Director of People Operations & Technology, Pie Insurance
$160-200k
+ Equity & Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members
Expert level
Remote from US
More information about location
Small business insurance
Be an early applicant
Small business insurance
201-500 employees
FintechB2BInsurance
Be an early applicant
$160-200k
+ Equity & Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members
Expert level
Remote from US
More information about location
201-500 employees
FintechB2BInsurance
Company mission
To make insurance less expensive, simpler, and more transparent for small business owners.
Role
Who you are
- 12 or more years of progressive experience in People (HR) with specific experience in people operations and tech stack ownership (Workday required), tier 1 team member relations, team member resource development and delivery, payroll management, and regulatory and compliance management
- 5 or more years of direct people management experience, including building, developing, and leading teams to consistent achievement of excellent business outcomes
- Prior experience preferred in a high-growth tech-forward environment with a mix of private and public company experience preferred
- You know what great looks like in a 1,000- to 5,000-person company and can also thrive in an earlier-stage environment that requires flexibility and building tools and resources, sometimes from scratch
- Prior experience in insurance, insurtech, fintech, healthtech, lending, or financial services preferred
- Workday certification(s) preferred
- Bachelor's degree or equivalent experience required
- Deep knowledge of HR workflow, regulatory, and compliance requirements across the employee lifecycle, with the capability to develop rigorous, highly efficient, compliant workflows, processes, and standard operating procedures
- Demonstrated capability of developing, testing, and implementing tech- and AI-enabled solutions that create a flywheel of continuous improvement for the team and company, both independently and with stakeholders
- Demonstrated capability to plan and execute HR transformation and/or system implementation projects leveraging agile and iterative methodologies
- Outstanding technical and analytical capabilities with specific experience in People (HR), Talent and organizational technology, metrics, reporting, and data visualization
- Has the knowledge, and cultivates the relationships, necessary to provide thoughtful insights on market trends, best practices, and benchmarking
- Ownership: Leads with a one-team, extreme ownership mindset, We Are The They
- Collaboration & Influence: Develops high-trust relationships org-wide and works collaboratively with cross-functional stakeholders to identify and consider a wide range of needs, creatively designing solutions that solve for the most needs
- Critical Thinking: Leverages first principles, integrative thinking, and Pie's Collaboration and Decision-Making Framework (CDMF) for designing the data-driven, maximum win/win solutions, considering all stakeholder needs
- Strategy: Demonstrates the ability to think integratively as an organizational leader, develops multi-year strategies and aligns multiple functions around cohesive strategic narratives; cultivates internal and external networks for identifying emerging opportunities and novel strategies that open new possibilities for their team and function; prepares for scale while identifying inefficiencies that solve functional challenge
- Growth Mindset: Leads with questions and curiosity, demonstrating self-awareness and humility, models continuous learning and growth through integration of personal, team, and cross-functional feedback, flexing and adapting as needs and context change; recognizes when behavior/thinking is below the line, and actively works to uplevel self
- Grit & Resilience: Persists through complex challenges while role modeling resiliency and supporting the team and peers
- Communication: Writes and speaks with accuracy, clarity and confidence with audiences at all levels of the company, including the CEO and Senior Leadership Team; demonstrates emotional control and role models Pie’s communication and feedback model; engages in constructive debate while actively listening; seeks and receives real-time candid feedback with kindness and positive intent
- Execution: Has high standards for performance and execution that continues to increase as you and the function develop and as the business requires it; willing and able to operate in detail mode, knowing when and how to flex between the strategic birds-eye view and the tactical details and providing direction and guidance to the team; fosters a culture of high accountability within team, leading by example
- Team Organization & Planning: Designs organizational structures that address business needs, team effectiveness, and team development and that can scale; develops operational rhythms that ensure functional alignment, develops monitoring systems that reduce complexity and provide real-time visibility into performance and enable risk identification
- Team Building & Performance Management: Builds and executes talent strategies to enable the function to achieve and maintain a level of performance; sets and measures against clear expectations at the individual and team level on a monthly, quarterly, and bi-annual basis
What the job involves
- With approximately 350 team members today, and scaling through people and technology for the future, Pie is seeking an exceptional Director of People Operations and Technology (Dir, POps & Tech) to join the People leadership team
- This role will elevate our human resources function through the strategic use of AI, technology, and a blend of business- and people-centered approaches
- The Dir, POps & Tech reports to the Chief People Officer (CPO). This Director role will serve as a critical member of the People, Talent & Executive Support (PTE) leadership team, working in a highly collaborative environment as a thought and execution partner
- The Director of People Operations and Technology is responsible for the ownership of post-hire team member lifecycle delivery and experience, providing the structure, data, and analysis necessary for Pie’s leaders and our People Talent teams to execute against Pie’s people-driven strategies
- Given the range of capabilities and responsibilities of the role, this position will also align with multiple centers of excellence across the organization, such as business intelligence, finance, analytics, and culture ambassadorship
- The Dir, POps & Tech will own the development of multi-year strategies that shape team direction, inform functional strategy, and are aligned to company objectives
- The Director leads a broad scope of people operations functions including people operations and tech strategy co-development with the CPO and execution through a multi-year roadmap; Tier 1 team member support; payroll management; management of the People and Talent technology stack with a strong focus on Workday configuration, maintenance, and data integrity; People workflow, process design and SOP management; reporting and analytics; and compliance
- At the outset, the role is also expected to partner closely with the Dir, Talent to support Talent Operations. Aligning all of these areas around cohesive, strategic narratives that connect to Pie’s market positions and competitive differentiation will be key to our collective success
- Ensure an innovative, effective, and inclusive work culture to retain and grow the best talent for the People Team and Pie as an organization
- Directly manage the People Operations team, currently comprised of three full-time team members with varying levels of experience and responsibility
- Responsible for all aspects of people management, including development, coaching, training, performance management, and the expected future growth of the team
- Lead and develop new People team leaders in order to build bench strength as the business grows over time
- Proactively establish and maintain strong collaborative working relationships across the organization with a focus on the following stakeholders: Finance & Accounting, Enterprise Technology, Internal Communications, Legal & Compliance, Product, the Pie Executive Team, the Senior Leadership Team, and the Office of the CEO
- Proactively partner with People Partners, Total Rewards, Talent, and the Executive Support and Space teams on strategy development and outstanding execution across all aspects of the People, Talent & Exec Support functions
- Leveraging Pie’s Collaboration and Decision Making Framework, you will often serve in a lead execution role, as well as in supporting and consultative roles on cross-functional, complex project and program management initiatives
- Lead the People Operations team through strategic processes, projects, and complex situations
- Design, deliver, and monitor the strategic roadmap for the People Operations function on a monthly, quarterly, and annual basis
- Oversee payroll approval for the biweekly pay cycle for non-exempt and exempt team members
- Own the strategic design, delivery, and administration of our HRIS (Workday) and have oversight for the People tech stack and resources (Culture Amp, Continu, Ethena, Carta (shared), etc.)
- Manage the People Operations and Technology budget as well as People-specific vendor relationships and service providers
- Serve as the security admin for Workday, managing user and role-based security groups
- Own configuration, testing, and deployment updates, process improvements, and business process updates in HCM, Compensation, Advanced Compensation, Benefits, Time Tracking, Absence, US Payroll, and Talent
- Manage the bi-annual Workday release cycle
- Serve as the integration administrator to troubleshoot integration enhancements, issues, errors, or vendor requests
- Partner across the PTE team and key stakeholders organization-wide to identify and prioritize system development needs
- Align system configuration goals with PTE goals to optimize the HRIS' value
- Plan and execute moderate to complex projects, partnering with cross-functional SMEs
- Oversee Tier 1 team member support provided by the People Operations team
- Develop capabilities to provide Tier 2+ support for end-users, inclusive of the People Partnering team and Tier 2 team member relations
- Continuously uplevel thought leadership specific to People Operations and Technology, leveraging emerging frameworks and technologies
- Keep our house clean through comprehensive documentation of process, workflow, system configuration, and integration
- Establish and train the team using best practice methods for People systems
- Lead, execute, contribute to and/or consult on projects, programs and work as needed
- Monitor, audit, maintain, and troubleshoot the HRIS system to ensure data integrity and system compliance
- Maintain data integrity by developing routine audit procedures, creating audit reports, analyzing data, and defining corrective solutions
- Respond to requests for systems support and reports
- Develop data management protocols and standards, including data entry, integration, validation, and quality assurance procedures
- Establish and document audit procedures for the People Systems tech stack
- Ensure People Systems align with internal technology, procurement, and retention policies
- Build custom reports and dashboards for key metrics; fulfill ad-hoc report requests
- Analyze complex datasets to ensure system functionality and set-up
Our take
Historically, it’s been extremely cumbersome to qualify, onboard and manage workers’ comp insurance, particularly for America’s small businesses which haven’t been prioritized by larger carriers. That’s left small businesses often stranded with expensive and low-quality coverage.
Pie Insurance is changing all that through its technology-first model. Using data and analytics to better comprehend risk and speed up the decision-making process, it reduces the time to make an underwriting decision to a few minutes. Facing only legacy competition in an industry ripe for disruption, Pie Insurance has enjoyed rapid growth and received significant investment funding from backers in the InsurTech space.
Having recently acquired a nationally licensed insurance company, Pie Insurance is now able to directly issue its own policies nationwide. Currently available in 38 states, it will be aiming to expand its operations into the remaining states and territories to provide insurance to small businesses across the entire USA.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Top investors
4% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Sep 2022
$315m
SERIES D
Mar 2021
$118m
SERIES C
Total funding: $620.3m
Company benefits
- Flexible work: Pie offers in-office, hybrid, and remote work options so you can create the work environment that's best for you
- Fully paid health care: Pie covers the health, vision, and dental premiums for full time employees and covers a percentage of premiums for spouses and children
- Equity and 401k: We think you should get a piece of the pie, so in addition to equity, Pie contributes to your retirement through a 401k
- Generous PTO: We want to make sure Pie-oneers have time to balance a rewarding work life and fulfilling personal life
- Parental leave: Pie knows your family is important, providing 100% compensation for the first three months of parental leave, as well as a generous return to work plan
- Caregiver leave: Pie offers caregiver leave so you have the time to dedicate to those who need your care
- HSA and Health FSA: Pie contributes $1,500 for individuals and $2,000 for family HSAs per year. Employees have the option to contribute to a Health FSA
- Dependent Care FSA: To help care for your dependents, Pie allows employees to set aside pre-tax dollars to be used for expenses like babysitters, daycare, summer camps, etc
- Pet insurance: Pie understands your pet is family and their care can be costly when they're not feeling well. The plans provide reimbursement for common needs like exams, vaccines, x-rays, prescriptions, and much more!
Company HQ
Union Station, Denver, CO
Leadership
Dax Craig
(Co-Founder & President)MD of 11x Holdings which invests in commercial and residential real estate. Also Co-founded Valen Analytics, a data and analytics provider for property and casualty insurance.
John Swigart
(Co-Founder & CEO)Previously CMO for RapidFinance. Also worked as CMO for Esurance, starting off as VP of Finance in 2000.
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