A single training day is enough to move the needle. A coaching relationship is what keeps it moving when the calendar gets real. Earnings, board meetings, the next press cycle, the all-hands after a hard quarter, the analyst day, the keynote, the activist letter that arrives on a Friday afternoon. Senior leaders do not face one high-stakes moment a year. They face one a month, sometimes one a week.
Success In Media's executive communication coaching is built around that calendar. We work as a named, on-call advisor to one leader at a time, with regular live sessions, on-camera reps, and short-notice prep before the moments that genuinely matter. The same person who watched you on tape in February is on the call before the September keynote. There is continuity, and continuity is the point.
Who We've Coached
Our coaching clients sit at AIG, the United Nations, Land Rover, State Street, American Express, and across additional Fortune 500 organizations in financial services, technology, healthcare, and consumer brands. We also work with senior leaders at trade and professional associations, mid-market CEOs in pre-IPO windows, and nonprofit executive directors heading into capital campaigns or congressional moments. Confidentiality is the default and most engagements are private.
"Jess is a pro at media training. He has broken it down to a science, but allows each person to find their unique way to deliver their message. He put me at ease as a novice. When I finished working with him, I felt like a pro and ended up doing a recurring TV spot for a local network."
Virginia "Ginny" Clarke, formerly Director of Executive Recruiting at Google. Conscious Leadership Expert, Speaker, Influencer, and Executive Coach
"Jess helped me immensely with one of the most seldom used but most difficult skills of being a non-PR business person, dealing with the media. After a robust one-day training I went from being a disorganized and hard-to-watch talking head to an authoritative brand steward ready to discuss our business publicly."
Daniel Peirce, Investor and Advisor (formerly Gatorade, Starbucks, Welch's, adidas Group, TJ Maxx, Save the Children)
Coaching versus training, in plain language
Some senior leaders hear the word "training" and read it as remedial. As if needing it implies a deficiency. The opposite is true. The top performers in the world all work with coaches alongside them, taking them from great to exemplary.
There is also a structural difference between most training programs and the way coaching works. Most communication training, presentation training, and media training is sold as a block of time. A day. Two days. Maybe a week. Coaches approach the same skills from a different angle: a steep increase in capability over a short window, followed by a continued growth pattern across the next year. We build a real relationship with the leaders we support. We watch them grow. When someone starts to drift on a particular skill, a quick touch-base puts them back on track immediately.
The feedback we hear most often is that this kind of guidance, showing up at the right moment, has helped clients land raises, secure promotions, and stand up well in front of investment banks during pivotal capital raises. We have a client right now who is in line to be the next CEO of a major company. She has told us a meaningful piece of that trajectory was taking her communication skills from good to great to top one percent.
What an engagement looks like
A typical executive communication coaching engagement runs six to twelve months. Inside that window:
- Live coaching sessions on a regular cadence, usually monthly, with the executive's real upcoming moments as the agenda
- Short-notice prep calls before specific high-stakes events (a board meeting, an interview, a keynote, an analyst day)
- On-camera repetitions (reps) with playback for the events where being on tape is part of the prep
- Message development support for new strategic narratives, repositioning, or quiet pivots
- Post-event debriefs so the recording from a real moment becomes the next session's material
The cadence flexes. Some quarters are heavy and we are on a call every other week. Other quarters are quiet and the executive only needs us before two specific moments. The point is to be there when the calendar calls.
Who this is for
- CEOs who do at least four high-stakes external communication moments per year
- CFOs in pre-IPO companies or in F500 IR-adjacent roles
- CMOs during a brand transition, repositioning, or major launch year
- CHROs and Heads of People in periods of restructuring or culture change
- Trade-association presidents and executive directors through their term cycle
- Founders who are entering a more public phase of the business
If a leader has three or more known high-stakes moments coming in the next twelve months, a coaching engagement usually pays back faster than a single training day.
Investment and pacing
Leaders who invest in themselves are the ones whose growth chart shows a spike instead of a plateau that year.
We do not publish prices on this page, but we will speak about investment in general terms. There are coaches and trainers who charge more than us. There are coaches and trainers who charge less. Because every engagement we run includes a full year of post-training support as standard, we believe what we offer is one of the strongest packages available. Our focus is on helping you get exactly what you want. We start with the end in mind. We find out what your short-term and long-term goals are, and we help build the path between where you are now and where you want to be a year from here.
People invest in what is important to them. People invest in what reduces pain and removes recurring problems. And people invest when they know the change will compound across the next year and beyond. If that is where you are, reach out and we will scope the right engagement.
What is included across the year
Every coaching engagement includes:
- A named senior coach as your point of contact (no rotating juniors)
- Quarterly assessments and a written progress summary
- Up to seven short-notice reach-outs for critique or pre-event pep talk
- Access to the multimedia learning library, refreshed every ten days
- Recordings of every session sent to the organizer
Clients have told us that a single short-notice reach-out, showing up at the right moment before a high-stakes event, was worth more than the price of the engagement.
A real coaching story
I was traveling internationally for the ongoing training work I do for the United Nations when a WhatsApp voice message came in from an executive director at a prominent financial services organization. He had not done a media interview in the two months since our training, and he was set to be on Bloomberg the very next morning. I could hear the panic in his voice.
When some time passes between training and a high-stakes moment, this is exactly what happens. We are all human. Skills we worked on six or eight weeks ago start to feel further away. The good news is we plan for this. Every engagement includes systems that let our clients arrive at the important moment as good or better than the day they finished training.
I sent a voice message back, having remembered exactly what he shared in our session, and gave him the two most important strategies that would help him land the messages he wanted to deliver and look like a superstar delivering them. As I was boarding my next flight, the phone rang. He told me this was exactly what he needed to hear, at exactly the right moment. He committed to running through it a couple of times before going on, and to sending a first draft of the answers in front of the world the next morning.
By the time I landed home, there was a link to the interview, watchable worldwide. And from him, a two-word message:
Nailed it.