Wantrepreneur to Entrepreneur | Start and Grow Your Own Business 1209: The AI Tool That Turns 40-Hour Proposals into 2-Day Wins w/ Shelley Simkins
Tired of spending endless hours on proposals that go nowhere? In this episode, multi-time entrepreneur Shelley Simkins shares how a ruined Christmas vacation spent grinding on an RFP was the breaking point that launched her AI company, Proquesto. Shelley breaks down the hidden costs and complexities of the traditional proposal process and reveals how AI is the great equalizer for small and mid-sized businesses. This episode is a masterclass for any entrepreneur who wants to win more business, reclaim their time, and learn how to transform their own frustrations into a scalable, tech-driven solution.
💡 What You'll Take Away For YOUR Business
- How to implement a "Go/No-Go" framework to stop wasting time on the wrong RFPs.
- The secret to differentiating your proposals with authentic client stories instead of just competing on price.
- The strategy of building a co-founding team with diverse skills (sales, tech, operations) to create a well-rounded business.
- Why "drinking your own Kool-Aid" and using your own product is the ultimate tool for building credibility and refining your offer.
- How to turn your biggest professional pain point into a viable and scalable business idea.
📝 About Shelley Simkins
Shelley Simkins is a seasoned entrepreneur and former consulting executive who built a strategic health tech practice after years at firms like Huron Consulting, Accenture, and multiple startups. Motivated by firsthand frustrations with outdated RFP processes, she founded Proquesto to reimagine procurement workflows using AI. Drawing on deep experience in growth strategy and operational innovation, Shelley brings a forward-thinking, tech-enabled approach to solving entrenched industry inefficiencies. Her leadership emphasizes streamlining operations and maximizing client value through emerging technologies. Under her direction, Proquesto is redefining the RFP landscape with AI-powered solutions that raise the bar for efficiency and insight.
🎯 Shelley’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
"The more that you drink your own Kool-Aid of what you're selling, the better off you're going to resonate in the market because people trust people who utilize their own services and product."
📢 Memorable Quotes
- "I sat in a hotel lobby, in a hotel room 12 hours a day pushing out RFP content... and at that point I said, never again. I have to give people back their work life balance and not be spending an entire Christmas vacation or sacrificing time with your family in order to respond to an RFP."
- "Our product really gets you first draft 75% complete so that you can spend your time... leveraging their critical thinking and creativity without getting bogged down."
💡 Actionable Takeaways
- Before starting your next proposal, hold a "Go/No-Go" meeting to decide if the opportunity truly aligns with your company's skillset and resources.
- Rewrite a section of your standard proposal template to include a compelling, real-life client story that demonstrates your value beyond a list of services.
- Audit your weekly tasks and identify one repetitive, back-office process you can streamline using an AI or automation tool like ClickUp.
- If you're looking for a business partner, make a list of the skills you lack and intentionally seek out individuals who excel in those areas.
- Explore an AI proposal tool to understand how it can help you respond to more opportunities and increase your revenue stream.
🔗 Links & Resources