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We're Hiring!

We Have Big Hearts & High Standards

Are You Our Next Co-Creator?

We're a small & mighty collective, rewriting the rules of business by blending deep human care & liberation with shared high standards. If you're ready to ditch corporate masks, protect your peace, and do truly matterful work alongside people who hold each other to account, you’ve found your home.

We’ve been renting out our three large Muskoka lakeside cottages for about 20 years, and caringly shifting to a humanistic, teal organisation for the last ten. We excel by being unapologetically human - offering enlivening experiences and authentic connections to our guests and ourselves.

We're also at the beginning of a much larger journey. Our big, hairy, audacious goal is to grow thriving, humanistic businesses across the world - starting with this one!

“Old Rule: Lead with dominance. Create Followers.
New Rule: Lead with humanity. Cultivate Leaders.”
– Abby Wambach

OUR NON-NEGOTIABLES

We look for true, mutual alignment with our co-creators, ensuring the shared culture & peace of this space can continue to thrive. You'll be working alongside dedicated people who love digging deep, doing matterful work, and being their favourite version of themselves. Thriving here means naturally living and breathing these shared standards:

Love of People: You have a natural love & trust for humanity, bringing a genuine passion for real, heartfelt, human-to-human connection.
High Emotional Maturity: You are confident, humble, and deeply boundaried. You actively protect our shared space by refusing power plays, gossip, drama, or the belittling of yourself or others.
Integrity & Responsibility: You intentionally align your choices with your values. Highly self-aware, you take ownership of your entire reality - both your shining moments & your missteps - and deeply understand the power of mutuality in relationships.
Possibility Mindset: You believe in "can" over "can't." You show up trusting, optimistic, and relaxed because you naturally see opportunities everywhere.
Growth Mindset: You're energised by feedback and dedicated to evolution. You have the vulnerability to ask for help, the humility to recognise "I don’t know what I don’t know," and the drive to remain unstoppable.
Feminist & Open-Minded Core: Our space is diverse and proudly powered by deeply motivated, caring women. Bringing wholehearted respect, curiosity, and celebration to all human dynamics is just second nature to you.
Flexible Availability: You choose lifestyle fluidity and a flexible schedule (evenings, weekends, and holidays) over a strict 9-to-5, knowing that cottage rental peak moments happen when the world is resting.

If you've been embodying these standards for eons, let’s build community and make some great sh!t happen together.

“Daring leaders who live into their values are never silent about hard things”

– Brené Brown

Contribution Opportunities

Humanistic Business Care

(Entrepreneurship, Operations, Teal Leader)

THE OPPORTUNITY

Full-Time • WFH (80%) • In-Person (20%) • Muskoka, Ontario

The Humanistic Business Care contribution is for entrepreneurial, steady, boundaried folks who want to create & nurture a workplace where we all truly thrive. We're not interested in top-down control here. Instead, it’s about leading like a gardener - tending the soil so a healthy ecosystem can flourish, giving everyone room to grow their own talents while we all stay rooted in the same shared purpose. Caring for that ecosystem also means nurturing our livelihood - growing new products & offerings that keep our business resilient, sustainable, and flourishing.

If holding space for a thriving, abundant, and deeply human business is where you'd truly bloom, here's how we can make some great sh!t happen together:

RESPONSIBILITIES & DUTIES

At its heart, your contribution is about holding our business (also known as our livelihood) with a boat load of calm, deep emotional maturity, and an unwavering commitment to:

Protecting Our Integrity & Safety: Grounding all financial and operational decisions through a humanistic lens - focusing on abundance, long-term resilience, faithfully meeting tax, payroll, and legal requirements with precision and care, and steadfastly upholding our collective boundaries.
Sustaining Our Vitality: Bringing an entrepreneurial drive to build a resilient livelihood ecosystem - creating fresh offerings, nurturing organic growth opportunities, and keeping our financial metrics healthy (from balanced wage ratios to intentional spending) so every financial choice is deeply matterful and sustainable.
Nurturing Alignment & Belonging: Discovering & embedding shared clarity, anchoring our collective direction, championing open-hearted financial transparency, and fostering joyful co-creation where everyone can be their favourite version of themselves.
Cultivating Our Culture: Looking at and cultivating our livelihood from a relational perspective rather than a purely transactional, spreadsheet-driven lens; acting as a steady gardener to nurture overall conditions while leaving everyone else's growth completely in their own capable hands; bringing a steady, grounded presence that honours clear boundaries and takes ownership of your own energy; leaning into hard things with zero hesitation; and living our shared values with absolute consistency.

QUALIFICATIONS

We care far more about your emotional intelligence, life smarts, and alignment with teal organisational principles than any degrees or official certificates. To thrive here, you need to bring:

Quiet Self-Awareness: A deeply anchored, solid core that lets you meet challenging circumstances with humility, resilience, and steady, conscious choices.
Serious Relational Depth: An instinct for vulnerable, communal, and highly trusted relationships where we build mutual support and hold space together as co-creators.
Entrepreneurial Spirit: A natural instinct for bringing new products, offerings, and systemic improvements to life. You're experienced in growing a healthy business by cultivating authentic, trust-based relationships rather than resorting to high-pressure sales or growth-at-any-cost tactics.
Teal Operational Leadership: A steady, systems-minded approach to keeping our back-end rhythm, finances, and day-to-day ecosystem running smoothly, paired with the humanistic leadership style needed to guide a self-organising community.

CO-SUPPORTING & BENEFITS

Commitment: Full-time, permanent co-creator partnership. (Let's be the change we wish to see in the world!)
Location: 80% WFH and 20% in-person (Muskoka, Ontario). Every couple of months, we gather at the cottages for a Monday-to-Friday working getaway with overnight stays. Feel free to live wherever you feel most rooted, as long as you can cover your travel to our in-person time (and yes, your loved ones are always invited to share the magic!) Here, you’ll have the space - both virtually and in-person - to bring true human connection and care into how we work together.
Rhythm: Hospitality has its own natural flow, which means our working rhythm includes evenings, weekends, and holidays. If you thrive on variety and true control over your time, this freedom lets you build deep rest, personal space, and real-life living directly into your week.
Compensation: Starting from $60,000 per year, caringly scaled to the depth of contribution you choose to offer. (When we build shared prosperity, we all rise together, whoot whoot.)
Benefits: Personal/wellness leave days; hands-on leadership in building a humanistic business model - proving through our daily work that business can indeed be a vehicle for human thriving; and free cottage getaways to rest & recharge with your loved ones :) Explore more benefits here: https://www.trenanthiacottage.com/hiring#h.q4c97tec2wj5

UP FOR THE JOY & CHALLENGE?

We’re real people looking for real people. We don't expect perfection, but we are looking for entrepreneurial spirit, deep self-awareness, and the courage to co-create a better way to work & live. Here, you'll find a space built on shared high standards, mutuality, and the freedom to bring your whole heart while becoming your favourite version of yourself. So whaddaya say? Wanna build something beautiful together?

Pop over here to see how our application process flows: https://www.trenanthiacottage.com/hiring#h.3lynueb9wsl6. We can't wait to meet you!

All the best,
Ping (and the whole cottage caboodle)

Other Opportunities

If there are no matching listings in this section, our collective is currently full. We're always excited to connect with peeps who resonate with our way of being in the world though, so feel free to introduce yourself anytime. Check out our PAST Contribution Opportunities below.

Real People Looking for Real People

Benefits & Support

High Standards Require High Support

No need to check your human side at the door. Bring your full, authentic self, and join a collective that actively pours back into your growth, your peace, and your capabilities - both professional & personal.

Holistic Wellness & Peace of Mind

Comprehensive Health: A dedicated physical and mental health plan.
True Rest: Generous vacation and personal leave days designed to support your physical, mental, and emotional well-being.
Evolving Workspace: A working environment - including flexible WFH (work-from-home) structure where possible - continuously designed around collective wellness.
Financial Backup: Access to a repayable personal loan option for when life throws unexpected curveballs.

Deep Personal & Professional Growth

Custom Growth Plans: Personal & professional development maps to expand your horizons.
Decades of Mentorship: Direct access to over 30 years of humanistic, entrepreneurial, business, Agile/Lean, and technology wisdom.
Whole Engagement: Contribution opportunities designed to exercise your left brain (logic, systems, metrics) and your right brain (creativity, intuition, heart) in equal measure.

Our Favorite Perks

High Autonomy: Space to own your work, make choices, and execute with freedom.
A Culture of Care: A deliberate, everyday practice of noticing, acknowledging, and genuinely appreciating one another’s talents.
The Ultimate Closer: Free, restorative cottage getaways at our lakeside properties to enjoy with the people you love. 🌿

Wanna Join Us? Apply here!

We believe the truest picture of who you are comes from your core values, your knack for self-management, and your genuine interest in what we’re building here, rather than a traditional, functional resume.

Since we value clear boundaries and mutuality from day one, we ask that you hold responsibility for the first step of this process. To explore working together, please send an email to joinus@trenanthiacottage.com with the subject line "I'd Love to Contribute to Thriving Together! [Your Name]" and include the following:

Your Story: In whatever format feels most authentic to you (eg a short video, an audio note, a few written paragraphs, etc), tell us why the co-creator philosophy resonates with you, and how you see us thriving together.
Opportunity: Clearly share which Contribution Opportunity you're applying for.
Your Availability: Confirm that you have the lifestyle flexibility that matches the days & hours we need for the Contribution Opportunity you’re applying for.

A boundary we honour: To respect everyone's time and energy, we only review and respond to conversations that include all of these elements.

Next steps: If we feel a strong resonance, we’ll invite you into an intentional series of three to four co-impressions. This is a two-way exploration where we get to look at our real-world needs together, share ourselves authentically, and even dive into some hands-on co-working. It’s an organic process designed to ensure our values, culture, and dreams align, and that our unique offerings genuinely feed all of our souls.

A privacy note on our hiring process: As a teal collective, your application and our co-impression notes are shared and reviewed internally by our co-creators to ensure an aligned choice. By applying, you agree to this shared review process so the people you'll actually be working with can help welcome you in, whoot whoot.

We can’t wait to meet you!

Cottage Locations

Wanna see where we're tucked away? Map your route to the cottages right here.

PAST Contribution Opportunities

We keep past opportunities visible below so you can see how we co-create. If our ethos resonates with you, we’re always open to connecting.

[FILLED] Seasonal WOW

(Welcoming, Organizing, Whipping-into-Shape)

THE OPPORTUNITY

Part-Time • Kiddo & Doggy Friendly (with boundaries!) • In-Person • Muskoka, Ontario

The Seasonal WOW contribution is for active people who love a fast, physical rhythm and want a workplace that genuinely embraces their whole self (kids and fur babies included!) We don't do dominator management. Instead, we look for self-aware co-creators who take genuine pride in bringing the magic of Trenanthia Cottage to life.

We're looking for seasonal support over our busy summer season (May - October). We're open to hiring a Coordinator, Sr. Coordinator, or Lead, depending on the level of responsibility you choose to hold.

If you read our Non-Negotiables and thought, "Finally, a place that speaks my language," here’s how we can create some great sh!t together:

THE WORK SPLIT

Your core mission is to ensure every guest has a breathtaking first impression of the cottages. Across any given month, your time is split between two distinct areas:

90% Cottage Changeovers: This is the fast-paced, high-standard core of the job. You have a tight 5-to-6-hour window between checkout and check-in to restore absolute pizzazz, order, and visual beauty to the cottages for the next guests.
10% Team DIY Projects: Executed when there are empty days at the cottages. Projects range from straightforward (deep cleaning, paint touch-ups, yard work) to diy/renovation work (refinishing decks, laying flooring, or even building an indoor treehouse, wohoooo)

A Note on Kids & Fur Babies: We love wholeness and community! Bringing your kiddos or pets is highly encouraged. Because the cottage changeover window is tight and fast-paced, we trust you to self-manage this balance so that safety and our high standards flow seamlessly. We won't micromanage how you do it, as long as the magic happens!

RESPONSIBILITIES & DUTIES

First impressions: Create breathtaking first impressions of the cottages with gasps of, “Wow. Wow! WOW!” at every turn.
Changeovers: Care for day-to-day cottage changeovers with a big heart, high standards, and heartfelt consistency.
Inventory & Staging: Maintain meticulous organisation of supplies and create unforgettable moments of connection through heartwarming staging.
Safety & Fluidity: Communicate proactively to flag and remediate any safety or maintenance issues.
Evolution: Contribute creative ideas and hands-on energy to cottage improvement projects.

If entering at the Lead level, your stewardship extends to:

Managing supply logistics and equipment efficacy.
Facilitating planning and training to promote heartfelt consistency across the team.
Contributing to strategic and financial goals (minimizing issues, reducing refunds).

QUALIFICATIONS

We care far more about your emotional intelligence and life smarts than specific accreditations. To thrive here, you need to bring:

Passionate Cleaning & Staging: True skill in residential or hospitality cleaning, paired with a natural eye for visual harmony and order.
Basic DIY & Maintenance: Comfort with basic repairs, paint, and tools, executed with high attention to detail.
Root-Problem Solving: The instinct to see solutions instead of obstacles, and the courage to act on them.
Charming Communication: Laid-back, fun-loving, and collaborative communication skills - in person and through team tech tools.
Bonus: Past experience in tourism, hospitality, or short-term rentals.

SCHEDULE & SALARY

Commitment: Part-time, seasonal. Typically 2 to 3 six-hour shifts per week (though if you're FABulous and can commit to just 1 shift per week, we can chat!) Commuting to the cottages is at your own expense.
Days: Successful contribution relies on being available during our busiest changeover days: Fridays, Sundays, and Mondays (including holidays/holiday periods). Occasional Tuesdays and Thursdays.
Project Getaways: Larger DIY projects happen once a month in chunks of time (e.g., a Mon-Fri working getaway that includes staying overnight at the cottage - loved ones welcome!)
Pay: Between $18 (student rate) and $25 per hour, caringly scaled to the depth of contribution you choose to offer.
Benefits: Personal/wellness leave days, high autonomy, deep appreciation, and discounted cottage getaways with your loved ones :) Explore more benefits here: https://www.trenanthiacottage.com/hiring#h.q4c97tec2wj5

UP FOR THE JOY & CHALLENGE?

We're real people looking for real people. We don't expect perfection, but we do look for wholeness, self-direction, and the courage to co-create. We don't rescue, and we don't micromanage - instead, we share high standards and offer the space & trust for you to bring your best work, and be your favourite version of yourself. So whaddaya say? Wanna build something beautiful together?

Pop over here to see how our application process flows: https://www.trenanthiacottage.com/hiring#h.3lynueb9wsl6. We can't wait to meet you!

All the best,
Christine (and the whole cottage caboodle)

[FILLED] Humanistic Guest Connection

(Customer Care, Marketing, Events)

THE OPPORTUNITY

Full-Time • WFH (80%) • In-Person (20%) • Muskoka, Ontario

The Humanistic Guest Connection contribution is for big-hearted, boundaried people who want a workplace that actively nurtures their growth, peace, and whole-human potential. We don't do transactional customer service here. Instead, we look for self-aware co-creators who take genuine pride in forging authentic, soul-feeding relationships with our guests and each other.

If reading that brings a sudden sense of relief, you're right where you belong! We're looking for a highly sociable, deeply self-aware co-creator who thrives with true responsibility & liberation. Someone who genuinely craves understanding the why behind relationship building & business growth, embodies our Non-Negotiables, and brings rock-solid boundaries to the table. Sound like you? FABulous. Let's make some great sh!t happen together...

THE WORK SPLIT

However you choose the rhythm of your days - whether you prefer to dive into dedicated blocks of focus or move fluidly in the moment - your overall energy will be directed toward these two core areas:

40% Heartfelt Guest Care: This is about being entirely present with people. You’ll care for our everyday chats, wherever our guests reach out to us (phone, email, social media, livechat, etc.), with warmth and grounded presence, holding the space to guide guests into FANtastically memorable getaways with us. And because great care needs solid ground, you’ll bring your organisational magic and thoughtful attention to detail to the behind-the-scenes pieces that keep everything running like clockwork.
60% Creative & Community Projects: This is where you get to think big, experiment, and bring matterful ideas to life by combining your people-loving, marketing & event prowess. Projects range from the straightforward (freshening up our website, improving the guest experience) to the highly social (weaving connections with past guests, collaborating with local community partners) and the imaginative (crafting inspiring stories, or dreaming up unexpected surprises for our guests).

RESPONSIBILITIES & DUTIES

We don't do micro-management ‘round here. Instead, we trust you with true responsibility - inviting you to bring your unique skills & insights to life while helping us grow sustainably. Your daily contribution to our ecosystem will look & feel like:

Human-to-Human Connection: Meeting our guests exactly where they are with warmth, authenticity and a dash of vulnerability.
Navigating Friction with Care: Safely anchoring tricky or complex situations with a blend of deep empathy and clear, healthy boundaries.
Cultivating Financial Safety: Nurturing the health & safety of our ecosystem through proactive guest bookings, relational marketing initiatives, and meaningful community events.
Curating the Experience: Intentionally designing and refining the overall guest experience - before, during, and long after their getaways with us.

QUALIFICATIONS

We care far more about your self-awareness, life smarts, and how you show up for people than any degrees or official certificates. To thrive here, you need to bring:

Natural Sociability: A genuine ease in connecting with people, building relationships, and listening deeply, with a knack for seeing, knowing & understanding your fellow life travelers.
Empathy & Healthy Boundaries: The capacity to have conversations that are simultaneously kind and boundaried. You possess the inner grounding to remain calm & centered in moments of chaos, without being easily swept up or influenced by other people's emotional waves.
Relational Marketing: A natural eye for connective, meaningful marketing, community building and storytelling, including a comfort with weaving narratives across our social media spaces.
Experience & Event Design: A deep, intrinsic love for bringing people together, understanding feelings & needs, and creating lasting memories.

CO-SUPPORTING & BENEFITS

Commitment: Full-time, permanent. (Let's be the change we wish to see in the world!)
Location: A fluid hybrid balance - 80% Work-From-Home (WFH) and 20% In-Person (Muskoka, Ontario). About once every two months, we gather at the cottages for collective, hands-on projects (such as property refreshes or DIY upgrades). These are beautiful opportunities to connect in person and typically look like a Monday-to-Friday working getaway where we stay overnight at the cottage. And yes, your loved ones are invited - the more the merrier! You’re welcome to live wherever, and commuting to the cottages for our in-person gatherings is at your own expense.
Rhythm: Hospitality has its own natural flow, which means our working rhythm regularly shifts to include evenings, weekends, and holidays. If you lean into variety and a fluid schedule over a rigid 9-to-5 routine, this kind of freedom leaves a whole lotta breathing room to thrive.
Compensation: Starting from $50,000 per year, caringly scaled to the depth of contribution you choose to offer. (When we build shared prosperity together, we all rise together, whoot whoot.)
Benefits: Personal/wellness leave days, genuine autonomy, holistic mentoring, deep appreciation, and free cottage getaways to rest & recharge with your loved ones :) Explore more benefits here: https://www.trenanthiacottage.com/hiring#h.q4c97tec2wj5

UP FOR THE JOY & CHALLENGE?

We’re real people looking for real people. We don't expect perfection, but we do look for wholeness, self-direction, and the courage to co-create. We don't rescue, and we don't micromanage - instead, we share high standards and offer the space & trust for you to bring your best work, and be your favourite version of yourself. So whaddaya say? Wanna build something beautiful together?

Pop over here to see how our application process flows: https://www.trenanthiacottage.com/hiring#h.3lynueb9wsl6. We can't wait to meet you!

All the best,
Christine (and the whole cottage caboodle)