Controller

About SafeLease

At SafeLease, we're rethinking how P&C insurance is sold in an age of technological change. We believe the industry's biggest inefficiencies aren't technical problems — they're structural ones. And we're building the team to tackle them.

SafeLease is a profitable insurance business that designs, underwrites, and distributes specialty coverage for commercial property owners and their tenants. Most insurance companies either distribute products or bear the risk — we do both. We back our policies with our own capital, which means we control the full stack: product design, tech, and the speed at which we move. That end-to-end ownership lets us offer customers real flexibility, saving time and money for more than 4,000 properties insured for billions in value nationwide.

We're a team of 70, growing over 100% annually, and we've done it without sacrificing profitability or culture. Here, you'll get high discretion and a wide aperture of problems to solve. We embrace the newest technologies, move fast together, and operate with the intensity of a small company where every person's work is visible. If you're looking for a place to sharpen your craft alongside people who take their work seriously, you'll fit right in.

SafeLease is hiring a Controller to lead all accounting, financial reporting, and internal controls across the organization — with full ownership spanning our Managing General Agent (MGA) operations and our surplus lines insurance carrier. The role owns dual-track reporting: U.S. GAAP financial statements for SafeLease and its consolidated entities, and statutory financial statements filed with state insurance regulators under NAIC Statutory Accounting Principles. The ideal candidate combines a Big Four audit foundation with hands-on accounting experience inside an insurance carrier, and a track record of building and scaling finance functions in a high-growth environment. This is a high-visibility leadership role reporting to the CEO with direct exposure to senior leadership and strategic decision-making.

• Own and oversee all accounting operations across the MGA and the surplus lines carrier, including general ledger management, month-end / quarter-end / year-end close, and intercompany accounting between the producer and the underwriter.

• Prepare and deliver timely, accurate financial statements in accordance with both U.S. GAAP and Statutory Accounting Principles (SAP), including the NAIC P&C Annual Statement, quarterly statements, and audited statutory financial statements.

• Manage statutory reporting and regulatory filings: NAIC Schedules F (reinsurance), P (loss reserves), D (investments), and T (premium by state); Risk-Based Capital (RBC) calculations; IRIS ratios; and domiciliary and non-admitted / surplus lines state filings.

• Oversee MGA accounting under the NAIC Managing General Agents Act (Model #225), including premium trust / fiduciary accounts, the MGA-to-carrier reporting cycle, and quarterly accounting packages submitted to the carrier in a form usable for completion of the Annual Statement.

• Design, implement, and maintain robust internal controls and financial policies that scale with organizational growth (SOX-style frameworks preferred).

• Lead the annual statutory and GAAP audits and serve as the primary liaison with external auditors, tax advisors, state insurance examiners, and the engaged actuary.

• Build, mentor, and develop a high-performing accounting team; establish best-in-class processes and a culture of continuous improvement.

• Manage consolidated financial reporting across SafeLease entities, including intercompany transactions and eliminations between the MGA and the carrier.

• Partner with the CEO and senior leadership to provide financial insights, variance analysis, and strategic recommendations.

• Own premium and claims accounting cycles, ceded and assumed reinsurance accounting, deferred acquisition cost (DAC) treatment, and loss reserve accounting.

• Oversee cash management, treasury functions, investment accounting (including NAIC SVO-rated portfolios), and capital allocation reporting.

• Ensure compliance with federal, state, and local tax requirements, including premium tax filings and surplus lines tax compliance across multiple jurisdictions.

• Evaluate and enhance financial systems, tools, and technology infrastructure to support scalability and operational efficiency.

• Support fundraising, investor reporting, and due diligence processes as needed.

   

• Insurance carrier experience required, with responsibility spanning an MGA and a surplus lines (Excess & Surplus / E&S) or admitted carrier.

• Statutory accounting (SAP) and NAIC reporting experience required — including preparation or direct oversight of the NAIC Annual Statement and quarterly statements.

• Big Four background required — audit or assurance experience at Deloitte, PwC, EY, or KPMG.

• CPA designation required; Bachelor’s degree in Accounting, Finance, or related field.

• Minimum 7 years of progressive accounting and finance experience.

• Deep expertise in both U.S. GAAP and SAP, the differences between the two frameworks, and the bridging entries required to reconcile them.

• Demonstrated experience managing accounting functions across multiple legal entities and lines of business.

• Strong technical accounting skills including consolidations, intercompany eliminations, premium accounting (written / earned / unearned), loss reserve accounting, and reinsurance accounting (ceded and assumed).

• Hands-on familiarity with NAIC Schedules F, P, and D, and Risk-Based Capital reporting.

   

• Master’s degree in Accounting, Finance, MBA, or a related advanced degree.

• Experience inside a high-growth insurtech, specialty insurer, or scale-up environment.

• Prior responsibility for state-by-state premium tax filings and surplus lines tax compliance.

• Experience operating inside an insurance holding structure (HoldCo + carrier + MGA).

• Familiarity with investment accounting under SSAP No. 26R, SSAP No. 30R, and SSAP No. 43R (bonds, equities, structured securities).

• Proficiency with insurance-specific statutory reporting and ERP platforms (Workiva, EagleEye, SunGard EAS, SAP Insurance, or similar) and modern financial planning tools.

• SOX or SOX-style internal controls implementation experience.

Why SafeLease?

The tech: Our prospects convert fast because we’re solving real problems and delivering serious value to commercial real estate owners.

The team: We’re a team of seasoned pros and sharp operators who know how to move fast and build smart. High standards, low ego.

The stability: We’re well-funded, growing fast, and we make sure our team shares in that success with competitive pay and equity.

The employee experience: We also offer unlimited PTO, full health benefits, flexible work setups, and the kind of culture where people want to show up to do their best work.

If you don't have all the qualifications listed, don't worry! We understand everyone's career path is unique and still encourage you to apply if you feel this role is aligned with your career trajectory.

Employment at SafeLease is contingent upon a satisfactory verification of a general and criminal background check.