We will be closed on Thursday and Friday, November 22 and 23, for the Thanksgiving Holiday.

Careers

The career trek can often lead to an ultimate base camp. Experience the journey with us.

As we embrace the “small enough to know better” mantra, we work to guide each member on their individualized path to financial success. We believe in Portland, our hometown, and the unique people who live here. So we embrace their individuality and work to help them succeed.

At Trailhead we know that success is a result of our exceptional employees. Our respect for these individuals motivates us to provide staff with opportunities for professional development, as well as a competitive salary and a generous benefits package.

Benefits

Healthcare

  • 100% employer-paid Medical, Vision, and Dental insurance for full-time employees
  • Life and Accidental Death & Dismemberment Insurance
  • Salary Continuation Insurance
  • Health Care and Dependent Care Reimbursement Account (Flexible Spending)
  • Supplemental Insurance offered at group rates
  • Extended Leave Bank (ELB) accruing at eight hours per year

401(k) Retirement Plan

  • 100% vested
  • Participation begins after three months of employment
  • After one year of employment, Trailhead will contribute 3% of your salary AND will match 50% of your contribution up to the first 6% of your salary

Paid Time Off

  • Earn up to 20 days in the first year
  • 11 paid holidays per year

Continuing Education & Professional Development

  • Opportunities for workshops, seminars, classes, and conferences
  • Tuition support for college classes

Transit and Parking

  • Get reimbursed for the cost of a Tri-Met pass or parking equal to that amount

The Trailhead Difference

  • Casual Dress Code: we wear jeans every day!
  • Body-tattoos and facial piercings are a-okay – show your authentic self
  • The small perks: annual staff appreciation party, free coffee, free checks, frequent potlucks, Trailhead swag, annual logo-wear reimbursement, and more!

Please reference the Trailhead Employee Handbook for complete details on benefit policies. Not all benefits and reimbursements are available for part-time staff. Inquire with Trailhead management for further details.

Current Openings


No current openings

Apply Now

Please email your resume with a cover letter explaining your interest in the position to [email protected].

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