Director of Accounting

Founded in 2003, Roundstone is not your typical insurance company. We’re on a mission to help employers save on healthcare benefits so they can put those savings towards bettering their businesses and taking care of their employees.

Role Description: Director of Accounting

The Director of Accounting oversees all accounting and financial reporting functions across Roundstone’s captive insurance operations, reinsurance activity, and administrative entities, ensuring GAAP compliance, strong internal controls, and accurate reporting.

Key Responsibilities:

Overall Financial Leadership & Oversight

• Manage accounting operations including general ledger, multi-entity consolidation, captive accounting, and close cycles (journal entries and account reconciliations).
• Maintain GAAP-compliant accounting policies.
• Lead and develop the accounting team.
  
  
  

Captive / Risk-Bearing Entity Responsibilities

• Oversee captive premium accounting, pooling cash flow, and savings distributions.
• Manage stop-loss reinsurance accounting.
• Supervise reserve and liability accounting (IBNR).
  
  
  

Third Party Administrator Responsibilities

• Oversee accounting for administrative/management fees and revenue recognition.
• Manage fund/trust accounting and reconciliations.
  
  
  

Financial Reporting & Compliance

• Prepare consolidated financial statements and management reports.
• Ensure regulatory compliance, internal controls, and audit readiness.
• Coordinate internal and external audits.
  
  
  

Systems, Processes & Operational Controls

• Oversee accounting system integrations.
• Drive automation and process efficiency.
• Maintain strong internal controls.
  
  
  

Key Qualifications:

Core Skills

• Bachelor’s degree in Accounting or Finance; active CPA required.
• 10 years progressive accounting experience, preferably within insurance/captives.
• Strong GAAP, reinsurance, and captive accounting knowledge.
• Proven leadership and team management experience.
  
  
  

Core Competencies

• Integrity and Compliance
• Strategic Thinking
• Leadership & Team Development
• Business Partnering
• Adaptability & Innovation
  
  
  

Reporting Structure

Reports to the Chief Financial Officer and oversees the accounting and finance team.

Better Benefits:

We’re leaders in our industry, so naturally, we look out for our employees’ best interests with a robust benefits package. Roundstone employees are eligible for:

• Medical, dental and vision benefits
• Annual bonus
• Parental Leave
• Dependent care 100% match up to max allowable
• PTO beginning on Day 1
• Tuition reimbursement
• Health work/life balance
• Hybrid office schedule
• 401(k) plan with company match
• Employee Assistance Program
• On-site gym with personal trainer access
• Life insurance and short term disability insurance
  
  
  

More About Roundstone

Headquartered in Rocky River, Ohio, Roundstone is proud to be a Northeast Ohio Top Workplace as recognized by The Plain Dealer and cleveland.com, based on anonymous employee feedback. We foster a supportive, values-driven culture where employees feel engaged, valued, and celebrated. Roundstone has also been named an Inc. 5000 award recipient for eight consecutive years, reflecting our continued growth and success.

Our Core Values

• Live well: Be healthier and bring positive energy to all you do.
• Work smarter: Get things done, better.
• Own it: Accountability is your middle name. Be on time, do what you say, and finish what you start.
• Be intellectually curious: Always be learning. See opportunity everywhere and have a drive to know.
  
  
  

Culture and fit are integral to success and in an effort to achieve a better match both from a candidate's perspective and our organization, please take a minute, click on the link and take the really brief survey:

https://go.cultureindex.com/p/zOBX5CHw7lm2

Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Roundstone Insurance we are dedicated to building a diverse, inclusive, and authentic workplace, so if you're excited about this role but your past experience doesn't align perfectly with every qualification in the job description, we encourage you to apply anyways. You may be just the right candidate for this or other roles.