[All remote jobs](https://jobicy.com/jobs.md)[![Squarespace logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/02/WRILS-210217203348-525354.jpg)](https://jobicy.com/company/squarespace.md)[Squarespace](https://jobicy.com/company/squarespace.md) # Senior Product Director, Client Engagement Group Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/squarespace.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 323k–435k / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceDirectorPublished7 Oct 2026Apply before6 Nov 2026Listing views54Application actions4Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. This is an executive product leadership role responsible for the strategy, roadmap, and business outcomes of Squarespace's Client Engagement Group. The leader will oversee CRM, email campaigns, automations, transactional communications, segmentation, and emerging channels such as SMS. They will own the Email Campaigns business line, lead product managers across multiple product areas, and partner closely with engineering, design, growth, commerce, and go-to-market teams. The role reports to the President and requires strong revenue accountability, product-market strategy, and organizational leadership. Success depends on building a differentiated, data- and AI-enabled customer engagement platform that improves attach, adoption, retention, and merchant growth. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe position has enterprise-level strategic scope, direct executive visibility, and accountability for a revenue-generating multi-product portfolio. It requires balancing long-term platform vision with rapid execution, organizational leadership, and alignment across numerous senior stakeholders. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianHighly competitive$379,000US market range$280k–$450k0$495k AI insightThe disclosed US yearly cash compensation range is $323,000 to $435,000 USD, producing an offer midpoint of $379,000. This is a highly competitive range for a senior product director/executive leading a revenue-critical CRM and marketing-platform portfolio at a major US technology company. Estimated US market compensation for comparable senior product leadership base/cash roles is approximately $280,000 to $450,000 yearly, with total compensation potentially higher when equity and incentives are included. ## Core skills Skills and capabilities most closely associated with this opportunity. [Product strategy](https://jobicy.com/jobs?search_keywords=Product%20strategy.md)[Product portfolio leadership](https://jobicy.com/jobs?search_keywords=Product%20portfolio%20leadership.md)[CRM](https://jobicy.com/jobs?search_keywords=CRM.md)[Email marketing platforms](https://jobicy.com/jobs?search_keywords=Email%20marketing%20platforms.md)[Marketing automation](https://jobicy.com/jobs?search_keywords=Marketing%20automation.md)[Transactional communications](https://jobicy.com/jobs?search_keywords=Transactional%20communications.md)[Revenue ownership](https://jobicy.com/jobs?search_keywords=Revenue%20ownership.md)[People management](https://jobicy.com/jobs?search_keywords=People%20management.md)[Cross-functional leadership](https://jobicy.com/jobs?search_keywords=Cross-functional%20leadership.md)[Product experimentation](https://jobicy.com/jobs?search_keywords=Product%20experimentation.md) Sample interview questionsHow would you define a multi-year strategy for a unified customer engagement platform at Squarespace?I would begin with merchant segmentation, customer journey mapping, competitive analysis, and an assessment of current product adoption and retention data. I would define a clear platform thesis centered on the workflows where Squarespace's ecosystem data creates defensible advantages, then sequence investments across CRM, campaigns, automation, segmentation, and channels based on customer value, revenue impact, and delivery dependencies. The strategy would include measurable outcomes such as attach rate, activation, repeat usage, merchant retention, and incremental revenue. How have you managed a revenue-generating product line while preserving a strong customer-centric product culture? I connect product metrics to commercial outcomes without reducing the roadmap to short-term monetization. I establish a balanced scorecard covering acquisition, activation, engagement, retention, customer satisfaction, and revenue, and use it to make trade-offs transparently. This gives teams clear accountability for business impact while ensuring customer problems and durable product value remain central. What would you prioritize in the first year to improve Squarespace Email Campaigns and CRM capabilities? I would validate the highest-friction merchant workflows and identify gaps relative to the needs of growing service sellers. Likely priorities would include stronger audience and customer data foundations, more flexible segmentation, high-value automation templates, reliable transactional messaging, and simpler cross-channel orchestration. I would pair these investments with focused go-to-market and onboarding improvements to accelerate adoption and demonstrate measurable value quickly. How do you lead product managers across several product lines with different maturity levels? I set a shared product vision, operating principles, and outcome framework, while giving each product leader clear decision rights and ownership. I tailor coaching to the maturity of the product and leader, use regular portfolio reviews to surface dependencies and trade-offs, and maintain a high bar for customer evidence, hypotheses, and measurable results. This creates autonomy while keeping the organization aligned on the most important company goals. Describe how you would use AI and first-party platform data to differentiate customer engagement products. I would focus on practical merchant outcomes rather than AI features in isolation. First-party commerce, scheduling, website, and customer interaction data can improve audience suggestions, automate lifecycle triggers, recommend campaign content or timing, and surface next-best actions for merchants. Every use case would be evaluated for accuracy, explainability, privacy, merchant control, and incremental business impact through controlled experimentation. Opportunity details ## About this role. 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](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. #LI-Hybrid Thank you in advance for providing the following details about your work history from your resume! This helps us ensure that your candidate information is accurate and consistent during the hiring process. Squarespace will never solicit your personal banking information or ask you to transfer money in connection with a job offer or interview. We also will not reach out to you via phone or SMS without your permission or knowledge. If you plan to use AI in any capacity during your candidate journey, please review our [Candidate AI Policy](https://sqsp.link/Sxow3s). 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