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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.



  • 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

Member Services Tellers – Old Town & Mississippi Branches

Trailhead Credit Union has two open positions for a full-time Member Services Teller at the Old Town and Mississippi Branch locations. We hire people that have the skills to deliver high quality member service and need-based selling. The position would be responsible for assisting our members with their transactions while providing excellent service which includes identifying additional financial product needs and recommending Trailhead solutions.


  • Uphold the Trailhead service promises: Deliver, Engage, Anticipate, Respectful, Reward
  • Handle monetary transactions for our members
  • Assist members with financial services either by phone, mail, or in person
  • Use need-based selling to provide great service to our members
  • Interact and support other members of Trailhead staff and management in a positive, respectful, and professional manner


  • High school diploma
  • Cash handling and customer service experience
  • Great verbal and written communication skills
  • Knowledge of windows products

Preferred experience:

  • 2+ years of experience in the financial services industry

Executive Assistant & HR Specialist

Trailhead is looking for an experienced Executive Assistant – HR Specialist, who reflects our Credit Unions’ vision and shares the same passion for Portland. In this dynamic role, the Executive Assistant will be a part of Senior Team and is encouraged to propose and implement meaningful change. HR experience is highly-preferred. Executive Assistant level experience required.


  1. Deliver service to both internal and external members that are in alignment with the credit union’s Service Promises.
  2. Provide and distribute all materials requested by the Board; assist Board and Supervisory Committee with requests/questions/problems as lead liaison to Board & Committees.
  3. Manage Professional Adobe document preparation and editing of all forms utilized by Credit Union. Format, maintain, and create correspondence and various documents that are congruent to Brand Promises.
  4. Record and share official meeting minutes, including but not limited to: Board, ALCO, annual meeting, Senior Team, and staff meetings when necessary. Assemble, post, and save all related documents, agendas and packets for monthly meeting as necessary.
  5. Posts Board & Volunteer content to MyBoardPackett; responsible for monitoring and maintaining secure database of all Board related material.
  6. Maintains Credit Union calendar; and Board Calendar.
  7. Manage Volunteer and Staff Training Program (VAP for Board, and OnCourse Training for Staff, Board of Directors, and Supervisory Committee).
  8. Must comply with government and other regulations affecting the credit union industry including but not limited to the Bank Secrecy Act and The USA Patriot Act.
  9. Conduct official business with executives, volunteers, members, employee files, records, with confidentiality.
  10. Participant and active member of Senior Team.
  11. Prepare for and assemble documents, loan information, and or audit related requests for Supervisory Committee.
  12. Update and maintain Pertinent Information list, revisions to Policy Manual, Employee Handbook, Job Descriptions, Procedural Manual and Disaster Recovery Manual.
  13. Order all office supplies, notary commissions/seals, and other office related systems/machines/supplies.
  14. Approve invoices for payment as necessary.
  15. Coordinates and plans operation events, trainings, conferences, posts reimbursements, and travel arrangements for Board and Staff as needed.
  16. Manages onboarding training efforts; involved with recruitment, posting, interviewing, background checks, and orientation. Manages offboarding termination process for benefits and exit interview.
  17. Benefits coordination with VP Operations: medical, dental, standard, 401k.
  18. Promotes organization wellness for employees.
  19. Perform all other duties and responsibilities as assigned.

Skills and Abilities Required:

Education: Must have high school education or equivalent. At least two years of college experience required. Additional years of work history may substitute education requirement.


  • A minimum of five years of experience as an Executive or Senior-level Administrative Assistant (preferably in a credit union or financial institution) preferred.
  • Two years of experience in Human Resources highly preferred.
  • Proficient telephone and typing skills; minimum typing speed 55 words per minute.
  • Ability to fully utilize Microsoft Access programs, including Excel, Word, Outlook, PowerPoint, Publisher. Experience with Adobe Professional is ideal but not required.
  • Ability to provide candid feedback to Senior Management with a high level of professionalism and integrity.
  • Requires high-level of confidentiality and attention to detail.
  • Must demonstrate the ability to exercise good judgment, initiative and tact in dealing with Board, Management and staff.

COVID-19 considerations:
To keep our tellers as safe as possible, we’ve installed plexiglass dividers at our front counter and have supplied masks, gloves and hand sanitizer.

Apply Now

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

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