Dawnisha Taylor of OnPoint VA Connect on Building a Premium Executive Virtual Assistant Matching Agency

Dawnisha Taylor is the Founder and CEO of OnPoint VA Connect, a boutique Executive Virtual Assistant matching agency that connects CEOs and founders with highly experienced Executive VAs. Known as an Executive VA matchmaker, Dawnisha helps scaling business leaders reclaim their time by placing trusted, executive-level virtual support inside growing companies.

OnPoint VA Connect was built to solve a critical gap in the virtual assistant industry — matching high-performing executives with professional, well-paid Executive Virtual Assistants who operate at a strategic level. With a thoughtful vetting process and strong operational systems, Dawnisha has created a premium VA agency rooted in integrity, structure, and excellence.

Please share a brief introduction and your business:

I’m the Founder & CEO of OnPoint VA Connect, a boutique agency that matches CEOs and founders with highly experienced Executive Virtual Assistants (EVAs — pronounced ee-vah). I started the business after years of working behind the scenes supporting leadership and realizing how many incredible businesses struggle simply because the right support isn’t in place. OnPoint exists to give leaders their time back — and to create meaningful, well-paid opportunities for Executive VAs who deserve to be valued for their expertise.

Are you a mamaprenista?

Yes, I am. My biggest piece of advice is to let go of the idea that balance looks perfect. Some seasons require more from your business, others from your family, and that’s okay. I’ve learned to be honest about my capacity, build support where I can, and focus on what actually moves the needle instead of trying to do everything. Being present matters more than being perfect.

Take us back to when you launched? What was your marketing strategy?

When I first launched, I leaned heavily on The Online Business Blueprint to help me get started and shape my initial strategy. I used it as a guide to focus on the fundamentals first — getting clear on my offer, my process, and exactly who I serve before trying to do too much.

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My priority was building a strong foundation rather than chasing visibility right away. I did hire a social media manager early on to help establish a presence and get my brand out there, and that decision went exactly as planned. It took something off my plate that I knew I didn’t have the time, capacity, or desire to master myself, and it allowed me to stay focused on building the business behind the scenes.

Did you always know you wanted to be an entrepreneur?

Not at all. I was encouraged to play it safe — to get a stable job in healthcare or oil & gas and follow a traditional path. Early on, that felt like the right move. As I gained real workforce experience and began to understand my work ethic and the value I consistently brought to the table, my perspective started to change.

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Over the years, I explored different paths — food photography, video projects, and real estate investing — trying to find the right fit. Some ideas worked for a season, others didn’t, and there were a few dissolved LLCs along the way. What became clear over time was that I wasn’t failing; I simply hadn’t found the right problem to solve yet.

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Everything shifted once I recognized where I could create real impact. I understood how to support leaders, make them look good, and bring structure to what was happening behind the scenes. I also saw how often the people doing that work — the ones quietly keeping businesses running — are overlooked or underpaid. Building my VA agency became less about entrepreneurship itself and more about creating meaningful value for the leaders I had supported for years and for the professionals who deserve to be seen and paid accordingly.

What accomplishments are you the most proud of to date in your business?

I’m most proud of building a premium agency that’s rooted in integrity, intention, and excellence. Creating a thoughtful matching process, clear systems, and a brand that feels true to who I am — while still being early in the journey — is something I’m incredibly proud of.

What is one thing you wish you had known when you started your Entreprenista journey?

I wish I had been more prepared for how active and opportunity-rich the community is. There are so many incredible women, conversations, and resources that it’s easy to feel like you’re behind or not doing enough if you’re not careful. What I’ve learned is the importance of being intentional about how I engage. Building a “sister circle” and creating space in my processes to stay present — without trying to do everything — has been key to staying grounded and consistent.

What did you do before starting your own business?

I began my career in healthcare shortly after high school, where I spent years supporting executives in fast-paced, high-responsibility environments. That experience taught me how to anticipate needs, stay organized under pressure, and support leaders in ways that genuinely make their day-to-day easier.

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Over time, I also worked closely with a private client, which gave me a different perspective. Supporting a business owner helped me understand what it really takes to run a business — making decisions quickly, managing priorities, and needing support that adapts as things grow and change.

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Most recently, I’ve spent the last five years serving as the COO of my husband’s courier business, managing operations, systems, and daily execution. Being in that role gave me a front-row seat to what leaders actually need behind the scenes to grow and stay balanced. That combination of corporate, private, and entrepreneurial experience ultimately led me to create OnPoint VA Connect.

What made you take the leap to start your own business?

I reached a point where I knew I could make a bigger impact by building something of my own. I saw a gap between what executives need and how virtual support is often positioned, and I felt called to create a better way. Starting my own business allowed me to combine my experience, values, and vision into something that truly serves both clients and VAs.

Do you have any recent wins?

Launching my newly revamped website and fully stepping into my role as Founder & CEO has been a big win. I’ve also brought on a new Executive Virtual Assistant and have been encouraged by the number of experienced applicants showing interest in joining OnPoint VA Connect. Alongside that, I’ve continued refining my offer, building meaningful relationships, and laying the groundwork for sustainable growth — all while balancing family, life, and major personal milestones.

Who are your customers?

My clients are CEOs, founders, and business owners who are ready to stop doing everything themselves. They’re scaling, juggling a lot, and know they need trusted executive-level support to operate at a higher level. On the other side, I work closely with experienced Executive Virtual Assistants who want stable, aligned placements where their skills are truly respected.

What's your favorite business tool?

My favorite business tool is a well-built system — whether that’s workflows, calendars, or documented processes. Tools come and go, but having systems in place keeps things from living in your head and makes growth feel manageable instead of chaotic. Clear systems give you time back, and that’s invaluable.

What advice do you have for aspiring Entreprenistas?

Don’t rush the process or compare your chapter one to someone else’s chapter ten. Spend time getting clear on the problem you’re solving and the value you bring before worrying about visibility or scale. Building something sustainable takes patience, self-trust, and a willingness to learn as you go — and that’s more than enough.

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From building her foundation with The Online Business Blueprint to hiring a social media manager early so she could focus on backend systems, Dawnisha Taylor has approached entrepreneurship with clarity and intention. Her background in healthcare executive support and operational leadership uniquely positions her to understand both the CEO’s pressure and the Executive VA’s value.

Her advice to founders is simple: focus on the fundamentals first. Get clear on who you serve, build strong systems, and resist the urge to chase visibility before your foundation is solid.

If you are a woman founder building a service-based business and looking to grow alongside ambitious leaders who value structure, strategy, and sustainable success, Entreprenista connects you with the community and resources to scale with confidence. Learn more about joining Entreprenista League.