The Founder15 is a blog series where we profile founders of Work Tech companies in their own words. Today, we bring you Ben Brooks, the Founder and CEO of PILOT, an award-winning program structured around individual reflection, manager feedback, executive mentorship, and live group coaching sessions. Brooks is an award-winning HR executive and nationally recognized executive coach. He has seen the powerful impact of top-quality career development, and he developed PILOT to scale this impact. Whether your team is 20 people or 20K people, PILOT scales development to everyone — causing incredible growth in your entire organization.
- “Tell me about you.” How do you answer that question? Texas-born, Colorado-raised, adventure-seeker, a 15-year resident of NYC, former SVP of HR, gay, passionate, curious, intense, entrepreneur, and thoughtful. I don’t fit neatly into a set box or persona and am often described as “one of a kind,” which I take as a high compliment. Life has surprised me with blessings, adversity, detours, and experiences I could have never imagined possible, and looking backward, it all makes sense, but it was never some sort of grand plan I crafted. I describe my career as “Z-shaped” and that I know “a little bit about a lot,” which has served me well as an entrepreneur.
- What’s your company’s origin story? I founded PILOT with my life’s savings, and we’ve never taken a fundraising meeting in our history. The premise behind PILOT was me realizing how life-altering the process of executive coaching was with my private practice clients and wanting to figure out how to democratize that at scale. A good friend of mine, Brian Kelly, founded a massive travel blog called The Points Guy, and on a drive together one day, he pushed me to “think bigger.” I quickly started to shape what we could do to take the power of 1:1 executive coaching and scale it in a way that was affordable, inclusive, flexible, measurable, and sustainable. Our mission is “for everyone to feel powerful at work,” and it turns out that when employees feel powerful at work, that mojo often spills into other areas of life that matter to them.
- Why is your company different? One of our values at PILOT is being “Inventive,” which we define as “being creative yet grounded in our approaches.” That shows up in a variety of contrarian approaches we take to supporting HR as well as the employees they support. The two biggest competitive advantages we have are our unique product (methodology, technology strategy, myriad of tiny features that together make a huge measurable impact) and our crew + culture. Fellow founders and mentors have shared that most successful companies follow about 85% best practices and then do a few select things truly differentiated. The way we’ve built PILOT sets us apart — a remote-first culture sets up crew members to succeed, grow, feel connected, and make an impact with our mission. Great people working on a great product are core to our exceptional customer satisfaction and retention rates.
- Why do you do what you do? About a decade ago, I went through a week-long executive education program where we were asked to define a personal mission statement and KPI for life. Five long days netted out to a simple realization that “impact” was how I wanted to measure my life. As a society, we’ve resigned ourselves that work is going to be a drag, and in doing so that passivity, cynicism, and negativity infect how we run all aspects of our lives. I want people to feel large and in charge, confident, self-aware, and in action around what matters most to them.
- What do you know now that you wish you had known before you started your company? I could write a 300-page book on this prompt alone! It took me a while to unlearn the skills that made me successful in Fortune 500 companies, as they often didn’t port over to my entrepreneurial life. More often than not our initial experiments, hypothesis, or approaches haven’t worked out, which I now realize is part of a high rate of learning as an organization, but at first, it felt like we kept failing. Founding and building PILOT has been the hardest thing I’ve ever done, and together with our talented crew over the past 6+ years, we’ve figured out so much through a combination of brute force, persistence, quick experimentation, and a culture of continuous improvement.
- What’s your favorite Work Tech application that isn’t yours? Asana. The PILOT crew are power users (we run meetings/agendas from it, use it for recruiting, for 1:1’s, product feature development, customer health monitoring, invoice processing, and much more). I love Work Tech that’s thoughtful, intuitive, reliable, and, most importantly, highly useful and valuable to my real-world challenges. Plus, we delight in marking a task complete and hoping the unicorn catapults across the screen with the rainbow shooting out its a$$!
- Who is a company founder you admire and why? Mike Bloomberg. He leveraged his subject matter expertise, corporate experience, life savings, and network and used all of it to co-found an amazing company with a second-to-none product to this day. I’ve had many friends work for Mr. Bloomberg both at Bloomberg LP and in the city government, and the way he thinks, leads, and operates sets an incredibly high bar. Plus, he’s used his treasure, talents, and time for the greater good, with his super practically-rooted Bloomberg Philanthropies organization and in public service to New York City and beyond. I’d love to have 1% of the success and impact the mayor has earned.
- Who is your go-to person for professional advice? Myself. Nobody knows more about me, what I value, my circumstances, my experiences, my needs, my desires, my feelings, my thoughts, my opportunities, or my resources than me. Don’t get me wrong; I tap into a host of others I trust including advisors, mentors, coaches, therapists, trainers, and contemporaries, for perspective, benchmarking, inspiration, accountability, and support. But I’m the world’s leading expert on Ben Brooks. That’s why at PILOT, we build in self-reflection and situational awareness into the product as far too many professionals look outside of themselves for answers that they have the best information to determine.
- What professional accomplishment are you most proud of? As a second act to my involvement in LGBTQ+ equality in the aughts, I played a small role in the successful repeal of the United States military’s so-called Don’t Ask, Don’t Tell policy, in my role as Director and Chair of Development for OutServe-Servicemembers Legal Defense Network, a national legal services and lobbying non-profit. We led a coalition effort to repeal the law in congress. Transforming the world’s largest employer into an LGB-welcoming workplace was the change management case study of a lifetime, and was a domino for follow-on equality victories such as the freedom to marry. Nothing I have done in my corporate employment will compare to the satisfaction that I contributed to the defining civil rights victory of a generation.
- What’s one thing that people would be surprised to learn about you? That I don’t own a car (well for the last 15 years I’ve lived in NYC at least), rent a one-bedroom apartment, and have all of my “stuff” neatly fit into just two closets and some clever storage solutions at home. When I lived in Denver after college, I bought a lovely carpenter’s bungalow and drove a beloved Acura. But I much prefer the simplicity of city living, as it frees up so much of my time, energy, and wallet to focus on experiences in life and myself. I’ve been amazed at how far my own two feet, a Citibike, a taxi, or a $2.75 subway fare can get me, and the level of comfort, support, delight, and satisfaction a modest apartment can provide.
- What’s one moment that changed your professional life? About a year after I was hired at Lockheed Martin after college, my groovy classified spy plane development program was canceled by the Pentagon. I was issued a WARN notice that my job was being eliminated. Crap! I had worked so hard at getting this job after a stretch of searching after graduation, I liked where I worked, and I damn sure needed the paycheck. I’ll never forget realizing that not only was my career my responsibility but also that there was SO much I could do for myself. Before you know it I was networking with some colleagues I had met on the east coast and pitched supporting our growing supplier diversity efforts. Bam! I had a new role that was very satisfying, challenging, and dynamic. And it all happened because I spotted the need, advocated for myself, and kept following up. This mindset is what we’re seeking to instill with the PILOT product.
- What’s a question we should ask the next person we interview? What are your values? How will you measure your life? What causes or values would you protest in the street for? What causes/issues have you given your time/treasure/talents to? As a coach, I’m fascinated to get to the root of someone’s motivations, character, and decision-making.
- What do you hope people say about you when you’re not in the room? What a stud! I kid (mostly)! Generally, I aspire to be known as someone who has a profound positive impact on other people’s lives by being a source of inspiration, support, and delight. In doing so, I seek to be a leader that’s known for clear thinking, thoughtfulness, ambition, principled decision-making, generosity, and positive energy. These standards for me are “a mountain with no top” thus, I’m continuously working to grow, learn and mature in pursuit of being the best version of myself, and when I do leave this life, being able to declare that I was “used up” before I departed.
- What’s the biggest risk/bet you’ve taken and how did it work out? Packing up for an unexpected move to NYC nearly 15 years ago, only knowing two people in the city, with very little in my bank account, and having visited the city only twice before I interviewed. It has profoundly impacted my life professionally and personally. In fact, I consider it one of the top 5 most important decisions and influences on my entire life. I still can’t believe I was lucky enough to have wound up here, as being a resident is continuously life-altering and my favorite subscription of all time.
- What’s something you want to do professionally that confronts you? I’ve long admired comedy as an art form and the many diverse, brave, and talented comedians who generate one of the most precious resources in all of life — laughter. Learning how to do stand up and doing a set scares the crap out of me, and yet I can’t stop thinking about it. In fact, at the start of 2020, I set a goal to do a class … but the universe had other plans for me for the past 2+ years. I think it would help me develop and flex a bunch of new muscles, and I’m curious to explore if I can bring comedic skills or structures into my Work Tech/employee development efforts as a different, more engaging, and enjoyable way to reach, energize, and activate people at scale. I’ve even started writing a long list of jokes/material on my phone, including many about how hysterical work, co-workers, and the workplace can be.
Note to readers: This is a series for Work Tech Founders. If you’re interested in being a part of it, email us at ocho@thestarrconspiracy.com.
