Sarah E. Brown - Lead Upwards

1 Cover

2 Title Page SARAH E. BROWN

3 Copyright Copyright © 2022 by Sarah E. Brown. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per‐copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750‐8400, fax (978) 750‐4470, or on the web at www.copyright.com . Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748‐6011, fax (201) 748‐6008, or online at http://www.wiley.com/go/permission . Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Further, readers should be aware that websites listed in this work may have changed or disappeared between when this work was written and when it is read. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762‐2974, outside the United States at (317) 572‐3993 or fax (317) 572‐4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com . Library of Congress Cataloging‐in‐Publication Data is Available: ISBN 9781119833352 (Hardback) ISBN 9781119833376 (ePDF) ISBN 9781119833369 (ePub) Cover Design: PAUL MCCARTHY

4 Dedication Dedicated to Erin Rand, Colleen Blake, and Matt Harada, whose tremendous leadership examples, support, and friendship have profoundly impacted my career trajectory. Also, in memory of my late grandmother Zelda Lipman, who taught me the power of lifelong learning and unconditionally believing in people, including oneself .

5 Introduction: Why Startup Leadership Matters at Every Levelintroduction NOTES

6 PART I: BECOMING A STARTUP EXECUTIVE CHAPTER ONE: What It's Really Like to Be an Executive at a Startup—and How It's Different from Being a Director or Manager WHAT DOES A STARTUP EXECUTIVE REALLY DO? A STARTUP EXECUTIVE'S SCHEDULE: A WEEK IN THE LIFE, AT A GLANCE OTHER DIFFERENCES BETWEEN NON‐EXECUTIVE AND EXECUTIVE ROLES OWNING THE “WHY” OF THE WORK DEPARTMENTAL UNDERSTANDING BEYOND ONE NARROW AREA RESPONSIBILITY FOR BUILDING AND LEADING A HIGH‐PERFORMING TEAM SIMPLY PUT: IT'S A BIGGER COMMITMENT LESS COMPANIONSHIP AND CAMARADERIE WITH OTHER NON‐EXECUTIVE STARTUP EMPLOYEES EXECUTIVES HAVE THE MOST CONTEXT OF ANYONE IN THE DEPARTMENT WHO'S QUALIFIED TO BE A STARTUP EXECUTIVE? WHAT QUALIFICATIONS AND SKILLS ARE ESSENTIAL ON THE JOB AS A STARTUP LEADER MANY SCALING STARTUPS BRING IN LEADERS FROM BIG COMPANIES EXECUTIVE COACH AND FORMER MICROSOFT NORTH AMERICA CFO JOHN REX: ADVICE FOR SCALING STARTUP LEADERS SCALING IS HARD IN BOTH DIRECTIONS LEARN TO DELEGATE WITH CAPABLE TALENT AS YOU SCALE EARLY‐STAGE STARTUP VS. SCALE‐UP LEADERSHIP MINDSET STARTUP LEADERS CAN'T GET STUCK AT 30,000 FEET NOTES CHAPTER TWO: Bridging the Transition from Manager to Executive: How Leaders Got Their First Role MAKING THE LEADERSHIP TRANSITION: YOU DON'T HAVE TO BE “FULLY READY” TO GO FOR IT HOW THEY GOT THEIR FIRST EXECUTIVE ROLE: REAL STORIES FROM STARTUP EXECUTIVES MINDY LAUCK ON BEING A NON‐FOUNDER STARTUP TEAM MEMBER PROMOTED TO EXECUTIVE, AND THEN CEO (TWICE!) CHALLENGE FOR FIRST‐TIME EXECUTIVES: SAM MCKENNA SHARES HER STORY OF BEING PROMOTED TO VICE PRESIDENT OF SALES MAKING THE TRANSITION BY LEARNING TO WORK DIFFERENTLY FROM BIG COMPANY LEADER TO STARTUP EXECUTIVE: COO ERIN RAND'S STORY NAIL THE LEAP: START AS A “HEAD OF” AND MAKE THE TITLE OFFICIAL ONCE YOU'VE PROVEN YOUR SUCCESS CONSULTING AS A PATH TO DE‐RISKING YOUR FIRST EXECUTIVE ROLE NOTE CHAPTER THREE: Understanding and Evaluating Your Fit at Various Startups CHOOSING A STARTUP THAT'S RIGHT FOR YOU WHY QUESTIONS MATTER SOME SAMPLE QUESTIONS TO EXPLORE IN THE INTERVIEW PROCESS OTHER CONSIDERATIONS RESEARCH THE COMPETITION/MARKET RESEARCH THE TEAM THROUGH YOUR CONNECTIONS AND/OR PUBLIC REVIEW SITES LIKE LINKEDIN AND GLASSDOOR ASSESS THE CO‐FOUNDER RELATIONSHIP UNDERSTAND THE STARTUP'S STAGE AND HOW IT ALIGNS WITH YOUR GOALS DO YOU ALIGN WITH THE LEADERSHIP TEAM? OTHER KINDS OF FIT TO LOOK OUT FOR SOME EXAMPLES OF FIT ASSESS THE MATURITY OF YOUR STARTUP'S DIVERSITY AND INCLUSION WHAT'S YOUR STARTUP‐STAGE RISK TOLERANCE? HOW MUCH EXECUTION AND “GETTING YOUR HANDS DIRTY” ARE YOU COMFORTABLE WITH RIGHT AWAY? DETERMINING YOUR IDEAL STARTUP STAGE NOTES CHAPTER FOUR: Landing Your Next Startup Executive Role: Leveling Up Within Your Current Organization or Seeking a Role Elsewhere MY FIRST EXECUTIVE ROLE: JOINING AN EARLY‐STAGE STARTUP AND GETTING PROMOTED TO VP HOW ANALIESE BROWN, VP OF PEOPLE AT CAMPMINDER, GOT PROMOTED INTO HER FIRST EXECUTIVE STARTUP ROLE GENERALIST TO SPECIALIST: HOW TO “COME UP” AS AN EXECUTIVE IN YOUR AREA OF SPECIALIZATION LEARN TO BALANCE THE TACTICAL AND THE STRATEGIC UNDERSTAND BUSINESS AREAS OUTSIDE YOUR “COMFORT ZONE” EMBRACE A LEARNING OR “GROWTH” MINDSET HOW NICOLE WOJNO SMITH, VP OF MARKETING AT TACKLE, GOT HER FIRST EXECUTIVE ROLE BY LEVELING UP WITHIN HER THEN‐ORGANIZATION HOW SMITH “LEVELED UP” BY BUILDING A PARTNERSHIP WITH THE C‐LEVEL TEAM MASTERING DATA‐DRIVEN STORYTELLING AROUND BUSINESS OBJECTIVES GAIN A DEEPER UNDERSTANDING OF CROSS‐FUNCTIONAL PARTNERS AND THEIR ROLES PARTNER CLOSELY WITH YOUR FINANCE LEADERSHIP (UNLESS YOU'RE THE CFO; IN THAT CASE, PARTNER WITH EVERY OTHER EXECUTIVE TEAM) START UNOFFICIALLY RECRUITING YOUR “BENCH” DREAM TEAM FOR YOUR DEPARTMENT LEVELING UP IN THE ENGINEERING SIDE OF THE BUSINESS: JEFF AMMONS LEARNING TO LET GO OF BEING THE ONE TO WRITE CODE AND SHIFTING TO EMPOWERING HIS TEAM ON INTERNAL PROMOTIONS: NICK MEHTA'S PERSPECTIVE AS CEO OF GAINSIGHT GETTING HIRED: LANDING THE ROLE INTERNAL PROMOTIONS TO EXECUTIVE ARE POSSIBLE, BUT NOT AT EVERY COMPANY CHAPTER FIVE: Get the Offer and Secure Your Executive Seat FIND YOUR FIRST (OR NEXT) EXECUTIVE ROLE INTERVIEWING FOR YOUR EXECUTIVE ROLE NAVIGATING THE OFTEN BYZANTINE STARTUP HIRING PROCESS THE INTERVIEW PROCESS UNDERSTAND THE PRESENTATION TECH STACK AND PRACTICE YOUR PRESENTATION WITH FRIENDS MEETING WITH THE CEO: UNDERSTAND THEIR VISION WHEN THE STARTUP'S HIRING PROCESS GOES AWRY GETTING THE OFFER COMPENSATION BREAKDOWN NEGOTIATING THE OFFER DO YOUR RESEARCH RISK VS. REWARD: A NOTE ABOUT EQUITY FIND OUT THE PERCENTAGE OF EQUITY BEING RECEIVED AND ITS CURRENT VALUE UNDERSTAND YOUR VESTING SCHEDULE IN YOUR OFFER HIRE AN ACCOUNTANT AS SOON AS YOU ACCEPT AN OFFER A NOTE ON EARLY‐STAGE EQUITY HIRE A LAWYER TO REVIEW YOUR OFFER LETTER AND CONTRACT NEGOTIATING YOUR TITLE CASH VS. EQUITY: FOOD FOR THOUGHT MORE ON EQUITY AND CAP TABLES FOR UNDER‐REPRESENTED STARTUP LEADERS A WORD: IF THE DEAL GOES SOUTH WHILE YOU'RE IN NEGOTIATIONS AFTER YOU SIGN THE DEAL NOTES