Grow Your Startup Career By Mentoring And Giving Back

Photos: CC BY 3.0 US Mapbox Uncharted ERG

This post is adapted from my latest book, Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams.

When I became a mentor at Techstars, a leading accelerator with a presence around the world, I learned its manifesto “give first,” which means to give without an expectation of receiving (knowing we mentors will still likely receive a lot from the experience). I didn’t realize how important this was to my startup philosophy until I encountered ecosystems where that mentality wasn’t the case. It made me understand that generosity without expectation is truly the lifeblood of a successful startup ecosystem. There is so much to learn and limited resources to accomplish a startup’s mission and goals.

MENTORSHIP POWERS THE STARTUP ECOSYSTEM

I know what mentorship means both to myself as a mentor and to the founders with whom I have had the privilege of interacting. Techstars says that mentor relationships almost always become two-way. That’s definitely been true for me as I have been a lead mentor in Techstars Sustainability, Oakland Powered by J.P. Morgan, and Workforce Development accelerators.

One founder I mentored invited me to his baby shower two years after our mentorship relationship officially ended, and we regularly talk about life, relationships, as well as the startup world. Another mentor and I have a more formal relationship, but we have stayed in touch long after his program ended, and I consider all three of these founders as friends. They’ve helped me with life topics as much as I’ve helped their companies with their go-to-market strategies. That’s the gift of mentoring; whether you’re aiming to give or receive, know that it’ll be something that goes both ways.

MENTORSHIP IS ABOUT KNOWLEDGE AND CHEMISTRY

Mergelane co-founder Sue Heilbronner says a good mentor–mentee relationship needs personal connection and chemistry.

“Once you get through specific content and facts like ‘this person has great experience in finance’ and ‘this person could use some bolstering in their knowledge in this area,’ the connection is the thing,” says Heilbronner.

“Mentees are most successful when they think about identifying mentors as people who are already in their world with whom they have a big connection; it’s true for mentors also. We have formal structures in accelerators, incubators, and that’s all fantastic as a way to facilitate and enhance the power of mentorship, but informal opportunities can be very meaningful.”

MENTORS DON’T HAVE TO KNOW ALL OF THE ANSWERS

I’ve learned as a mentor to ask good questions and be open to how the recipient wants to navigate their answers, releasing ideas of how I think they “should” handle a situation, and trusting them to be the best judge of their own course of action. Mentors can advise and provide guidance but don’t oversteer. There’s great power in also knowing that when I receive mentorship, I can choose to listen to what resonates and discard the rest.

For example, I once was talking to a founder about a challenge with one of his co-founders around their average sales price (ASP) and how he was feeling about their difference of opinion. I didn’t try to tell him what to do or even push him to decide what action to take. I had my own opinion about what ASP would work best for their target market, but that wasn’t what he needed. Instead of pushing an agenda, I was there to listen to what he wanted to share on the topic and come to his own answers.

He ended up solving his problem by engaging a coach to facilitate some difficult conversations with him and his co-founder about their company vision and how they wanted to go to market. He found our chats helpful to clarify his own needs and thinking. I’m proud that they took these insights into their next successful fundraising event, now on the same page about the why behind their pricing strategy.

PURSUE MENTORSHIP THAT PROMOTES EQUALITY

Trier Bryant is Co-Founder and CEO of Just Work, a strategic executive leader with distinctive Tech, Wall Street, and military experience spanning over 15 years. She’s previously held leadership roles at Astra, Twitter, Goldman Sachs, and served as a combat veteran in the United States Air Force as a Captain leading engineering teams while spearheading diversity, equity, and inclusion (DEI) initiatives for the Air Force Academy, Air Force, and DoD. She says that as a Black woman, finding mentors who “guide her the same as a white man” is important.

SIGN UP TO MENTOR AT AN ACCELERATOR

I’ve learned so much from mentoring at Techstars accelerators and deeply value those relationships. I proudly use my swag from their orgs and refer other mentors regularly who could be a good fit for the programs. If you want to get involved with mentoring in a more formal way, offering your departmental expertise and/or industry expertise to founders at an accelerator is a great avenue.

At Techstars, we first meet the founders of each cohort and hear their pitches in what’s called “Mentor Madness.” It’s basically a half-day of hearing back-to-back conversations where you get to see if you both have chemistry. Whether in-person or virtual, I always end the day exhausted, because I’m an introvert, and it requires being “on” with a lot of new people in one day. Yet it’s satisfying to get to help early stage founders and companies find their way.

I mentor at Oakland Powered by J.P. Morgan and Workforce Development accelerators at Techstars. There are now many accelerators around the world that specialize in different things and markets. Chances are, there’s an accelerator near you that includes companies tackling something you care about and can provide value to. It’s worth a shot if you feel it would be fulfilling.

MENTOR THROUGH AN OFFICIAL ORGANIZATION

Mentor Spaces founder Chris Motley believes in mentorship’s power to transform lives. Through his platform, professionals from underrepresented backgrounds can support others and get support for their own career growth. Motley’s organization works with the National Black MBA Association (NBMBAA) and other organizations. Other organizations to consider becoming a mentor at include Lesbians Who Tech, Girls Who Code, and other affinity groups.

FIND COMMUNITY AND SHARE MUTUAL SUPPORT AS A “PEER MENTOR”

Nicole Wojno Smith says finding peers and building a supportive community around you is paramount to finding and succeeding in an exec role.

“The biggest thing that I’ve found is that it’s lonely,” says Smith. “Most of the time, your CEO expects you to know how to do the job. You can’t really go to them and say, hey, I really don’t know how to do this. When you were director, you had your VP to ask these questions or you might have had three other peers on the same level that you could just chat with about some of this. It’s kind of like overnight some of that goes away,” says Smith.

Smith asks her global group of CMO peers how to handle situations, sending them messages when in doubt (and fielding them from others). When she owned a new function within marketing recently, she turned to this group for counsel, and they are always willing to get on calls or answer messages to help her succeed.

AFFINITY ORGANIZATIONS

Having people whom you can trust to turn to outside of your company when you don’t know something or just need support is crucial, especially if you’re a member of an under-represented minority. Groups like People of Color in Tech, Lesbians Who Tech, or other affinity groups can help you find like-minded peers and mentors with whom you can draw and give support. Scale-up startups often have organizations like Employee Resource Groups (ERGs) around identities like LGBTQ+, Latinx, Black in Tech, Women in Tech, and more that you can join and be a part of.

To read more on this topic, check out my latest book, Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams.

 

Startup Leadership Fireside Chat With Brad Feld And Sarah E. Brown [Watch The Recording]

Recently, I had the honor and privilege of joining VC, Techstars co-founder, and author Brad Feld to discuss our perspectives on startup leadership and career development to empower the next generation of startup leaders.

From the beginning, Brad has been an incredibly generous supporter of my books focused on startup employees, Power to the Startup People and Lead Upwards. I am grateful to get to learn and benefit from Brad’s work focused on building startup communities and ecosystems, both locally in Colorado and globally.

Brad has written many excellent books; two of my favorites, Startup Communities and The Startup Community Way, have particularly influenced my perspectives on how to foster more inclusive, diverse startup ecosystems.

Our fireside chat explored what it takes to build diverse startup communities and the role of startup employees in thriving startup ecosystems. Our discussion covered many topics that will hopefully resonate with many startup joiners who are interested in growing their careers and getting more involved in the ecosystem.

Watch the recording below.

Featuring:

Brad Feld: Partner, Foundry Group; Co-founder, Techstars; Author of Startup Communities

Sarah E. Brown: Author of Lead Upwards

Moderated by: Megan Barbour, Head of Network, Foundry

For those who want to read along, books can be ordered:

Startup Communities

Lead Upwards

You’re Invited: Startup Leadership Fireside Chat Featuring Brad Feld

What does it take to build thriving, diverse startup communities?

I’m co-hosting a virtual workshop on March 8th with Brad Feld (Author of Startup Communities: Building an Entrepreneurial Ecosystem in Your City) to explore this topic.

In Startup Communities and his follow up book The Startup Community Way, Feld sheds light on the ingredients for successful startup communities and how to cultivate diverse and thriving ecosystems.

In my book Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, I share a guide to maximizing your impact and delivering results in a startup leadership role. The book explains how to prepare for, earn, and succeed in an executive role at a startup company.

Join us as we discuss our perspectives on startup leadership and career development to empower the next generation of startup leaders.

RSVP to join us. Hope to see you there.

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

9781119833352.pdf

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