Cowbell is signalling a new era in cyber insurance by harnessing technology and data to provide small and medium-sized enterprises (SMEs) with advanced warning of cyber risk exposures bundled with cyber insurance coverage adaptable to the threats of today and tomorrow. Championing adaptive insurance, Cowbell follows policyholders’ cyber risk exposures as they evolve through continuous risk assessment and continuous underwriting. In its unique AI-based approach to risk selection and pricing, Cowbell’s underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue to less than 5 minutes. Founded in 2019 and based in the San Francisco Bay Area, Cowbell has rapidly grown, now operating across the U.S., Canada, U.K., and India. This growth was recently bolstered by a successful Series C fundraising round of $60 million from Zurich Insurance. This investment not only underscores the confidence in Cowbell’s mission but also accelerates our capacity to revolutionize cyber insurance on a global scale. With the backing of over 25 prominent reinsurance partners, Cowbell is poised to redefine how SMEs navigate the evolving landscape of cyber threats. Cowbell is signaling a new era in cyber insurance by harnessing technology and data to provide small and medium-sized enterprises (SMEs) with advanced warning of cyber risk exposures bundled with cyber insurance coverage adaptable to the threats of today and tomorrow. Championing adaptive insurance, Cowbell follows policyholders’ cyber risk exposures as they evolve through continuous risk assessment and continuous underwriting. In its unique AI-based approach to risk selection and pricing, Cowbell’s underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue to less than 5 minutes. Founded in 2019 and based in the San Francisco Bay Area, Cowbell has rapidly grown, now operating across the U.S., Canada, U.K., and India. This growth was recently bolstered by a successful Series C fundraising round of $60 million from Zurich Insurance. This investment not only underscores the confidence in Cowbell’s mission but also accelerates our capacity to revolutionize cyber insurance on a global scale. With the backing of over 25 prominent reinsurance partners, Cowbell is poised to redefine how SMEs navigate the evolving landscape of cyber threats. What you will do: - Ensure timely and accurate financial reporting in accordance with U.S. GAAP, including oversight of the monthly and quarterly close and entity consolidations - Leverage resources to ensure completeness and accuracy of insurance financial results and related disclosures - Maintain and strengthen internal control frameworks and accounting policies to support audit readiness and mitigate financial reporting risk - Lead all statutory accounting and reporting, including preparation and review of quarterly and annual statutory financial statements and related regulatory filings - Oversee insurance accounting across premium, loss and LAE reserves, reinsurance, and related balance sheet accounts, ensuring alignment and reconciliation between GAAP and statutory results - Direct accounting and reporting for ceded and assumed reinsurance and fronting arrangements, including premium settlements, ceding commissions, reinsurance recoverables, and collateral balances - Coordinate and review periodic reporting and settlement deliverables to fronting and reinsurance partners (e.g., bordereaux, accounts current, and related treaty reporting) and ensure compliance with contractual reporting requirements - Partner with actuarial, underwriting, and operations teams on reserve roll-forwards, premium recognition, and statutory disclosures and related insurance schedules - Serve as primary accounting liaison for statutory audits and insurance-specific reporting matters - Experience building scalable accounting processes and reporting infrastructure - Drive automation and system enhancements across ERP and insurance accounting workflows (e.g., NetSuite and policy/reinsurance data integrations) - Establish and document accounting policies and procedures across insurance finance activities - Serve as a key partner to insurance operations, underwriting, actuarial, and compliance teams - Support external audits (GAAP and statutory) and regulatory inquiries - Mentor and develop accounting staff as the insurance accounting function grows What Cowbell needs from you: - Bachelor’s degree in Accounting or Finance or related field; CPA required - Audit experience with insurance industry clients strongly preferred - 3-5 years of Insurtech or Insurance experience - 5–7 years of accounting experience, including insurance or financial services accounting - Strong technical expertise in U.S. GAAP and insurance/statutory accounting frameworks - Demonstrated experience with insurance company reporting and financial close processes - Experience with ERP and financial systems (e.g., NetSuite or similar); ability to work across data and reporting platforms - Experience with statutory filings or insurance carrier accounting preferred - Ability to operate effectively in a dual GAAP/statutory accounting environment Pay Transparency: The annual base salary range for this position based in the United States is listed below. This salary range is an estimate , and the actual salary may vary based on Cowbell’s compensation practices, job related skills, depth of experience, relevant certifications and trainings, in addition to geographic location. Based on the factors above, Cowbell utilizes the full width of the range. Annual base salary range for this role: $170k-$240K Equal Employment Opportunity: We are committed to equal opportunity in the terms and conditions of employment for all employees and job applicants without regard to race, color, religion, sex, sexual orientation, age, gender identity or gender expression, national origin, disability, or veteran status. Cowbell is a leading innovator in cyber insurance, dedicated to empowering businesses to always deliver their intended outcomes as the cyber threat landscape evolves. Guided by our core values of TRUE—Transparency, Resiliency, Urgency, and Empowerment—we are on a mission to be the gold standard for businesses to understand, manage, and transfer cyber risk. At Cowbell, we foster a collaborative and dynamic work environment where every employee is empowered to contribute and grow. We pride ourselves on our commitment to transparency and resilience, ensuring that we not only meet but exceed industry standards. We are proud to be an equal opportunity employer, promoting a diverse and inclusive workplace where all voices are heard and valued. Our employees enjoy competitive compensation, comprehensive benefits, and continuous opportunities for professional development. Cowbell is an E-Verify employer. E-Verify is a web-based system that allows an employer to determine an employee's eligibility to work in the US using information reported on an employee's Form I-9. The E-Verify system confirms eligibility with both the Social Security Administration (SSA) and Department of Homeland Security (DHS). For more information, please go to the USCIS E-Verify website. For more information, please visit https://cowbell.insure/. Cowbell Cyber does not permit the use of AI tools during any stage of our interview process. By submitting your application, you agree to complete all assessments and interviews without the use of generative AI assistance.

• Oversee all accounting functions, including accounts payable, accounts receivable, payroll, and general ledger management • Prepare monthly, quarterly, and annual financial statements in accordance with GAAP • Manage budgeting, forecasting, and cash flow analysis • Ensure compliance with all local, state, and federal tax filings and reporting requirements • Oversee property-level accounting and reconciliations for owned and managed assets • Coordinate annual audits and maintain strong internal controls • Review and approve construction draw packages and loan compliance reports • Partner with executive leadership to provide strategic financial insights and recommendations • Implement and optimize accounting systems and software (e.g., Yardi, Buildium, QuickBooks, etc.) • Supervise and mentor accounting staff, fostering accuracy and professional growth

• You oversee account monitoring and reporting, including investigating and reconciling unknown transactions/discrepancies, processing payroll transfers, and maintaining financial data • Prepare financial plans, annual budget planning and statistics for categorizing income and expenses • You are responsible for risk management • You work closely with the CEO, HR, Operations and Support teams and monitor & control all incoming and outgoing payments • You serve as the point of contact for all financial matters at both team and company level and represent the finance department in meetings

Assistant Controller (CPA) Remote U.S. (designated states) Department: Finance Reports to: Corporate Controller This position is fully remote and may be performed from one of the following U.S. states: AL, AZ, FL, GA, IN, KS, MA, MI, MS, NC, NV, OR, PA, SC, TN, TX, VA. At Raintree, we’re not just shaping the future of therapy technology – we’re creating it. This is your chance to be part of something bigger, where your career will have game-changing, career-defining moments that propel you to new heights. We aim to be the best place for the best people, and we’re looking for ambitious, creative thinkers ready to make an impact. Whether you’re advancing AI solutions or enhancing user experiences, your work here will shape the future of therapy technology while advancing your career alongside dedicated professionals who are as committed to your success as you are. At Raintree, your ideas drive real change, your growth is limitless, and the work you do will touch millions of lives. Ready to ignite your career and leave a lasting legacy? Join us and be part of something extraordinary. We are currently seeking an exceptional Assistant Controller to join our Finance leadership team. Reporting to the Corporate Controller, this individual will be responsible for managing the daily operations of the finance department for our fast-growing, PE-backed software company. This role is designed for a lead-by-example professional who possesses the technical sophistication to manage the financial audit and the operational willingness to support the team’s foundational work as we scale our department. As a lead-by-example working manager, you will ensure our financial records are flawless, our reporting is efficient, and our annual audits are seamless. During your first year, you will serve as a key functional stakeholder in our digital transformation, helping to implement our new ERP, billing, and AP software systems to support our rapid expansion. You will be a working manager, providing both strategic oversight and direct execution to ensure our department's success. Duties and Responsibilities: Financial Operations - Close Management: Lead the end-to-end month-end close process, serving as the primary project lead to ensure a timely and accurate ledger. You will be responsible for maintaining the close calendar, monitoring progress against key milestones, and providing transparent status updates to the Controller. Your goal is to compress the close cycle while ensuring all key deliverables —including departmental P&Ls and variance analyses— are ready for executive review. - Accounting Support: While this is a leadership role, you will be expected to support the team by performing select reconciliations, preparing complex journal entries, and assisting with data entry as needed. As the manager, you will set the standard for documentation, ensuring all reconciliations meet rigorous criteria for completeness and accuracy. You don't just review the work; you define what "audit-ready" looks like through hands-on leadership and a "roll-up-your-sleeves" mentality. - Treasury & AP: Oversee daily cash positioning and the Accounts Payable function, balancing vendor relationships with strategic liquidity management. Audit & Reporting: - Audit Liaison: Serve as a key internal lead for the external auditors, ensuring all PBC (Provided by Client) requests and supporting schedules are delivered with high integrity. - Financial Reporting: Collaborate with the external audit firm to draft annual financial statements, ensuring all footnote disclosures are accurate and GAAP-compliant. - GAAP: Serve as the internal lead for GAAP inquiries. You will research and document accounting treatments for complex areas—such as revenue recognition and capitalization—to ensure our financial reporting remains accurate and compliant as the business evolves. Systems Transformation (Year 1 Focus): - Functional Stakeholder: Act as a key contributor in the implementation of a new ERP, Billing System, and AP platforms. - Process Design: Leverage your hands-on work with the current ledger to help map and configure the new tech stack for maximum efficiency and ASC 606 compliance. Professional Credentials - CPA required. - Bachelor’s degree in Accounting or Finance Experience & Background - Experience: 6–10 years of progressive accounting experience, ideally starting in Public Accounting (Big 4 or Mid-Tier). Experience in the Software/SaaS industry is preferred - Operational Willingness: You are a seasoned professional who understands that in a fast growing company, no task is too small if it ensures a clean close. You are comfortable navigating an ERP and entering data when the situation requires it. - PE Environment: You are comfortable with high-velocity reporting and managing through change. Competencies to Drive Success: Technical Skills - Deep expertise in U.S. GAAP (specifically ASC 606). - Advanced Excel skills; high comfort level learning and "power-using" new accounting software. - Experience with SaaS billing engines (e.g., Rillet, Sage Intacct, NetSuite) and automated collection/AP tools (Ramp, Bill.com, Stampli, Tipalti). The "Soft" Skills - Resilience: You thrive in the "building phase" where processes aren't yet perfect. - Detail-Obsessed: You catch the outlier in the spreadsheet that everyone else missed. - Communicator: You can translate complex accounting treatments into plain English for non-finance stakeholders. Our Perks Remote Work/Work From Home Paid Time Off/11 Paid Holidays/Year-End Holiday Break Health, Dental, Vision, HSA/FSA, 401K with Company Match Disability & Life Insurance Employee Assistance Program Paid Parental Leave About Raintree Systems​ Raintree is the preeminent provider of electronic health records (EHR) and revenue cycle management (RCM) software for the therapy and rehabilitation industry. Founded in 1983 and headquartered in Chandler, AZ, Raintree serves enterprise and mid-sized organizations across physical therapy, occupational therapy, speech-language pathology, and ABA specialties. Our award-winning, all-in-one platform empowers therapy professionals to deliver superior patient care through innovative clinical documentation, automated billing, and actionable business intelligence. With over 2,500 implementations and a commitment to "Software-as-a-Relationship," we are a mission-driven team dedicated to transforming healthcare technology and improving outcomes for everyone. Our Core Values We put our Clients First - We are Open and Honest - We are Disciplined, Yet Flexible We love to Solve Problems - We are Committed to Greatness - We are a High Performance Team Raintree Systems provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.