Holiday Season Book Pairing Recommendation: Startup CXO + Lead Upwards

As the winter holiday season kicks off, I’m still smiling from a fireside chat I had the privilege of co-hosting a few weeks ago with the one and only startup CEO and author Matt Blumberg and the fantastic team at Bolster, including Cathy Hawley and Andrea Ponchione. 

The chat was a conversation between Matt and me focused on topics in our complementary books, Matt’s outstanding Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams and my book Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams.

I’ve long admired Matt and his work and have dogeared copies of each of his books on my shelves, including the excellent new Second Edition of Startup Boards by Brad Feld, Mahendra Ramsinghani, and Matt Blumberg.

As a primer for startup leaders who want to succeed in their functions, and for startup CEOs and others who want to better manage their CXOs/build functions up, Startup CXO is an invaluable resource. I wrote Lead Upwards hoping that it would be a helpful way finder for people like me – growing startup executives who want to make an impact. CXO is an essential exec startup leadership functional guide, and our books as companion reading just makes sense.

Holiday gift idea: Startup CXO by Matt Blumberg and Lead Upwards by Sarah E. Brown

Order Startup CXO HERE and Lead Upwards HERE

Matt, the Bolster team, and I had the idea to host our session as a fireside chat in order to explicitly put our experiences and our books in conversation, calling it “Startup Leadership: Startup CXO Meets Lead Upwards,” tackling topics for startup leaders like:

  • Career Progression – creative paths/journeys we’ve seen to the executive level in startups and why those paths work.
  • “Managing the CEO” – As a startup leader, how do you manage the work relationship with your CEO? As a CEO, how do you attune to your teams and decide the cases it’s time they attune to you? Is it certain roles that must attune to you (ex. An EA) but your direct reports you learn their styles?
  • How to quit as a CXO or let a CXO go – Two weeks’ notice is not the way to go, as Matt and I agree. Executives can’t just up and quit with “two weeks’ notice” — AND executives need to be mentally prepared to be shown the door when they resign. Also, as a CEO, how do you know when an exec isn’t scaling or working out? How do you think about exiting them from the business?
  • And more!

[Watch The Recording] Startup Leadership: A Fireside Chat

I hope you enjoy these as a part of your holiday reading for yourself or perhaps as a gift to your team. Full disclosure: Matt and I share the same incredible editorial team at Wiley (shout-out to Bill Falloon and the team). Happy holidays!

P.S. Matt recently published a generous and thoughtful review of Lead Upwards on his fantastic blog. Check it out

Book Review: Startup Boards (Second Edition)

I recently finished reading the new second edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors by Brad Feld, Mahendra Ramsinghani, and Matt Blumberg. I loved it. It is a highly useful tome for startup operators and investors alike. I found it to be particularly helpful in preparation for a recent board meeting.

Many startup leaders can relate to the flurry of activity prior to a board meeting; the data collection, the slide preparation, the cross-functional alignment meetings, and the presentation prep itself. The new edition of Startup Boards is packed with useful insights, including board fundamentals (what is a board’s purpose, and what are the roles and responsibilities of members?), steps towards creating inclusive boards, and the overall background on how boards can have a role in important company milestones like fundraising, selling or buying a company, IPOs, or closing down the business.

Startup Boards has great advice for independent or aspiring board directors. As we work towards making boards more diverse and inclusive, this is something our entire industry can benefit from.

As an LGBTQ woman startup executive, this particularly resonates with me, as I am often still the “only” person or one of a handful from a minoritized group at board meetings. Thankfully, things are changing. We all need to work towards making boards more inclusive and effective.

In my book Lead Upwards, I included a chapter for startup leaders on how to prepare for and present at board meetings, including advice from investors, seasoned CEOs, and executives. I’ve previously referenced the first edition of Startup Boards as recommended reading. The new edition is even better and more helpful for aspiring and current startup execs to be successful in their board communication.

Startup Boards is a must-read to understand the “why” behind the board meetings, the board priorities, and the structures that are present at your startup. Highly recommended reading. Get your copy.

Announcing my new book Lead Upwards

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In my new book Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, learn how to maximize your impact and deliver results in a startup leadership role. Get insights into 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

Written for current and aspiring executives at startup firms, Lead Upwards is also a guide for startup board members, founders, funders, and managers seeking a singularly insightful discussion of business leadership. Available now!

Order your copy

Introducing my next book: Lead Upwards

9781119833352.pdf

It’s an honor to officially introduce my next book, Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, which will be published by Wiley in Spring 2022.

In Lead Upwards, readers will learn how to maximize impact and results in a startup leadership role. 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. Learn 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

Written for current and aspiring execs and leaders at startups, Lead Upwards is also a guide for startup board members, founders, funders, and managers seeking an insightful discussion of business leadership. Available May 2022.

Order your copy

Join Us For Boulder Startup Week 2021

While it seems like both a lifetime and no time at all since the first all-virtual Boulder Startup Week in 2020, I am excited to share that I have the privilege of being the marketing track captain for Boulder Startup Week 2021. It is an honor to support the vibrant Boulder startup ecosystem, especially during a time that has been challenging for so many. The theme this year is resilience, and our spotlight marketing event will focus on the role that marketing plays in driving revenue for today’s cloud companies.

Boulder Startup Week 2021 Event: Marketing = Revenue

A panel of marketing leaders from the startup ecosystem including Carly Brantz, CMO of DigitalOcean, Cate Lochead, CMO of JumpCloud, Lizelle van Vuuren, CMO of Undock, Olivia Omega, Strategist at Wallace Marketing Group, and I will discuss the topic of how marketing contributes to pipeline and revenue. This event is aimed at those who want to align marketing, sales, product, and customer success teams, understand how to take a revenue marketing approach and the role that data and account-based marketing play in successful go-to-market programs.

Watch the recording

Join Us For Boulder Startup Week 2020

Life has changed a lot in the past few months. In personal news, I moved back to Boulder late last year, and am thrilled to share I recently started a new role as the head of marketing at Intricately, the leading provider of product adoption, usage, and spend intelligence for cloud sales and marketing teams.

While this is a time of hardship for so many in our community in Boulder and beyond, I’m inspired by the resilience of the Boulder Startup Week team, who have been working hard to ensure the success of this year’s online-only festival. A special shout-out to Ben Travis, who runs the Boulder Marketing Meetup, and Rendl Clark, Director of Boulder Startup Week, for their amazing organizing efforts!

I’m looking forward to hosting two events (all-remote!) during this year’s Boulder Startup Week:

BSW ’20 Panel discussion: How To Grow Your Startup Marketing Career 

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A panel of marketing leaders from the startup ecosystem (Rachel BeiselSimone Johnson, and Victoria Stitt, MBA. ) will discuss the topic of how marketers can level up and achieve their goals along their startup career path. Watch the Recording

BSW ’20 Film Screening: Chasing Unicorns (“Ükssarvik”) 

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One of the most successful Estonian movies of 2019, Chasing Unicorns is a semi-satirical narrative feature about a female founder trying to make it a male-dominated tech world, from Estonia to Silicon Valley. RSVP to join us

Why an Estonian startup film? After traveling to Tallinn, Estonia in February, I was inspired by Estonia’s thriving startup ecosystem, including their innovative e-residency program. After watching the satirical Estonian startup film Chasing Unicorns, I reached out to the filmmakers Tõnu Hiielaid and Rain Rannu about the possibility of sharing the film with our Boulder startup community. Several months later, we’re partnering to host a virtual film screening during this year’s BSW. While Tallinn and Boulder are distant, I’m grateful for this opportunity to connect our startup communities through the film.

Looking forward to seeing folks (virtually) at BSW! For those interested, consider supporting Colorado’s COVID Relief Fund.

Introducing my new book Power to the Startup People: How To Grow Your Startup Career When You’re Not The Founder

Power to the Startup People: How to Grow Your Startup Career When You're Not the Founder

I’m thrilled to share that my new book Power to the Startup People: How to Grow Your Startup Career When You’re Not The Founder launches today! This book has been two years in the making and would not have been possible without the incredible help and support of so many of my friends, family, and members of our startup community.

In today’s tech startup world, career paths are nonlinear. A startup career can be rewarding, but it often can be challenging and confusing. While a ton of ink has been spilled on how to “crush it” as a founder or startup leader, there’s very little in the way of guidance for how employees can hack our own careers. If we’re lucky, we find mentors who have had careers we admire. But we may never find these people. Or, if we do, it may be too late, or their expertise in the particular area with which we need help may be limited.

Entrepreneurs get the lion’s share of glory, but much of the work is done by us: the contributors, the team. This book was born out of my desire to find answers to my own questions about how to have the best startup career possible, while ideally avoiding some pitfalls that, unfortunately, are hard to foresee unless you have a direct mentor relationship with someone who has experienced a similar situation.

I wrote this book from the vantage point of being a startup employee who wants to navigate my career as successfully as possible, while enjoying the journey along the way. While this book is not by any means exhaustive, it will hopefully help readers make more sense of the world of tech startups and make better decisions about their careers along the way.

I have a greater purpose for sharing this information. I truly believe that we, the startup people, hold the power of the tech industry in our hands. By taking command of our own startup careers, we will make a greater impact at the companies that are shaping our future. As the world grapples with questions about the nature of technology in our lives, with concerns about privacy and data and our looming automated economy, we, the employees who make this ecosystem work, will have to decide which companies deserve our time, sweat, and tears. My goal for publishing this book is to give us more choices and more power to shape our own destiny, so that we can in turn enrich the tech ecosystem with our talents. Power to the startup people!

Order now on Amazon

Thank you for reading! I look forward to hearing what you think of the book. If you enjoy the book and find it to be helpful, please leave a review on Amazon–it truly helps. Thank you! Sarah

We Need To Start Talking About The Debt of Withheld Feedback At Startups

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I was on a walking meeting with my colleague Erin when she gave me feedback on a talk she had just seen me rehearse. For an instant, I wanted to rebut it, but instead I thanked her and integrated the feedback, and it made my talk better.

The feedback Erin gave me was relatively easy to receive; I was asking for it, and the feedback involved was something I could (and did) easily adjust. Honestly? Even then it was hard to receive.

In many cases, the kind of feedback we desperately need to give each other is much harder to give and receive. And so, we avoid it, and the pain accumulates over time.

The difficulties we face in giving and receiving feedback leads to an epidemic of withheld feedback at an organizational scale — feedback debt.

Just as a startup can incur financial and technical debt, withheld feedback is an insidious and often unaddressed issue that is responsible for a myriad of problems at companies. Conceptualizing withheld feedback as debt makes it easier to understand it as an untapped source of organizational value.

Withheld feedback is a resource. Like capital, it holds tangible value, and comes with interest.

The sum of feedback not given among individuals and teams at your startup is creating a strain on your company’s outputs. Thus, it is a kind of organizational “potential energy” and has the capacity to reveal issues so that they can be addressed. When people have insights for each other — good, real, constructive insights that could make a person, project, or team better–and then don’t give it, that depreciates the total value of your organization.

Like technical debt, the debt of withheld feedback may actually keep an organization working smoothly in the short-term but sets it up for major long-term problems.

Technical debt is a term coined by Ward Cunningham to explain the consequences of a shoddily-done short-term technical solution. According to Atlassian:

“Constantly procrastinating on bugs that need to be fixed is a dangerous way to make software. As the bug count grows, tackling it becomes increasingly daunting–resulting in a vicious death-spiral of technical debt.”

Withheld feedback has a similar impact. Procrastinating on discussing issues that need to be fixed is a major issue. On individual, team and organizational levels, the consequences of not giving feedback can be devastating:

  • A subordinate doesn’t disclose a potential security issue she notices in a new feature that could put customers at risk because of fear of upsetting her manager.
  • A CEO doesn’t tell her VP of Sales she’s afraid he isn’t right to scale with the business, watching the company performance lag until finally the situation becomes unsalvageable.
  • A head of HR doesn’t follow up on getting feedback about major allegations of discriminatory behavior at the company because she’s afraid the founder won’t listen, or worse, may be implicated.
  • And more…

Withheld feedback debt must be repaid eventually

If you haven’t told someone the truth about something, chances are you’re going to skirt the issue and that’s going to be wasteful in some way vs. directly addressing it. That’s a debt that accumulates over time–with interest.

Uber has come under fire recently for missing the opportunity to receive feedback about its cultural issues. Companies that just don’t want to face the truth will have to pay up at some point, with interest, and usually publicly.

Winning companies will become adept at maximizing the flow of healthy feedback at every level of their organization.

My hope is that by conceptualizing withheld organizational feedback as debt, startups squash it on their way to increased profitability and success, and improve culture along the way.

Startup Employees: Here’s What To Do If Your Startup Is Acquired

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Imagine you’re working for a fifteen-person startup known for its tight-knit, values-driven, outdoorsy culture, and suddenly, one day, you’re pulled into an all-hands meeting letting you know that your company has just been acquired by a big company headquartered across the country. You may know a little or a lot about this company, but either way, very soon, you will become their employee.

For startup employees, an acquisition can be a nerve-wracking time due to the number of unknowns.

Some questions that may arise:

  • What will change, and will any of it markedly affect my work experience?
  • Will the parent (acquiring) company share the same values as my current startup?
  • Will my job become redundant and/or will I no longer be needed?
  • More immediately, what will happen to my PTO, benefits and will my spouse still be covered on my health insurance?

In addition to the potentially negative consequences of an acquisition, it’s important to remember that there can be many positive outcomes. For instance, you could get a promotion. Or perhaps you had equity that you could turn into cash in the acquisition. Regardless of whether you have equity, there may be an opportunity for you to leverage the value you bring to the transition to negotiate a nice windfall. Acquisitions and their resulting transitions can be highly emotional times, and no two acquisitions look quite the same. That being said, there are some ways you can empower yourself to make the most of an acquisition.

In 2015, Analiese Brown was the HR Manager at the time of acquisition of ShipCompliant, then an approximately forty-person self-funded, privately-held SaaS company headquartered in Boulder, CO. During the acquisition, Analiese’s role involved helping ShipCompliant through the transition, and much of her work centered around trying to help employees feel empowered throughout the process. Analiese oversaw changes in employee benefits, policies, and procedures such as well as the integration of HR systems and record-keeping with the acquiring company, Sovos. But Analiese also managed the “human” side of the transition, which involved helping employees grapple with the emotional elements of the transition. Read Analiese’s blog post sharing lessons learned from working at ShipCompliant.

“The CEO filled me in as it became more of a reality that it was going to happen,” said Analiese. “At that point, my focus became understanding  the acquiring company’s processes, employee benefits policies and handbook, and other things that might potentially affect our team once acquired.”

For Analiese, being on the team spearheading the integration was challenging; she oversaw details such as how to honor everyone’s time off balance and roll it over into the new policy, and also had to determine how to communicate the changes to employees. Analiese learned that the key to successfully navigating a startup acquisition as an employee is to focus on how you can shape what’s happening, and to find ways to re-frame it from something happening “to” you to something you have the power to shape to better your future.

Here’s what Analiese recommends if you’re a startup employee finding yourself in an acquisition scenario:

Upon learning of an imminent acquisition, take it upon yourself to learn as much as you can.

While there will be much that you don’t know and can’t know right away, obtain as much information as you can about the acquiring company. Research the acquiring company’s leadership, financials, and key customers and stakeholders. Editor’s note: You can search for recent press releases about them and check Crunchbase and Angellist to determine whether they’ve fundraised and/or if they plan to one day go public. Try to find out what happened when they bought another company; did the founders stay, and if so, how long? How many employees stayed?

Some of this information won’t be readily available, but you’d be surprised what you can dig up with some modern sleuthing. You can learn from internal resources, too. There might be a designated go-to person at your startup (the company being acquired) you can ask questions of who may be CEO of the company, startup’s founder, or whomever is managing HR or Finance. Whoever it is, there is probably some designated go-to resource you can look to who will be able to provide you with information to help you feel empowered, but remember they may not have all the answers or may be unable to share information one-on-one before announcing it to the whole group.

For as long as you’re planning on sticking around, commit to doing an outstanding job.

Don’t let the shifting sands environment of an acquisition be an excuse not to be a stellar performer. Keep up the great work — regardless of how long you plan to stay, you need to put in extra effort during this period because upon staying or leaving, you will have new people to impress either at the acquiring company or a new role very soon.

Sam Altman of Y Combinator says, “Most acquisitions are not smooth sailing. Go into it knowing it’s going to be hard.” Sam recommends employees wait at least six to nine months before making a decision that it’s not going to work (Source). In many cases, you’ll benefit from staying long enough to fully explore the opportunities present in an acquisition.

Empower yourself by becoming actively involved in the transition.

Your company may form a group of employees who are interested in shaping the transition. If there are ways to get involved, you’ll have access to information and will be in a place to shape the transition process. Every acquisition and integration is structured differently – the more you can be actively involved, the better chance you’ll feel positively about the outcome.

Sam Altman recommends adopting the mindset of “bridge builder”. “You don’t want two warring factions,” says Sam. “You want the new company to support you and you want people to like each other.” He advises making it your personal business to develop strong relationships with as many people as you can at the acquiring companies and be a bridge as tensions inevitably rise. (Source)

Give up on trying to keep things the same.

Things will change. That’s a given. The only thing you can control is what you do about the changes. Take time to mourn or celebrate the startup experience you had, and then roll up your sleeves, learn and decide whether you want to stay and/or if you need to go. Sam Altman says that often agreements will be reached with acquired companies to stay fairly autonomous, which can be a great thing if you already like your work and its processes.

“I would push the founders to make sure you got such an agreement to operate as independently as possible,” said Sam. (Source)

Unfortunately, even if such an agreement is reached, the reality of what “staying independent” looks like can be vastly different in each scenario. There may be certain processes like vacation time or required internal systems that will bend towards the parent company’s way of doing things. Figure out what will change as soon as that information becomes available.

Determine whether the new reality aligns with what’s important to you, and determine which things are non-negotiable for you.

Analiese recommends reading What Color Is Your Parachute?, a classic career discovery book, which can help you do the crucial work of discovering what’s important and what ultimately will be most fulfilling to you in your career.

Upon deciding to join the company, you probably have evaluated a number of factors that you’ll now have to re-evaluate. This includes: preferred geographic location, office environment you thrive in, and essential company values. Analiese says coming back to our own needs and desires provides a framework to evaluate whether the new reality of your acquired company will support and fulfill these things (or not). This personal inquiry is valuable regardless of whether you’re currently undergoing an acquisition, but is especially crucial when your company is experiencing major change.

Analiese reminds us that it is a human impulse to fear change. Figure out what’s important to you personally. Are you unwilling to move to a new city? Will you draw the line if the acquiring company doesn’t value inclusiveness?

If you have equity, understand how it works.

Understanding the impact to you as soon as you can will equip you with information about whether there’s a choice to be made, whether there’s an obligation to you around how that is paid out. If you don’t have equity you may feel the ship has sailed, but there may be some individuals who were very involved in transition or contributed heavily to the company’s success in the recent past  who may be then be in a position to be rewarded in some other way. That can be discretionary. It’s worth having the conversations. If in doubt, consider hiring a lawyer or business advisor who specializes in startup equity; you’ll be glad you did.

You may be acquired by a parent company with bonus or Management by Objectives (MBO) culture and if you’re in a key position, you can negotiate with the parent company for a favorable compensation structure or bonus. If you’re someone integral to transition, whether or not equity is part of your current compensation package, you may have some leverage.

Consider negotiating for a new role or a promotion.

If you’re planning to stay, once the shock wears off and people wrap their heads around what’s happening, incredible opportunities may surface. It may not even be something you have to ask for; you may see a restructure and be asked to take on a new role, or perhaps travel more or be based out of an office in a more desirable location. Analiese suggests looking for potential opportunities to learn and grow and develop as much as you can during an acquisition process. You may need to explicitly ask for a promotion if you’re being assigned more responsibilities or your role is being enhanced. Often larger companies acquiring smaller ones  may have more well-articulated career paths, or may look at the role you’re doing in a new way. At smaller companies, you may be a Jack or Jill of all trades, but upon acquisition, you may find that in this new reality, your multi-faceted role puts you a peg higher in an organizational chart.

You may also find that you are qualified to be in a higher-level role, and the acquiring company will likely have more funds or resources for learning and development. This may include going to conferences, workshops, or perhaps an internally-created leadership development program. There may also be more structured rewards and incentive program.

In the early post-deal stages, Analiese reminds us that it may not be totally clear what new career paths will be available or who will be impacted and how. Analiese says, in an ideal scenario, managers are a good first line of contact to ask for information and discuss how you’ll be impacted along the way. Hopefully, your manager will have the inside track (or be able to point you toward the right resources) to explore promotions or other opportunities.

Final Thoughts

If you’re facing an acquisition, adopt a learner’s mindset and find ways to become an active participant in the transition. Your goal is not to try to resist the change or preserve status quo, but to understand what the new scenario will be and to determine if the new company “reality” aligns with your values and needs.

If you’re resourceful, the acquisition of your startup can be an incredibly powerful catalyst for your career and personal development.