How Shelley Simkins Turned Proposal Chaos Into a Scalable Solution

After years of building programs within corporate walls, Shelley Simkins finally listened to the inner voice—and her friends—telling her it was time to build something of her own. That leap of faith birthed Proquesto, a platform transforming the chaotic RFP process into a streamlined, empowering experience. Her turning point came during a family Christmas break lost to RFP deadlines, sparking the mission behind her company. In this Wantrepreneur to Entrepreneur Spotlight, Shelley shares how simplifying the complex and honoring time became the foundation of her business—and how becoming an entrepreneur required more than skills; it demanded reinvention.

Hi, Shelley Simkins! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

Who do you serve?

Proquesto serves businesses and organizations that frequently respond to Requests for Proposals (RFPs). This includes sales teams, proposal managers, bid teams, pre-sales directors, and subject matter experts across various industries. Essentially, anyone involved in the complex and time-consuming process of creating and submitting proposals for new business opportunities.

How do you serve them?

Giving Time Back to Teams: Instead of spending countless hours searching for information, manually drafting responses, and ensuring consistency, Proquesto takes on the heavy lifting. Users experience an immediate surge in efficiency, freeing up valuable time that can be reinvested into strategic thinking, client relationships, or personalizing their bids for maximum impact. Imagine transforming days of work into just hours.

Minimizing Stress and Maximizing Focus: The pressure of tight deadlines and complex RFPs can be immense. Proquesto alleviates this burden by automating the mundane, allowing proposal managers and sales professionals to concentrate on what truly matters: understanding client needs, crafting persuasive arguments, and ultimately, closing more deals. It's about working smarter, not just harder.

Boosting Proposal Quality with Intelligent Assistance: Our platform acts as an intelligent co-pilot for proposal creation. It doesn't just store information; it actively guides users to craft compelling narratives. This means consistently high-quality proposals, even for complex RFPs, without the need for extensive training or constant oversight. Users gain confidence knowing their proposals are backed by best practices and relevant, approved content.

Fostering Seamless Teamwork: The traditionally siloed nature of proposal writing is eliminated. Proquesto provides a shared, intuitive workspace where teams can collaborate in real-time. This reduces communication bottlenecks, ensures everyone is working from the same page, and brings proposals to completion faster and with less friction.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

For many years of my career I was always building programs & offerings in the jobs I had and many times either my husband or friends would tell me you need to go out and do this on your own instead of for everyone else. At that time I was in a leadership role at a large consulting firm, working 50+ hour weeks. This began taking a toll on me and my family. After spending about 6 mons reflecting on what I wanted for my future I decided to take a step of faith and start my own business. To my surprise, my friends & family were correct, I did have what it takes to be a successful entrepreneur. 

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

It was Christmas Break 2 yrs ago, I was in Colorado with my husband and two kids excited to go skiing and enjoy the Colorado Mountains, when I received an urgent text message to get on a RFP call. That call lead to me working 12 hr days over my kids entire Christmas Break to turn a very large RFP around that was due January 2nd. That moment impacted me so significantly, I said there has to be a better way to do this. No one should have to spend Christmas break working long hours and sacrificing time with their family.

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

We utilize automation tools where we can, especially with back office operations. It helps to keep operating cost in check, so we can pour more into our product and services to provide high value to our customers. 

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

I think I answered that in two of the questions above

What unconventional strategy did you employ that significantly impacted your business?

Our most impactful, and perhaps unconventional, strategy at Proquesto has been our unwavering commitment to ruthless simplicity and user-centric design, specifically by actively refusing feature bloat. While many in the tech world believe more features equate to more value, we've instead obsessed over alleviating the acute pain points of the RFP process for every single user by making proposal generation genuinely easy and intuitive.

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

It's a very personal experience that requires shedding certain aspects of yourself that won't serve you in this new chapter. You can't simply layer new skills onto your current self and expect to become the leader your vision demands; this journey requires demolishing the old structure to build an entirely new foundation. Trying to force a new identity onto an old framework creates friction and stagnation, making it essential to consciously divest from the ego and habits that no longer serve your higher purpose to truly innovate and inspire.

Want to dive deeper into Shelly's work? Check out the links below!

• Visit Proquesto's website: proquesto.com
• Follow Proquesto on LinkedIn.