Senior Program Manager, Commercial Strategy

Webhosting; New York (NY); On-site; USD 126,500 - 203,550; Full time

Benefits offered by this job

Free lunch and snacks

Dog-friendly workplace

Private rooftop

Headspace mindfulness app subscription

Flexible PTO

Job summary

Squarespace is seeking a Senior Program Manager to empower the Commercial Strategy team in accelerating revenue growth. You will drive planning, tracking, risk mitigation, and scalable delivery across cross-functional groups in a hybrid NYC setting.

You’ll lead initiatives from project lifecycles to executive updates, leverage AI tools for outputs, and align pricing and monetization strategies with business goals. The role reports to the Director of Commercial Strategy.

Qualifications

• Lead and manage complex programs across multiple product areas.
• Design sustainable processes and playbooks for transparent execution.
• Coordinate cross-functional work with Product, Engineering, Analytics, UXR, Tax, Legal & Finance.
• Manage A/B test pipelines and interdependencies.
• Incorporate AI-assisted workflows to improve speed and quality.

Responsibilities

• Build and maintain clear project plans with scope, milestones, owners, risks, dependencies and issue tracking.
• Break down silos and ensure coordinated, multi-area launches.
• Track and communicate project status; lead executive updates with AI-assisted outputs.
• Facilitate cross-functional collaboration across teams.
• Manage value-driven pricing and packaging reviews with emphasis on optimization.

Skills

Project management

Cross-functional collaboration

AI tooling

Roadmapping

Risk management

Stakeholder communication

Job description

Hybrid Full-time Senior Operations

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.
• 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
• 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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