Find a speaker / Ilana Esterrich
Ilana Esterrich
Strategy and Growth

Ilana Esterrich, Listed

Why Transformation Fails, What Leaders Miss, and How to Turn Strategy into Lasting Results

Keynote speaker, workshop leader, subject-matter expert, and moderator and emcee · Co-author of The ROI Lie

Strategy and GrowthLeadership and CultureOperations and Execution
+2 moreFinance, Investing, and the EconomyInnovation and the Future

Sending an inquiry is free. You confirm the date, fee, and terms with Ilana before anything is booked.

Speaking fees
$7,500, or custom quote
3 sessions below
Formats
Keynote, Workshop
In person
Based in
Boston, MA
Travels internationally.
Organizer feedback
None collected yet
Reviews appear on Verified profiles. How we collect feedback

Sessions and fees

Every fee below is published by Ilana. Custom quote means Ilana prices that session for your event.

The ROI Lie: Why Transformation Fails and What to Measure Instead

Custom quote
KeynoteUnder 1 hourIn person
For entrepreneurs and business owners, CEOs and senior executives, executive peer groups, general corporate audiences, and boards and nonprofit leaders.

Drawing on real-world executive experience and insights from The ROI Lie, Ilana challenges conventional approaches to evaluating transformation success. Through compelling stories, practical frameworks, and audience reflection, she reveals why promising investments stall, how organizational attention and capacity shape outcomes, and what leaders should measure to turn ambitious strategies into lasting results. Participants leave with questions they can apply to their next major investment or transformation decision.

  • A practical way to recognize the hidden costs that derail transformation, including decision delays, competing priorities, and capacity constraints.
  • A framework for evaluating investments beyond projected financial ROI to include organizational readiness and execution capacity.
  • Three questions leaders can use immediately to determine whether a transformation initiative is positioned to deliver lasting value.
Session details and terms
Promotion: None proposed. Required purchases: None. Attendee follow-up: None.

The Decision Drag Workshop: Why Good Strategies Stall

$7,500
WorkshopHalf dayIn person
For entrepreneurs and business owners, CEOs and senior executives, executive peer groups, and boards and nonprofit leaders.

Why do capable leadership teams struggle to turn decisions into action? In this interactive workshop, Ilana explores how competing priorities, unclear decision rights, and limited organizational capacity create hidden costs and slow execution. Participants apply practical diagnostic tools to their own challenges, discuss organizational tradeoffs, and identify actions to move an important strategic decision forward.

  • A diagnostic for identifying where critical decisions are stalled and what is preventing progress.
  • A practical approach to clarifying decision rights, accountability, and organizational capacity.
  • An action plan to accelerate one real strategic decision without adding unnecessary work or complexity.
Session details and terms
Promotion: None proposed. Required purchases: None. Attendee follow-up: None.

Built to Adapt: Leading Organizations Through Uncertainty and Change

Custom quote
KeynoteUnder 1 hourIn person
For CEOs and senior executives, executive peer groups, general corporate audiences, and boards and nonprofit leaders.

Organizations face relentless pressure to adapt, but their structures, processes, and resource commitments often make change difficult. Drawing on decades of executive leadership across corporate and mission-driven organizations, Ilana explores how leaders can build the operating capacity to pivot, scale, and sustain performance. Through real-world examples and guided reflection, audiences examine where their organizations are vulnerable and what needs to change to become more resilient.

  • A framework for assessing whether their organization's operating model can adapt to changing conditions.
  • A practical method for identifying capacity constraints, structural barriers, and competing priorities.
  • Three leadership actions to strengthen organizational resilience, adaptability, and long-term performance.
Session details and terms
Promotion: None proposed. Required purchases: None. Attendee follow-up: None.

About Ilana

I'm a three-time Chief Financial Officer, author, advisor, and Harvard Advanced Leadership Initiative Fellow who has spent more than 30 years helping organizations navigate complex decisions, transformation, and growth. My career spans corporate leadership, management consulting, and the nonprofit sector, including serving as CFO of Planned Parenthood Federation of America.

As co-author of The ROI Lie: Why Transformation Fails and What to Measure Instead, I challenge conventional thinking about how organizations invest, execute, and measure success. I bring a CFO's financial discipline, an operator's understanding of organizational complexity, and a practical perspective on what makes change stick.

My goal is to help leaders ask better questions, confront difficult tradeoffs, and turn ambitious strategies into lasting results.

Media and books

Cover of The ROI Lie
The ROI Lie
Why Transformation Fails and What to Measure Instead. Published 2026. Co-author. Attention Shift OS LLC. Paperback and ebook. Copies $24.99 per person.
Related books, services, and programs
Books, Consulting or advisory, Courses or training

Books: The ROI Lie: Why Transformation Fails and What to Measure Instead, co-authored with Vincent Messina. Consulting: Esterrich+Associates provides strategic advisory services to mission-driven organizations. Attention Shift OS helps businesses improve decision-making and transformation outcomes. Workshops & Training: Executive workshops on strategic leadership, organizational transformation, decision-making, financial leadership, and sustainable performance.

Organizer feedback

No organizer feedback collected yet. Reviews appear on Verified profiles, collected by Short List Speakers from organizers who booked the speaker and published regardless of sentiment. How we collect feedback