Squarespace is seeking a Director of Sales & GTM Operations to be the chief architect of the systems and intelligence that will power our new B2B upmarket growth engine. This is a unique opportunity for a systems-first leader who thrives in creating order from ambiguity and is passionate about building a truly modern, AI-native revenue infrastructure from the ground up.

You will play a pivotal role in shaping our entire GTM strategy, laying a scalable foundation for rapid growth across Sales, Agency Partnerships, and Customer Success. We are looking for a strategic builder who can architect a well-oiled, intelligent revenue machine. You have the vision to design what a next-generation, AI-powered GTM motion looks like and the technical-mindedness to roll up your sleeves and build it.

This role reports to the VP of Sales and is based out of Squarespace's NYC Headquarters (hybrid).

You'll Get To...

• Architect an Intelligent GTM Future: Design and implement a scalable, end-to-end GTM systems architecture. Your primary focus will be on building a tech stack that is not only integrated and usable but is infused with AI and automation to create a competitive advantage.
• Build a Predictive Engine from Day One: Establish and scale core RevOps functions, including predictive forecasting, dynamic pipeline management, data-driven compensation design, and optimized territory planning. You will ensure every GTM touchpoint is measurable, actionable, and informs our strategy.
• Lead with an Engineering Mindset: Own the GTM technology stack as if it were a product. You will drive the roadmap, evaluation, implementation, and optimization of our tools. This includes leveraging AI-native platforms for conversation and deal intelligence, process automation, predictive scoring, and data integration to maximize rep productivity and deal velocity.
• Champion AI-Driven Insights: Move beyond traditional reporting. You will lead the charge on data governance and hygiene to create a pristine data foundation, enabling the use of AI for predictive analytics, lead scoring, and identifying new revenue opportunities. You will own the strategy for data enrichment and the generation of high-intent target accounts.
• Drive Strategic & Operational Cadence: Partner with GTM leadership to establish and run the operating rhythms of the business, including QBRs, performance tracking, and strategic planning. You will ensure these forums are grounded in data and forward-looking insights.
• Innovate and Automate: Constantly seek out opportunities to streamline processes and automate workflows across the customer lifecycle. You will be expected to reduce friction for our sales and success teams, allowing them to focus on high-value activities.
  
  

Who We're Looking For

• 12-15+ years in Revenue or Sales Operations, with at least 5 years in a leadership role—ideally in a high-growth B2B SaaS environment.
• A Proven "Builder" Track Record: You have successfully built and scaled a modern RevOps function for a large organization, demonstrating your ability to design systems and processes from scratch.
• Deep AI & GTM Tech Stack Expertise: You are a power user of Salesforce and possess a strong, opinionated view on the modern GTM technology landscape. You have hands-on experience implementing and optimizing AI-driven tools for conversation intelligence, predictive forecasting, and workflow automation.
• An Engineering and Systems Mindset: You are a strategic thinker with a bias for execution. You naturally gravitate towards systems-thinking, automation, and applying engineering principles to solve operational challenges and ensure data integrity.
• Data-First and Analytically Rigorous: You have a proven ability to translate complex data into actionable business insights and strategic recommendations. Experience with BI tools (e.g., Tableau, Looker) and a fundamental understanding of data warehousing concepts is essential.
• Cross-Functional Leadership: You excel at managing complex, cross-functional initiatives and building strong relationships with senior leaders in Sales, Marketing, Finance, and Product to drive unified, revenue-focused outcomes.
• A passion for simplification, elegant system design, and achieving measurable impact in a fast-paced environment, structure, and driving measurable business outcomes.

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
• 20 weeks for parental leave and up to 12 weeks to care for an ill family member
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 8 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $203,500 - $327,750 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 on-target commissions or overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock.

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 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and Australia. For more information about our company culture, 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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