Start date: October 16th at the latest

Applications due: September 9th 

About Round Sky:

Round Sky Solutions is a worker cooperative facilitating and teaching about cooperative leadership and management. Our training programs incorporate both individual and collective  growth to support organizations in their shared leadership to do great work! 

Over the past ten years, Round Sky Solutions has become one of the leading trainers in cooperative management and self-directed management practices. Round Sky offers collaborative leadership practices at many scales: short webinars, conference sessions, workshops, and longer intensive trainings, like the Cooperative Leadership Certification Program

We believe that collaborative leaders benefit from both tools and structures to facilitate their teams and personal development practices. We approach the work through concrete processes (tools), personal development practices, somatics, and connection grounded in our methodology we call Collab. 

Learn more by looking at our website:

About the Position – Part Time (20 hours/week to start)

We are seeking a fast learner, hard-working, and creative individual excited to support leaders and teams in their collaboration. We are looking for someone who envisions themselves staying in this role long term (3+ years) and becoming a worker owner.

Your main roles would be in the area of teaching and facilitating, although as a small, worker cooperative we all wear multiple hats. Our cooperative thrives through development, innovation, and growth, and we welcome new, exciting ideas about how best to accomplish our goals.

Our main training, the (online) Cooperative Leadership Certification Program has grown in popularity in our community. We are seeking a trainer to become the lead on this key aspect of our work. The trainer will be an assistant to the course shadowing and working alongside one of our trainers before taking full lead. The trainer will also be invited and encouraged to participate in webinars open to the public. 

Our work environment is a highly collaborative space and we expect the trainer to have autonomous and creative power over the delivery of the material in communication with the Round Sky Instructor team. We have an environment where challenges, opportunities, problems, and ideas are welcome in meetings. 

Additionally, the ideal candidate is also excited to step into roles that contribute to running the business, which can look like supporting accounting, outreach, legal, video production, graphic design, and other areas key to the business. 

Main Responsibilities:

As an instructor/trainer (70% of time):

  • Genuine excitement to support (adult) participants/students in their learning in an online format
  • Delivering on curriculum and connecting to student needs and learning styles 
  • Listening, noticing, and following up with students to give them support
  • Offering direct input, feedback, and insight during course sessions and in written form through the forums
  • Communicating with students via email to support their completion of the course
  • Tracking and relaying feedback from sessions to the Round Sky team for improving the course
  • Producing and evolving training materials for curriculum with Round Sky team as needed
  • Commenting on assignments and grading exams in a timely manner 


As a Round Sky Team Member (30% of time):

  • Admin, Communication, & Relationship Building:
    • Participating in weekly meetings and project tracking
    • Responding to emails
    • Offering and receiving feedback 
    • Building relationships with Round Sky workers and partners
    • Participating in personal development work, relationship building, anti-racism work, and more areas of the work internally at Round Sky
  • Marketing & Outreach:
    • Participating in webinars, workshops, and/or conference sessions especially as it relates to relevant programs
    • Supporting outreach and marketing, which could include (not limited to)… 
      • Reaching out to past students, groups, lists, and contacts about events
      • Producing written materials (like blogs)
      • Posting on social media outlets as relevant to your social media presence
    • Building relationships as a Round Sky representative
  • Program Development:
    • Visioning and producing new products
    • Evolving current products including incorporating participant feedback
  • Desired capacity for other projects related to finances, legal, and other business needs:
    • This could be.. 
      • Bookkeeping
      • Bill paying
      • Legal research

Essential Skills/Capacities/Qualities:

  • Instruction or education experience
  • Group facilitation experience
  • Excitement for building relationships with the students through the courses and beyond
  • Capability (and willingness) to reflect on your previous meeting facilitation and project management experience to connect to the learning materials
  • Willingness to work within a collaborative structure and process
  • Ability to give and receive constructive feedback
  • Commitment to racial, social, and economic justice
  • Ability to thrive in a remote workplace as a self-motivated, independent worker who can prioritize tasks and manage multiple projects at once
  • Flexibility and adaptability to change and growth
  • Proficiency with Google Office Suite (Slides, Sheets, Docs)
  • Must have own computer and equipment including a stable and consistent internet connection to hold several video meetings per week

Preferred Qualities/Capacities, not required:

  • Coaching or consulting background
  • Familiarity with Collab and Round Sky’s teaching, Level I Certified
  • Fluency in Spanish
  • Connection to or/and knowledge of the cooperative, new economy, racial justice and/or solidarity economy movements
  • Familiarity with teaching in online course platforms
  • Video editing experience
  • Bookkeeping or financial background

Compensation & Benefits:

  • A starting hourly rate of $20.17/hour 
  • 20+ hours a week with potential for full time
  • Paid time off for Vacation and Sick Days
  • Office expense reimbursement 
  • Personal development opportunities within and outside of Round Sky
  • Remote Work
  • Flexibility and power over your schedule and work (with communication)
  • Path to worker-ownership
  • Informal support during taxes season
    • Note: your pay is not subject to employee withholding taxes; during tax season, you will receive a K-1 as a ‘provisional owner’



This is an opportunity to join a business as an owner and share in the profits, successes, responsibilities, and co-shape the direction. This is not a conventional job and you will not be an employee. After a trial period of 2000 hours  you will become eligible to apply to the cooperative as an owner. As a worker owner you will have equal voice in decision making and legal ownership and will receive a share of profits or losses based on the hours you have contributed.

How to Apply:

Accepting applications through September 9, 2022 

Note: Applications accepted and processed on a rolling basis.

Send the following in PDF form to with the email title “Trainer Application” for consideration:

  • Resume or CV
  • Cover letter
    • Tell us what excites you about this role and working with Round Sky.
  • At least two references (contacted after interviews)
  • Optional: 
    • Lesson Plans
    • Curriculum or images you’ve created to help students/audience understand what you’re teaching


Round Sky Solutions is an equal opportunity employer and does not discriminate on the basis of race, ethnicity, national origin, age, familial status, military status, religion, disability, medical condition, sex, sexual orientation, or gender identity and expression. 

We welcome and encourage applications from Black, Indigenous, and people of color, and queer, transgender, and gender non-conforming people.