From Executive Assistant to Entrepreneur: How Darcy Bennet Turned Operational Excellence into Leadership
- Elizabeth Sutkowska
- Feb 24
- 5 min read
Darcy Bennet is a powerful example of how an Executive Assistant career can become the foundation for intentional entrepreneurship. For over a decade, she supported senior leaders in fast-paced environments, managing high-level events and complex business operations, often behind the scenes. Today, as the Founder of DB Executive Services and the Elevating Administrative Professionals initiative, Darcy builds strategic bridges between the administrative profession, business, and the MICE industry, demonstrating that EA expertise is not just operational support, but true strategic value. In this conversation, she shares her journey from EA to entrepreneur, her approach to leadership, and her philosophy of preventing chaos rather than fighting it.
Darcy Bennet is the Founder of DB Executive Services, LLC, and the Elevating Administrative Professionals initiative. Drawing on eleven years of experience in high-stakes event planning and executive support, Darcy launched her company to address the critical gap in MICE procurement. Today, she leads this strategic platform to empower Administrative Professionals, connecting them to global hospitality partners through exclusive FAM Trips and the Leaders & Talent Connect series.
Elizabeth Sutkowska: Darcy, from Executive Assistant to Entrepreneur, that’s a big leap. You spent over a decade supporting senior leaders in fast-paced industries before launching DB Executive Services. What moment or realization made you feel ready to take that step from being the one behind the scenes to becoming the one leading the vision?
Darcy Bennet: My journey from Executive Assistant to entrepreneur was driven by a single realization after 11 years in the industry: my high-level strategic skills, particularly in event and MICE procurement, were constantly hitting a ceiling and treated as logistical tasks instead of revenue-generating assets.
The leap was fueled by frustration over a glaring market gap: Administrative professionals were managing high-value events without dedicated resources. Simultaneously, hotels and CVBs struggled to reach these high-value decision-makers.
My mission became clear: to build the strategic bridge. I launched DB Executive Services, LLC to elevate the administrative profession by making these crucial connections.
This is achieved not only through introductions and referrals, but also by ensuring professional development opportunities are directly funded by event sponsors. This guarantees high-end resources and strategic training for admins while delivering qualified leads for our partners.
I chose to stop managing the problem from behind the scenes and start leading the vision to fix it.
Elizabeth: Building a business rooted in EA excellence is such a powerful choice. How have the skills and instincts you developed as an Executive Assistant shaped the way you now run your company, especially when it comes to strategy, client relationships, and leadership?
Darcy: I can say with absolute certainty that I would not possess the fundamental knowledge or necessary instinct to run my company were it not for my career as an Executive Assistant. My 11 years behind the scenes served as my specialized business school, providing insight that formal education cannot match.
By supporting senior executives across departments, I gained an unparalleled, holistic view of how a business functions, from managing financial projections to optimizing operational workflows. I learned how to manage complex budgets and make critical resource allocation decisions, directly informing the sponsorship and pricing strategy of my company today.
My previous roles demanded mastery of marketing and negotiation. I learned how crucial networking and strategic marketing really are. Daily duties involved managing vendor contracts and high-stakes negotiations.
By being the one "behind the scenes," I acquired the detailed, operational knowledge to manage my own vision and lead my company effectively from day one.
Elizabeth: You’re also known for creating experiences that bring people together, from corporate events to your Elevating Administrative Professionals initiative. What are your golden rules for planning high-stakes events that run smoothly and make a lasting impact, without burning out in the process?
Darcy: The core of running high-stakes events that make a lasting impact without leading to burnout is relying on a strategic, rather than a purely logistical, framework.
Here are my three golden rules for high-stakes planning:
I keep myself grounded by strictly setting blocks of time to dedicate to each project. This disciplined approach ensures I am working on the strategic vision of the event rather than constantly reacting to problems. This is the only way to manage multiple high-impact events and avoid the constant firefighting that leads to burnout.
I am never afraid to ask for help. My strategy is to immediately tap into my network, both my community of admins and fellow business owners, to get advice on everything from forming an LLC to vendor performance. This process immediately mitigates risk by ensuring I have peer-vetted solutions before presenting them to the client.
The event must be valuable for everybody involved. My events are structured to serve a triple purpose: empowering the admin with professional development, giving the sponsor measurable ROI with qualified leads, and ensuring the client receives a flawlessly executed final product. This mutual value is what creates a successful and lasting impact.
Elizabeth: The EA community looks up to you as someone who turned operational mastery into entrepreneurial success. What advice would you share with other Executive Assistants who dream of starting something of their own, whether it’s a business, a brand, or a community?
Darcy: Starting is the hardest part. My first piece of advice is fundamental: believe in yourself and believe that you will be successful. That self-belief is what allows you to survive the inevitable financial stress and logistical fear of the early days. Negativity is just noise, and you cannot let it detract you from reaching your goals.
Remember, you are not alone. The administrative community is incredible and extremely supportive.
The game changer is realizing that networking with those inside and outside the administrative profession accelerates growth exponentially.
Internal Support: Leverage your core administrative community for practical support and morale.
External Strategy: Join groups with other business owners and talk to people who have done what you want to do. This external collaboration provides high-level business strategy and prevents entrepreneurial isolation.
This blend of internal support and external strategic guidance is what ultimately accelerates growth and creates a sustainable business.
Elizabeth: You often talk about preventing chaos rather than conquering it; what a beautiful mindset. What does that philosophy look like in your daily work and leadership? And how do you help others find calm and confidence when everything around them feels high-stakes?
Darcy: Preventing chaos means eliminating friction points before they ever escalate to high-stakes problems. In my daily work and leadership, this looks like having an organizational structure that is strict, disciplined, and non-negotiable. Being strict with my structure and schedule keeps me on track and prevents chaos.
I help others find calm and confidence when everything feels high-stakes by enforcing two principles:
Actionable Tasks: I focus on breaking down overwhelming problems into actionable tasks. This provides a path forward with less stress.
Vulnerability and Support: I am open about my experiences in the hopes that it will help others. By leading with empathy and shared experience, I build a sense of confidence and assure them that if they ever need a hype girl, I'm here for them.
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