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 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
