Milestone Systems
Benefits at Milestone Systems
Milestone offers a comprehensive benefits package designed to support employee health, financial wellness, and work-life balance. Eligible employees can enroll in medical, dental, and vision coverage starting the first of the month following their hire date, with additional employer-paid benefits like disability and life insurance provided. Milestone provides two medical plan options through Regence, including a High-Deductible Health Plan with generous HSA contributions. Employees also enjoy access to flexible spending accounts, a 401(k) with 100% employer match up to 6%, paid vacation and sick leave, parental leave, and 12 paid holidays including floating holidays. Additional perks include internet and fitness subsidies, education assistance, and a paid volunteer day.
Financial + Retirement
401(K) matching
Auto enrollment at 4% after 90 days only if no other action taken. Milestone matches 100% of earnings up to 6% plan compensation. Vesting is immediate and is always 100%
Pay transparency
Office Perks
Company-sponsored outings
Varied by team.
Fitness stipend
Employees may be reimbursed up to $120 annually for expenses related to gym memberships and/or fitness app subscriptions.
Company-sponsored happy hours
Onsite gym
Onsite office parking
Free snacks and drinks
Home-office stipend for remote employees
Full Time Employees will be provided $50/ month to help support home internet access.
Mother's room
Professional Development
Continuing education stipend
Provides reimbursement for courses related to your job or to progress toward your career goals. Repayment provisions may apply if terminate employment within 2 years of receiving assistance.
Job training & conferences
Promote from within
Tuition reimbursement
For college degree programs.
Personal development training
Health Insurance + Wellness
Dental insurance
Principal Dental Plans - Milestone pays 90% of premium.
Disability insurance
Short- and long-term disability, along with state paid leave programs.
Flexible Spending Account (FSA)
Allows you to save pre-tax dollars to pay for eligible health dependent care and eligible health care expenses.
Health insurance
Regence Blue Cross Blue Shield - Milestone pays 90% of premium.
Life insurance
Basic Life and ADD and Voluntary Life and ADD
Vision insurance
Regence Blue Cross Blue Shield - Milestone pays 90% of premium.
Mental health benefits
Canopy Employee Assistance Program
Culture
Volunteer in local community
Open door policy
Open office floor plan
Remote work program
Live near Portland, OR? Join us in a hybrid role at our Lake Oswego office! Outside the area? You’ll still be part of an innovative, highly connected remote team that thrives on collaboration.
Employee-led culture committees
Quarterly engagement surveys
Hybrid work model
In-person revenue kickoff
Employee awards
Child Care + Parental Leave
Family medical leave
Generous parental leave
Vacation + Time Off
Generous PTO
Regular employees accrue 1.67 days’ vacation per month, which is 20 days per calendar year. Unused vacation time may be rolled over to the next year, subject to a cap of 20 days.
Paid volunteer time
Full time employees receive 1 paid day off per calendar year to volunteer with the non-profit / 501c3 organization of your choice. Pre-approval needed by your manager.
Paid holidays
Paid sick days
Full time employees receive 10 paid days of sick leave at the beginning of each calendar year. For new hires, they are prorated depending on your start date. Sick time does not rollover.
Floating holidays
Bereavement leave benefits
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