About The RoleWe're hiring a CFO who can be a genuine operating partner to the business. Someone who is a strategist, and comfortable in the details when the situation calls for it. You'll own financial strategy, planning, compliance, and reporting across a multi-entity global structure, while also building the operational infrastructure (controls, processes, close cadence) that a company our size and trajectory needs.
This is a hands-on leadership role. You'll have a small team to develop, but you should expect to roll up your sleeves alongside them.
What You'll Own- Financial strategy & planning: Lead forecasting, budgeting, and long-range planning across our consulting and product business lines.
- Compliance & tax: Ensure the company stays compliant across all entities and jurisdictions, including tax filings and reporting requirements.
- Multi-entity financial management: Oversee financial reporting and controls across our growing entity structure, including our Puerto Rico entity, as we expand into new markets including London and Asia Pacific.
- Digital asset accounting & treasury: Manage the accounting, tax treatment, and treasury implications of consulting contracts paid in digital assets.
- Institutional client requirements: Support the sales and delivery teams by meeting the financial diligence expectations of large institutional clients i.e insurance requirements, security standards, and financial performance disclosures.
- Process & controls: Build (or rebuild) the financial infrastructure i.e. close process, controls, reporting cadence
- Team leadership: Manage and develop a small finance team (currently a controller and a bookkeeper), with plans to grow the team as needed.
- Year-end close & audit readiness: Own the FY close process and ensure the company is audit-ready as our reporting requirements increase.
- Board & founder reporting: Provide clear, digestible financial reporting to the founders and other stakeholders as needed.
Key Requirements- Proven experience scaling a finance function through significant company growth- ideally through the 100 150+ employee range, not just operating at that size.
- Genuinely hands-on. You should be as comfortable building a model in a spreadsheet yourself as you are directing a team to do it.
- Multi-entity, global experience. You've dealt with the complexity of financial reporting and compliance across multiple entities and countries.
- Compliance and risk fluency. Experience navigating insurance requirements, security/compliance standards, and the financial diligence expectations of large financial institutions as clients
- Crypto/digital asset experience is required. Our consulting contracts include payment in digital assets, so you should be comfortable with the accounting, tax, and treasury implications of crypto-denominated revenue.
- Process builder. You've stood up financial controls and operating rhythm from scratch, or significantly matured an existing one.
- Team leadership with realistic expectations. You can manage a small team while still being willing to do the work yourself when needed.
- Global expansion experience. We're expanding into London and Asia Pacific and will have clients based in those regions. Experience with international entity structuring, reporting, and compliance across these regions is a strong plus.
- Puerto Rico entity experience preferred. One of our entities is based in Puerto Rico; familiarity with Puerto Rico's tax and compliance requirements is a plus.
- Experience in professional services / consulting business models is a plus.
How We WorkAt Obsidian Systems, we believe great work comes from thoughtful people who take ownership, communicate openly, and enjoy solving difficult problems together. These principles guide how we work every day.
Own Your Work, Protect Your Team
- We take full ownership of our responsibilities while supporting the people around us. We believe accountability creates trust, and clear ownership allows teams to move quickly without stepping on one another's work.
Don't Settle for Superficial
- We aim to understand problems deeply rather than treating symptoms. We ask questions, challenge assumptions, and make unknowns explicit so we can build durable solutions instead of temporary fixes.
Be Honest Proactively
- We communicate openly and early. Raising risks before they become problems helps our team and our clients make better decisions. We value transparency over avoiding uncomfortable conversations.
Get to It
- Many of the challenges we solve have never been solved before. We don't wait for perfection; we start, learn, iterate, and move forward. Progress comes from taking the next concrete step.
If you're excited by continuous learning and playing a real role in building the next generation of financial market infrastructure, you'll feel at home at Obsidian.
