Today we’d like to introduce you to Jonathan Taylor.
Hi Jonathan, so excited to have you with us today. What can you tell us about your story?
My journey into entrepreneurship and technology consulting began with a simple, recurring pattern: people consistently coming to me for help solving complex problems. Whether it involved technology, operations, branding, or business strategy, I was drawn to breaking challenges down, building practical solutions, and helping others move forward.
As that skill developed into a career, I spent years consulting across a range of industries. Along the way, James Leggs and I became partners and co-owners, bringing together our combined strengths to better serve small and growing businesses. Together, we launched the TaylorMade family of brands—each one focused on solving real-world problems with clarity, strategy, and technology.
What began as freelance advisory work has since grown into a portfolio of service-based companies united by a single mission: helping small businesses operate smarter, grow sustainably, and use technology in ways that truly support their goals.
We all face challenges, but looking back would you describe it as a relatively smooth road?
It definitely hasn’t been a smooth road — and that’s exactly what built my resilience.
Early on, the biggest challenge was wearing every hat: the strategist, the developer, the brand designer, the project manager, the accountant… you name it. As the business grew, maintaining quality while scaling services required discipline and smarter systems. Another challenge was helping clients understand the value of technology — not just the tools themselves, but how those tools create efficiency, automation, and competitive advantage.
Each obstacle forced me to refine my processes, elevate my standards, and build service offerings that are both high-impact and sustainably delivered.
Thanks – so what else should our readers know about TaylorMade Consulting Group?
Professionally, we focus on technology advisory, consulting, and digital transformation. Our work spans across business operations, automation, AI integration, brand development, and technical strategy.
A typical client comes to us because something in their business isn’t working — processes are inefficient, systems don’t talk to each other, workflows break, or they feel overwhelmed by software options. We step in to diagnose, architect a solution, and help implement it in a way that fits their long-term goals.
What’s next?
In the near future, James Leggs and I are expanding TaylorMade into a full-service technology advisory and solutions partner designed to support organizations at every stage of their technology journey. While strategic consulting will always be the foundation of our work, the future of TaylorMade is focused on owning the entire lifecycle of technology decisions—from assessment and planning to sourcing, implementation, and ongoing management. Our goal is to simplify an increasingly complex technology landscape by giving clients one trusted partner who understands both their business objectives and their technical needs. As technology continues to evolve, so must businesses; they need guidance, clarity, and a roadmap that aligns their technology investments with their long-term growth.
A key part of this growth is the expansion of our Tech Advisory services, which allows us to pair unbiased guidance with best-in-class solutions. Together, James and I are leading efforts to help organizations move away from legacy phone systems through modern POTS replacement options, while also offering UCaaS solutions that unify voice, messaging, and collaboration. We are also expanding into CCaaS platforms that enhance customer experience and improve operational efficiency. In addition, TaylorMade provides connectivity advisory services, including internet and network solutions designed for reliability, performance, and scalability. These offerings are supported by managed services to ensure that once technology is implemented, it continues to perform, adapt, and evolve with the business—rather than becoming another unmanaged expense.
What truly defines this next phase for TaylorMade is our advisor-first approach. As co-owners, James Leggs and I do not begin with products; we begin by understanding the business, identifying gaps, and designing the right strategy. From there, we help clients select, implement, and manage technology that supports how they operate and grow. By combining advisory, implementation, and ongoing support, we reduce vendor complexity while increasing accountability. For our clients, this means clearer direction, fewer technology headaches, and systems that actually work together. Ultimately, the future of TaylorMade is about building long-term partnerships and helping businesses create a smarter, more resilient technology foundation for what comes next.
Pricing:
- Tech Advisory & Strategy Consulting: Starting at $250/hr
- Process Optimization & Business Systems Buildout: Custom project-based pricing
- Automation & AI Integration: Packages start at $1,500
- Brand Strategy + Digital Development: Starting at $2,500
- Monthly Retainers: Available for ongoing advisory + support
Contact Info:
- Website: https://www.taylormadeconsultinggroup.com/
- Facebook: https://www.facebook.com/taylormadeconsults/
- LinkedIn: https://www.linkedin.com/company/taylormadeconsultinggroup
- Yelp: https://m.yelp.com/biz/taylormade-consulting-group-mansfield
