Senior Systems Architect & GTM Operations Manager

Squarespace is at a pivotal 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 the architect 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.

You'll Get To...

Architect & Deploy the GTM Tech Stack

• 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.

Lead High-Impact Implementations

• 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.

Champion Data Integrity & Workflow Reliability

• 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.

Unlock AI-Powered Productivity

• 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.
  
  

Who We’re Looking For

• 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.

Why This Role at Squarespace

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.

Benefits & Perks

• A choice between medical plans with an option for 100% covered p