Executive Coaching · Strategic & Marketing Advisory · Team Development

Results matter.
So does how you get there.

Leadership, execution, and executive judgment — shaped through years of operating at scale.

I coach senior leaders and advise the teams they run — as they take on broader scope, navigate complexity, and lead through the moments that actually test them.

Greater Boston · Engagements worldwide
Rachel Levy
The Setup

Leadership is high-pressure, lonely, and fast-moving. Leaders are trained to deliver outcomes — not to build alignment and followership across teams.

That gap is where careers stall, teams burn out, and good strategies fail to land. My work begins there.

Leadership can be isolating. One of the most valuable things coaching provides is protected space to think — to examine assumptions, challenge patterns, and see choices more clearly.

How I Partner

Three ways I work with leaders and the organizations they lead.

01

Executive & Leadership Coaching

I work one-on-one with senior leaders taking on broader scope or operating at the edge of what they've done before. The work is confidential, results-focused — and deliberate about how you show up, decide, and lead.

02

Strategic & Marketing Advisory

I advise companies and leadership teams on growth, marketing strategy, and organizational effectiveness — bringing two decades of operating experience, including running a 115-person marketing organization and doubling the Amex Offers business.

03

Workshops & Team Development

I work with teams that need to translate strategy into disciplined, aligned execution — and with leadership groups sharpening their collective effectiveness.

What I Help Leaders Do

Six places this work matters most.

01 / Uncertainty

Leading through uncertainty to accelerate growth

I help leaders stay decisive and restore focus when clarity is scarce — preventing team burnout and drift.

02 / Influence

Shaping high-impact leaders to elevate performance and followership

I help leaders deepen self-awareness, sharpen presence, and expand influence.

03 / Change

Driving strategic change to align stakeholders and deliver results

I help leaders and teams turn direction into disciplined, aligned execution.

04 / Culture

Turning values into action to strengthen culture and results

I help organizations turn values into action and drive credible, measurable impact.

05 / Complexity

Navigating complexity to drive clarity, alignment, and confident decisions

I help leaders tackle complex decisions where clarity, judgment, and risk tolerance align.

06 / Growth

Sharpening growth and marketing strategy to move the business

I help leaders translate strategic ambition into go-to-market execution that drives revenue and market share.

How I Think

The posture underneath the work.

Judgment over certainty

Sound calls when the data's incomplete and the stakes are real.

Clarity over noise

Alignment isn't agreement — it's a clear call, understood.

Tension over slogans

The real answer lives in the trade-off, not the tagline.

Reality over the org chart

Who really decides, and how work moves through a matrixed org.

Discipline over intensity

Leading hard moments by holding the line, not the volume.

Ambiguity over false precision

Moving work forward without pretending the fog has lifted.

From the Room

Notes from the work.

Pattern recognition from inside consequential rooms.

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On Signals

"I accidentally changed the dress code."

Months into a new leadership role, someone thanked me for "letting" the team wear jeans. I had no idea what she meant — the previous leader had been more formal, and I'd just shown up as me. But to the team, that was policy. Leaders communicate culture constantly, even when they don't realize they are. People watch what gets rewarded, ignored, interrupted. And apparently — what the boss wears.

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On Conviction

"I still think the product decision was wrong."

That's the uncomfortable part of "disagree and commit" — sometimes you commit without changing your mind. I argued hard for a product decision and lost; I wasn't the CEO. At some point, continuing to fight stops being productive and starts being destructive. Not every business decision is a moral battle. I fought relentlessly on people, ethics, and values. Learning the difference points you toward the fights worth having.

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On Starting

"My starting point was a blank spreadsheet."

I was asked to build operating procedures for a confidential new business model and had no idea where to begin. So I locked myself in a conference room and typed — not answers, questions. What do we need to decide? Who would know? That spreadsheet became a map of what I didn't know and who I needed to talk to. It became hundreds of pages of procedures.

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On Presence

"You're tinier than I expected."

A Group President said this the first time we met off Zoom. I'm five feet tall — but in her mind I was bigger. People form a read on your presence long before they meet you: how you speak, how you carry a point, what you choose not to say. That becomes your size in the room — not your title, not your tenure. The only question is whether you're shaping it.

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On Ambiguity

"I want to NDA you."

I got staffed on a high-stakes M&A deal I had no business being on — a few months of vaguely relevant experience from a decade earlier, just back from maternity leave. When I asked the GM why he picked me, the answer was simple: he needed someone who could operate in ambiguity and move work forward. At senior levels, trust isn't built on the perfect résumé. It's built on whether you deliver when things get messy.

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On Org Design

"Your absence won't move the stock price."

My husband said that years ago, when I was stressed about turning off my BlackBerry for two weeks. He was right — not just about me, but about how I was operating. The real test of leadership isn't how you show up. It's how things run when you're gone. If everything stalls when you step away, that's not a workload problem. It's a design problem. Vacation doesn't create strong teams. It reveals them.

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On Judgment

"I hired you because you ask the right questions."

A month into my most senior role, my division head said that — and it reframed how I saw the job. Your team often has the deepest expertise; you're in the seat to create clarity. The hardest leadership skill isn't intelligence or strategy. It's judgment: knowing when to sound the alarm, when to make the call, which data points actually matter. It's the difference between momentum and swirl.

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On Pressure

"Pressure doesn't build character. It reveals it."

Most leaders don't lose their teams during growth — they lose them during ambiguity. When pressure rises, standards quietly erode: deadlines slip, clarity blurs, accountability softens. It rarely happens dramatically; it happens incrementally. Strong leadership in those moments isn't about intensity. It's about discipline — protecting clarity, holding the line, refusing to let "good enough" become the norm.

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On Resilience

"The corporate equivalent of the Post-it breakup."

I once found out I didn't get a job from a voicemail — left by a hiring manager who worked on the same floor. I was mortified. But here's what people don't say enough: successful people get passed over. A lot. For jobs, promotions, visibility — sometimes for good reasons, sometimes political ones, sometimes reasons you never understand. Careers are far messier than they look in hindsight. Eventually you stop treating rejection as a verdict on your worth.

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What Others Say

From the people who've worked alongside me.

She transformed her team into a powerhouse, while elevating her brand and impact. A great colleague and a tremendous professional.
SVP · American Express
An exceptionally skilled and effective leader. She has the unique ability to balance innovative thought leadership with flawless process management and execution.
VP/GM · American Express
Rachel Levy
About Rachel

I learned how leaders actually grow — at scale, under pressure, in the room.

I spent nearly two decades in leadership roles, including leading large-scale marketing organizations at American Express — driving growth, leading large teams, managing P&Ls, and operating inside highly matrixed organizations. I doubled the Amex Offers business over three years, and was entrusted with establishing the guardrails for a first-of-its-kind business-model transformation during a core M&A initiative.

Today I work with senior leaders and the teams they run — to drive results, build followership, and navigate complexity. I bring commercial rigor, principled leadership, and human depth to high-stakes environments, and I'm known for high standards, candid feedback, and the kind of trust that lasts. I'm a certified Co-Active Training Institute (CTI) Coach Practitioner.

Beyond client work, I serve on the Board of Directors of the Crohn's & Colitis Foundation (New England chapter) and on the Lexington Human Rights Committee.

2 decades Leading
at scale
115 Person
organization led
3 countries Lived &
worked in
Global Teams &
strategy led
On stage & on camera

Two decades in front of teams, boards, panels, and cameras — the experience behind the coaching.

Rachel Levy speaking on a keynote stage
Keynote stage
Rachel Levy on a studio set
On set
Rachel Levy speaking at the Women in Payments Symposium
Women in Payments Symposium · 2023
Rachel Levy speaking at a Crohn's & Colitis Foundation event
Crohn's & Colitis Foundation · 2025
Let's Talk

Tell me about the leadership challenge you're facing.

The best engagements start with a conversation. Share what's on your mind — a leader stepping into more, a team that needs to align, a decision that doesn't have an obvious answer — and let's see if there's a fit.