Category

Leadership

Why the Startup Sales Function Starts With Whiteboards

(This post was inspired by Startup CXO and was originally published by Techstars on The Line.) In most startups, one of the founders is the first salesperson — often out of necessity as much as passion. But as startups scale they add sales reps or maybe some form of a Sales Manager once there are more than a couple of reps. But how do you know when to bring on a senior sales leader? Too soon and you have a very expensive employee, too late and your sales reps are creating their own processes and approaches. As a CEO there are several telltale signs that you need to hire a CRO, for example: You wake up in the middle of…

Five Misperceptions of the CCO Role

This post was inspired by Startup CXO and was originally published by Techstars on The Line. If you’re new to the Chief Customer Officer role, we’d like to share some advice we wish we had learned earlier in our careers. There are a few common misconceptions about customers and the service organization. If you don’t realize these as misperceptions, you can spend a lot of time dealing with issues that are not real, but perceived. We have identified five of these common misperceptions, although we are sure there are more. Misperception #1: The service organization fully controls churn (customer attrition) In a lot of organizations you’ll see the service organization be measured solely on customer churn. If you really think about…

Signs your critical functions aren’t scaling – three webinars

This is a topic we write about obsessively in Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams — in fact, it’s basically the whole point of the book! I’ll write some more specific posts here in the coming weeks that take some excerpts from the book, but Bolster is putting on three free and open webinars we’re calling our “Bolster-up Series” over the coming weeks that I want to share with everyone who reads StartupCEO.com. In this series, I’ll be doing short interviews with CEOs who we work with at Bolster on the different aspects of scaling specific functions, how they diagnosed those problems, and how they leveraged on-demand executive talent to solve those…

How to get the most out of working with a CEO Mentor or CEO Coach

(This is the third in a series of three posts on this topic.) In previous posts (here, here) , I talked about the difference between Mentors and Coaches and also how to select the right ones for you. Once you’ve selected a Mentor or Coach, here are some tips to get the most out of your engagement. Starting to work with a CEO Mentor is fairly easy. Give them some materials to help understand your business, and then come prepared to every session with a list of 1-2 topics that are keeping you up at night where you want to benefit from the person’s experience. Kicking off a CEO Coach engagement is more in-depth. I always recommend starting to work…

The Startup Ecosystem Needs More Independent Board Members – That’s the Clearest Path to Having Better and More Diverse Boards

I love having independent directors on my Board.  They are a great third leg of the stool alongside a CEO/Founder and VCs.  They provide the same kind of pattern matching and outside point of view as VCs — but from a completely different perspective, that of an operator or industry expert.  The good ones are CEOs or CXOs who aren’t afraid to challenge you.  Equally important, they’re not afraid to challenge your VCs.  At Return Path, I always had 2 or 3 independent directors at any given time to balance out VCs, and some have become great long term friends like Scott Petry, Jeff Epstein, and Scott Weiss.  At Bolster, we’re already having a great experience with our first independent,…

How to Select a CEO Mentor or CEO Coach

(This is the second in a series of three posts on this topic.) In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them. Selecting a CEO Mentor is…

The Difference Between a CEO Coach and a CEO Mentor and Why Every CEO Needs Both

(This is the first in a series of three posts on this topic.) Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys. All of us would benefit from having an Albus Dumbledore in our lives.  But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is.  Why work with a Coach or a Mentor?  I’ll start…

Addicted to Ruthless Efficiency

Last week I wrote about The Tension That Will Come With the Future of Work.  No one knows what the post-pandemic world of office vs. remote work will look like, but there are going to be some clear differences between how people will respond to being in offices or not being offices going forward.  As I said in that post, I think the natural, gravitational pull for senior people will be to do more remote work, because of a combination of their commutes, their personal time, their work setups at home, and their level of seniority…but with the possible exception of engineers, “all remote” may actually not be in the best interest of a number of junior or more introverted…

OnBoards Podcast

My podcast with OnBoards is live, talking with Raza and Joe about the importance of adding independence, first-time directors, and diversity to startup boards, and how Bolster helps companies achieve that quickly and inexpensively. I’m writing a lot about Boards at the moment on the Bolster blog. We’re compiling all of those posts into a couple of eBooks. Once all of that is done, I’ll put some digests up here on StartupCEO.com as well as make the eBooks available for download. But the gist of it is that we are working hard to break the logjam of diversity on startup boards, and we’re starting to meet with some great success with our clients.

The Tension That Will Come With the Future of Work

The Tension That Will Come With the Future of Work A lot has been written about the Work From Anywhere life that knowledge workers are leading right now due to the pandemic, and what will come next.  Fred has a great post on it, and I’m curious to see how his and Joanne’s “Home Office Away From Home” space called FrameWork does when it opens.  In that post, he references a few other posts and articles worth reading: Imagine Your Flexible Office Work Future – Anne Helen Petersen We’re Never Going Back – Packy McCormick The Future of Offices When Workers Have Choice – Dror Poleg Instead of entering the debate about what the future will look like, which no…

Soliciting Feedback on Your Own Performance as CEO

(Excerpted from Chapter 12 of Startup CEO) As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things: Asking for feedback Accepting feedback gracefully Acting on feedback Asking for follow‐up feedback on the same topic to see how you did In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a…