Head of Strategic Finance

We’re a team of immigrants and experts who have struggled with our own journeys through the complex, high‑stakes U.S. immigration system. That is why we are building deeply customer‑centric products and experiences to become the default trusted partner for all businesses and families. Across both business and consumer segments, we’ve aided over 1,000 businesses and 100,000 individuals to successfully navigate the convoluted immigration process.

We're a growth‑stage technology company backed by influential venture investors around the country, including Silver Lake Waterman, High Sage Ventures, Foundry Group (led by Brad Feld), Trilogy Equity Partners, Pioneer Square Labs, Emerson Collective (Laurene Powell Jobs’ foundation), Two Sigma Ventures, and Jerry Yang.

Today, we are a dynamic growth‑stage technology company with 300+ employees across the U.S., Europe, and Asia. We are growing both organically and through strategic acquisitions. We are well‑capitalized and on our way to becoming the largest immigration company in the world and the first trusted brand in the industry.

Boundless is seeking a Head of Strategic Finance & Analytics who will lead the function with an explicit AI‑first mandate. This leader will architect, build, and oversee an automated, always‑current financial system that uses AI and advanced tooling to drastically reduce manual work, accelerate insights, and enable data‑driven decision‑making across the company.

You will own forecasting, financial communications, evolving our KPIs, building our board decks, overseeing our business analytics function, and partnering with execs to make better strategic decisions. To build that foundation, you will design and implement a self‑updating financial ecosystem—leveraging AI agents, automated data pipelines, and intelligent planning models to unlock real‑time visibility, smarter decision‑making, and 10x operating leverage.

If you love building systems as much as building models, and get excited about leveling up a finance organization through automation, this role is for you.

• Architect an AI‑first finance engine: Design automated systems for all business‑as‑usual strategic finance activities leveraging SaaS tools, AI copilots, structured agents, and integrated data flows. Build self‑service capabilities for business teams with AI‑enabled financial tools.
• Month‑end analysis and insights: Build self‑updating dashboards and “continuous planning” capabilities that reduce manual work and enable high‑frequency decision support. Own month‑end analysis, transforming today’s manual workflows into an automated system capable of financial statement analysis, KPI analysis, and AI‑generated commentary. Deliver crisp insights and actionable recommendations to help our leaders understand the ROI of our various investments.
• Financial communications: Prepare all leadership, investor, and employee communications about financial results, leveraging AI automation for all communications. Ensure succinct, consistent, and compelling messaging, tailoring messaging for different audiences. Facilitate our monthly leadership discussion about financial results.
• Financial modeling: Own and evolve the company’s rolling 12‑month plan, annual budget, and 3‑year financial model. Develop forward‑looking financial insights and scenario models that guide CEO decision making.
• Strategic initiatives: Surface and champion initiatives to achieve our financial goals (e.g. evolving pricing/packaging, gross margin optimizations, synergy achievement, vendor negotiations, changes to resource allocation, changes to our KPIs, M&A). Support other team members’ initiatives with pro forma analysis, narrative development, and self‑service tools.

• 5+ years of experience delivering strategic and analytical impact in high‑performance environments (management consulting, investment banking, private equity, FP&A, AI automation role at a tech company, or similar).
• Expert‑level financial modeling skills with deep knowledge of economic concepts, GAAP, and SaaS benchmarks.
• Systems‑oriented thinker with hands‑on interest in AI,…