We're Hiring

Investment Associate Position

Full-time  ·  Remote-friendly, with travel for management meetings and site visits  ·  Investments / Deal Team


About ORANGE JUICE

ORANGE JUICE is a permanent-capital acquisition company built for the era of AI and Bitcoin. We acquire durable, cash-generative businesses, strengthen them through technology and operational improvement, and hold them indefinitely. Unlike traditional private equity, we have no fund-expiration date or obligation to sell. Instead, we build a long-term compounding platform designed to grow free cash flow per share and responsibly build a Bitcoin treasury.

We are assembling a small, high-caliber deal team to execute acquisitions across a wide range of industries. We are seeking an Investment Associate to help drive the analytical work behind our acquisition program, working directly with the CEO and Investment Committee to evaluate, underwrite, diligence, and close transactions.

This is a rare early seat for a transaction-experienced professional who wants more than a traditional analyst / associate role. You will have direct exposure to investment decisions from day one, unusual ownership of live deals, and a clear path to help build — and ultimately lead — ORANGE JUICE’s deal team as the company scales.


The Role

As ORANGE JUICE's Investment Associate, you will own the analytical work stream behind every acquisition. You will screen opportunities, reconstruct and normalize financials, build transaction models, coordinate diligence, and translate complex findings into clear recommendations for the Investment Committee.

You will report directly to the CEO and work closely with the Investment Committee, business owners, and external advisors across a growing pipeline spanning multiple industries. From day one, you will have unusual ownership of live transactions and visibility into how investment decisions are made.

This is a high-impact, high-autonomy role designed for someone who wants to develop beyond financial analysis into full deal leadership. The successful candidate will help build the firm’s underwriting infrastructure, train future team members, and take on increasing responsibility for the deal function. As ORANGE JUICE scales, strong performers will have room to grow, whether by deepening their craft in deal evaluation or taking on broader leadership over time.


What You Will Do

  • Screen inbound and proprietary opportunities, identify the issues most likely to determine whether a deal advances, and recommend when to proceed, pause, or pass.
  • Build and maintain acquisition models, including three-statement projections, sources and uses, pro forma capitalization, debt capacity, return scenarios, and sensitivity analyses.
  • Consolidate, reconcile, and normalize complex multi-entity and, where relevant, cross-border financials into a single reliable view.
  • Determine normalized owner earnings and free cash flow by distinguishing maintenance from growth capital expenditures, scrutinizing add-backs, reconciling EBITDA to cash, and quantifying working-capital, related-party, and other distortions.
  • Lead the financial underwriting workstream, independently rebuilding and pressure-testing seller-reported results from source materials.
  • Coordinate diligence across management teams, data rooms, site visits, third-party advisors, financing sources, and internal stakeholders, keeping open items and decisions moving toward resolution.
  • Prepare and present clear, decision-ready Investment Committee materials, including the underwriting case, principal risks, key assumptions, sensitivities, and recommendation.
  • Build reusable models, templates, and sector-specific normalization playbooks that make each successive transaction faster and more rigorous.
  • Help advance qualified opportunities from initial review through closing and maintain a complete, searchable record of both completed and passed transactions.
  • After closing, help identify, quantify, and track opportunities to improve cash flow, working capital, pricing, procurement, and operating efficiency.
  • Support thesis-driven sourcing and outreach to founders, business owners, intermediaries, and private equity firms as the acquisition program grows.
  • Use AI and other tools to increase speed and analytical depth while independently verifying and standing behind every material number and conclusion.
  • Contribute to the broader needs of an early-stage company, including operational, administrative, and communication work as required


What Success Looks Like (first 2-3 years)

  • Drive the underwriting and diligence process across the deal pipeline, producing rigorous, decision-ready analysis that the Investment Committee actively tests, challenges, and builds on.
  • Have built a scalable underwriting system and trained additional team members so the firm can run more deals without proportional headcount growth.
  • Play a central role in originating and closing proprietary transactions, not just evaluating inbound opportunities.
  • Become a trusted voice in the investment process, with growing influence on decisions and the opportunity to take on more over time.


What We Are Looking For

Required

  • 2+ years of experience in investment banking, private equity, corporate development, or a comparable transaction-oriented investment role. You have lived inside company financials for weeks at a time and personally contributed to live transactions through underwriting and execution.
  • Elite financial modeling skills. You can build a clean, auditable model from messy inputs without leaning on a template.
  • Strong accounting depth. You can normalize owner earnings, tell a real add-back from a cosmetic one, reconcile EBITDA to cash, and spot related-party and working-capital issues, especially in founder and family-owned businesses.
  • Transaction judgment. You can explain what drove an investment or financing decision, which assumptions mattered most, what could have killed the deal, and how the conclusion changed through diligence.
  • Intellectually curious. You ask targeted questions and can identify the operating and accounting drivers that matter without relying on a generic sector playbook.
  • Clear written and verbal communication. You can translate complex financial analysis into a concise recommendation and defend it with senior decision-makers, business owners, and external advisors.
  • High ownership and comfort with ambiguity. You can manage multiple live workstreams, pursue missing information, and keep decisions moving without waiting for perfect instructions.
  • Intellectual honesty and independent judgment. You actively seek disconfirming evidence and surface the facts that could invalidate an investment thesis, not merely those that support it.

Candidates should be prepared during the interview process to walk through at least one live transaction in detail, including the business, transaction structure, model, investment or financing thesis, key diligence findings, major risks, outcome, and their specific personal contribution.


Preferred, but not required

  • Experience in an investment banking product group, such as M&A, or a thesis-driven buy-side strategy such as special situations, value, distressed, or restructuring.
  • CFA, or progress toward it.
  • Comfort integrating AI tools into an analytical workflow.


Compensation & Benefits

We offer a competitive total compensation structure consistent with Wall Street and financial services standards, including a competitive base salary, performance-based bonus, and benefits. As an early member of a scaling firm, you will also have meaningful upside and a clear path to increasing responsibility and economics over time.


How to Apply

To apply, complete our short application form using the button below. You will be asked to submit your resume.

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ORANGE JUICE is an equal opportunity employer. We evaluate every applicant on merit.