Principal Financial Analyst

OutSystems•Boston, MA

About The Position

The Principal Financial Analyst, GTM is a senior individual-contributor role on OutSystems’ GTM Finance team, reporting to FP&A GTM Leadership. The role serves as an expert on complex GTM financial questions, building models, analyses, and frameworks that support investment and capacity decisions across Sales, Marketing, and Revenue Operations. It has significant influence without formal people-management responsibilities and leads high-stakes projects while shaping GTM decision-making and translating strategy into executable financial plans. The position supports bookings and nARR forecasting, maintains ARR driver models and pipeline analytics, develops customer lifetime value frameworks, and evaluates scenarios for campaigns, channel investments, and sales coverage. It leads GTM variance analysis and owns the commissions and sales compensation model, including plan-design support, cost forecasting, and accrual alignment with Accounting. The analyst leads global quota-capacity modeling and partners with Sales Operations to improve planning precision. The role also designs dashboards and KPI frameworks, prepares recurring GTM financial analysis and executive-review materials, advances automation and analytics, and leads cross-functional finance projects. It establishes analytical standards for the GTM Finance team and mentors analysts without formal management responsibility.

Requirements

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

Nice To Haves

MBA or CPA.
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.

Responsibilities

Support the Sales bookings and nARR forecast, reconcile with Sales Operations and Clari calls, and explain variances to plan.
Design and maintain ARR driver models, pipeline analytics, and customer lifetime value frameworks connecting GTM activity to multi-year revenue outcomes.
Build and stress-test scenario models for campaigns, channel investments, and sales coverage changes, and recommend expected returns and risks.
Lead variance analysis on GTM performance and provide forward-looking commentary on performance drivers and actions.
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 and use 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.
Promote 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 modeling and analytical standards for the GTM Finance team, review complex work, and mentor analysts on storytelling and business judgment.
Contribute to Finance’s AI-enabled ways of working by standardizing repeatable analysis and reusable model templates.