Senior Program Manager, Commercial Strategy

Squarespace; New York (NY); Hybrid; USD 127,000 - 204,000; Full time

Benefits offered by this job

Medical plans with premiums covered

Fertility and adoption benefits

Headspace app subscription

Retirement with employer match

Flexible paid time off

Parental leave

Job summary

Squarespace is seeking a Senior Program Manager to accelerate revenue growth within the Commercial Strategy team. You will plan projects, track progress, mitigate risks, and streamline delivery across Product, Engineering, Analytics, and Finance.

The role supports a hybrid NYC-based schedule with 2-3 days in the office. You will manage multiple launches, surface opportunities for optimization, and leverage AI tools to draft communications and reports for executives.

Qualifications

• 5+ years of program or project management experience in SaaS or software.
• Familiarity with Agile, Scrum, and Waterfall methodologies.
• Experience with A/B testing methodologies and data analysis.

Responsibilities

• Build and maintain clear project plans with scope, milestones, owners, risks and dependencies.
• Break down silos and coordinate multiple launches across product areas.
• Track status and lead executive communications; synthesize outputs with AI tools.
• Facilitate cross-functional collaboration across Product, Engineering, Analytics, and Finance.
• Manage the A/B test pipeline and flag downstream schedule impacts.

Skills

Program management

Cross-functional leadership

Stakeholder management

Communication

Agile methodologies

Tools

Jira

Google Workspace

Excel

Looker

Amplitude

Statsig

Job description

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 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: $126,500 - $203,550 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 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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