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Training Specialist - $21.77-$27.23 per hour

  • Location: NE Glisan
  • Position Reports To: Training Manager
  • Full-Time Equivalent: 1.0 FTE


Ride Connection is looking for a collaborative and uplifting relationship builder, teacher, and lifelong learner to join our Training team as a Training Specialist.

The Training Specialist focuses on classroom instruction and driver training that offers coordinated, appropriate, frequent, accessible training to volunteer, paid, and staff drivers for community transportation, shuttles, and non-emergent medical transportation programs within the Ride Connection network and across the state. The Training Specialist works in collaboration with the Training team members to deliver Ride Connection’s training programs and curriculums. The Training Specialist reports to the Training Manager.

This is a full-time, non-exempt position with a starting salary of $21.77-$27.23 per hour depending on experience. May require occasional evening and weekend hours. Ride Connection offers an excellent benefits package, including comprehensive medical, dental, and vision insurance, an Employee Assistance Program, 403(b)-retirement plan with full vestment on day one, Flexible Spending Accounts with a $500 employer contribution, 10 days of paid vacation in your first year with increases every three years, six floating holidays that can be used at any time, a sick leave bank separate from your time off bank, and Trimet annual public transportation passes.


Who You Are

  • You enjoy teaching people sharing your experiences and expertise to help others add new toys to their toyboxes.
  • Teaching and training are passions for you, regardless of the class size. You deliver the same energy and support, whether you are teaching one person via Zoom or 25 people in a physical classroom.
  • You’re a lifelong learner. You find learning new ideas and perspectives from those you work with, people you meet in the community, and even your family members invigorating.
  • You value relationships and believe that relationship-building is about cultivating and sustaining meaningful connections that support and uplift everyone.
  • You are a community builder by nature. You view collaboration as key to supporting underserved communities and working with your team and teams across an organization or agency for the common good.
  • You understand the importance of empowering others and the impact that making sure people feel like they are an active part of a project or mission can have on someone’s confidence and performance. 
  • Once you start a teaching project, you can’t help but see it through to the end. And you know that “seeing it through” includes all the behind-the-scenes documentation, paperwork, and other particulars that aren’t always as exciting as the teaching itself.
  • You have the kind of internal clock and calendar that keeps you reliably on time, present, and honoring your commitments – but you’re not afraid to use a calendar or scheduling program for peace of mind.
  • You do your work through an equity lens.


What You’ll Do

  • Facilitate and perform scheduled training opportunities for Drivers. Trainings include Defensive Driving, Passenger Assistance, and Wheelchair Securement.
  • Perform vehicle orientation and behind-the-wheel training including on-the-road testing.
  • Provide curricular design support to Training Manager.
  • Generate and send monthly emails to Drivers with tips and learning points to continue learning and development outside of the classroom.
  • Develop training materials and monitor training content to ensure it is accurate and current.
  • Build, co-build, and develop training courses for in-person and online learning.
  • Adapt current training courses for online learning settings as needed.
  • Educate drivers and staff on how the Americans with Disabilities Act (ADA) applies to transportation access.
  • Identify safety risks and recommend learning-based solutions.
  • Represent Ride Connection in the community and model Ride Connection’s commitment to students, service partners, our funders, and the community.
  • Develop and maintain relationships with Ride Connection staff, partners, customers, and supporters.



A minimum of three years of experience training adult learners, building curriculum and training modules. Experience working with and training diverse communities. The ability to communicate key information to customers as well as trainees in ways that resonate. The ability and willingness to work occasional nights and weekends. The ability and willingness to travel throughout the Portland metro area to deliver training courses as needed. Occasional overnight travel throughout Oregon to deliver training courses may be scheduled well in advance. Experience with using office suite software, including word processing and spreadsheet creation. Must pass a National Criminal Record Check, which includes fingerprint identification.


Preferred Qualifications

  • Bilingual.
  • Multi-lingual.
  • Associates degree or teaching certification.
  • Degree in, certification in, or experience working in social work or community-based support settings.
  • Some course instruction certifications. Examples include Drivers Education instructor certification, CPR certification, and the Community Transportation Association of America’s Passenger Assistance Safety and Sensitivity (PASS) Driver and Trainer Certification.
  • Experience, lived or otherwise, working with older adults and people with disabilities.


Application Instructions

To apply for this position, please send your resume and cover letter to You can submit these documents in any format, but pdf works best. Please share what skills and experiences you would bring to this role in your cover letter. Also, please address the following:

  • How would you use your skills and experiences to contribute to equity, inclusion, accessibility, and community engagement internally and externally as part of Ride Connection?

Applications will be considered as submitted, so you are encouraged to apply early. Applications will continue to be accepted until the position is filled.

Please note: if you are chosen to move forward in the process for a second-round panel interview, for the first half of the interview, you will be expected to showcase your training skillset by presenting a short training of your creation on the topic of your choice.


About Ride Connection

Ride Connection is a private, non-profit organization based in Portland, Oregon. We offer ways for people to access the goods and services they need to survive and thrive. By giving people the means to get around, we offer independence, health, and inclusion.

The Ride Connection network comprises a collection of agencies that serve older adults and people with disabilities and low-income individuals, and the public by offering a variety of transportation options in Clackamas, Multnomah, and Washington counties.

Together, we provide over 500,000 rides and support more than 2,000 individuals with training and access to public transportation each year.

You can learn more about Ride Connection at