Benefits & Insurance
Owner: Director of Finance & Operations (DFO) – with input from all Directors Audience: All OWL staff
Purpose
This document provides an overview of OWL's benefits, stipends, and insurance coverage.
Benefits and Insurance
Open Way Learning offers a range of benefits to support the personal well-being and long-term financial security of our team. Our benefits reflect OWL's commitment to supporting our employees in a sustainable, equitable, and transparent way.
Retirement Plan - 403(b)
All full-time employees are eligible to participate in OWL's 403(b) retirement plan, administered by Newport Group, with investment options through Vanguard ETFs and mutual funds.
OWL provides a non-elective employer contribution of 5% of the employee's base salary, deposited each pay period—regardless of whether the employee contributes.
Employees may elect to make additional voluntary contributions (pre-tax and/or Roth) up to the IRS annual contribution limits (e.g., ~$20,500 in 2022; updated annually).
Enrollment support and plan details are provided upon hiring and are available upon request.
Why this matters: This benefit supports your long-term financial well-being and grows automatically over time, even if you choose not to make additional contributions.
Health Insurance Stipend
Until OWL reaches the scale to support a group health plan, all full-time employees receive a monthly $500 health insurance stipend to help offset the cost of individual coverage.
Employees are encouraged to use this stipend to purchase insurance through Healthcare.gov or a private provider.
The stipend may be:
Included in your paycheck as taxable income, or
Redirected as a contribution to your 403(b) plan
To select your preference, contact the OWL Administrative Associate. If no preference is submitted, the default will be paycheck inclusion.
Note: This is a reimbursement-style stipend, not a formal group health plan, but it is designed to offer flexibility while keeping costs manageable for both employees and OWL.
Other Benefits
Government-Mandated Programs: OWL complies with all legal benefit programs, including Social Security, Medicare, and Medicaid. Employee contributions are withheld from each paycheck, and OWL contributes the required employer match.
OWL offers full-time employees an $80/month technology stipend to help offset mobile phone and internet expenses necessary for remote work, collaboration, and virtual facilitation. Note that OWL may alternatively cover the cost of these services directly via a company credit card if the account is registered in the organization's name and used exclusively for OWL business.
OWL provides a one-time moving stipend of up to $1,000 for new full-time employees or for existing employees who are relocating in a way that provides strategic benefit to OWL's regional presence or client services. This stipend may help cover the cost of transportation, shipping, or temporary housing during the transition. While OWL is a remote-first organization, proximity to key partner regions, school districts, or conference hubs may enhance program delivery, outreach, and visibility, making relocation support an appropriate and mission-aligned investment. Approval is granted on a case-by-case basis by the OWL Leadership Team.
Workers' Compensation Insurance: All employees (except directors) are covered under OWL's workers' compensation policy for work-related injuries or illnesses.
Prompt reporting is required for any incident, no matter how minor. Notify a Director immediately in such cases.
OWL will provide instructions for submitting a claim and, if needed, refer you to an approved medical provider.
Note that failure to report promptly may result in denial of benefits.
Claims are administered by an external insurance carrier, whose representatives may contact employees directly during the claims process.
Benefit Eligibility Summary
Flexible Paid Time Off (PTO)
✔️
❌
❌
Vacation
N/A
✔️
❌
Sick Days
N/A
✔️
✔️ (Prorated)
Holidays
✔️
✔️
✔️ (Unpaid)
Personal Days
N/A
✔️
❌
Expense Reimbursement
✔️
✔️
✔️
403(b) Retirement Plan (w/ 5% employer)
✔️
✔️
❌
Health Insurance Stipend ($500/month)
✔️
✔️
❌
Technology Stipend
✔️
✔️
❌
Business Phone Expense Coverage
✔️
✔️
❌
One-Time Moving Stipend (up to $1,000)
✔️ (case-by-case basis)
✔️ (case-by-case basis)
❌
Workers' Compensation Insurance
✔️
✔️
✔️
Paid Leave (Medical, Civic, Parental, etc.)
✔️
✔️
Eligibility varies
Unpaid Leave (Extended/Personal)
✔️
✔️
Eligibility varies
Year-End Bonus (Surplus Sharing)
✔️
✔️
❌
Social Security / Medicare / Medicaid
✔️
✔️
✔️
Note: Eligibility for benefits like vacation, sick time, and insurance stipends is based on your employee classification. Employees working in hybrid roles should refer to their primary classification or consult the OWL Leadership Team for clarification.
Benefit Disclaimer
OWL reserves the right to revise, modify, or discontinue any benefit at any time, consistent with organizational needs, legal requirements, and financial conditions. Any material changes to employee benefits will be communicated in writing and discussed as appropriate.
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