Sr Director of Product, Client Engagement Group

At Squarespace, we empower our product teams to solve hard problems in ways that our customers love and strengthen our business. As Senior Director of Product for the Client Engagement Group (CEG), you will lead the product strategy and execution for Squarespace's customer engagement platform: the CRM, email campaigns, automations, and transactional communications that enable our merchants to build lasting customer relationships and grow their businesses on Squarespace.

The Client Engagement Group sits at the center of Squarespace's growth strategy. Our marketing tools are a critical lever in increasing product attach, reducing merchant churn, and building a differentiated position in the service commerce landscape. You will own the vision for transforming our current communications offering into a unified customer engagement hub… one that competes with best-in-class tools while leveraging Squarespace's unique data and ecosystem advantages.

You will report directly to the President of Squarespace and serve as a member of the Product leadership team. You will have the option of working on-site (hybrid) at our NYC headquarters or remotely within the U.S.

You’ll Get To… 

• Define and drive the multi-year product vision and strategy for CEG - spanning CRM, email campaigns, automations, transactional communications, and emerging channels including SMS - with a clear line of sight to revenue growth and platform impact
• Own the Email Campaigns business line end-to-end: report on revenue performance, develop engagement and GTM strategies, and lead roadmap decisions in close partnership with commercial and marketing stakeholders
• Build toward a competitive, full-featured customer engagement platform by prioritizing investments in business CRM, transactional automations, flexible communication channels, and advanced segmentation that meet the sophisticated needs of today's service sellers
• Lead, grow, and mentor a team of product managers across multiple product lines, setting a high bar for hypothesis-driven development, roadmap rigor, and customer-centricity
• Partner with Engineering and Design functional leads to deliver outcomes across the team; step in to remove blockers and maintain velocity on high-priority initiatives
• Collaborate across the Squarespace ecosystem - with Commerce, Growth, Financial Solutions, and GTM - to ensure CEG products are deeply integrated into the broader platform
• Champion the use of Squarespace data and AI to create smarter automation flows, personalized outreach, and differentiated customer engagement experiences that competitors cannot easily replicate
• Shape the process, craft, and standards for senior product leadership at Squarespace

Who We’re Looking For 

• 12+ years of product management experience, with a meaningful portion spent building and scaling customer engagement, CRM, marketing, or communications products
• 5+ years leading and developing teams of product managers in complex, multi-product environments
• Deep familiarity with the customer engagement and email service provider landscape; informed perspective on what it takes to compete with and differentiate from best-in-class marketing and CRM tools
• Demonstrated ability to own a revenue-generating product line with accountability for business outcomes, not just product delivery
• Strong strategic instincts paired with a bias for execution; comfortable operating at the intersection of vision-setting and unblocking day-to-day team work
• Excellent communicator and cross-functional partner with the credibility to influence senior leadership and align stakeholders across product, engineering, commercial, and marketing functions
• Experience applying hypothesis-driven development and experimentation to accelerate product-market fit and grow adoption

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
• Supplemental Life and Disability Insurance plans
• Fertility and adoption benefits
• 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

US Cash Compensation Range

Cash Compensation Range: $323,000 - $435,000 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 customers, but we also work toward 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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