Director, Actuary
Confirmed on the employer's own hiring board on Oct 30, 2026. First seen by Alion on Jul 9, 2026.
Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.
Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.
The Director, Actuary is responsible for leading Corporate Actuarial functions for workers' compensation and other P&C lines of business. This leadership position will manage a growing team of actuaries responsible for actuarial analyses in the areas of reserving, reinsurance, pricing, ratemaking, analytics, and systems integration in support of Pie's pricing and financial goals. Duties also include enhancing enterprise risk management capabilities, applying predictive models, researching workers' compensation industry trends, and developing and delivering presentations to a senior level audience. This work is used to develop financial forecasts and influence decisions of senior management; the results are communicated to a broad group of stakeholders, including Claims, Underwriting, Business Development, Actuarial and Product; this role will have significant visibility with the senior leadership group. Strong technical background, the ability to dig into details and find early indicators of problems, and communication skills to a wide audience, written and oral, will distinguish the ideal candidate.
How You’ll Do It
Execute Company Strategy:
- Ensure the consistent use of methods and assumptions across all lines of business as part of loss trends deep dives and regularly recurring work.
- Guide team members in developing the loss trends storylines for Workers’ Compensation and other lines of business.
- Manage regular reporting deliverables including competitor commentary and pure premium relativity.
- Establish relationships and collaborate with cross-functional areas to better prioritize work within the team and support the development of insurance trends.
- Collaborates with other actuaries and business units within Pie to ensure effective execution of actuarial data driven initiatives.
Actuarial Analysis:
- Responsible for high quality and reproducible predictive and descriptive tools for business use.
- Closely reviews innovative models and recommends regulatory approach to innovation.
- Monitors business portfolio KPIs such as frequency and severity trends and proactively informs senior management.
- Collect, aggregate, and analyze data from multiple internal and external sources.
- Write and maintain code to build and maintain data pipelines for production models.
- Use and develop advanced actuarial techniques to discover patterns, insights, and trends in Pie data.
- Produce sound rate level indications with advanced understanding of actuarial ratemaking methodology.
- Work with Pie’s reinsurers and reinsurance broker to optimize Pie’s reinsurance program and create reporting, including bordereau materials, for reinsurance partners.
- Work with external partners like AM Best, auditors, and external consultants, as necessary.
- Partner with the Data team to identify and establish actuarial data requirements.
- Provide regular status updates to Pie’s senior leadership.
- Identify issues and recommend mitigation strategies.
- Ensure key stakeholders are identified and regularly informed of project status.
- Lead in the development and documentation of actuarial department processes.
Leadership:
- Support, mentor, and coach as well as provide professional development for your team. Provide continuous feedback and opportunities for career development.
- Work in partnership with the People Partner on performance improvement and coaching plans.
- Identify hiring needs and be the hiring manager for recruiting high quality analysts.
- Work through conflict management needs and team member relations needs with the help and direction from the People Team.
- Work collaboratively with the People Partner throughout the team member lifecycle, including, but not limited to hiring, onboarding, performance management, team member relations, and offboarding.
The Right Stuff
- Bachelor’s Degree required.
- 10+ years of progressive insurance Actuarial experience required.
- Fellow of Casualty Actuarial Society
- Experienced leader, with 6+ years of people leadership. Strong ability to motivate others to take initiative, as well as, establish psychological safety for team members to test, learn, and grow.
- Experience using SnowFlake, SQL, Python, and other programming languages is a plus.
- Master communicator: Ability to communicate up and down the organizational levels, strong executive presence. Expressing self effectively by where applicable, presenting their own, team, and cross functional perspectives and requests in a clear, direct and open manner. Foster open communication and dialogue by uncovering and resolving conflicts within the team and among cross functional groups, where applicable, in a constructive manner.
- Highly Collaborative: Understands others by seeking and understanding multiple points of view and needs of multiple cross functional groups.
- Strategic Thinker & Problem Solver: Demonstrates the ability to translate business segment strategy into functional plans and guiding execution. Can consistently apply integrative thinking skills to solve underlying needs and find the best possible solution.
- Proactive Operator: Surfaces issues early. Manages stakeholder expectations directly. Anticipates rather than reacts.
- AI-Native: Actively uses AI tools to accelerate analysis, drafting, and team productivity. Comfortable making AI adoption a stated team expectation.
- Independent Judgment: Brings well-reasoned actuarial positions to senior leadership and defends them under scrutiny.
The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.
Base Compensation Range
$180,000—$240,000 USD
Compensation & Benefits
- Competitive cash compensation
- Comprehensive health plans
- Generous PTO
- Future focused 401k match
- Generous parental and caregiver leave
- Our core values are more than just a poster on the wall; they’re tangibly reflected in our work
Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.
Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.
Location Information
Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.
Additional Information
Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.
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