Deal Operations Manager - Squarespace

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 and help scale operations for our expanding B2B service-seller market, serving as the critical connective tissue between our Go-To-Market strategy and our financial controllership.

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

You’ll Get To…

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

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

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
• 12 weeks paid parental leave and 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 and 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, and 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 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 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and 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 and experiences with the world. Not only do we embrace and 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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