Assistant Controller - Skyward Group

Skyward Group is seeking an experienced Assistant Controller to support the accounting and financial reporting activities of its non-insurance companies. This role Reports to the Senior Vice President, Controller for the Skyward Group. The ideal candidate is a hands-on accounting leader who is comfortable operating in a complex, multi-entity public company environment. This role partners closely with finance leadership to drive timely and accurate close processes, maintain strong internal controls, and deliver reliable management reporting across a multi-entity structure. Responsibilities include oversight of the internal MGA, service company, cost sharing allocations and intercompany. The role operates in a public company environment and plays a key part in maintaining SOX-compliant processes and scalable finance operations.

Key Responsibilities

• Lead monthly, quarterly, and annual close activities for Skyward Group’s non-insurance entities, ensuring accuracy, consistency, and timeliness across the organization.

• Review journal entries, account reconciliations, and supporting schedules to maintain accurate financial reporting and well-supported balances.

• Oversee accounting and reporting for the internal MGA, service company, including intercompany transactions, eliminations, and support for shared-service activities.

• Manage and enhance expense allocation methodologies across entities to ensure transparency, consistency, and alignment with internal policies and management reporting needs.

• Support the accounting integration and ongoing reporting needs of the company’s U.K. and other international entities, including coordination across jurisdictions and intercompany processes.

• Assist in the preparation of financial statements, management reports, variance analyses, and materials supporting external reporting in a public company environment.

• Maintain and strengthen internal controls, accounting policies, and documented procedures, including direct involvement in SOX compliance, control execution, testing support, and remediation activities.

• Coordinate external audit support, including schedules, documentation, and timely responses to auditors and other stakeholders.

• Supervise, mentor, and develop accounting staff, including review of work product, workload prioritization, and reinforcement of accountability and continuous improvement.

• Serve as an escalation point for accounting issues across the non-insurance structure and partner with cross-functional teams to resolve issues, improve processes, and enhance reporting accuracy.

• Drive system, workflow, and close-process improvements that increase efficiency, control, and scalability, including the effective use of BlackLine for account reconciliations and OneStream for consolidation and reporting.

Qualifications, Education and Experience

• Bachelor’s or Master’s degree in Accounting.

• CPA designation required.

• Leadership experience required.

• Progressive accounting experience, including significant experience with month-end close, reconciliations, and financial reporting in a multi-entity environment.

• Public company accounting experience preferred.

• SOX experience required, including internal controls, documentation, support, and remediation.

• Strong understanding of GAAP and experience operating in a controlled financial reporting environment.

• Experience with service company accounting, shared services, cost allocations, and intercompany accounting required.

• Experience supporting a U.K. entity and/or other international entities preferred, including coordination across jurisdictions and post-acquisition integration considerations.

• Experience with MGAs, insurance-adjacent entities, or regulated financial environments strongly preferred.

• Proficiency in ERP/accounting systems and advanced Excel skills; experience with BlackLine for reconciliations and close management and OneStream for consolidation and reporting strongly preferred.

• Strong analytical, organizational, and problem-solving skills with close attention to detail.

• Ability to manage multiple priorities, meet deadlines, and communicate effectively with stakeholders across the organization.

Compensation & Benefits

The applicable base salary for this opportunity is $150,000 - $175,000. The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. In addition to the base salary, this opportunity may be eligible for performance-based incentives.​  We are excited to offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401k savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance. ​

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