Lead Upwards E-Book

Sarah E. Brown

• Herausgeber: John Wiley & Sons
• Kategorie: Fachliteratur
• Sprache: Englisch

Seitenzahl: 382

Veröffentlichungsjahr: 2022

Beschreibung

In Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, startup marketing leader Sarah E. Brown delivers an illuminating and accessible guide to maximizing your impact and delivering results in a startup leadership role. The author draws on over a decade of experience scaling SaaS companies as she explains how to prepare for, earn, and succeed in an executive role at a startup company.

The book describes every step on the way to realizing your goals—and the goals of your startup—as you navigate the gap between a management role and the executive team. It covers what to do in your first 90 days, how to build and sustain a healthy team culture, and the art of communicating results to your leadership team and board. You’ll also learn:

• How to manage the challenges posed by leading a remote, distributed, or hybrid team
• Management strategies based on inclusive and diverse teambuilding, alignment with business objectives, and inspirational leadership
• Effective ways to level up your skills and stay current as your company grows

A must-read book for current and aspiring executives at startup firms, Lead Upwards will also earn a place on the bookshelves of startup board members, founders, funders, and managers seeking a singularly insightful discussion of business leadership.

Leseprobe

Table of Contents

Cover

Title Page

Copyright

Dedication

Introduction: Why Startup Leadership Matters at Every Levelintroduction

NOTES

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

PART II: GETTING STARTED: NAIL YOUR FIRST 90 DAYS

CHAPTER SIX: Define Your Goals and Align with Your CEO and Board on Success

YOUR FIRST 90 DAYS: ONBOARDING TO YOUR NEW ROLE AND PROVING YOUR VALUE TO THE ORGANIZATION

DON'T BE SHY ABOUT MAKING AN IMPACT RIGHT AWAY

GET POINTS ON THE BOARD EARLY BY FOCUSING ON ACCOMPLISHING SEVERAL LOW EFFORT, HIGH IMPACT INITIATIVES IN YOUR FIRST 90 DAYS

WORK WITH YOUR CEO TO IDENTIFY SUCCESS

“ARE WE SEEING THE SAME GAME?”

ADVICE FROM A CEO TO STARTUP EXECUTIVES: REMEMBER THAT THE CEO ROLE IS TOUGH

ONBOARDING SUCCESSFULLY AS A STARTUP LEADER REQUIRES BALANCING SHORT‐TERM WINS WITH LONG‐TERM PRIORITIES

SETTING YOUR OBJECTIVES AND KEY RESULTS (OKRs)

SETTING OKRs—EXAMPLE: SAMPLE MARKETING OKRs

OKRs AND BONUS COMPENSATION

DELIVERING YOUR FIRST QUARTERLY BUSINESS REVIEW (QBR)

HERE'S A GUIDE FOR WHAT TO INCLUDE IN YOUR FIRST 90‐DAY QBR PRESENTATION

NOTE

CHAPTER SEVEN: Build Key Relationships: CEO, Board, Team

BUILDING A RELATIONSHIP WITH YOUR CEO AND/OR CO‐FOUNDER

HERE'S A SAMPLE CEO 1:1 AGENDA

BUILDING TRUST WITH YOUR CEO: VALUES ALIGNMENT

SET UP COMMUNICATION EXPECTATIONS WITH YOUR CEO AND LEADERSHIP TEAM

GET TO KNOW YOUR CROSS‐FUNCTIONAL PARTNERS AND BUILD RAPPORT

LEARN HOW YOUR KEY STAKEHOLDERS LIKE TO WORK

DON'T BE AFRAID TO DISAGREE—RESPECTFULLY

WHY COMPANIES BRING IN “BIG COMPANY EXECUTIVES” AND HOW TO WORK WITH THEM IF YOU'RE COMING FROM A STARTUP BACKGROUND

BUILDING STRONG RELATIONSHIPS WITH YOUR BOARD

MANAGING TO YOUR BOARD'S EXPECTATIONS

LEARN THE INTERESTS, HOBBIES, AND FAMILY MEMBERS OF YOUR EXECUTIVE TEAM

NOTE

CHAPTER EIGHT: Know Thyself: Strengths, Weaknesses, and Areas to Improve

YOUR RELATIONSHIP WITH YOURSELF AS A STARTUP LEADER

IDENTIFYING YOUR STRENGTHS

WEAKNESSES: THINGS THAT MAKE YOU FEEL IMPOSTER SYNDROME UNTIL YOU ADDRESS THEM

EXPECT TO HIRE AROUND YOUR WEEKNESSES BUT SEEK TO UNDERSTAND THEM AND NOT AVOID THEM

UNDERSTANDING HOW TO HANDLE WEAKNESSES

MEASURING YOUR EFFECTIVENESS AS AN ENGINEERING LEADER: GET HONEST ABOUT YOUR SKILLS AS YOU TRY TO LEVEL UP

BEING HONEST ABOUT OUR STORTCOMINGS: ENTREPRENEUR RAND FISHKIN'S PERSPECTIVE

IDENTIFY: WHAT ARE YOU NOT STRONG AT THAT YOU'LL WANT TO IMPROVE?

HIRING FOR COMPLEMENTARY SKILLS

GOING DEEPER: GETTING TO KNOW OUR MOTIVATIONS

FOCUSING ON ADDING VALUE, REGARDLESS OF TITLE

EMBRACE IMPROV AS A WAY TO BECOME A MORE PRESENT, COLLABORATIVE LEADER

GET TO KNOW YOURSELF THROUGH “PERSONAL RETROSPECTIVES”

UNDERSTANDING OUR PRIVILEGE AND HOW IT IMPACTS OUR WORK

EMBRACING ALL OF OURSELVES, INCLUDING OUR “SHADOW” SIDES

ARE YOU OUTSOURCING A PART OF YOURSELF TO YOUR TEAM?

CREATING HEALTHY BOUNDARIES

NOTES

CHAPTER NINE: Learn the Company Culture and Define It with Your Team

UNDERSTANDING STARTUP VALUES

COMPANY VALUES DRIVE BEHAVIOR

OTHER WAYS CULTURE IS IMPACTED BY VALUES

BUILDING TRUST AMONG YOUR TEAM AS A STARTUP LEADER

CREATING A CULTURE THAT ISN'T “ALWAYS‐ON”

CREATING INCLUSIVE TEAMS WHERE INDIVIDUALS FROM DIVERSE BACKGROUNDS CAN EXCEL TOGETHER

CREATING “BALANCE” ON TEAMS

CREATING HEALTHY WORK EXPECTATIONS THAT SUPPORT INCLUSIVITY AMONG YOUR TEAM

CULTIVATE PSYCHOLOGICAL SAFETY ON YOUR TEAMS

COMPASSIONATE BOSSES MAKE PEOPLE'S LIVES BETTER, SO ASPIRE TO BE ONE OF THEM

GET TO KNOW YOUR TEAM AS INDIVIDUALS

NOTES

PART III: BUILDING AND MANAGING YOUR TEAM AND DEPARTMENT

CHAPTER TEN: Recruit Smart and Build Belonging

RECRUITING NEW TEAM MEMBERS

WHAT TO DO IF YOU'VE INHERITED A TEAM

HIRING YOUR TEAM

DESIGNING YOUR ORGANIZATION CHART

HIRING TIP: CREATE A SCORECARD

REDUCING BIAS IN THE HIRING PROCESS

CULTIVATING EQUITABLE, DIVERSE, AND INCLUSIVE TEAMS

HIRING PEOPLE: HOW TO RETAIN TALENT ON YOUR TEAM IN TODAY'S COMPETITIVE LABOR MARKET

NOTES

CHAPTER ELEVEN: Alignment: Set the Strategy to Get Your Team Working Toward the Same Vision and Goals

HELP YOUR TEAM TO UNDERSTAND THE MISSION AND THE “WHY” BEHIND THE STRATEGY

SETTING OKRS WITH YOUR TEAM

BONUSES TIED TO OKRS

UNDERPERFORMING TEAM MEMBERS

GET IN THE WEEDS IN ORDER TO UNDERSTAND THE NATURE OF PROBLEMS

LEAD WITH THE BEHAVIOR YOU WANT TO SEE

CONFLICTS ON YOUR TEAM: HOW TO IDENTIFY AND WORK THROUGH THEM

PAY ATTENTION TO THE DETAILS LONGER THAN FEELS NECESSARY

NOTES

CHAPTER TWELVE: Attunement: Creating a Culture Where People Contribute Their Best Work

BEGIN WITH THE GOAL IN MIND: EMPLOYEE EMPOWERMENT

MAKE BUILDING A HEALTHY CULTURE A TEAM PRIORITY

TEAM EMPOWERMENT STARTS WITH BUILDING TRUST

GET SUPPORT ALONG YOUR JOURNEY THROUGH A SUPPORT CIRCLE

ENSURE YOUR TEAM HAS ENOUGH RESOURCES TO BE SUCCESSFUL

LET YOUR TEAM KNOW YOU, TO THE DEGREE YOU FEEL COMFORTABLE WITH

EMPOWERING YOUR TEAM TO DELIVER AND LET GO OF TASKS IN YOUR “ZONE OF EXCELLENCE”

BUILD PSYCHOLOGICAL SAFETY BY CREATING AN ENVIRONMENT WHERE MISTAKES ARE HANDLED WITH CARE, NOT BLAME

CONSIDER INSTITUTING A “NO MEETING” DAY

A WORD ON BEING A MEMBER OF AN UNDER‐REPRESENTED GROUP AND NAVIGATING MAKING MISTAKES

CREATE A ROADMAP WITH INDIVIDUAL PREFERENCES AND AGREEMENTS FOR WORKING TOGETHER AS A TEAM

NOTE

CHAPTER THIRTEEN: Building a High‐performance Team Culture

STEPS TO BUILDING A CULTURE OF SUCCESS

CREATING A PERFORMANCE CADENCE WITH YOUR TEAM

THE 1:1S WITH YOUR DIRECT REPORTS

CREATE BETTER 1:1S BY ASKING BETTER QUESTIONS

GOAL SETTING AND OKRs

CARVE OUT TIME TO TALK CAREERS AND GIVE FEEDBACK

SMALL GESTURES ADD UP TO A CARING MANAGEMENT STYLE

MEETINGS: HOW MANY DO YOU REALLY NEED TO BE IN?

IS THIS MEETING SET UP TO FAIL? HERE ARE WARNING SIGNS THIS WON'T BE A PRODUCTIVE MEETING

MANAGEMENT TIP: DON'T SEND “CAN WE TALK” MESSAGES TO YOUR TEAM

BE EMPATHETIC TO WHAT PEOPLE ARE GOING THROUGH WHILE SETTING HEALTHY BOUNDARIES

BUILD FEEDBACK INTO YOUR REGULAR COMMUNICATION AND PROCESSES

BEWARE THE PITFALLS OF “SKIP LEVELS”

SOLVING CONFLICTS ON YOUR TEAM

ENSURING YOUR TEAM (INCLUDING YOU) TAKES ADEQUATE TIME OFF

TAKE TIME TO REALLY UNPLUG YOURSELF TO SHOW YOUR TEAM THAT'S THE CULTURE

CULTIVATE AS FLEXIBLE A WORK ENVIRONMENT AS POSSIBLE

EMBRACE FEELINGS WHILE ESTABLISHING HEALTHY BOUNDARIES AROUND HOW YOU DEAL WITH THEM

DEFINING SUCCESS AND TRUE OWNERSHIP

GET YOUR REPORTS TO THINK LIKE OWNERS

A NAVY VETERAN SHARES THE CASE AGAINST COMMAND AND CONTROL LEADERSHIP

HAVE YOUR TEAM'S BACK

LET YOUR TEAM KNOW IT'S SAFE TO MAKE MISTAKES, AS LONG AS THEY LEARN FROM THEM

TEACH YOUR TEAM TO PROBLEM‐SOLVE AND LET THEM DO THINGS IN DIFFERENT WAYS THAN YOU WOULD

IF YOU'RE GOING TO BE A MANAGER, DECIDE TO CARE ABOUT PEOPLE PROBLEMS

INVEST IN LEARNING HOW TO BECOME A MORE INCLUSIVE LEADER

HAVE FUN AS A TEAM!

PRACTICE REPAIR AND BUILD IT INTO YOUR TEAM RHYTHM

DO RETROSPECTIVES TO ENSURE THE TEAM SHARES THEIR VOICES AND GROWS WISER

RETROSPECTIVE PROCESS (START–STOP–CONTINUE)

NOTES

PART IV: MANAGING YOURSELF AND YOUR EXECUTIVE COMMUNICATION

CHAPTER FOURTEEN: Level Up to Scale with Your Startup

MAKE AN INVENTORY OF THE THINGS YOU'D LIKE TO WORK ON

HOW TO GET THE MOST OUT OF WORKING WITH AN EXECUTIVE COACH

BEYOND COACHING: THERAPY IS A GREAT OPTION

YOUR GROWTH IS UP TO YOU

CHAPTER FIFTEEN: Leading in a Post‐covid World

AS THE WORLD HAS CHANGED, PRIORITIES HAVE SHIFTED FOR MANY OF US

SINCE REMOTE WORK IS HERE TO STAY, HERE'S HOW TO DO IT: IDENTIFY AND SOCIALIZE THE SYSTEMS YOU'LL USE FOR COMMUNICATION AND TRACKING WORK

PLAN TO WORK AROUND TEAMS' SCHEDULES AND TIME ZONES

CREATE PREDICTABILITY IN YOUR OPERATING CADENCE

LEVERAGE OKRs TO KEEP EVERYONE ALIGNED

TAKE EXTRA TIME TO CHECK IN ON HOW PEOPLE ARE DOING

SET SAFETY PROTOCOLS AND CONSIDER HIRING A COVID SAFETY OFFICER TO GATHER IN PERSON

JOSH ASHTON'S STORY: LEADING HIS TEAM AS CHIEF PEOPLE OFFICER AT TRINEO DURING THE PANDEMIC

REMEMBER THAT EVERYONE IS STRUGGLING WITH SOMETHING DIFFERENT

NOTES

CHAPTER SIXTEEN: Managing Up: How to Work with Your CEO and Board

WORK WELL WITH YOUR CEO BY UNDERSTANDING THEIR PREFERRED WORK STYLE: FOUNDER HITEN SHAH'S STORY

NOTE: YOUR CEO MAY NOT BE AWARE OF ALL OF THEIR PREFERENCES (BUT THEY STILL HAVE THEM)

GETTING TO KNOW THE BOARD BY CONNECTING DIRECTLY WITH AT LEAST ONE MEMBER

ALWAYS BE CONCISE IN YOUR COMMUNICATION WITH YOUR BOARD

NICK MEHTA'S ADVICE: FOCUS ON THE METRIC THAT THE BOARDS CARE MOST ABOUT

MANAGE YOUR TIME WELL DURING THE BOARD MEETING

UNDERSTANDING WHAT YOUR BOARD REALLY CARES ABOUT

A WORD OF ADVICE: DON'T OVER‐PROMISE TO THE BOARD

CHAPTER SEVENTEEN: When Things Go Pear‐shaped: Navigating Challenges, Setbacks, Failure, and Departures

LEARN TO PRACTICE COMPASSION TOWARDS YOURSELF WHEN DIFFICULTY AND FAILURE HAPPEN (BECAUSE THEY WILL)

PRACTICE SELF‐COMPASSION WHEN THINGS ARE HARD AT WORK

UNDERSTAND THAT PEOPLE REACT DIFFERENTLY UNDER STRESS

TREAT PEOPLE WITH RESPECT, ALWAYS

WHAT TO DO IF A COLLEAGUE QUESTIONS YOUR IMPACT

IF YOU FAIL AND GET LET GO, OR MESS UP IN A BIG WAY, YOU STILL BELONG IN THE STARTUP WORLD AND YOU'RE GOING TO BE OK

WHEN YOU GET PASSED OVER FOR A PROMOTION OR A ROLE

NORMALIZING SET‐BACKS AND GIVING YOURSELF PERMISSION TO FAIL AND LEARN

IS IT TIME TO CALL IT QUITS? NO ONE GETS TO DECIDE WHEN YOU STOP BEING A STARTUP LEADER BUT YOU

REFRAMING FAILURE AS ANOTHER LEARNING OPPORTUNITY

OTHER TYPES OF SETBACKS

OTHER THINGS THAT CAN GO WRONG AND HOW TO DEAL WITH THEM

ADVERSITY IN THE STARTUP WORLD IS A FEATURE, NOT A BUG

NAVIGATING PIVOTS SUCCESSFULLY AS A STARTUP LEADER

TREAT PIVOTS AS A CHANCE TO BECOME A BETTER COMPANY

IN TIMES OF CRISIS, UNDERSTAND YOUR CIRCLE OF CONTROL

STAY AND ACCEPT, TRY TO CHANGE THINGS, OR LEAVE?

IN TIMES OF MAJOR CHANGE, CONSIDER HAVING AN “ON THE BUS OR OFF THE BUS” CONVERSATION WITH YOUR TEAM

IF YOU STAY, KNOW YOU WON'T AGREE WITH ALL DECISIONS

TURNING A STARTUP PIVOT INTO A STARTUP LEADERSHIP ADVANCEMENT OPPORTUNITY: MINDY LAUCK, CEO OF BROADLY

DON'T TRIANGULATE: IDENTIFY “YOU TWO” PROBLEMS

ON THE FAME/BLAME CYCLE—WHEN THE HIGHS ARE HIGH AND THE LOWS ARE LOW

DEPARTURES: WHEN IT'S TIME TO MOVE ON FROM YOUR ROLE

DECIDING WHEN IT'S TIME TO MOVE ON

QUESTIONS YOU CAN ASK WHEN DECIDING WHETHER TO LEAVE YOUR EXECUTIVE ROLE

HOW TO LEAVE A ROLE LIKE AN EXECUTIVE

HOW TO GIVE NOTICE

WHEN YOU GIVE NOTICE: BE PREPARED TO BE ASKED TO CLOSE YOUR LAPTOP ON THE SPOT

A WORD OF ADVICE: RESPECT THE COMPANY'S INTELLECTUAL PROPERTY (IP) AND DON'T TAKE IT UPON DEPARTURE

ANOTHER WORD OF ADVICE: BE CAREFUL ABOUT POACHING EMPLOYEES (AT LEAST RIGHT AWAY)

EXERCISING YOUR VESTED EQUITY AROUND YOUR DEPARTURE

TAKING TIME OFF IN BETWEEN JOBS

MAKE A COMMUNICATION PLAN

KEEP IT POSITIVE

BEWARE THE “DILBERT PRINCIPLE” AND LEAVE WITH GRACE ANYWAY

NOTES

PART V: PROVING, SUSTAINING, AND EXPANDING YOUR IMPACT AS A LEADER

CHAPTER EIGHTEEN: Measuring Success: How to Know If Things Are Working

WHO CARES ABOUT LEADING AND LAGGING INDICATORS?

UNDERSTANDING THE METRICS THAT SET UP YOUR DEPARTMENT FOR SUCCESS

FOCUS ON MEASURES THAT SHOW OUTCOMES VS. ACTIVITY

GETTING COMFORTABLE WITH QUANTITATIVE MEASUREMENT TOOLS

HOW THE BOARD THINKS ABOUT YOUR INDICATORS

MEASURE WHAT COUNTS AT A REGULAR CADENCE

OTHER “SUCCESS” MEASURES

LETTING LEADING INDICATORS GUIDE YOUR EARLY‐STAGE STARTUP GROWTH

RAND FISHKIN'S ADVICE FOR METRICS: KEEP IT SIMPLE

HOW TO WORK WITH YOUR CEO ON MEASURING YOUR PERFORMANCE

BUILDING ACCOUNTABILITY INTO YOUR TEAM REPORTING

CHAPTER NINETEEN: Communicating Your Results to Your CFO, CEO, Company, and Board

WHY BOARD MEETINGS EXIST (AND NO, THEY'RE NOT JUST TO TORTURE STARTUP FOUNDERS AND EXECUTIVES!)

COMMUNICATING AT THE BOARD LEVEL

COMMUNICATING AT THE “ALTITUDE” OF THE BOARD

HOW IS YOUR BUSINESS PERFORMING WITHIN THE CONTEXT OF THE GREATER MARKET (OR THE VC'S PORTFOLIO?)

DO YOUR HOMEWORK

BUILD RELATIONSHIPS WITH THE BOARD PRIOR TO YOUR FIRST MEETING

TAKING A STORYTELLING APPROACH TO BOARD PRESENTATIONS

COMMUNICATE WITH YOUR DEPARTMENT TEAM TO GET WHAT YOU NEED FROM THEM

CREATING YOUR BOARD SLIDES: THINK AT A HIGH ALTITUDE

HOW TO CREATE YOUR BOARD SLIDES

EXAMPLE DEPARTMENT OKR SNAPSHOT SLIDE REPORTING RESULTS WITH R/Y/G

OTHER TYPES OF SLIDES TO INCLUDE IN YOUR BOARD DECK

THE PURPOSE OF YOUR APPENDIX AND/OR PRE‐READ MATERIAL

TIP: ENSURE EVERY SLIDE HAS A NARRATIVE‐DRIVEN TITLE

PRESENTATION TIPS: BEFORE, DURING, AND AFTER THE BOARD MEETING

CHAPTER TWENTY: Mentorship: How to Further Grow Your Career by Networking and Giving Back

MENTORSHIP POWERS THE STARTUP ECOSYSTEM

MENTORSHIP'S ROLE IN SUPPORTING DEVELOPING LEADERS

MENTORSHIP IS ABOUT KNOWLEDGE AND CHEMISTRY

MENTORS DON'T HAVE TO KNOW ALL OF THE ANSWERS

ENLISTING YOUR OWN MENTORS: DEVELOPING A GROUP OF PERSONAL ADVISORS

MENTORS CARE ABOUT YOU PERSONALLY AND CAN KEEP YOUR PRIORITIES STRAIGHT

SEEK MENTORSHIP THAT PROMOTES EQUALITY

SIGN UP TO MENTOR AT AN ACCELERATOR

MENTOR THROUGH AN OFFICIAL ORGANIZATION

FIND COMMUNITY AND SHARE MUTUAL SUPPORT AS A “PEER MENTOR”

AFFINITY ORGANIZATIONS

OTHER TYPES OF SUPPORT: SPONSORSHIP AND COACHING

DON'T DISCOUNT INFORMAL MENTORSHIP

TAKE MENTORSHIP TO THE NEXT LEVEL: SCALE YOUR IMPACT

AFTERWORD

ACKNOWLEDGMENTS

ABOUT THE AUTHOR

INDEX

End User License Agreement

Guide

Cover Page

Title Page

Copyright

Dedication

Introduction: Why Startup Leadership Matters at Every Level

Table of Contents

Begin Reading

AFTERWORD

ACKNOWLEDGMENTS

ABOUT THE AUTHOR

INDEX

WILEY END USER LICENSE AGREEMENT

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SARAH E. BROWN

LEAD UPWARDS

HOW STARTUP JOINERS CAN IMPACT NEW VENTURES, BUILD AMAZING CAREERS, AND INSPIRE GREAT TEAMS

Copyright © 2022 by Sarah E. Brown. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey.

Published simultaneously in Canada.

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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.

Introduction: Why Startup Leadership Matters at Every Level

So, why haven't you been an executive before? It looks like you were qualified years ago.

The venture capitalist's remarks were part of his due diligence in determining whether the early‐stage startup he invested in should hire me for a marketing leadership role. But upon hearing his backhanded compliment, my heart sank. While I was grateful for his affirmation that I was qualified to be considered for the position we were discussing, it made me wonder: why had I waited when my resume suggested I had enough experience for a startup executive position years earlier?

Fast forward several years later, and I'm a vice president of marketing at an early‐stage venture—a startup executive. That conversation with the VC was a wake‐up call, motivating me to learn how to transition from mid‐level manager to department leader, which I have done thanks in great part to the support of my executive coach, friends, my CEO, and peer network.

In hindsight, I didn't aspire to become a startup executive earlier in my career because I didn't know it was possible. I didn't understand what qualifications were required or which skill gaps I might need to address. I knew that there was a startup leadership tier I wasn't yet part of, but I didn't know how to reach it. I was also unable to picture myself as a startup executive, with so few role models in the industry who were like me, an openly LGBTQ+ woman. Lack of visibility does make a difference and can be a self‐perpetuating cycle.

Although we've seen progress in recent years, the technology industry is still overwhelmingly homogeneous at the leadership level. At the time of publishing, nearly half of all startups don't have a single woman on their executive teams.1 A 2019 study from the National Center for Women and Information Technology (NCWIT) shows that while women are about 60 percent of the total workforce in the US, they are only 25 percent in the computer technology industry.2

Within tech, people of color are fewer and egregiously rare in startup leadership. According to a study conducted by the Ascend Foundation, numbers of Black women in tech declined by 13 percent from 2003 to 2017.3 According to Deloitte, approximately 2 percent of the tech workforce is Black, 3 percent is Latino or Latina.4 Note: for a book specifically focused on the challenges women of color in tech face that includes fantastic resources; I highly recommend Susanne Tedrick's book Women of Color in Tech: A Blueprint for Inspiring and Mentoring the Next Generation of Technology Innovators.

The information technology industry is one of the crucial drivers of economic prosperity worldwide. It is a multi‐trillion dollar industry.5 In 2021, the global cloud computing market alone was worth $270 billion. The tremendous wealth and opportunity in technology have been unevenly distributed. Inclusivity at all levels of startups drives economic equality.

I didn't have a great response for the investor all those years ago, but if I could go back in time, I would share these statistics with him (and my younger self), about systemic challenges that historically have led to capable, qualified people from under‐represented backgrounds being under‐represented in startup leadership. I would have also thanked him for inadvertently pushing me to see myself as the kind of startup leader I'd always wanted to be but didn't believe was possible.

Early in my career, I developed a passion for B2B SaaS and the cloud and its promise to provide tremendous value to businesses and users across the ecosystem. I've been a B2B SaaS marketer ever since. More than a decade later, I still love the space and feel grateful to be a part of it. At the time of publishing, I've had the privilege of being a marketing leader at five startups that have been sold for more than $300 million combined.

Along the way, I became interested in improving diversity and inclusion throughout our startup ecosystem. I founded an LGBTQ+ technology group called Flatirons Tech in Boulder, CO, which is part of the NCWIT Affinity Group Alliance and partners with startups and global technology companies like Google, Splunk, Twilio, Twitter, Workday, and other technology companies to increase tech inclusion across the Front Range and beyond. I've also become a mentor at Techstars, a global accelerator with more than $19 billion in market cap, and Backstage Capital, which funds and champions founders from under‐represented backgrounds. Both organizations aim to increase inclusion within the startup landscape. I've discovered a calling supporting joiners from under‐represented backgrounds, and helping us achieve our best careers and lives possible within the startup ecosystem.

The startup road isn't easy. A startup career can be rewarding, but navigating it can be challenging and confusing, as few resources exist to help startup employees advance. Unlike established companies, startups are disrupting markets or creating new ones, and career trajectories are often nonlinear. Startup employees must forge their own paths.

As they grow and mature, startups are expected to behave more like enterprises, and this presents a challenge and an opportunity for rising leaders. How do you scale your own leadership to meet the demands of the market, including customers and shareholders, as your company grows?

There were more than 12 million tech employees in the US in 20196 and more than 800,000 technology startups operating in the US alone in 2020.7 Most startup resources focus on helping founders and chief executive officers succeed. But for every CEO at a startup, there are multiple executives charged with leading and scaling the company's departments. Forbes reports that Leadership Development is a $366 billion industry, yet surprisingly few resources aim directly at helping startup executives succeed in their roles, which can be challenging and with high turnover. According to industry group Pavilion, the average tenure for a startup revenue executive is just 16 months.8

As the people who oversee making and selling products that are forging our future, CEOs and founders aren't the only ones making an impact. For every founder, there are many people who are “startup joiners,” a term coined and popularized by venture capitalist and author Jeffrey Bussgang. Startup joiners have the power to shape their companies and the market. This book offers advice about being a top performer in a startup leadership role, whether you're already one, or are looking for your first executive‐level job.

Perhaps you're a manager or director at a startup and would like to know how to transition into an executive role. I want to demystify what the role entails to do it well. I will also share the skills, experiences, deliverables, and presentations that a startup executive needs to know how to execute in order to be successful, including presenting at your first board meeting or creating an annual plan for your department and getting cross‐functional stakeholder buy‐in. You might already be a startup executive, and want more tips and advice for being successful at navigating an ever‐changing startup environment.

This book includes real‐world stories from leading executives, venture capitalists, and founders, alongside frameworks and practical guidance that executives outside the CEO role can benefit from. It shares clear frameworks for success, practical advice, in‐the‐trenches stories, and crucial guidance that will help current and aspiring startup leaders land and excel in their roles.

Doing well in this environment takes a special set of skills. This book describes how to navigate predictable, crucial executive areas, such as how to land your first executive role at a startup, succeed within your first 90 days on the job, how to manage relationships with your CEO, team, fellow executives, and board of investors. It also discusses how to scale your impact and role as your company grows, and navigate challenges and setbacks.

After reading this book, you'll have insights into the following questions:

What is it really like to be a startup executive?

How will I know if I have what it takes or even want to be a startup executive?

What differentiates startup executive roles from management or other contributor roles, and what does it take to make the leap?

How can I leverage my nonlinear path or under‐represented background to become a startup leader?

How do I manage my first 90 days in a startup executive role successfully?

What does it take to effectively manage my team and myself in our remote, post‐Covid world?

How do I successfully communicate my results to our CEO or our board?

How can I scale my impact with the company as the company grows?

While this book is not by any means exhaustive, it should help you make more sense of the world of tech startup leadership and make better decisions about your career along the way. I believe making the successful leap from startup manager or director to executive should be demystified to make the path more accessible and inclusive to the widest and most diverse range of talent. New employees look at the executive team to see if it is inclusive at the highest levels; this book specifically addresses barriers for under‐represented leaders and how to overcome them.

Becoming an executive should be within reach of far more rising startup leaders. I hope to help empower the next generation of executives with tools to excel. For those who lead startup joiners, the founders and investors, this book provides tools for supporting, promoting, and fostering executive talent. Stronger leaders benefit our entire startup ecosystem. It's time that we focus on up‐leveling the next generation of startup leaders, which this book aims to do through the inclusion of relevant case studies, examples, voices from startup leaders from diverse backgrounds, with tested, practical advice readers can put to use in their own careers on their journeys to “lead upwards.” Let's get started!

NOTES

1.

   Silicon Valley Bank (n.d.), “Half of Startups Have No Women on Their Leadership Team.” Sil Retrieved October 5, 2021, from:

https://www.svb.com/trends-insights/reports/women-in-technology-2019#:~:text=Just%2056%20percent%20of%20startups,the%20UK%2C%20China%20and%20Canada

.

2.

   Tedrick, S. (2020),

Women of Color in Tech: A Blueprint for Inspiring and Mentoring the Next Generation of Technology Innovators

. John Wiley & Sons, Inc., p. viii.

3.

   Ibid.

4.

   “Women in IT: Five Strategies for Making it to the Top,” Deloitte United States, August 2, 2018. Retrieved October 5, 2021, from:

https://www2.deloitte.com/us/en/pages/technology-media-and-telecommunications/articles/women-in-it.html

.

5.

   CompTIA (n.d.).

2020 IT “

Information Technology) Industry Trends Analysis: Business of Technology: Comptia.” Retrieved October 5, 2021, from:

https://www.comptia.org/content/research/it-industry-outlook-2020#:~:text=Industry%20Overview,to%20the%20research%20consultancy%20IDC

.

6.

   Mendoza, N. F. (2020, April 21), “US Tech Industry Had 12.1 Million Employees in 2019,”

TechRepublic

. Retrieved November 6, 2021, from:

https://www.techrepublic.com/article/us-tech-industry-had-12-1-million-employees-in-2019/

.

7.

   Statista Research Department (2021, January 20), “New Entrepreneurial Businesses U.S. 2020.

Statista

. Retrieved November 6, 2021, from:

https://www.statista.com/statistics/235494/new-entrepreneurial-businesses-in-the-us/

.

8.

   Written by Chris Orlob, who is a Director of Sales at Gong.io. (2019, January 17). “The VP Sales’ Average Tenure Shrank in 7 Months—Here's Why. Gong.” Retrieved November 6, 2021, from:

https://www.gong.io/blog/vp-sales-average-tenure/

PART IBECOMING A STARTUP EXECUTIVE

CHAPTER ONEWhat It's Really Like to Be an Executive at a Startup—and How It's Different from Being a Director or Manager

Is being a startup executive really that different from being a manager or director? Yes. But probably not in the ways you think.

Prior to becoming a startup executive, my view into the role was limited. I saw how the “executives” behaved in our one‐on‐one meetings and while presenting to our entire company during all‐hands meetings. I noticed how they emailed, messaged, and comported themselves at the office. I observed how they spoke in our companies' all‐hands and how they behaved at holiday parties. I watched them, as most startup employees do their leaders. (If you're reading this, know that people are paying attention to your behavior.) But my view wasn't close to the full picture of what their roles demanded.

At various companies I'd worked for, many of the executives' calendars were fully booked in meetings so often I wondered how they got any work done. What were they doing during these blocks? Beyond their busyness, I wondered what that translated to in terms of what their jobs required on a day‐to‐day, weekly, or quarterly basis.

Now that I'm an executive, I understand that the bulk of work done by an executives team is challenging to grasp as an individual contributor or even mid‐level manager. While there's been a movement to increase transparency across the startup ecosystem and more companies openly share their operating principles and salaries to their employees and even to the public, much of the inner workings of a startup leadership team are hard to see if you're not a part of it. This chapter covers what a startup executive role involves behind the scenes, including insights from executives on what their work‐life entails on a daily, weekly, and monthly basis.

“The more senior you are, you execute less, and you have to be efficient with your time and need to empower your team to achieve your goals,” says marketing executive Rachel Beisel. “You're in a lot of meetings because you're often the facilitator between departments and between employees in those departments.”

The reason that executives spend so much time in meetings is that decision‐making is their most important responsibility. While startup leaders will always execute to some degree at earlier‐stage companies (including the founders and CEO), their ability to strategize and decide is why they exist at the company.

“As a founder, I have decision fatigue,” said AQUAOSO CEO and co‐founder Chris Peacock. “I expect my executives to constantly make good decisions in their areas, even in the absence of all of the data.”

Executives are charged with managing managers, meaning their direct reports generally have their own reports. This “skip level” hierarchy requires executives to empower their reports to make good decisions and own their areas.

The level of hands‐on work you do as an executive will vary based on your startup's stage and maturity. Early on in a startup, you'll be spending more time on execution, doing things like shipping a new landing page, or editing copy, or creating financial models. These deliverables are a big part of how your success is measured early on. But as your company grows, you'll need to delegate and manage other people who can do those things while you manage their productivity.

WHAT DOES A STARTUP EXECUTIVE REALLY DO?

Each week, executives spend the bulk of their time communicating with each other and their teams to align the strategy and programs with business goals. They collaborate across departments, incorporating new data to adjust the course as needed. Many startup executives who come from working at larger companies struggle with the balance of execution and strategy. You have to “zoom in and out” as executive coach and former Microsoft North America CFO John Rex calls it, and do execution as well as strategic work.

In addition to the general management of others and their team, a startup executive owns a department or “function” and its goals. A department is usually a team of teams and the overall strategy, vision, and goals that this person sets for their department must roll up to the overall business goals, which are translated to their team's sub‐goals.

A STARTUP EXECUTIVE'S SCHEDULE: A WEEK IN THE LIFE, AT A GLANCE

A sample startup executive schedule:

Daily

Checking dashboards to view metrics and results measured against quarterly and/or yearly goals.

Providing feedback to campaigns or other work products of teams within your team, usually at key milestones—early to verify direction (e.g., this product roadmap change aligns to our strategy for the business/team) and “buy‐off” at final stages of delivery (yes, this press release has my seal of approval for publication, and my job is on the line if we screw it up).

Cross‐functional meetings with other executives or departments.

Reading up on the latest news in your market or industry vertical.

CEO syncs and department team meetings.

Checking in on project management updates from your team on Slack, Asana, or another communication tool.

Weekly

1:1 with your direct reports; ensuring your reports and *their* reports are succeeding, and the team is tracking to Objectives and Key Results (OKR); troubleshooting any issues; and tracking their career goals.

Weekly updates cross‐functionally to other teams and your CEO.

Measuring progress against OKRs.

Feedback and/or sign off on key projects in your department.

Monthly

1:1s with your direct reports; ensuring your reports and *their* reports are succeeding, and the team is tracking to OKRs; troubleshooting any issues.

All‐hands presentations to the entire company and/or business unit.

Board updates.

Updates to your CEO and/or cross‐functional stakeholders.

Quarterly

Reporting on a Quarterly Business Review (QBR) and/or Objectives and Key Results (OKRs).

Evaluating strategic decisions weighing performance and/or new data.

Board updates—deck, pre‐read materials, and/or live presentation in a board meeting.

Setting OKRs for the next quarter or half.

Annually

Annual reviews and retrospectives, including reporting wins, failures, and what you've learned to your CEO, fellow executives, and the board.

Annual planning, forecasting, headcount, and budgets.

Financial models and planning—tracking CAC and LTV.

Supporting fundraising efforts.

Performance reviews for your teams and yourself (sometimes semi‐annually).

Your daily, monthly, quarterly, and annual activities depend on the maturity of your department and company. Smaller startups may forgo annual planning and instead rely on quarterly planning cycles. You and your CEO may meet three times per week vs. once, so take the above with a grain of salt. Note: for more detail on running effective 1:1s with your CEO, team, and board, see the chapter on building relationships.

OTHER DIFFERENCES BETWEEN NON‐EXECUTIVE AND EXECUTIVE ROLES

Accountability at the Highest Business Levels

Startup executives are accountable for delivering business results to company shareholders, including your co‐founders, fellow executives, the board and investors (your founders' bosses), and other employees. As an executive, you have the most ownership (including, likely, equity) and accountability of anyone on your team. Unlike individual contributors or mid‐level management, startup executives must build business strategies and execute them. Pavilion leader Jennifer Rice refers to the concept of building business opinions (vs. being an order taker) as “having a theory of business.”

As a marketing executive I am expected to form and communicate data‐driven opinions on how to generate demand within target accounts to increase my startup's market share and grow revenue. My CEO and cross‐functional peers can help and my team will provide input, but, ultimately, I own and put my name on a plan. I need others to believe in the plan, but first I have to believe in it and champion it. When it succeeds or fails, I am the one who's responsible. No one will hand these plans to us to go execute as startup leaders as they did when we were mid‐level managers (although great ideas can and do come from anyone on the team). It's on us to strategize and enable our teams to deliver results.

OWNING THE “WHY” OF THE WORK

As business leader Peter Drucker would say, there is a difference between doing the right work and work done right. Your job is to make sure that the programs, tactics, and tools your team uses roll up to the overall business goals of your organization. Own the “why” of the work—not just “should I run this PR campaign?” but “should we run *any* PR campaigns, and is that the best investment of our limited budget, and why?” This is how executives need to think. You'll constantly be making tradeoffs.

How will your department's strategy and tactics lead to the business achieving goals? What have you learned in previous quarters or even recent weeks and days that informs the work you're doing? These are the types of questions executives are expected to answer. Continuing to think through “why” is just as important as “how.” The best startup leaders constantly learn to improve and achieve faster, better results.

DEPARTMENTAL UNDERSTANDING BEYOND ONE NARROW AREA