Controller

JOB DESCRIPTION

Controller

Counterpart is an insurtech platform reimagining management and professional liability for the modern workplace. We believe that when businesses lead with clarity and confidence, they become more resilient, more innovative, and better prepared for what's ahead. That's why we built the first Agentic Insurance™ system --- where advanced AI and deep insurance expertise come together to proactively assess, mitigate, and manage risk. Backed by A rated carriers and trusted by brokers nationwide, our platform helps small businesses grow with confidence. Join us in shaping a smarter future, helping businesses Do More With Less Risk®.

Counterpart is entering a new chapter of growth with strong backing from world-class investors, a growing network of distribution partners, and a passionate team of industry veterans and innovators. As Controller, you will serve as the operational backbone of our finance function, ensuring accurate, timely, and compliant financial reporting while building scalable accounting processes that support our transition to a risk-bearing insurance entity. You will oversee all accounting operations, regulatory compliance, and financial controls, working closely with our functional leads to establish the financial infrastructure necessary for sustainable growth. This role is critical as we scale our operations, implement new financial systems, and navigate the complex regulatory requirements of the insurance industry.

YOU WILL:

Financial Reporting & Accounting Operations

• Own the monthly, quarterly, and annual close processes, ensuring accurate and timely GAAP-compliant financial statements.
• Manage all aspects of general ledger accounting, including journal entries, account reconciliations, and variance analysis.
• Oversee accounts payable, accounts receivable, and cash management processes with particular focus on insurance-specific transactions.
• Prepare and review financial statements, management reports, and board packages in partnership with the functional leads.
• Lead annual audit processes with external auditors and manage relationships with accounting firms and tax advisors.

Insurance & Regulatory Compliance

• Navigate complex insurance accounting standards including SAP (Statutory Accounting Principles) and GAAP reporting requirements.
• Manage regulatory filings, including quarterly and annual statements for insurance entities and state insurance departments.
• Oversee bordereaux reporting, claims reconciliation, and carrier settlement processes across all reinsurance relationships.
• Ensure compliance with insurance regulations across multiple jurisdictions and maintain documentation for regulatory examinations.
• Implement controls and processes for premium recognition, loss reserves, and unearned premium calculations.

Systems & Process Optimization

• Design and maintain internal controls, policies, and procedures that scale with business growth and regulatory requirements.
• Collaborate with engineering and operations teams to integrate billing, underwriting, and claims systems with accounting workflows.
• Establish automated reconciliation processes for high-volume transactions and complex insurance cash flows.
• Build reporting infrastructure that provides real-time visibility into financial performance and operational metrics.
• Lead the optimization of our ERP system to support insurance operations and growth.

Operational Excellence & Systems

• Build and manage a high-performing accounting team, including vendors, contractors, and offshore resources.
• Partner with cross-functional teams including underwriting, claims, operations, and data analytics to ensure seamless financial operations.
• Establish training programs and documentation to maintain institutional knowledge and operational excellence.

YOU HAVE:

• 7+ years of progressive accounting experience, with at least 3 years in a Controller or senior accounting role.
• CPA certification with strong technical accounting knowledge in both GAAP and insurance-specific accounting principles (SAP experience strongly preferred).
• Direct experience in the insurance industry, including familiarity with premium accounting, loss reserves, bordereaux reporting, and regulatory filings.
• Proven track record implementing and managing ERP systems (NetSuite, QuickBooks, or similar) in high-growth environments.
• Experience with insurance billing systems and payment processing platforms, particularly in managing complex cash flows and reconciliations.
• Strong knowledge of internal controls, SOX compliance, and audit processes.
• Advanced proficiency in Excel/Google Sheets and experience with financial reporting tools and business intelligence platforms.
• Experience managing and developing accounting teams, including remote and offshore resources.

WHO YOU WILL WORK WITH:

• Tanner Hackett, CEO & Founder: Having founded two other major startups, including Button and Lazada, Tanner now spends his time focused on mental health through his philanthropy, Open Minded.org, in addition to reading, surfing, yoga, and enjoying the outdoors. 
• Tobias Schuler, Head of Data & Analytics: Tobias was previously the Head of Data and Analytics at Digital Partners, a Munich Re company. Tobias led a team that built out data integrations, business intelligence and advanced analytics across all insurtech partners spanning various P&C lines of businesses. Tobias is also a FCAS and has built systems to enable leading class insights for underwriting, actuarial, claims and finance experts while focusing on democratizing data. He enjoys traveling internationally and spending time with his 2 young daughters.
• Mike Foster, Insurance Operations Lead: MIke has over two decades of experience in insurance operations, strategy, transformation, and customer experience. Before joining Counterpart, Mike led a 120+ person team at Lincoln Financial, overseeing strategy, analytics, and service operations for group benefits. Earlier in his career, he spearheaded digital transformation efforts and managed large-scale operations teams at both Lincoln and Liberty Mutual, where he launched new service models and built cloud-native platforms from scratch. Mike is known for his thoughtful leadership, data-driven decision-making, and ability to scale operational excellence in complex environments.

• Stanley Wang, Director, Pricing Analytics: Before joining Counterpart, Stanley worked as an actuary within the pricing solutions and methods team at USAA to combine actuarial pricing with data science models. Before that, he was a leading data scientist for Digital Partners, a Munich Re Company where he specialized in building data science models and insights for leading insurtech companies. He has had many other relevant roles such as capital modeling, risk management etc. He lives in New York with his growing family.

• Chris Shafer, Special Projects: Chris is a published scientific author, having studied the neural correlates of gratitude at the lauded Brain and Creativity Institute. He has since helped to launch numerous businesses in which he held a variety of critical roles from product management to business operations to strategic partnerships. Chris received his bachelor’s degree in Biological Sciences from the University of Southern California.

WHAT WE OFFER

• Stock Options: Every employee is able to participate in the value that they create at Counterpart through our employee stock option plan. 
• Health, Dental, and Vision Coverage: We care about your health and that of your loved ones. We cover up to 100% of your monthly contributions for health, dental, and vision insurance and up to 80% coverage for family members.
• 401(k) Retirement Plan: We value your financial health and offer a 401(k) option to help you save for retirement.
• Parental Leave: Birthing parents may take up to 12 weeks of parental leave at 100% of their regular pay following the birth of the employee’s child, and can choose to take an additional 4 unpaid weeks. Non-birthing parents will receive 8 weeks of parental leave at 100% of their regular pay.
• Unlimited Vacation: We offer flexible time off, allowing you to take time when you need it.
• Work from Anywhere: Counterpart is a fully distributed company, meaning there is no office. We allow employees to work from wherever they do their best work, and invite the team to meet in person a couple times per year.
• Home Office Allowance: As a new employee, you will receive a $300 allowance to set up your home office with the necessary equipment and accessories.
• Wellness stipend: $100 per month to spend toward an item or service that supports your wellness (i.e. massage or gym membership, meditation app subscription, etc.)
• Book stipend: To support your intellectual development, we offer a book stipend that allows you to purchase books, e-books, or educational materials relevant to your role or professional interests.
• Professional Development Reimbursement: We provide up to $500 annually for you to invest in relevant courses, workshops, conferences, or certifications that will enhance your skills and expertise.
• No working birthdays: Take your birthday off, giving you the opportunity to relax, enjoy your special day, and spend time with loved ones.
• Charitable Contribution Matching: For every charitable donation you make, we will match it dollar for dollar, up to a maximum of $150 per year. This allows you to amplify your charitable efforts and support causes close to your heart.

COUNTERPART'S VALUES

• Conjoin Expectations - it is the cornerstone of autonomy. Ensure you are aware of what is expected of you and clearly articulate what you expect of others. 
• Speak Boldly & Honestly - the only failure is not learning from mistakes. Don’t cheat yourself and your colleagues of the feedback needed when  expectations aren’t being met. 
• Be Entrepreneurial - control your own destiny.  Embrace action over perfection while navigating any obstacles that stand in the way of your ultimate goal. 
• Practice Omotenashi (“selfless hospitality”) - trust will follow.  Consider every interaction with internal and external partners an opportunity to develop trust by going above and beyond what is expected. 
• Hold Nothing As Sacred - create routines but modify them routinely.  Take the time to reflect on where the business is today, where it needs to  go, and what you have to change in order to get there.
• Prioritize Wellness - some things should never be sacrificed. We create an environment that stretches everyone to grow and improve, which is fulfilling, but is only one part of a meaningful life.

Our estimated pay range for this role is $150,000 to $170,000. Base salary is determined by a variety of factors, including but not limited to, market data, location, internal equitability, and experience. 

We are committed to being a welcoming and inclusive workplace for everyone, and we are intentional about making sure people feel respected, supported and connected at work—regardless of who you are or where you come from. We value and celebrate our differences and we believe being open about who we are allows us to do the best work of our lives.

We are an Equal Opportunity Employer. We do not discriminate against qualified applicants or employees on the basis of race, color, religion, gender identity, sex, sexual preference, sexual identity, pregnancy, national origin, ancestry, citizenship, age, marital status, physical disability, mental disability, medical condition, military status, or any other characteristic protected by federal, state, or local law, rule, or regulation.