Executive coaching in Miami.

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 Miami 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 Miami and South Florida: 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 Miami companies: transformation leadership, integration after a relocation or an acquisition, board counsel and work with private equity portfolio companies.

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.

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 Miami’s headquarters and regional offices

Carnival, Lennar and Norwegian Cruise Line are headquartered in the Miami area, and more than 1,400 multinational firms are located here, many running their Latin American operations from the city. Leading across countries is its own seat: at New Relic I led 450 people across four countries.

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 of companies that just moved here

Citadel and Citadel Securities moved their headquarters from Chicago to Miami in 2022. A relocated headquarters is a leadership problem before it is a real estate one: a new team, a new city and the old company’s habits. I led transformation inside an 80-year-old enterprise at Cox Automotive.

Miami has been called the Gateway to Latin America. It is a major center of commerce and finance with a strong international business community: more than 1,400 multinational firms are located here, many of them running their Latin American operations from the city, and in 2022 Citadel and Citadel Securities moved their headquarters here from Chicago. That is leadership across borders and through a move: a team spread over several countries, and a headquarters that brought its old habits to a new city. At New Relic I was EVP while it grew from $300M to $500M and led 450 people across four countries, and I led transformation inside an 80-year-old enterprise at Cox Automotive.

Florida is where I started. Convinced that every business was going to run on the internet, I founded my first company, WIPC.NET, in Deerfield Beach: a $5,000 server rented for close to $5,000 a month, and by the second month we were doing more than $25,000 a month. The limit was the pipe: the backbone to the whole South Florida market was one T3, a 45-megabit connection to the internet, so I moved to Atlanta, where the fiber was, founded Interland, the company that became Web.com, and took it to 650 people and a Nasdaq IPO. Ironically, WIPC.NET was acquired by MicronPC, the same company Interland later merged with. When we talk about your Miami company, the seats are the ones I have held.

Thanks. Your note's on its way.

Ken will get back to you personally. If it's time-sensitive, feel free to grab a slot above.