Career Transition Coach (Marketplace Contractor)
Company shown to members 🔒 · Remote · US only
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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- Experience not stated
- Where you can live
- US only
- Skills and tools
- outreach
- Job type
- Contract or freelance
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Job details
- Where you can work
- United States
- Employment type
- Contract
- Advertised pay
- Not stated by the employer
- Experience
- Experience not stated
- Employer publication date
- 25 August 2026
- First recorded by Psst
- 12 October 2026
- Last checked at the source
- 7 November 2026
About the job
About the company
The company is reimagining outplacement for the AI era.
We support people who have lost their jobs by combining human coaching, AI, and community to help them regain confidence, clarify what comes next, activate their networks, and move forward with purpose.
Our mission is simple
No one should experience a career transition alone.
The Role
As a Career Transition Coach, you will work one-on-one with candidates who have lost their jobs.
You will meet with each candidate weekly and become their best friend in transition: someone who listens deeply, remembers what matters, challenges when needed, and helps them move forward.
Your job is not to run candidates through a template.
It is to understand them deeply enough that their strategy, resume, Career Prayer™, networking approach, and next steps feel uniquely theirs.
What You’ll Do
- Meet with candidates weekly throughout their engagement.
- Understand their career story, strengths, motivations, values, and goals.
- Help each candidate develop their Career Prayer™: who they are, what they do best, what they want next, and how others can help.
- Partner with candidates to build and strengthen resumes, LinkedIn profiles, and professional narratives.
- Activate their network through Career Prayer and targeted outreach.
- Help identify target roles, companies, industries, and opportunities.
- Prepare candidates for interviews and important career conversations.
- Use AI and research tools to improve preparation, insight, and personalization.
- Collaborate with other coaches, operations, and the founder to continuously improve the candidate experience.
Who Thrives Here
At the company, we hire for perspective, not pedigree.
The best coaches are intellectually curious, adaptable, and able to understand that people are complicated.
A candidate may be confident in one moment and uncertain in the next. They may be grieving a job loss while also feeling relieved. They may want another version of the role they just lost, or they may need someone to help them see that an entirely different path is possible.
You have to be comfortable working with all of those parts.
Someone who needs a rigid script, waits for a checklist, or simply moves people through a process is unlikely to thrive here.
We want coaches who can think independently, make connections quickly, and hack the transition with the candidate: understand the person, diagnose what is getting in the way, identify leverage, experiment with approaches, and help create momentum.
Requirements
We are looking for people who bring a combination of career depth, human insight, and modern problem-solving ability.
You should have
- An undergraduate degree.
- Meaningful professional experience across more than one company, environment, industry, or stage of business.
- A strong understanding of how careers are built, changed, and reinvented.
- Experience navigating organizations, leaders, teams, hiring processes, or career decisions.
- Exceptional listening, communication, and relationship-building skills.
- High emotional intelligence and self-awareness.
- The ability to build trust quickly and ask thoughtful, sometimes difficult questions.
- Strong judgment and the ability to operate without a rigid playbook.
- Comfort adapting your approach based on the individual in front of you.
- The ability to recognize patterns, identify obstacles, and help candidates find creative paths forward.
- Strong follow-through and reliability.
- Comfort working independently while staying highly collaborative with the company team.
- Availability during business hours for candidate sessions.
Career and Human Insight
We are especially interested in people who have spent meaningful time thinking about careers, strengths, motivation, and human potential.
You may have experience with tools or frameworks such as
- MBTI
- Enneagram
- CliftonStrengths
- DISC
- Working Genius
- Hogan
- Emotional Intelligence
- Other behavioral, coaching, or career-development frameworks
The tools themselves are not the requirement.
The curiosity behind them is.
We want people who naturally ask
- What makes this person different?
- What do they do better than most people?
- Where have they been underestimated?
- What is holding them back?
- What could they become next?
Tech Savvy
Technology is part of the work.
You should be comfortable learning and using different platforms, experimenting with AI tools, improving your prompting, researching quickly, and figuring out how technology can make you a better coach.
You do not need to know every tool on day one.
But you should want to understand the difference between tools such as ChatGPT, Claude, Gemini, Perplexity, NotebookLM, and AI agents and know when one may be more useful than another.
If new technology intimidates you or you prefer to wait for someone else to show you exactly what to do, this role will probably feel uncomfortable.
Curiosity matters more than expertise.
Our Values
Deep Empathy
- We believe empathy starts with knowing yourself.
- You should be comfortable reflecting on and sharing the experiences that shaped you, because authentic connection often begins with self-awareness.
Community
- Great coaching should not happen in isolation.
- You will collaborate with other coaches, the founder, operations, and the broader the company team. We share ideas, ask for help, challenge each other, and learn together.
Artificial Intelligence (AI)
- We expect curiosity about technology.
- You should be willing to learn different AI platforms, improve your prompting skills, experiment with new tools, and understand when one system is better suited for a particular problem than another.
- You do not need to arrive as an AI expert.
- You do need to want to become one.
Benefits
This is a 1099 independent contractor role paying $38–$50/coaching session/hour
It is designed for experienced professionals who may be
- Building fractional HR, coaching or consulting practice.
- Growing a portfolio book of business.
- Working fractionally across multiple organizations.
- Transitioning from corporate leadership into independent work.
- Looking for meaningful supplemental client work.
Because the company operates as a marketplace, hours may vary based on candidate demand, availability, and fit.
Build With the company
For the right person, this can become much more than a coaching role.
Every coach has the opportunity to grow into a broader builder role with the company.
You may choose to
- Build your own book of business in partnership with the company.
- Develop relationships with HR leaders, companies, and referral partners.
- Create the company community in your geography.
- Host local events, roundtables, and gatherings.
- Help grow candidate and client relationships in your market.
- Earn additional revenue through business development and marketplace growth beyond coaching hours.
- Mentor other coaches and help shape the candidate experience.
- Partner directly with the company founder on market development, community, and growth.
Coaches who consistently create exceptional candidate experiences and demonstrate the ability to build relationships, community, and revenue may have a path toward becoming a Founding Partner or founding employee as the company grows.
We are looking for people who do not simply want assignments.
We are looking for people who may want to build something with us.
Why This Work Matters
A great coach cannot guarantee someone their next job.
But they can help someone regain confidence, understand their strengths, activate their relationships, and rediscover what they are capable of.
That is the work.
If you are curious about people, comfortable thinking without a script, technologically adventurous, and want to become someone’s best friend in transition while building meaningful work of your own, we would love to meet you.
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