jordan eaton, boss assistants, helen siwak, portfolioyvr, vancouver, bc

Jordan Eaton: Scaling Small Businesses Without Burnout Through BOSS Assistants

Jordan Eaton is the founder and CEO of BOSS Assistants, a marketing and administrative support agency serving entrepreneurs across North America. As a single parent navigating ongoing health challenges, Jordan built BOSS Assistants out of necessity — creating a business model that proves you do not have to choose between professional success and quality of life.

Jordan started her career in administration straight out of high school. After studying Computer Systems Technology, she held multiple positions supporting CEOs and business owners across diverse industries, including software, real estate, construction, healthcare, and more. This foundation built deep expertise in how successful businesses operate, and what not to do.

Jordan’s entrepreneurial journey began over a decade ago when traditional employment became impossible due to health limitations and the demands of parenthood. Starting as a freelance virtual assistant on Upwork, Jordan discovered remote work before it became mainstream, eventually building steady client relationships with companies across the United States.

In 2022, Jordan officially launched BOSS Assistants as the company’s strategic positioning became clear. The rebrand reflected a fundamental shift from task-based assistance to growth partnership — helping entrepreneurs reclaim their time and grow sustainably.

Jordan’s mission is personal: to prove that entrepreneurship does not require sacrificing your enjoyment, your health, or your values.

jordan eaton, boss assistants, helen siwak, portfolioyvr, vancouver, bc

THE BUSINESS.

BOSS Assistants is a strategic growth partner based in Vancouver, BC that helps ambitious entrepreneurs across North America reclaim their time and scale without burnout. Founded in 2022, the company specializes in helping coaches, consultants, solopreneurs, and small business owners grow their businesses without sacrificing their personal lives.

Unlike traditional virtual assistant services, BOSS Assistants provides comprehensive support in social media management, targeted outreach, content creation, podcast editing, executive assistance, and administrative optimization. The agency works exclusively with entrepreneurs who view marketing and administration as investments in sustainable growth.

BOSS Assistants emphasizes hiring Canadian team members to support the local economy. Each client works directly with team members who understand their business goals and use strategic thinking to achieve them. Clients typically see measurable results within weeks — such as new client acquisition, five to ten hours of reclaimed time weekly, and process improvements.

Having worked with countless entrepreneurs across multiple industries, BOSS Assistants has built a reputation for delivering transformational results through reliable execution and genuine investment in client success. The company’s mission is clear: help overwhelmed business owners delegate effectively so they can focus on what gives them enjoyment and build businesses on their terms.

jordan eaton, boss assistants, helen siwak, portfolioyvr, vancouver, bc

IN HER WORDS.

I still remember the moment the first big idea landed with absolute clarity. I realized that I could take the skills I had honed in traditional roles, offer them remotely, and finally control my own schedule. That idea became the spark that pushed me onto Upwork, where I started side hustling long before I dared call myself an entrepreneur. I learned how to write proposals that captured attention, deliver results that made clients return, and build relationships grounded in reliability. My first steady client was a SaaS company in the United States, and that early partnership showed me that if I kept showing up with consistency, I could build something real.

ROOTS OF ENTREPRENEURSHIP

Entrepreneurship felt familiar long before it became my career. As a kid, I was the one running lemonade stands, shovelling snow, selling handmade bracelets, and looking for any opportunity to create income. Those small ventures taught me initiative, resourcefulness, and the freedom that comes from building something of your own. Working with my uncle in his construction business expanded that learning. From client management to supplier issues to unexpected job-site problems, I saw what running a real business looked like. Those experiences revealed that the strongest businesses are built on relationships, follow-through, and the willingness to solve problems before they become disasters. Watching family members create something from nothing made entrepreneurship feel possible, even when it felt frightening.

LEARNING TO GROW

As my own journey evolved, I moved from pure survival mode into intentional growth. In the beginning, I had no idea what I was doing, so I sought support anywhere I could find it. Organizations such as WeBC, CEED, and Community Futures became sources of education and encouragement. I found mentors who understood the emotional terrain of entrepreneurship, and I forced myself into situations that terrified me. In my second year of business, I attended more than two hundred networking events. I walked into rooms where I knew no one, pitched my services even when my voice shook, and learned that growth always waits on the other side of fear. The hardest part, however, has always been navigating my own health. Some days I can barely function, and those moments pushed me to work smarter because working harder was simply not an option.

SCALING WITH COURAGE

As I gained confidence, I learned that scaling required a different kind of courage. I had to stop doing all the work myself and start building the systems that would carry the business forward. I invested in Canadian employees and service providers because supporting the local economy matters to me. I shifted our messaging from “hire a virtual assistant” to “partner with a growth team,” and that simple change repositioned us in the market. Clients began to view marketing and administration as investments rather than expenses. We built relationships, remained consistent on social media, and grew entirely through word-of-mouth and organic content. Every decision became about creating leverage so the business could grow without pushing me back into burnout.

SACRIFICES MADE

The sacrifices I made in the early years were significant. I lost sleep, gave up social time, and let go of any illusion of work-life balance. I worked after my kids went to bed, squeezed client calls between school drop-offs, and learned to accept “good enough” when perfection did not matter. I missed events, and I felt guilty constantly—guilty about time, guilty about effort, and guilty when my health did not cooperate. Those sacrifices changed me. I discovered that rest is not optional, it is essential. Now I teach entrepreneurs that delegation is not a luxury. It is a survival strategy, and it is how you maintain both ambition and well-being.

MANY SMALL REMINDERS

There has never been one dramatic moment when I knew the business would succeed. Instead, there have been many small, powerful reminders. When someone says, “What you provide is really valuable,” something in me shifts. The biggest validation comes from the messages clients send when they win—landing a new client, launching a podcast, or celebrating a breakthrough. Those messages prove that our model works. They remind me that success is not about proving anything. It is about making a measurable difference in someone else’s business.

POWER OF MENTORSHIP

Mentorship has played a critical role during moments when quitting felt like the easiest option. Marshall Stern has had a profound impact on my personal and professional growth. His honest, strategic, no-nonsense approach has challenged me to think bigger and believe in what is possible. Rick Martens changed how I understand money, teaching me that financial security is not just about earning income, but about making wise decisions with it. Both saw potential in me long before I fully saw it in myself. That kind of support does not just influence your business. It reshapes who you become.

jordan eaton, boss assistants, helen siwak, portfolioyvr, vancouver, bc

EVOLVING AS LEADER

As the business grew, my leadership had to evolve. I shifted from being the operator who clung to every task to becoming the delegator who trusted the team. It was ironic, because delegation is exactly what we teach our clients, yet I was burning out by refusing to let go. I had to realign with my core values, especially the value of sustainable growth. Today, my leadership is about creating systems, empowering my team, and modelling the balance we encourage our clients to pursue. Leading this way honours my health and my role as a parent, and it allows us to guide others toward building businesses that do not consume them.

MY BEST ADVICE

If I could give one piece of advice to aspiring entrepreneurs, it would be this: start before you are ready, but build systems from the beginning. Perfection will slow you down. Your clients will teach you more than any course ever could. Run your business as if it were already large. Document everything. Create repeatable processes. When help arrives—and it will—you will not become the bottleneck. My own definition of success has changed dramatically. In the early days, success meant survival. Now it means sustainability, impact, and having a business strong enough to function even when I need to step away.

TODAY’S MISSION

At the heart of BOSS Assistants is a simple belief: no two entrepreneurs are alike, and neither are their goals. We are a marketing and administrative support agency built on personalization and partnership. Our subscription model is month-to-month because we want clients to stay due to results, not contractual obligation. What we need now is to connect with entrepreneurs who have big messages, coaches and consultants who want to reclaim time, and business owners ready to elevate their visibility. We welcome conversations about investment for North American expansion, and partnerships with agencies and CMOs serving aligned audiences.

THE FUTURE AHEAD

Looking ahead, I envision BOSS Assistants becoming the go-to growth partner for purpose-driven entrepreneurs across North America. By 2026, I see our team expanded, partnerships formalized, and operations established in key Canadian and American markets. I want us to be known for strategic thinking, integrity, and genuine investment in our clients’ success. Most importantly, I hope my work helps shift the narrative around entrepreneurship. I want to show that burnout is not a badge of honour, and that success should support your life, not consume it. If my legacy is proving that you can build a thriving business without sacrificing your well-being, then I will have done something meaningful.

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Helen Siwak, Collaborator: This story is created in collaboration between Helen Siwak and the featured subject. As the founder and publisher of Portfolio.YVR Business & Entrepreneurs Magazine, Helen works closely with entrepreneurs to share their paths of innovation, resilience, and growth. Each story in this series is co-developed through interviews and first-person insights, blending authentic voices with Helen’s editorial expertise to highlight the remarkable individuals shaping British Columbia’s business landscape.