Lead Upwards

How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams

Sarah E. Brown

• Publisher: Wiley
• Year: 2022
• Print ISBN: 9781119833352
• eBook ISBN: 9781119833369
• Edition: 1
• Topic: Business
• Subtopic: Business General
• Index: Business

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.

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

---

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...

Table of contents

• Cover
• Table of Contents
• Title Page
• Copyright
• Dedication
• Introduction: Why Startup Leadership Matters at Every Levelintroduction
• PART I: BECOMING A STARTUP EXECUTIVE
• PART II: GETTING STARTED: NAIL YOUR FIRST 90 DAYS
• PART III: BUILDING AND MANAGING YOUR TEAM AND DEPARTMENT
• PART IV: MANAGING YOURSELF AND YOUR EXECUTIVE COMMUNICATION
• PART V: PROVING, SUSTAINING, AND EXPANDING YOUR IMPACT AS A LEADER
• AFTERWORD
• ACKNOWLEDGMENTS
• ABOUT THE AUTHOR
• INDEX
• End User License Agreement