Lead Upwards. Sarah E. Brown
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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 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 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 3. Ibid.
4 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 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 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 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 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/
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
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