The Art of the Pivot: An important lesson from the start-up trenches
About the Author
Will Cromarty is the founder and CEO of Kirkwall, a venture-backed software company using data analytics and AI to safeguard critical infrastructure and prevent costly equipment failures. His deep experience in national security, systems resilience, and high-stakes decision-making gives him a rare perspective on what it takes to build adaptable, mission-driven startups.
Will is also an Entrepreneur-in-Residence at Startup Sioux Falls, where he mentors early-stage founders and facilitates programs like BootCamp and the 10-Week Accelerator.
Part of a startup journey is embracing adaptability if you want to survive.
When we launched Kirkwall, our sights were set on cybersecurity for autonomous systems—especially in aerospace. We had the right team, strong backing, and a plan to get there. Direct outreach was our short game; value-added resellers were the long game. Early customer interviews backed us up.
But then the market spoke—and we listened.
When the Market Talks, Pay Attention
During those early conversations, the message from customers was clear. They were curious about our cybersecurity stack, but their eyes lit up when we mentioned preventative maintenance, sensor monitoring, and system resilience.
We realized we were sitting on something more useful, more immediate. Something they’d actually pay for.
That’s when we pivoted.
From Cybersecurity Roots to Operational Resilience
The shift took us from drone-centric messaging to solving broader problems in industrial and agricultural settings. We began applying our tech to detect early signs of equipment failure, utility issues, and environmental threats, before they triggered downtime.
And we widened our sales strategy in the process. Federal contracts are powerful but slow. A single win can fund a year, but the cycle runs 12–18 months. Private sector deals, by contrast, often close in under 90 days. The blend helped us stabilize revenue and keep momentum during longer government timelines.
Letting Go Without Losing Sight
One of the tougher parts of any pivot is emotional. We didn’t want to abandon our original mission. The threats we saw in autonomous systems are still there. But the market wasn’t ready to solve them the way we envisioned. So we adapted, without losing our north star: protecting critical operations. The problems changed. Our commitment didn’t.
Four Lessons That Stuck
- Discovery Never Ends
We treat customer interviews as standard operating procedure—not a one-time launch activity. Every demo, conversation, or casual feedback loop is a chance to learn. A pivot that sticks doesn’t end. It keeps evolving. - Your Message Can Trap You
Early on, we got labeled as a “drone cybersecurity” company. That wasn’t wrong—but it wasn’t complete. Reframing that took discipline. Words matter, and sometimes the hardest thing to change is the story people think they already know. - Ego Kills Agility
Inside Kirkwall, we judge ideas by merit, not by title. We’ve had some of our best breakthroughs come from interns. If you want to move fast and stay sharp, you’ve got to be willing to be wrong—and let others be right. - Fast Failure Saves Time
A clean “no” beats a vague “maybe.” We’ve learned to value speed, even when the answer isn’t what we hoped. It lets us refocus energy on the things—and people—that are actually moving forward.
For Founders in the Thick of It
- Thinking about a pivot?
Don’t just guess. Talk to real people. Especially those outside your niche. Look for the signal—where people lean in and ask for more. - Pivoting and stuck?
Beta test with friendlies. Try an A/B approach. Or bounce ideas off founders in completely different sectors. That cross-pollination can trigger big insight. - And always—build in more time and budget
However long you think it’ll take, double it. However much you think it’ll cost, pad it. Even if you hit your estimates (we did), you’ll be glad for the breathing room.
At the end of the day, at Kirkwall, pivots aren’t failures. We see them as a discipline: a way to stay sharp, relevant, and resilient, no matter what the market throws our way.
If Will’s insights on adaptability and founder mindset resonated with you, you can learn directly from him and other Entrepreneurs-in-Residence through Startup Sioux Falls’ Bootcamp and 10 Week Accelerator programs. These hands-on experiences are designed to help founders like you refine your business model, validate your market, and build resilience for whatever comes next.