Squarespace is seeking a Director of Sales & GTM Operations to be the chief architect of the systems & 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 & 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, & 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 & the technical-mindedness to roll up your sleeves & build it.

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

You'll Get To...

• Architect an Intelligent GTM Future: Design & implement a scalable, end-to-end GTM systems architecture. Your primary focus will be on building a tech stack that is not only integrated & usable but is infused with AI & automation to create a competitive advantage.
• Build a Predictive Engine from Day One: Establish & scale core RevOps functions, including predictive forecasting, dynamic pipeline management, data-driven compensation design, & optimized territory planning. You will ensure every GTM touchpoint is measurable, actionable, & 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, & optimization of our tools. This includes leveraging AI-native platforms for conversation & deal intelligence, process automation, predictive scoring, & data integration to maximize rep productivity & deal velocity.
• Champion AI-Driven Insights: Move beyond traditional reporting. You will lead the charge on data governance & hygiene to create a pristine data foundation, enabling the use of AI for predictive analytics, lead scoring, & identifying new revenue opportunities. You will own the strategy for data enrichment & the generation of high-intent target accounts.
• Drive Strategic & Operational Cadence: Partner with GTM leadership to establish & run the operating rhythms of the business, including QBRs, performance tracking, & strategic planning. You will ensure these forums are grounded in data & forward-looking insights.
• Innovate & Automate: Constantly seek out opportunities to streamline processes & automate workflows across the customer lifecycle. You will be expected to reduce friction for our sales & 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 roleideally in a high-growth B2B SaaS environment.
• A Proven "Builder" Track Record: You have successfully built & scaled a modern RevOps function for a large organization, demonstrating your ability to design systems & processes from scratch.
• Deep AI & GTM Tech Stack Expertise: You are a power user of Salesforce & possess a strong, opinionated view on the modern GTM technology landscape. You have hands-on experience implementing & optimizing AI-driven tools for conversation intelligence, predictive forecasting, & workflow automation.
• An Engineering & Systems Mindset: You are a strategic thinker with a bias for execution. You naturally gravitate towards systems-thinking, automation, & applying engineering principles to solve operational challenges & ensure data integrity.
• Data-First & Analytically Rigorous: You have a proven ability to translate complex data into actionable business insights & strategic recommendations. Experience with BI tools (e.g., Tableau, Looker) & a fundamental understanding of data warehousing concepts is essential.
• Cross-Functional Leadership: You excel at managing complex, cross-functional initiatives & building strong relationships with senior leaders in Sales, Marketing, Finance, & Product to drive unified, revenue-focused outcomes.
• A passion for simplification, elegant system design, & achieving measurable impact in a fast-paced environment, structure, & driving measurable business outcomes.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility & 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 & 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 & 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, & 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 & businesses online. We empower millions of customers in more than 200 countries & territories with all the tools they need to create an online presence, build an audience, monetize, & scale their business. Our suite of products range from websites, domains, ecommerce, & marketing tools, as well as tools for scheduling with Acuity & creating & managing social media presence with Bio Sites & Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & 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 & experiences with the world. Not only do we embrace & 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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