Looking to work With Us?
At Head First Health, it is our mission to empower our clients to have a better relationship with themselves in order to optimize their potential and live a meaningful life.
We believe in a holistic way of healing. We know that making changes to our lifestyle has profound effects on the way we feel. We honor the brain-body connection by exploring ways to heal our body, in order to feel more peace in our mind.
Current Available Jobs:
Brand Ambassador Position
Are you the friend who always knows what wellness event is happening in Chicago? Do you love talking about therapy, and creating connections that actually matter?
We're looking for a warm, engaging, and well-connected human to represent Head First Health at wellness events and in-person outreach opportunities across Chicagoland. This is a part-time, flexible 1099 position designed for someone who already lives and breathes the world of wellness & mental health.
YOU WILL BE A GREAT FIT IF:
You already go to wellness pop-ups, sound baths, or full moon circles — for fun.
You love therapy. You talk about your therapist like she’s a mentor.
You follow your favorite therapists and coaches on Instagram.
You know where the best matcha is and which boutique gyms are vibe-y.
You want to be a part of a therapy practice that’s grounded, smart, and deeply human.
You're comfortable pitching ideas, speaking warmly to strangers, and working independently.
You are comfortable being in direct communication with the CEO and thrive in collaborative relationships.
WHAT YOU WILL DO:
Act as the face of the brand
Generate brand awareness
Attend 1 tabling event per week (on average)
Setup and break down events
Engage passersby with warmth, curiosity, and clarity about what we do
Research and pitch new events and pop-ups for HFH to attend
Communicate directly with event organizers
Brainstorm outreach strategy and new ideas for building brand awareness
Take photos and short videos at events for social and internal use
Track basic event data (leads collected, notable convos, photos taken)
WHO THIS IS PERFECT FOR:
A wellness-obsessed connector who thrives at events and cares about mental health
A former (or current) marketing/outreach specialist who wants more purpose + less grind
A new mom who wants something flexible, fun, and emotionally meaningful
A therapist-in-training, social worker, nurse, or doula looking for flexible side income
POSITION DETAILS
Title: Brand Ambassador / Community Outreach Partner
Type: 1099 Independent Contractor
Hours: 5–10 hours/week
Pay: $27/hour
Location: Chicago + Surrounding Suburbs
HOW TO APPLY:
Send an email to jenna@headfirsthealthcc.com with:
A short intro about who you are + why this stood out to you
1–2 sentences about your favorite wellness event you’ve attended recently
A link to your LinkedIn, IG, or anywhere we can see your vibe
We can't wait to meet you!
We specialize in evidence based, short term therapies to help our clients challenge their limiting beliefs, retrain their thought patterns, and become more curious and accepting of their emotions.
We use a combination of western psychology, values-based techniques, mindfulness, and lifestyle changes, to help our clients gain clarity, set intentions, and accomplish their goals.
Head First Health, is a coaching + counseling practice for Millennial Women looking to navigate their relationships, life transitions & daily stressors. As far as jobs in telehealth go, you’ll find that our clients are yearning for a deeper connection to themselves, and to find a greater purpose in their lives.
Our Values
MIND, BODY & SPIRITUAL HEALTH
We recognize all of these parts within ourselves. We believe they are intricately connected, and we do our best to acknowledge & care for them.
CURIOSITY
We are continually learning. We have a growth mindset and are excited by challenges.
COMMUNITY
We take care of our community both in and out of the therapy room. We know we have the ability to make the world a better place, and we act on it.
COLLABORATION
We know we will never have all the answers; we learn so much from others, and that excites us! We lean on trailblazers in the Mind/Body field to support us in our mission.
KINDNESS
Our views vary; it helps us learn and grow from one another. Kindness allows us to feel safe to express our viewpoints, and have fruitful connections & conversations.
INTEGRITY
Standards—we’ve got them. “Always be bettering” is our way. Honesty flows through our practice both with our team and within our client relationships.
Our Hiring Process
01: Apply
Complete form on website & upload documents
02: Phone Screen
A phone call to sort out logistics
03: Video Interview
Meet with owner
04: Background Check
Required by insurance companies to have on file
05: Offer Letter
Congratulations! We are so happy to have you!
Curious what it's like working at Head First Health?
Here’s the team’s favorite part:
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The support! It truly feels like everyone is in your corner & always willing to go out of their way to help others.
Rachel Nicholson
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"Actually feeling cared for and heard. It's nice to have my needs met."
Jenna Riem
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"Flexibility and autonomy. Feeling fulfilled in my work as a clinician. I love what I do!"
Paige Boser
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"The flexibility and support from the team!"
Katie Hochleutner
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"I love working with an all-women team that uplifts and supports one another every day!"
Vildana Baker
Remote Therapist Position
At Head First Health, we do things differently. Therapy should feel like a conversation—not a cold, clinical exchange. We’re all about real talk, real connection, and real change for our clients.
If you’re a therapist who is warm, relatable, and passionate about helping Gen Z and millennial women ditch self-doubt, embrace their full potential, and live meaningful lives—we want you on our team.
Who We’re Looking For:
A fully licensed (LCSW, LCPC, LMFT, PhD, PsyD, etc.) or provisionally licensed (LSW, LPC, etc.) therapist who:
✔ Shares our values—We believe in authenticity, a holistic mind-body approach, and empowering clients to build better relationships with themselves.
✔ Wants to work with clients struggling with anxiety, OCD, trauma, eating disorders, relationships, perinatal/postpartum issues, or substance use.
✔ Loves evidence-based therapy like CBT, ACT, ERP, EMDR—or wants to get even better at these modalities.
✔ Is collaborative and eager to grow—We’re a team of high-achieving, down-to-earth clinicians who support each other.
✔ Wants to work remotely with a steady stream of referrals—No hunting for clients or managing your own marketing. We’ve got you covered.
What You’ll Be Doing:
💡 Providing individual and/or couples therapy remotely.
💡 Building and maintaining a caseload of 22 client hours per week (10 for part-time).
💡 Completing progress notes and treatment plans on a weekly basis.
💡 Pursuing ongoing training and professional development (we cover unlimited CEUs!).
What We Offer:
💰 Competitive Pay – $45 per session (provisionally licensed), $50 per session (fully licensed).
🩺 Full-Time Benefits (22 client hours/week):
Medical, dental, and vision with BCBS PPO.
2-4 weeks of PTO/sick time
Retirement plan with a 3% match.
Life insurance & short-term disability.
Supervision provided for provisionally licensed therapists.
Unlimited CEUs through PsychHub
Quarterly in-person team outings—(our favorite part!).
🏡 Remote Flexibility & Freedom – Work from anywhere.
💡 A Supportive, Growth-Oriented Team – An amazing group of clinicians who actually like working together and want to make a difference.
Ready to Dive In?
If this sounds like your dream job, we’d love to hear from you. Apply today and let’s make an impact—Head First.
