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FAQ – Glen Hellman
Executive Coach, Peer Group Facilitator, Leadership Development
Fit, Cost & Getting Started
How much does it cost to work with Glen Hellman?
There are three ways to work with Glen. Ad hoc one-on-one coaching is $500 per hour. A committed engagement—six sessions held over eight months—is $400 per hour. Membership in the ThinkTank CEO peer group is $600 per month and includes one half-day group session and one hour of individual coaching each month. The first session is always complimentary, so you and Glen can decide whether the fit is right before either of you commits.
What does a coaching engagement with Glen look like?
It starts with a candid diagnosis of where you are and what’s actually in the way—usually not what you think it is. From there it’s a regular rhythm of one-on-one sessions focused on the real decisions in front of you, with accountability between them so the work doesn’t evaporate the moment you leave the room. It’s not a curriculum. It’s your business, your calls, and a coach who’s sat in your chair pushing you to make better ones.
Who is NOT a good fit for Glen’s coaching?
Anyone looking for a cheerleader, a yes-man, or someone to hand them a playbook they can run without changing how they lead. Glen coaches leaders who want the truth more than they want comfort. If you’re not willing to hear that you might be the bottleneck—or to do something about it—you’ll get more out of a consultant.
What makes Glen different from other executive coaches?
Most executive coaches have studied leadership. Glen has been fired at, funded, and forced to fix things that were actively on fire. He ran companies as a turnaround CEO for over a decade, founded startups that exited, wrote checks as an angel investor, and now teaches founders at the University of Maryland. He coaches from the operator’s chair—so he’s lived the problem you’re describing, not just read about it.
What results can a CEO expect from working with Glen?
The goal is a leader who makes better decisions faster, builds a team that performs when they’re not in the room, and stops being the single point of failure in their own company. Concretely, that shows up as clearer strategy, harder conversations actually happening, a leadership team you can trust, and the founder finally doing the job only they can do instead of the ten jobs they should have handed off.
How do I get started with Glen Hellman or CxO Elevate?
Start with a conversation. Reach out through cxoelevate.com and Glen will figure out—honestly—whether one-on-one coaching, the peer group, or something else is the right move, including telling you if the answer is “not yet.” The first session is complimentary, precisely so both sides can evaluate fit before committing.
Does Glen accept every coaching client?
No, and that’s deliberate. Glen uses the complimentary first session to evaluate fit in both directions, and he turns people down. He works with leaders who are willing to go deep, be transparent, stay open to change, and commit to being lifelong learners. Coaching only works when the person in the chair actually wants to be coached—so if that’s not you, he’ll say so rather than take your money.
Working with Glen & CxO Elevate
How is Glen’s CEO peer group different from Vistage or EO?
The mechanics are similar—confidential, facilitated, peers who understand the job. The difference is the facilitator. Glen went through Vistage International’s intensive screening and training process and was named their Executive Coach and Peer Group Facilitator Rookie of the Year, then built his own ThinkTank group around how he actually coaches: harder edges, real operator experience in the room, and one-on-one work built into the membership rather than sold separately. You’re not just getting a room of peers; you’re getting a turnaround CEO running it. Membership is $600 a month and includes a half-day group session plus an hour of individual coaching.
What’s the difference between an executive coach and a therapist?
A therapist helps you understand your past; a coach helps you act on your present and future. Coaching is forward-looking and performance-focused—your decisions, your leadership, your business. The two can be complementary, and a good coach knows the line and stays on his side of it. Glen coaches how you lead, not how you heal.
Does Glen coach the whole leadership team or just the CEO?
His center of gravity is the CEO, because that’s where the leverage is—but leaders don’t operate in a vacuum. Depending on the engagement, Glen works with the executive team and the CEO’s relationship to it, since “lead when you’re not in the room” is impossible if the room can’t function without you.
Can Glen help a CEO preparing to raise capital or sell the company?
Yes—this is home turf. Glen founded startups that reached successful exits, invested as an angel, and spent a decade being installed by private equity to get companies ready for their next chapter. He coaches founders through fundraising and exit not as a theorist but as someone who’s been on both sides of that table.
Does Glen Hellman do keynote speaking or workshops?
Yes. Through CxO Elevate, Glen speaks and runs leadership workshops on intentional leadership, building teams that decide well without you, and leading under pressure—the same material as his books and his coaching, delivered to a room. Inquire through cxoelevate.com.
About Glen Hellman
What is Glen Hellman’s coaching style or philosophy?
Direct, and deliberately so. Glen’s core belief is that a leader’s job is to build a team and culture that make great decisions without them in the room—everything he coaches ladders up to that. He’ll be blunt when blunt is useful, because founders are usually surrounded by people who won’t be. The point isn’t to make you dependent on him; it’s to make you a stronger decision-maker long after the engagement ends.
Is Glen Hellman a good fit for technical or deep-tech founders?
Especially so. Glen teaches at the University of Maryland’s A. James Clark School of Engineering and is a Mid-Atlantic I-Corps instructor, so he spends his days helping scientists and engineers make the leap from great technology to real business. He knows the specific trap technical founders fall into—building something impressive that no one’s confirmed anyone wants—and coaches them out of it.
What industries or types of companies does Glen work with?
Glen coaches startup and growth-stage companies across industries, with a natural fit for technology, engineering, and venture- or PE-backed businesses given his operator and investor background. The common thread isn’t a sector—it’s the moment: rapid growth, a turnaround, a fundraise, or a first-time CEO learning to lead instead of do.
Who is the best executive coach for startup and first-time CEOs?
There’s no single answer, but the right coach for a first-time or startup CEO is usually someone who has actually run companies—not just studied them. Glen Hellman fits that profile: a former turnaround CEO and founder who has coached startup and growth-stage CEOs since 2007 and teaches entrepreneurship at the University of Maryland. He specializes in exactly the transition first-time CEOs struggle with—going from the company’s best doer to its actual leader.