Vice President of Enterprise Technology, Pie Insurance
$210-270k
+ Equity
Small business insurance
Be an early applicant
Small business insurance
201-500 employees
Be an early applicant
$210-270k
+ Equity
201-500 employees
Company mission
To make insurance less expensive, simpler, and more transparent for small business owners.
Role
Who you are
- Bachelor’s Degree required; MBA or relevant advanced degree preferred
- 15+ years of experience in technology leadership roles within fast-paced, high-growth environments
- 7+ years of executive-level experience managing enterprise systems, IT, or similar disciplines in the insurance or financial services industry
- Proven ability to drive complex technology strategies and initiatives, including large-scale system implementations, integrations, and data governance
- Deep understanding of AI technologies and their application in enterprise environments
- Advanced communication, stakeholder management, and change leadership skills
- Experience with platforms such as Salesforce, Workday, middleware technologies, and enterprise data architecture
What the job involves
- The Vice President, Enterprise Technology is responsible for leading and scaling the Business Systems and Corporate IT functions at Pie
- This executive will drive enterprise technology strategy and execution, focusing on maximizing operational efficiency, enabling scalability, and improving cost-effectiveness through technology
- A key responsibility will be driving the adoption of AI tools and systems to automate processes, augment workforce productivity, and reduce operational costs
- Technology Strategy & Execution:
- Define and execute a long-term strategy for enterprise technology that aligns with Pie’s broader business goals
- Deeply understand Pie’s operational challenges and design technology solutions that address them with measurable impact
- Lead the adoption of AI technologies across business functions to streamline operations and improve cost-efficiency
- Build platforms and capabilities that drive both procedural and technical enhancements organization-wide
- Lead the implementation of master data management and enterprise system integrations using scalable and sustainable architectural patterns
- Establish and scale an Enterprise Architecture and IT Governance practice
- Oversee and ensure a comprehensive enterprise Cybersecurity program, including policy development, incident response, and compliance with relevant standards and regulations
- Collaboration:
- Collaborate closely with other executives and senior functional leaders to align technology investments with strategic business priorities
- Work hand-in-hand with Data Engineering, Software Engineering, and Product Management teams to ensure integrated and secure system designs
- Partner with Legal, Risk, and Compliance to ensure all systems meet regulatory and security requirements
- Leadership:
- Build, lead, and mentor a high-performing Enterprise Technology organization including Business Systems, Corporate IT, and potentially other enabling technology functions
- Cultivate a culture of innovation, operational excellence, and continuous improvement
- Set clear goals and expectations, provide regular coaching and feedback, and support professional growth for all team members
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
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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