Workforce Director Jobs in Portland, OR (NOW HIRING)

About Cultivate Initiatives:

We are a group of people who work alongside those on the margins to empower individuals and communities through an inclusive range of services and support. We build communities from the inside out through workforce development, housing & homemaking, and supportive sheltering.

Summary

The Employment Specialist
is responsible for the end-to-end support, professional development, and successful career transition of timebound staff (Apprentices) within the Workforce Department. Acting as both a coach and an advocate, this role ensures participants are equipped with the skills, resources, and employer connections necessary to secure stable, full-time employment after their Apprenticeship ends.

Compensation/Benefits:

• $25-28 per hour
• Comprehensive benefits package including health, dental and retirement plans.
• Opportunity to make a meaningful impact by contributing to the success of a non-profit organization.
• Collaborative and inclusive work environment that values diversity and professional growth.

Accountability:

Accountable to the Workforce Director.

Duties/Responsibilities:

• Lead and facilitate the Intern Employment Pathways program, guiding timebound staff (Apprentices) through their onboarding and entire program lifecycle.
• Conduct regular 1-on-1 meetings with Apprentices to establish accountability, set professional goals, and monitor progress.
• Partner with the Program Managers and Workforce Director to support Apprentices with their transition back to full-time employment and with goal setting.
• Design and deliver tailored professional development workshops, activities, and curriculum optimized for marginalized populations.
• Provide individualized coaching in resume and cover letter writing, job search strategies, and interview preparation.
• Identify individual growth opportunities to effectively prepare Apprentices for their next career steps.
• Collaborate with the other Employment Specialist and Workforce Director to cultivate relationships with external employers, building meaningful and sustainable job placement pathways.
• Partner with community organizations to connect Apprentices with vital external resources, helping them navigate and mitigate systemic barriers to employment.
• Maintain accurate, timely records and data tracking systems to monitor Apprentice progress, milestone achievements, and resource utilization.

• Provide cross-functional support to the broader Employment Services team and Intern Program initiatives as needed.
• Support neighbors in the External Employment Pathways program as needed.
• May perform other duties as assigned by supervisor

Qualifications:

• Experience working with marginalized communities particularly those who have been unhoused or who are currently unhoused.
• Strong interpersonal skills and ability to communicate effectively with a diverse group of people.
• Must be able to work independently and collaborate well with a team.
• Must be able to provide proof of Driver's License.
• Demonstrated ability to use word processing, database, calendar, spreadsheet, e-mail, remote meeting software (Zoom/Google Meet).

Preferred Qualifications:

• Have at least 2 years of experience in career coaching or resource navigation for marginalized populations.
• Knowledge of local organizations and resources such as expungement clinics, work programs, and housing support.

Work Conditions and Physical Requirements:

• Being physically present at CI offices Monday-Friday from 8:30am-4:30pm
• Work is performed primarily indoors with occasional interactions outdoors in all types of weather.
• Ability to work in environments with varying noise levels, from quiet offices to louder, industrial settings.
• Ability to sit, stand or walk for prolonged periods, and ability to stoop and kneel occasionally.
• Ability to occasionally lift and/or move objects weighing up to 30 pounds.

• Work requires the ability to perform repetitive movements of the wrist, hands, or fingers due to continuous use of computer keyboards and other office equipment.
  

How to apply:
Please submit acover letter and resume
electronically.

The position is open until filled. Applications received by July 24, 2026, will receive priority consideration. If a suitable candidate is found during that screening, later applications will not be considered. We look forward to speaking with you!

CI is committed to maintaining a safe and secure work environment for employees and neighbors. As part of our hiring process, we conduct criminal history checks for the top candidates of all recruitments and driving history checks for candidates of positions that require operating company vehicles. CI also conducts routine drug tests.

CI is an Equal Opportunity Employer. CIvalues a diverse, inclusive workforce and provides equal employment opportunity for all applicants and employees. All qualified applicants for employment will be considered without regard to an individual's race, color, sex, gender identity, gender expression, religion, age, national origin or ancestry, citizenship, physical or mental disability, medical condition, marital status, domestic partner status, sexual orientation, genetic information, military or veteran status, vaccination status, or any other basis protected by federal, state, or local laws. If you require accommodation to apply, please contact Emily Hutsell at the following number or email.

Questions: employment@cultivatepdx.org or (503) 719-6135