Director of Sales Compensation & Revenue Reporting

The Opportunity

Swoop is looking for a Director of Sales Compensation & Revenue Reporting to build and own our sales compensation function within Revenue Operations. Today, sales compensation sits within RevOps without a dedicated owner. This person will take ownership of the function end-to-end — including compensation plan design and administration, rate and quota modeling, CaptivateIQ, forecasting, reporting, governance, and commission issue resolution. This is not simply a plan administration role. Swoop has multiple compensation structures, revenue-based commission models, new products coming to market, and a growing sales organization. We need someone who can bring structure and consistency to the function while remaining hands-on in the details.

What You’ll Do

• Own compensation plan design and administration across multiple sales roles and product lines, including commission rates, quotas, accelerators, guarantees, ramp provisions, coverage bonuses, and new product incentives.
• Lead the annual compensation planning process from modeling and plan architecture through stakeholder review, Legal approval, and distribution.
• Own CaptivateIQ as Swoop’s compensation platform, including plan configuration, automated commission calculations, data integrity, rep-level dashboards, attainment reporting, and ongoing platform optimization.
• Partner closely with Finance to transition manual commission and rate-modeling processes into CaptivateIQ and maintain accurate revenue and payout data across systems.
• Build financial models to evaluate compensation expense at varying levels of attainment and model the impact of rate changes, quota adjustments, accelerators, new product incentives, and senior-level compensation packages.
• Partner with Finance and Sales leadership on annual quota setting, territory-level revenue potential, attainment distribution, compensation forecasting, and comp-to-revenue analysis.
• Own commission issue resolution, including disputes, retroactive corrections, rate changes, and exceptions, while establishing a clear and consistent process for managing them.
• Manage compensation governance across Finance, Legal, HR, and Sales leadership, ensuring plans are reviewed, approved, documented, signed, and maintained with a complete audit trail.
• Standardize compensation plans and processes across the organization, including new-hire guarantees, ramp schedules, plan templates, offer-letter alignment, and compensation policies.
• Partner with Sales, Finance, and Partnerships to improve monthly revenue reporting and attribution across data partners, identifying and resolving missing, delayed, or inaccurate revenue that impacts commissions.
• Build reporting for Sales and Finance leadership around rep and team attainment, projected payouts, variable compensation accruals, plan performance, and areas of financial risk.
• Establish a more scalable compensation operating model, including regular cross-functional compensation reviews, greater rep-level transparency, and ongoing analysis of plan effectiveness and internal equity.
• Revenue Reporting (LiveRamp, Throtle): Standardize monthly data usage reports from various partners (LiveRamp, Throtle, iHeart, TransUnion, etc.) to support accurate revenue attribution across accounts and sales reps.

What You Bring

• 5+ years of experience in sales compensation, Sales Operations, or Revenue Operations, with direct ownership of commission plan design and administration.
• Hands-on CaptivateIQ experience required - ideally including building or significantly configuring an instance, not simply using the platform as an end user.
• Strong financial modeling skills with the ability to build scenario models from scratch in Excel or Google Sheets and confidently present recommendations to senior leadership.
• Experience with revenue-based commission structures, including rates tied to recognized revenue and quota attainment.
• Experience designing and administering multiple compensation plans simultaneously across different roles, products, or sales motions.
• Experience writing and managing compensation plan documents through Legal review and approval.
• Strong cross-functional skills with the ability to work effectively across Finance, Legal, HR, Sales, and executive leadership.
• Experience building or improving compensation processes in a high-growth environment where not everything is already defined.
• Healthcare, pharmaceutical, or ad tech experience is a plus, as is experience designing compensation for new product launches.
• SQL proficiency or an interest in developing it is a plus.

We’re looking for someone who can move comfortably between strategy and execution - someone who can build the model, understand what the numbers mean for the business, and communicate the recommendation clearly to Sales and Finance leadership