Founder Interview: Minnesota-based Kelly Sayre is on a Mission

Her company, the Diamond Arrow Group, teaches woMEN the art of identifying threats and mitigating risk

I first met Kelly Sayre around mid-2015, at the Brentwood Baptist Church just outside Nashville, Tennessee. Neither of us lived in Brentwood—at the time, I was still living in the Bay Area and she in Saint Cloud, Minnesota—nor were either of us Baptists. Nonetheless, we found ourselves at some sort of conference for retailers, where we were introduced by a mutual connection with the typical networker’s generality: “You are both smart, driven, and fun, I think you should know each other!” 

In the midst of tech startup entrepreneurship, where my days stretched into weeks, and weeks into months, with barely a moment of personal time, I felt anything but fun. I was glad someone saw me differently; and I was hoping Kelly was actually fun to take the heat off me. Within minutes of the introduction, I liked her. She was plucky, clearly up for a good time, and also wondered why we were in a church for a retail conference. “It’s Tennessee!” said our mutual friend. “That’s how they do it here.”

We both shrugged, then decided it was time to hit the nearby swanky bar for cocktail hour. Instantly, the seeds of friendship were planted. 

I learned that Kelly was from a blue collar family in Minnesota, her father was a truck driver who was away from the family for weeks at a time. She became self-sufficient at a young age, and had high hopes and dreams of doing something larger than life in her career—even though this wasn’t necessarily the environment in which she grew up. In her late twenties, she married a Saint Cloud, Minnesota police officer, and soon after they started a family. Kelly naturally fit into marketing, communications, and sales roles—given her love of people, natural creativity, and gift of storytelling. But she knew, eventually, she wanted to build something of her own. Something with more meaning. 

Given her observations of the police force and first responders through her then-husband’s work, finally a lightbulb went off when she was working at a company that specialized in empowering women through executive peer groups, coaching, and leadership events. While she was helping women build confidence in both their work and home lives, what she realized is that personal safety was never discussed. 

What if she could help reduce the blindspot in “psychological safety”— which is that 75 to 85 percent of attacks on women come from someone they know. If she could train women to be more aware of their surroundings, to watch for signs of a threat, then empower them with tools to mitigate those risks, wouldn’t this help reduce the instances of assault and sexual violence against women? So much emphasis was put on the aftermath, the recovery of an assault; but what if more focus was put on prevention. 

In 2017, with this idea in mind, she founded The Diamond Arrow Group, and committed herself to helping women understand what it means to increase their situational awareness in order to support their personal and professional development. Her refreshing angle on women’s safety emphasizes non-physical, proactive situational awareness techniques that recognize and avoid threatening situations before they happen. 

With a grounded approach and high energy, today Kelly works with law enforcement, nonprofit, corporate, and youth organizations on emergency preparedness, situational awareness training, and personal safety training. She offers this training globally: in-person, virtually, and through her online programs in the Stay Sharp Corporate Training Educational Community. Frequently, she is a guest speaker at national events and regularly appears on international podcasts where she talks about the importance and nuance of situational awareness. To top it off, Kelly is trained in FEMA’s Community Emergency Response Team program, the Department of Homeland Security’s Active Shooter Preparedness Workshop, and Texas A&M Extension Service’s crisis communications; and she is also a valued member of the Association of Threat Assessment Professionals.

In February 2022, Kelly released her first book, Sharp Women: Embrace Your Intuition, Build Your Situational Awareness, and Live Life Unafraid. Coincidentally, my first book, Champagne for One (who’s the fun one now?) was released the same month—so, Kelly invited me to join as a guest author and speaker at her book launch event. Despite the time and distance, our paths have mysteriously and magically continued to cross. 

I believe God puts certain people in our lives for a reason; sometimes it’s nothing more than just good, old-fashioned inspiration. I’ve watched Kelly trudge through dark waters, unsure if she was making the right move with her career. Over the past ten years, I’ve witnessed her overcome obstacle after obstacle, both personally and professionally—always with the same optimistic attitude. And to me, this is truly inspirational. 

She is a shining example of the thousands of entrepreneurial Americans who work behind-the-scenes, doing the hard-not-glamourous things; helping others, often with little or no recognition. Kelly is the epitome of what it means to live with integrity, and I am so grateful to be sharing her story as our very first Palomino County Founder Interview. 

Kelly Sayre, founder of The Diamond Arrow Group

Rebekah Iliff: What makes your approach to this type of training different from others who perhaps provide something similar?

Kelly Sayre: I think being a woman in this line of work gives me a unique perspective; and my training sessions allow women to feel more at ease—talking about threats in a way that is about giving them practical tools to handle these threats, versus fear-mongering. 

Most male trainers in this space unintentionally create a sense of fear by invalidating or misunderstanding the experiences of women. We move through the world very differently than men, and they don’t necessarily know what it’s like. How could they?  My personal experiences have shaped my training approach, and I focus on practical solutions to the things that women experience every day. So, while I’m making women feel at ease, I’m simultaneously providing the men in the organization with a new perspective. 

RI: What is your company mission? 

KS: We aim to help prevent trauma and save lives through Situational Awareness training. Our mission is simple: we cannot prevent bad things from happening, but there are so many things we can, and must, do to sharpen our own situational awareness and put our personal safety top of mind in all interactions we have—both at work and at home. 

RI: What is uniquely American about your organization? 

KS: Taking control of your destiny is a very American idea. The Stay Sharp Corporate Training Program is designed to give corporate leaders and their teams practical tools that puts them in the driver’s seat. It allows them to assess the risks of their unique experiences at work, on their way to and from work, while traveling for work, and in their personal lives. Also, when people are trained in my program, it naturally impacts those around them because they share the tools they’ve learned; I think most Americans appreciate having bulletproof ways to help more people in their community feel safe. 

RI: What is your definition of the American dream? 

KS: To me, the American dream is the freedom to dream boldly and the opportunity to turn those dreams into reality through hard work and grit. It’s not about guarantees, but rather about having the space to try, fail, learn, and try again. It’s knowing that no matter where you start, you have the ability to carve your own path and define success on your own terms.

RI: Speaking of, what is your definition of success?

KS: Success isn’t about being perfect, and it isn’t about having my shit together. It’s about figuring things out on my own terms, making mistakes along the way. I trust my intuition and use my fears as motivators to improve my life by empowering myself with tools to overcome those fears. 

RI: Does faith and spirituality play a key role in how you operate your business, and how you conduct your professional life? What about your personal life?

Faith, for me, is less about specific religious doctrines and more about a deep belief in something greater than myself—a guiding presence that keeps me aligned with my values. I was raised in a particular faith, but over time, my understanding has evolved beyond those specific teachings. What remains constant is my commitment to doing the right thing, leading with integrity, and treating people with kindness and respect. In both business and life, I rely on that foundation to guide my decisions and navigate challenges with integrity.

RI: What hard lessons have you learned along the way, on your road to founding The Diamond Arrow Group?

KS: Success isn’t a destination; it’s a continuous journey, and that journey is filled with highs and lows. One of the hardest lessons I’ve learned is that neither the wins nor the losses define me. Wins are great, but they’re fleeting. Losses sting, but they’re not permanent. What truly matters is how I show up every single day, how I push forward despite setbacks, and how I stay committed to my goals regardless of the obstacles in my way.

RI: What do you love most about being an American-based organization?

KS: What I love most is the freedom to challenge outdated narratives and create real change. I have the opportunity to redefine what personal safety education looks like for women: I can empower them instead of instilling fear. In some parts of the world, simply speaking up for my beliefs would be dangerous. Here, I have the ability to advocate, educate, and disrupt systems that no longer serve us. That’s something I never take for granted.

RI: For those aspiring founders out there, what are some key challenges to growing a business?

KS: One of the biggest challenges of growing a business, especially as a solopreneur, is managing my own mindset. The way I think about myself and my work directly impacts my decisions, my energy, and my ability to keep pushing forward. When things go well, it’s easy to ride that momentum, but when challenges arise, it’s just as easy to fall into doubt and frustration. I’ve learned that the faster I can shift my mindset from problems to solutions, the faster I can move my business forward.

RI: Do you have any inspirational quotes or ideas that support and inspire you? 

KS: One quote that deeply resonates with me is from Paulo Coelho: "An arrow can only be shot by pulling it backward. So when life is dragging you back with difficulties, it means that it’s going to launch you into something great. So just focus, and keep aiming." 

An arrow through a diamond can symbolize courage or confidence moving forward, so I chose "Diamond Arrow Group" to signify individuals building confidence in their personal safety skills to live life on their terms.

Another quote that has stayed with me since high school is: "Courage is relaxed by delay." I firmly believe that hesitation kills ambition. The longer we wait, the harder it becomes to take action. If you feel called to do something, don’t wait. Try, fail, learn, and try again. That’s how success is built.

RI: What’s new and what’s next for you? Anything exciting you can share?

KS: I’ve recently been contracted with the local school district to work with students, teachers, staff, and parents to increase their situational awareness skills. In order to help prevent violence in our schools, everyone needs to be taught what early warning behaviors to pay attention to and how to articulate those observations in an objective and actionable way. Getting the right resources and assistance to struggling individuals before they head down the wrong path is key to creating safe environments where kids can grow and thrive. 

The Diamond Arrow Group team is also working on a new project that combines the latest advancements in VR and AI technology to bring impactful training to the everyday person on a broad scale. My vision for the future is to make situational awareness a common term, one that becomes an integral part of a person’s toolbox. Technology can help us do that, but it also takes every person seeing the world just a little bit differently. 

***

To learn more about Kelly Sayre or to set up a training session, please visit the organization website: Diamond Arrow Group.