Deal Operations Manager

Squarespace•New York, NY

4h•$126,000 - $165,000

About The Position

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.

Requirements

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

Responsibilities

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.