Principal Financial Analyst

OutSystems is hiring a Principal Financial Analyst (GTM) in Boston, MA (onsite). This senior individual contributor role in the GTM Finance team supports Sales, Marketing, and Revenue Operations with model building, forecasting discipline, and decision-ready analysis. You will partner closely with GTM leaders and cross-functional teams to improve planning precision, strengthen performance measurement, and reduce manual effort through automation and advanced analytics.

In this position, you will report to FP&A GTM Leadership and help shape the modeling standards for the GTM finance function, with opportunities to mentor analysts on storytelling and business judgment without formal people management responsibility.

Responsibilities

• Support bookings and NRR forecasting for Sales, reconciling results with Sales Ops and Clari calls, and explaining variances to plan.
• Design, own, and maintain ARR driver models, pipeline analytics, and customer lifetime value frameworks that connect GTM activity to multi-year revenue outcomes.
• Build and stress-test scenario models for campaigns, channel investments, and sales coverage changes, then provide recommendations on expected returns and risk.
• Lead variance analysis on GTM performance and provide forward-looking commentary on what is driving results and what to do next.
• Own the commissions and sales compensation model, including plan design support, cost forecasting, and accrual alignment with Accounting.
• Lead global quota capacity modeling across roles and regions using sales productivity benchmarks and market coverage analysis to inform headcount and territory decisions.
• Partner with Sales Operations to improve planning precision, incorporating AI-enabled analytics to shorten planning cycles.
• Design and own dashboards and KPI frameworks for ARR growth, margin expansion, and sales productivity, and drive adoption across GTM leadership.
• Prepare and present monthly, quarterly, and annual GTM financial analysis and contribute materials for CFO, executive, and Board reviews.
• Champion automation and advanced analytics (including agentic tools and process automation) to reduce manual work and improve data quality.
• Lead cross-functional finance projects, including planning platform migration work in Pigment, from scoping through delivery.
• Set the modeling and analytical standard for GTM finance, review complex work, and mentor analysts on executive-ready storytelling.
• Contribute to Finance's AI-enabled ways of working by standardizing repeatable analysis and reusable model templates.

Requirements

• Deep command of SaaS and GTM metrics: ARR, NRR, CAC, LTV, quota capacity modeling, pipeline conversion, and unit economics.
• Bachelor’s degree in Finance, Accounting, Business, or a related field; MBA or CPA preferred.
• 7+ years of progressive experience in FP&A, GTM finance, or sales finance, including senior analytical or project leadership responsibilities.
• Proven track record supporting Sales, Marketing, or Revenue Operations in a SaaS or subscription environment.
• Expert-level ability to translate complex business dynamics into clear, executive-ready insights.
• Strong communication skills to influence senior stakeholders and simplify financial narratives for non-finance audiences.
• Hands-on experience with EPM and planning tools (Pigment, Anaplan, or equivalent) and CRM and GTM tools (Salesforce, Clari, Xactly, or comparable).
• Advanced proficiency in BI and data tools such as Power BI, Tableau, or advanced Excel.

Technologies

Pigment, Anaplan, Salesforce, Clari, Xactly, Power BI, Tableau, advanced Excel

Preferred

• Experience driving a financial planning platform migration.
• Experience preparing Board-level materials and presenting to CFO or executive leadership.
• Background operating in a multi-currency, global SaaS environment.