Senior Systems Architect & GTM Operations Manager

Squarespace is at apivotal moment of growth, building a brand-new B2B commercial sales organization from the ground up. We’re seeking a Systems Architect, GTM Operations to design and launch the foundational technology stack that will power this next chapter.

This isn’t just another systems role—you’ll be thearchitect behind a world-class, AI-enabled GTM engine that empowers high-velocity sales and success teams to move faster, smarter, and at scale. Your work will directly shape how Squarespace acquires, grows, and retains SMB and Mid-Market customers, establishing the infrastructure that drives our future success.

If you’re excited by zero-to-one building, thrive at the intersection of technology and go-to-market strategy, and want to make your mark at a company known for design and innovation, this is your opportunity to have outsized impact from day one.

You'll be a foundational pillar of Squarespace’s next stage of growth.You'll work hybrid 2-3 days/week from our NYC Headquarters and report directly to the Director of Sales & GTM Operations.

• Build and scale Squarespace’s B2B GTM systems, anchored in deep expertise in CRM processes and integrated tech stack across leading AI field GTM tooling (i.e. Salesloft, Momentum, Onum, Seismic, Slack, etc.)
• Serve as the solution architect for tooling, integrations, workflow automation, and data pipelines that keep GTM teams operating at scale across sales, agency partnerships, and customer success.
• Design infrastructure that supports high-volume inbound and outbound motions while remaining flexible for future growth.

• Own end-to-end execution of GTM infrastructure: lead routing, territory modeling, usage-based scoring, attribution, and forecasting.
• Ensure systems enable fast-moving reps to engage thousands of leads and accounts with speed and accuracy.
• Partner with Product & Engineering to integrate product usage insights directly into GTM workflows.

• Establish and enforce enterprise-grade data governance across GTM systems.
• Build proactive monitoring, error-handling, and automation safeguards to ensure reliable workflows.
• Deliver a single source of truth that gives executives, sales leaders, and reps clear visibility into pipeline and performance.

• Deploy AI-native tools to accelerate forecasting, lead scoring, personalization, and enablement.
• Implement automations that reduce manual work, shorten speed-to-lead, and increase rep efficiency.
• Drive experimentation with new AI approaches and scale those that deliver impact.

• 5-7+ years in Revenue Operations, Salesforce Administration, or GTM Systems Architecture.
• 2+ years supporting SMB or Mid-Market SaaS sales motions in a high-growth environment.
• Deep Salesforce Sales Cloud expertise (admin certifications strongly preferred), including advanced flows, Lightning, and custom object design.
• Strong background in revenue stack integrations (Salesloft, ZoomInfo, Outreach, Seismic, Workato, etc.).
• Proven success designing workflows for high-volume lead management and account-based plays.
• Ability to communicate technical design to non-technical stakeholders and influence senior decision-making.

Experience with usage-based GTM models, CPQ, CLM, or BI tools (SQL, Looker, Tableau). Apex / SOQL familiarity — not necessarily heavy coding, but the ability to partner with developers or write lightweight logic/queries. API-based integrations — understanding how to connect tools and move data between systems. CPQ / CLM tools (Salesforce CPQ, Ironclad, DocuSign CLM, etc.) for contract/billing workflows.

This is a rare opportunity to join Squarespace at an inflection point. You’ll:

• Be the architect of a brand-new GTM stack powering SMB and Mid-Market growth.
• Lead the adoption of AI-first sales and success workflows that set us apart.
• Build the systems foundation that will scale as Squarespace reaches new heights in B2B.
• Have visibility and influence across GTM leadership and cross-functional partners.

If you thrive in zero-to-one environments, love building elegant systems for high-velocity teams, and want to redefine how a modern SaaS company scales its B2B GTM engine, this role is for you.

• 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
• 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

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.

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.

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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