Show Up to Win: How to Land the Leadership Role You Want

by Kelly O. Kay and Jeff Sanders

A practical playbook for senior leaders to sharpen how they prepare, show up, and follow through when they seek new roles, so their every move in the executive job market builds trust, accelerates performance, and helps them build the career they really want.

 

“In a business context changing faster than ever, it’s difficult for leaders to consider their next move strategically. Kelly and Jeff have created an invaluable guide to the professional and personal questions leaders need to ask—and answer—to build careers with lasting impact.”

Robin Washington, President & Chief Operating and Financial Officer, Salesforce

Sample chapter
Download “Step 1: Get Ready to Show Up”

Endorsements

Salesforce

“In a business context changing faster than ever, it’s difficult for leaders to consider their next move strategically. Kelly and Jeff have created an invaluable guide to the professional and personal questions leaders need to ask—and answer—to build careers with lasting impact.”


— Robin Washington, President & Chief Operating and Financial Officer, Salesforce

Visa

Show Up to Win is candid and actionable. It helps leaders clarify their strengths, position themselves as the best candidate for the roles they want, choose the right path, and confidently navigate each step of their career transition.”


— Ryan McInerney, CEO, Visa

Rockwell Automation

“Kelly and Jeff present a compelling, highly credible process for executives to evaluate the case for personal change at various points in their careers, and to make the most of their experience, insight, and desire for positive impact over the long run.”


— Blake Moret, CEO, Rockwell Automation

Microsoft

“Kelly and Jeff have played a significant role in my leadership development and have been terrific partners in helping me find the strongest executive talent over the years. This is a must read for senior leaders looking to advance their career.”


— Judson Althoff, CEO, Commercial, Microsoft

Databricks

“Kelly and Jeff are the best in the industry! They’ve developed an amazing roadmap for senior executives navigating their next career challenge. This book delivers the clarity, strategy, and confidence needed to succeed in today’s challenging environment.” 


— Ali Ghodsi, Co-Founder and CEO, Databricks

Thrive Capital

“Jeff and Kelly articulate something every great leader eventually realizes. Opportunities do not always go to the most accomplished or most deserving, but to those who want it the most.”


— Josh Kushner, Founder and Managing Partner, Thrive Capital

What’s inside

Show Up to Win is a straight-talking playbook for senior leaders considering their next big move. Drawing on decades inside CEO and executive searches, Kelly O. Kay and Jeff Sanders explain why the leaders who land the right roles aren’t just the most accomplished on paper—they are the most intentional about how they prepare, show up, and connect in the moments that matter most—and they explain how you can do the same.

What readers will learn
  • How to clarify your “where and why next” so you pursue roles that truly fit your value and ambition—not just the loudest opportunities.
  • How executive hiring really works behind the scenes—across boards, search firms, references, and investors.
  • How to build a clear, differentiated leadership narrative that stands out among equally qualified peers.
  • How to run your own search process with discipline, from first conversations through offers and exit timing.
  • How to show up in the first 90 days so your new role compounds your impact instead of capping it.
Why it matters now
  • Senior searches are slower, tougher, and more scrutinized than ever, with more candidates, more data, and more stakeholders involved in every decision.
  • A single misstep in transition can set both a leader and a company back years.
  • Most executives still treat their own career decisions less rigorously than their day jobs; this book gives them an end-to-end playbook to match today’s market expectations.

Meet the authors

Kelly O. Kay

Kelly O. Kay is a partner in Heidrick & Struggles’ San Francisco office and the global managing partner of the firm’s Enterprise Software and AI Practice.

With 22 years in executive search, Kelly conducts searches worldwide for a wide range of technology companies, from high-growth private and public enterprises with revenues up to $100 billion.

Kelly specializes in senior go-to-market leadership roles, including board, CEO, COO, CRO, and worldwide sales. He co-founded Heidrick’s Sales & Commercial Officers Practice and is a leading voice on executive talent trends in B2B software. Before executive search, Kelly was a partner at the Center for Corporate Innovation (CCI), a CEO development and strategy organization sponsored by McKinsey & Co., and earlier held senior roles at IBM Corporation and Gemini Management Consulting.

A sought-after talent adviser and public speaker, Kelly’s writing has appeared in Harvard Business Review, Forbes, and The Wall Street Journal. His HBR article on resignation best practices “Leave Smart, Land Well” was based on a national survey of more than 6,000 CHROs and senior executives and became one of the publication’s most widely read
pieces on executive career management.

Kelly holds an MBA from the University of Southern California’s Marshall School of Business and a bachelor’s degree in Marketing from the University of San Francisco.

Jeff Sanders

Jeff Sanders is a vice chair and co-managing partner of the Global CEO & Board of Directors Practice at Heidrick & Struggles.

A member of the firm’s Global Management Committee, Jeff has spent nearly three decades specializing in CEO and board succession for some of the world’s most consequential organizations.

Jeff has led CEO and board searches for companies including Adobe, Airbnb, Apple, BlackRock, Dell, Home Depot, Microsoft, Salesforce, ServiceNow, Starbucks, Uber, and Visa, among many others. He has also advised leading private equity and venture capital firms on portfolio company executive talent, including Accel Partners and Benchmark.

Fortune named Jeff to its “40 Under 40—Ones to Watch” list in 2010, and BusinessWeek named him one of the “100 Most Influential Executive Recruiters in the World.”

He has authored widely read articles on CEO succession planning, board selection, and executive transitions, including for Forbes and Directors & Boards. He serves on the board of trustees for Catholic Charities of New York.

Jeff holds a Bachelor of Business Administration from the University of Arizona and joined Heidrick & Struggles in 1997.

Media inquiries

For media inquiries, please contact Bianca Wilson.

Bulk order inquiries

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