I am an executive coach for CEOs, founders and senior executives in Chicago, and I held the seats before I coached them: founder and CEO of the company that became Web.com, taken to a Nasdaq IPO; EVP at New Relic while it grew from $300M to $500M; VP at Cox Automotive through a cloud and DevOps transformation inside an 80-year-old enterprise; COO in a VC-backed turnaround. I am CEC and ICF certified, with a BS in Psychology and a master’s in CMHC underway.
My practice runs nationally: standing coaching calls on video with leaders everywhere, and on-site work, offsites, working sessions and consulting, anywhere in the country when the engagement books time for it. Chicago companies get the same terms and the same operator.
Three ways to work with a Chicago company.
Executive coaching, on a standing cadence
A standing cadence on video, weekly, every other week or monthly, with access between calls, on the same terms as all my executive coaching: a practical, candid thought partner who has held the seat you sit in. Executive coaching in Chicago for CEOs, founders and senior executives, and leadership team coaching when the team is the unit.
Offsites, in your room
Executive offsites, strategic planning sessions, retreats and leadership alignment workshops, run by an operator, not a moderator. See facilitation for how the room works. Executive offsite facilitation in Chicago: strategic planning sessions, leadership retreats and executive team alignment, in your room or the venue your team chooses.
Consulting, on your site
Operational work happens where the work is: your floor, your standups, your board meeting. From strategy consulting to AI consulting, on site when the engagement calls for it. Strategy consulting for Chicago companies: transformation leadership inside large enterprises, board counsel and work with private equity portfolio companies.
What you get from executive coaching.
Executive coaching is leadership development built around the seat you are in, not a course. Here is what an engagement delivers, as leadership development for Chicago executives built around the company you actually run.
Success, defined up front
Before the work starts we agree what success looks like and how we will both know, and we check the work against that measure at set points along the way, not only at the end.
A thinking partner who has held the seat
Standing calls weekly, every other week or monthly, in person or on video, and access between calls, because the hard things do not wait for the calendar.
A sharper view of your own patterns
Blind spots named early, and a clear view of how you lead under pressure. We can work on the board meeting and the person walking into it in the same hour.
Executive presence and stakeholder management
Presence with a board, investors, PE operating partners and the peers who wanted your job, and a plan for the transition into a bigger seat before it arrives.
Progress on the problems that do not fit on a slide
The team that worked at the last size and does not at this one. The difficult conversation you have been putting off. Accountability that does not backfire. Alignment across a leadership team.
Habits that outlast the coaching
The right formula, the right tactics, and repeatable actions: the rhythm that keeps the change alive after we finish. Insight alone does not survive a real quarter.
Your company can fund it. Most of my clients are funded by their company as leadership or professional development, because companies invest in the leaders they intend to keep. If you need to make that case internally, I will help you build it.
Who I work with in Chicago.
I have sat on every side of the table, so I understand how the whole organization moves, not just the seat you are in.
Technology founders and CEOs
CEO coaching for founders and first-time CEOs: scaling past the team you started with, investor expectations, and the move from founder-led to a real leadership team. I have made that move myself, and I was EVP at New Relic while it grew from $300M to $500M.
Leaders of PE- and VC-backed companies
A sponsor with a playbook and a clock, and a board that wants the plan delivered. I spent a decade as a managing partner at a venture firm, and I was COO in a VC-backed turnaround.
Executives inside Chicago’s Fortune 500
Chicago and its suburbs are home to 35 Fortune 500 companies, second only to New York City: McDonald’s, United Airlines, Kraft Heinz, Motorola Solutions and Exelon among them. Change inside a large enterprise is its own seat: I led transformation inside an 80-year-old enterprise at Cox Automotive.
Leadership teams
Leadership team coaching: the team as a unit, not only its leader. Executive team alignment, clear decision rights, and an offsite that turns into follow-through. More on facilitation.
COOs, presidents and product leaders
The second in command, whether the title is chief operating officer or president, and the most senior product leader. I have held the COO seat and the product seat. More on coaching for COOs and coaching for Chief Product Officers.
Leaders in finance and trading
Chicago has the largest and most diverse finance derivatives market in the world, home to the Chicago Mercantile Exchange, the Chicago Board of Trade and the Chicago Board Options Exchange. Executive coaching for leaders in trading, banking and financial services. As a VP at Unqork I led implementations for Goldman Sachs, Marsh and State Street.
What is different about leading a company in Chicago.
Chicago runs on large enterprises. The city and its suburbs are home to 35 Fortune 500 companies, second only to New York City, among them McDonald’s, United Airlines, Kraft Heinz, Mondelez, Motorola Solutions, Exelon and Archer Daniels Midland, and the metro’s economy is the third largest in the country. Leadership inside companies that size is its own discipline: a long history, a big org chart, and change that has to move through both. I led a cloud and DevOps transformation inside an 80-year-old enterprise at Cox Automotive, and as EVP at New Relic I sold to 15,000-plus enterprise accounts and led customer advisory boards with Disney and Capital One in the room.
Chicago also has the largest and most diverse finance derivatives market in the world, with the Chicago Mercantile Exchange, the Chicago Board of Trade and the Chicago Board Options Exchange. I led implementations for Goldman Sachs, Marsh and State Street as a VP at Unqork, and I took the company I founded to 650 people and a Nasdaq IPO as Web.com. Since then I spent a decade as a managing partner at a venture firm and board member across 35 deals and 18 exits, and sat in the COO seat of a VC-backed turnaround. When we talk about your Chicago company, the seats are the ones I have held.
Executive coaching in Chicago: the questions people actually ask.
How do I choose an executive coach in Chicago?
Start with which seat the coach has held and what happened to the company, then the credentials, then how the cadence works week to week. I wrote up six questions to ask any executive coach, including me.
How is your coaching different from other Chicago executive coaches?
I held the seats before I coached them: founder and public-company CEO, EVP, VP inside an 80-year-old enterprise, and COO. You work with me directly for the whole engagement, not a matched associate. I am CEC and ICF certified, a member of the APA, ACA and LPCA, and the author of the Amazon best seller Business Breakthrough 3.
How much does executive coaching cost in Chicago?
Most of my clients are funded by their company. The price depends on cadence, length and how much of the work is on site; you get a scope and a number on the discovery call. What the market charges is in my guide to executive coaching costs.
Is executive coaching worth it?
It is when there is a real problem on your desk and a leader willing to change how they work. The discovery call is where we find out, and if coaching is not the answer, I will tell you.
What industries in Chicago do you coach?
Leaders inside large enterprises and the Fortune 500, finance, trading and financial services, technology and software companies, and PE- and VC-backed companies: CEOs and founders, COOs, presidents and product leaders, and whole leadership teams.
What are the signs a leader could benefit from coaching?
A seat that got bigger faster than the leader did, a team that keeps stalling decisions, a board or a CEO asking for something the leader has not done before, or a transformation that was announced and is not holding.
Do you coach executives inside Chicago’s large enterprises?
Yes. Change inside a large enterprise is its own seat: the history, the org chart and the pace all push back. I led a cloud and DevOps transformation inside an 80-year-old enterprise at Cox Automotive, and at New Relic I worked with 15,000-plus enterprise accounts.
Do you coach leaders in finance and trading?
Yes. The coaching is about the seat you hold: the board, the regulators’ pace, the risk function, the peers and the team. As a VP at Unqork I led implementations for Goldman Sachs, Marsh and State Street, so I know how change moves inside a regulated firm.
Do you coach founders and venture-backed CEOs?
Yes. I founded the company that became Web.com and took it public, spent a decade as a managing partner at a venture firm and board member across 35 deals and 18 exits, and sat in the COO seat of a VC-backed turnaround. See coaching for startup CEOs.
Is executive coaching confidential?
Yes. If your company is funding the engagement, it will know the engagement is happening and may want to agree the goals up front, but what is said in a session stays in the session.
Do you work with Chicago clients remotely or in person?
Both. Most of my clients work with me on video on a standing cadence, with access between calls. On-site work, an offsite, a strategic planning session or a working session with your team, happens where your team is, anywhere in the country, when the engagement books time for it.
Do you coach leadership teams and run offsites in Chicago?
Both. Leadership team coaching treats the team as the unit: decision rights, how the team disagrees, and the follow-through after an offsite. Executive offsites and strategic planning sessions run in your room or the venue your team chooses. See facilitation for how the room works.
How do we start?
The same way every engagement starts: a discovery call. Forty-five minutes on video, the real problem on your desk, and a straight answer on whether I am the right person for it.
Start with the real problem.
Forty-five minutes, no pressure, no pitch. Bring the real problem on your desk and you will leave with a sharper version of it, and a straight answer on whether I am the right person for it.
- Send the note, or book the call if you would rather pick a time.
- Forty-five minutes, on video.
- A scope and a number if it makes sense to work together, and a straight no if it does not.
Or reach me directly:
(629) 304-8755
ken@kengavranovic.com
In person, or remote. City by city.
Executive coaching across a table, offsites in your room, consulting on your site. Based in Alpharetta, Georgia; remote everywhere.
- Alpharetta (home base)
- Atlanta (home market)
- Nashville (travel, remote)
- Dallas (travel, remote)
- Austin (travel, remote)
- Charlotte (travel, remote)
- New York City (travel, remote)
- San Francisco (travel, remote)
- Chicago (travel, remote)
- Miami (travel, remote)
- Washington, DC (travel, remote)
- Boston (travel, remote)