EXECUTIVE & LEADERSHIP COACHING
Clarity for the High stakes conversations of your career.
Jessica Weiss coaches C-suite executives, rising managers, and professionals at a crossroads — privately, candidly, and one relationship at a time.
A private practice, built around one client at a time.
Jessica Weiss works with a deliberately small number of clients at a time. There is no fixed curriculum and no one-size program — every engagement is built around the person in front of her: their role, their pressures, and the specific rooms they need to walk into.
What clients come for is rarely more information. It is a sharper, more honest conversation than they can have anywhere else — with someone who has sat across from leaders at the top of their fields and knows that the hardest part of any role is rarely the strategy. It is the person carrying it.
WHO JESSICA WORKS WITH
Three kinds of clients. One standard of work.
Most engagements begin in one of three places. You don’t need to know exactly where you fit — that’s part of the first conversation — but you will likely recognize yourself in one of these.
01
FOR THE C-SUITE
When you’re the one everyone is reading.
You have already proven you can do the job. What changes at the top is that everything you say is interpreted, amplified, and remembered. A board wants confidence without spin. An investor call rewards composure under pressure. A leadership team spanning functions you have never personally run still needs you to be credible to every one of them. Jessica coaches accomplished executives on the parts of the role that no promotion prepares you for: holding a room, managing a board, navigating interdisciplinary relationships where you can’t be the expert, and communicating with the kind of clarity that earns trust in seconds.
You’re a CEO, founder, or senior executive — and the stakes of how you show up have outgrown the instincts that got you here.
02
FOR RISING LEADERS
Being good at the work isn’t the same as being seen as a leader.
You were promoted because you are capable. But executive presence — commanding a room, presenting with authority, being taken seriously by people more senior than you — is a separate skill, and almost no one is actually taught it. Jessica works with managers and emerging leaders to build genuine presence: how to speak so people lean in, how to present without shrinking or overcompensating, how to lead former peers, and how to grow into the version of yourself the next role requires — without performing someone you’re not.
You’re a manager or rising contributor, and you can feel the gap between the work you do and the way you’re perceived.
03
FOR PROFESSIONALS AT A CROSSROADS
You’re good at your job. You’re also unhappy in it.
It is one of the least-discussed realities of working life: people who are capable, accomplished, and quietly miserable in their roles. Maybe the job has drained something out of you. Maybe you have outgrown it. Maybe you genuinely can’t tell yet whether the problem is the role, the organization, or something in how you are working. Jessica gives that situation the serious attention it deserves. This isn’t venting, and it isn’t a pep talk. It is honest, structured work to name what is actually wrong, decide what is worth fixing, and define what you want next — so you can make a deliberate choice instead of staying stuck or leaving in frustration.
You’re successful on paper and unhappy in practice — and you’re ready to do something about it.
HOW ENGAGEMENTS WORK
How coaching with Jessica works
A.
It starts with a conversation
Every engagement begins with a private conversation — for Jessica to understand what you are facing, and for both of you to decide whether she is the right person to help. Nothing is booked from a form.
B.
A minimum of three sessions
Real change doesn’t happen in a single meeting. Every engagement begins with a minimum of three sessions — enough to get past the surface, find the actual pattern, and start doing the work that matters.
C.
In person or virtual
Sessions can be held in person or virtually — whichever suits your location, your schedule, and the nature of the work. Many clients combine the two.
D.
An ongoing partnership, when you want one
For leaders who want sustained support — through a transition, a board cycle, a demanding year — Jessica offers ongoing engagements on a 3, 6, 9, or 12-month basis. A longer commitment means she is there as a steady advisor rather than only for scheduled sessions: a sounding board before the hard conversation, not just after it.
Engagement Options
MINIMUM
Three-session engagement
A specific, defined challenge — a looming board presentation, a key relationship, or a decision you need to think through clearly.
ONGOING PARTNERSHIP
3, 6, 9, or 12-month subscription
An ongoing partnership through a period of change or growth, with Jessica as a continuous advisor and sounding board.
Both formats are available in person or virtually. The three-session minimum applies to every engagement.
INVESTMENT
Tailored to the scope of the work.
Coaching with Jessica is a tailored engagement, and the investment reflects that. Rather than a single published rate, engagements are structured in tiers — scoped to who you are, what the work involves, and who the coaching ultimately serves.
An individual investing in their own development is a fundamentally different engagement from an organization sponsoring coaching for its leaders. A private equity firm engaging Jessica to coach and advise leaders across its portfolio — where the work informs performance, value, and high-stakes decisions — sits in a different tier than a professional paying out of pocket for their own growth. Both are genuinely welcome. They simply aren’t the same engagement, and aren’t priced as though they were.
Individual
A professional investing privately in their own development, presence, or career direction.
Organization-sponsored
An employer, board, or investor sponsoring coaching for one or more of its leaders.
Advisory & portfolio
Private equity firms and similar organizations engaging Jessica to coach and advise leaders across a company or portfolio.
Specific rates are shared directly, once Jessica understands the scope of what you need — which is exactly what the introductory conversation is for. There is no cost or obligation to have it.
WHAT TO EXPECT
What working with Jessica is like
CANDID.
She will tell you what she sees. The value of an outside coach is the honesty no one inside your organization can offer you.
CONFIDENTIAL.
What is discussed in coaching stays in coaching. [Confirm how confidentiality is framed for organization-sponsored engagements, where a sponsor is involved.]
TAILORED.
No curriculum and no template. The work is built around your role and the decisions actually in front of you.
PRACTICAL.
Coaching is tied to the real rooms, relationships, and conversations you are walking into — not theory.
Frequently asked questions
Every engagement begins with a minimum of three sessions — the smallest amount of time in which meaningful work can realistically be done.
Both are available. You can work entirely in person, entirely virtually, or combine the two — whatever fits your schedule and the work.
Confirm standard session length — for example, 60 to 90 minutes.
Yes. Organization-sponsored engagements are common, whether for a single leader or several. They are scoped and structured differently from individual engagements — see Investment above.
Not at all. Most people don’t arrive with a clear label. Identifying what you actually need is part of the first conversation.
Engagements are tiered rather than fixed-rate. Once Jessica understands the scope of what you need, she will share specific rates directly. The introductory call carries no cost or obligation.
It is a private, candid conversation about what you are facing — and an honest read on whether Jessica is the right person to help. If she isn’t, she will tell you.
Start with a conversation
Every engagement begins the same way: a private, no-obligation conversation about what you are facing and whether Jessica is the right person to help.
Or write directly: [email protected]