Mike Duffield’s path from leading the first sales team at Workday to founding a company offers a clear view into what it really takes to build and scale a business. In this conversation, he shares candid insights on early-stage challenges, growth missteps, and the mindset shift required to move from founder to operator.
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Ever wonder what it takes to build a company from the ground up, navigate seismic shifts, and lead a team to success?
In a recent conversation with Workday’s Callie Zeifang, seasoned entrepreneur and business leader Mike Duffield shared a wealth of insights collected over the course of a fascinating career that spans from childhood hustles to the highest echelons of tech.
Currently, Duffield is the co-founder of Alchemy and the vice president of go to market at Ridgeline, but his journey to these roles offers invaluable lessons for anyone looking to explore building a business, regardless of its size.
Duffield's entrepreneurial spirit was evident even in childhood. His earliest ventures, like caddying on a golf course and running a paper route, hinted at a promising sales acumen—and it was soon proven true.
His professional journey began at PeopleSoft, an ERP company. Starting at the very bottom as an associate consultant, Duffield got to learn the business from every angle, including customer service, sales, marketing, and development. His uncle, a top sales leader there, became a huge influence, teaching him much through observation.
After about a decade at PeopleSoft, Duffield became Workday's first global sales leader.
Leading sales at Workday at its start meant Duffield faced the daunting task of introducing cloud-based software at a time when people were deeply skeptical about moving their data online. He described this challenge as taking off in an airplane "with no landing gear," forcing him and his team to "build a landing gear along the way."
After more than a decade scaling Workday’s sales team, Duffield decided to take a leap. He founded Alchemy, a company that helped colleges and universities use Workday. This marked a turning point in his career: from executing within a larger system, to creating one from scratch.
Starting a company is rarely a clean process. For Duffield, founding Alchemy meant stepping into a market with no playbook. Workday’s product was still new and the demand was high, but there were no examples to follow—no reference customers, no standard implementation process, and no official training to lean on.
Demand from higher education clients pushed Alchemy to grow fast. But without stable infrastructure, the company scaled ahead of its own readiness. When the COVID-19 pandemic hit, the consequences were immediate: projects paused, revenue dried up, and 30% of the workforce had to be laid off.
Duffield’s reflection was candid and direct: the company grew too fast, too soon. And when you grow ahead of your capacity, especially without a financial buffer, you expose your team to serious risk. Raising additional capital under pressure also meant dilution, both for himself and for his early investors and employees.
These challenges tested Duffield’s resolve and shaped his perspective. The hard-won lessons that followed now guide how he thinks about growth, leadership, and building a business that lasts.
Early growth often relies on one or two individuals who carry most of the sales and delivery. That model doesn’t scale. You’re only ready to grow when the broader team can replicate success without heavy reliance on those early “deal heroes.” Build repeatable processes, ensure the message is understood company-wide, and confirm that performance doesn’t drop off when the founder steps back.
Prospects are more influenced by what current customers say than by anything in your pitch deck. Prioritize making your first customers successful, and then actively involve them in your sales process—through testimonials, referrals, or case studies. The more your customers can validate your value, the less convincing you have to do yourself.
Sales and leadership aren’t about speaking clearly, they’re about hearing accurately.
Active listening helps you understand real pain points, hidden objections, and unspoken priorities. Pay attention to how your message lands. Empathy and adaptability in conversation will earn more trust than persuasion ever could.
Every sales conversation needs to address:
Without clear answers to all three, deals stall. Build your pitch—and your product—around solving for these questions directly and confidently.
Early-stage companies don’t have the luxury of waiting for ideal conditions. Acting quickly—even without all the answers—builds momentum, surfaces lessons faster, and helps teams adapt in real time. The goal isn’t flawless execution; it’s fast learning and fast iteration.
Your first 5 to 10 customers will shape everything that follows—your reputation, your playbook, your internal training. Don’t optimize for margins at this stage. Be hands-on. Solve problems with urgency. Absorb mistakes and learn fast. The effort you put in now will pay off in credibility, repeatability, and referenceability later.
Growing too fast—especially without solid infrastructure—can put the business at risk. Every hire, expansion, or investment decision should be weighed against cash flow, operational capacity, and worst-case scenarios. Maintain a tight handle on burn. Momentum is important, but sustainability is essential.
Duffield always had an entrepreneurial spirit, but translating that into building a company was a different kind of challenge.
Moving from individual contributor to founder requires stepping out of execution mode and into ownership. You’re no longer responsible for closing deals, you’re responsible for creating the conditions in which others can.
For Duffield, that meant launching his own entrepreneurial journey with no roadmap, no playbook, and no guarantees.
But founding a company is just one phase. To build something that lasts, founders have to evolve again—into operators. That shift is where many get stuck. The urgency that helps you launch a business can work against you when it’s time to scale one.
Here’s what that evolution looks like in practice:
The founder-to-operator shift isn’t about giving up control. It’s about building something that doesn’t rely on your control in the first place, and that’s what makes a company durable.
Through every step of Duffield’s journey—from the earliest childhood hustles to navigating the complexities of major tech companies and the harsh realities of rapid startup growth—Duffield was continually learning. Each experience, whether a triumph or a setback, equipped him with invaluable insights into how to lead, how to scale a business effectively, and perhaps most importantly, how to stay true to core values through it all.
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