fulfilled. Our customers and employees alike are imaginative with the confidence to put their ideas out into the world and welcoming input and iteration. And our people run towards the next frontier to create our success motivated by the unknown and inspired by “first-ever” opportunities truly embracing a sense of possibility.

Why Work With Us

Squarespace employees are ownership-minded builders tenacious resourceful hands-on humble self-motivated experimental curious resilient inclusive and empathetic.

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