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Glen Hellman is a highly accomplished executive coach with over 15 years of experience, boasting a remarkable track record of leading startups to successful exits, rescuing struggling companies, and guiding founders through complex challenges. With a remarkable career spanning over four decades in the technology industry, Glen has navigated various leadership roles, from sales and marketing to executive leadership positions, including CRO, COO, CEO, and board member. As a certified executive coach and faculty member at the University of Maryland’s A. James Clark School of Engineering, Glen empowers leaders to drive business growth and teaches PhDs and postdocs how to build real companies through programs like NSF I-Corps. He also runs CEO peer groups, where leaders share experiences and insights, and blogs on CXO Elevate, where he offers unfiltered advice on leadership and celebrates impactful leaders. Glen’s distinctive blend of startup expertise, executive experience, and coaching skills makes him a trusted advisor for leaders seeking growth and transformation.
Glen’s Transformative Journey: From Specialist to Coach
Glen’s career path has been anything but linear. With a diverse background as a CEO, board member, investor, and turnaround specialist, he has navigated a winding journey that has led him to become a seasoned executive coach. Glen excels at propelling startups to successfully exist, revitalizing underperforming companies, and mentoring founders through obstacles, leveraging his expertise to drive growth and transformation. Now, as a coach, he focuses on empowering leaders to reach their full potential, driven by a passion to ignite growth and possibility in people.
A Transformative Role for Glen
As Glen reflects on his diverse career, he identifies coaching as the role that has the most profound impact. While his experience as a CEO taught him the importance of making tough decisions, coaching has humbled him by showing him the value of asking the right questions. Through coaching, Glen has come to realize that his role is not to provide all the answers, but rather to empower his clients to discover their solutions.
The Personal Lessons that Shaped Glen’s Leadership
Glen’s approach to leadership and coaching has been profoundly shaped by his personal experience. Life events such as divorce, fatherhood, public humiliation, and redemption have taught him valuable lessons that transcend business metrics. These experiences have instilled in him the importance of resilience, perspective, and empathy—essential tools that he brings into every coaching session, enabling him to connect with and support his clients on a deeper level.
The Key Driving Force behind Glen’s Passion
After decades in the tech and startup landscape, Glen remains energized by the opportunity to empower others. He finds excitement in helping smart people take bold action, witnessing the transformative “click” moment when chaos becomes clear, and, of course, enjoying a good cup of coffee.
The Distinction of Great Leadership
Glen believes that what sets great leaders apart is their ability to create possibility. While good leaders focus on driving performance, exceptional leaders foster cultures that encourage risk-taking, innovation, and growth. By empowering others and multiplying leadership, they achieve a lasting impact that extends beyond their tenure.
Coaching Approach to High-Pressure Decision-Making
Glen helps leaders navigate failure and high-pressure decisions by debunking the notion of perfection. His coaching approach focuses on defining success, committing to action, and owning the outcome. By trusting the process over instincts, leaders can make clear decisions under chaos. Glen also teaches leaders to prioritize the first “if,” avoiding analysis paralysis and staying grounded in the face of uncertainty.
Uncovering Blind Spots with a Unique Approach
Glen confronts C-suite executives with unflinching honesty, asking the tough questions others may avoid. Prioritizing outcomes over ego, he creates a space for growth and improvement. By challenging leaders to confront their blind spots, Glen helps them become better versions of themselves, driving meaningful results.
The Notable Evolution in Glen’s Leadership
Glen’s leadership approach has undergone a significant transformation. From his early days as a sales manager, where he focused on being the authority, to his current role as an executive coach, where he empowers others to grow. His style has shifted from command-and-control to coach-and-coax, recognizing that true leadership lies in making others smarter and more capable.
Glen’s Measure of Success
Glen takes pride in numerous achievements throughout his career, including a notable $100M acquisition. However, his true measure of success lies in the growth and independence of his clients. When they outgrow him and no longer need his guidance, that’s the ultimate testament to his impact as an executive coach.
Timeless Advice for Career Growth
Glen advises his younger self to prioritize listening over showcasing intelligence. By speaking less and absorbing more, he would foster deeper understanding and growth. He would also continue cautioning against chasing titles, instead emphasizing the importance of seeking roles that offer valuable learning experiences.
The Principles behind Glen’s Coaching Framework
Glen’s coaching and mentorship approach is built on three core principles: radical honesty, structured accountability, and a bias toward action. He emphasizes tangible growth by requiring clear plans with specific details—a noun, a verb, and a deadline—driving leaders to take decisive action and achieve meaningful results.
Cultural Obstacles to Growth
Glen identifies common pitfalls that hinder organizational growth, including a lack of honest feedback, leaders isolating themselves from diverse perspectives, teams driven by urgency rather than purpose, and cultures that prioritize individual heroics over building robust systems. These obstacles can stifle innovation, collaboration, and long-term success.
From Reactive to Proactive Leadership
Glen helps teams transition from reactive to proactive leadership by first slowing down the pace and separating signal from noise. He guides them in defining clear objectives and building systems that translate insights into actionable results. This disciplined approach may not be glamorous, but it delivers a tangible impact.
The Future of Executive Coaching
Glen envisions a future where executive coaching prioritizes tangible results over vague theories. Effective coaches will possess a deep understanding of business models, helping leaders bridge the gap between product expertise and customer needs. The integration of AI will further enhance coaching by analyzing session data, identifying opportunities, and informing future strategies. The fusion of human intuition and technological insight will drive meaningful growth and leadership development.
The Leadership for Younger Generations
Glen notes that younger generations of founders and leaders approach mentorship with a unique mindset. They crave direct, substance-rich feedback and value wisdom without the ego.
By prioritizing the “why” over “how,” they demonstrate a deeper understanding and a more discerning approach to learning, making them both eager students and challenging clients.
Innovations in Tech Commercialization
Glen is excited about the convergence of academia and industry in tech commercialization. When universities transform intellectual property into viable startups, innovation truly flourishes. He looks forward to witnessing research translate into tangible revenue, driving growth and impact.
