Squarespace is seeking an experienced Deal Operations Manager to join our growing Revenue Operations team. This role covers some traditional Deal Desk responsibilities while also driving cross-functional projects that shape our quote-to-cash processes. You will act as a strategic partner in the support of our existing Enterprise customers & help scale operations for our expanding B2B service-seller market, serving as the critical connective tissue between our Go-To-Market strategy & our financial controllership.

Working closely with Sales, FP&A, Billing, Accounting, & Commercial teams, this role balances deal execution with a broader mission of Revenue Governancedevising workstreams that drive greater sales velocity, deal transparency, & cost optimization. We are looking for a professional who understands the end-to-end "order-to-revenue" journey & can translate complex business needs into clear, actionable processes.

Youll Get To

• Ensure smooth deal execution while maintaining commercial guardrails & internal policy compliance.
• Maintain & continuously improve Finance documentation for Deal Operations, ensuring custom contracting & non-standard billing processes are well-understood & easily auditable.
• Partner with Business Development & Accounting to formalize billing workflows for strategic partnerships, ensuring revenue sharing & payout processes are accurate & scalable.
• Source, scope, & lead projects that drive measurable impact across Revenue Operations, anticipating & mitigating project roadblocks.
• Identify bottlenecks in the quote-to-cash workflow & propose strategic, data-backed solutions.
• Support new product, pricing, & packaging launches by ensuring downstream processes & documentation are ready.
• Monitor deal trends & exceptions to guide policy updates, while investigating revenue expansion opportunities & leakage risks.

Who Were Looking For

• 6 - 7+ years of relevant experience in Revenue Operations, Deal Desk, or Sales Finance, ideally within a multi-product SaaS environment.
• Proven ability to design, document, & improve complex revenue workflows across Sales, Legal, & Finance
• Bachelor's degree in Business Administration, Finance, Sales, or a related field.
• Hands-on expertise with Salesforce, Netsuite, Figma, Atlassian tools, & subscription billing platforms
• Advanced analytical capability using Excel and/or SQL to diagnose revenue issues & prevent leakage (BigQuery & Looker)
• Strong command of SaaS pricing, bundling, billing, payments (Stripe, PayPal), & dunning workflows
• Ability to adapt quickly, take initiative, & drive work forward without waiting for direction
• Skilled at driving consensus among stakeholders with competing priorities
• Proven ability to influence cross-functional teams & work effectively with Sales, Legal, & Finance
• Able to lead initiatives while maintaining process integrity, compliance, & internal controls

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
• 12 weeks paid parental leave & 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 & snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $126,000 - $165,000 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 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 & 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 1,700 is headquartered in New York City, with offices in Dublin, Ireland, & Aveiro, Portugal. For more information about our company, 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 customer base, but we also strive for 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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