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

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