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...