Deal Operations Manager

<p>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.</p> <p>Working closely with Sales, FPA, 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.</p> <h2><strong>You’ll Get To…</strong></h2> <ul> <li>Ensure smooth deal execution while maintaining commercial guardrails and internal policy compliance.</li> <li>Maintain and continuously improve Finance documentation for Deal Operations, ensuring custom contracting and non-standard billing processes are well-understood and easily auditable.</li> <li>Partner with Business Development and Accounting to formalize billing workflows for strategic partnerships, ensuring revenue sharing and payout processes are accurate and scalable.</li> <li>Source, scope, and lead projects that drive measurable impact across Revenue Operations, anticipating and mitigating project roadblocks.</li> <li>Identify bottlenecks in the quote-to-cash workflow and propose strategic, data-backed solutions.</li> <li>Support new product, pricing, and packaging launches by ensuring downstream processes and documentation are ready.</li> <li>Monitor deal trends and exceptions to guide policy updates, while investigating revenue expansion opportunities and leakage risks.</li> </ul> <h2>Who We’re Looking For</h2> <ul> <li>6 - 7+ years of relevant experience in Revenue Operations, Deal Desk, or Sales Finance, ideally within a multi-product SaaS environment.</li> <li>Proven ability to design, document, and improve complex revenue workflows across Sales, Legal, and Finance</li> <li>Bachelor's degree in Business Administration, Finance, Sales, or a related field.</li> <li>Hands-on expertise with Salesforce, Netsuite, Figma, Atlassian tools, and subscription billing platforms</li> <li>Advanced analytical capability using Excel and/or SQL to diagnose revenue issues and prevent leakage (BigQuery Looker)</li> <li>Strong command of SaaS pricing, bundling, billing, payments (Stripe, PayPal), and dunning workflows</li> <li>Ability to adapt quickly, take initiative, and drive work forward without waiting for direction</li> <li>Skilled at driving consensus among stakeholders with competing priorities</li> <li>Proven ability to influence cross-functional teams and work effectively with Sales, Legal, and Finance</li> <li>Able to lead initiatives while maintaining process integrity, compliance, and internal controls</li> </ul> <h2><strong>Benefits Perks</strong></h2> <ul> <li>A choice between medical plans with an option for 100% covered premiums </li> <li>Fertility and adoption benefits</li> <li>Access to supplemental insurance plans for additional coverage</li> <li>Headspace mindfulness app subscription</li> <li>Global Employee Assistance Program</li> <li>Retirement benefits with employer match</li> <li>Flexible paid time off</li> <li>12 weeks paid parental leave and family care leave</li> <li>Pretax commuter benefit</li> <li>Education reimbursement</li> <li>Employee donation match to community organizations</li> <li>7 Global Employee Resource Groups (ERGs)</li> <li>Dog-friendly workplace</li> <li>Free lunch and snacks</li> <li>Private rooftop</li> <li>Hack week twice per year</li> </ul> <h3>Cash Compensation Range: $126,000 - $165,000 USD</h3 ... (truncated, view full listing at source)