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Bolster

Grow or Die

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post: My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company. Let me put it in starker terms: Grow or Die….

Announcing The Daily Bolster (You DO NOT want to miss this new Podcast)

I’m thrilled to announce The Daily Bolster — a quick-hitting podcast for startup leaders scaling their businesses. It’s the actionable insight you need to scale—in about 5 minutes. The first episode drops this coming Monday. Our team created The Daily Bolster for folks in the startup world who — like me — want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed (which usually ends up sounding like Alvin & The Chipmunks, anyway). Instead, we’re getting straight to the point. GTTFP, as Brad says. Starting next week, I will be joined every day by experienced operators and industry experts who share their real-world experiences and…

Patience vs. Impatience

Patience and Impatience are both critical tools in the founder toolbelt. That sounds kind of funny since they’re at odds with each other. Let me explain. Patience is hard, but there are some things that require it. As they say metaphorically about Product, nine women can’t make a baby in a month. Products needs to be built, tested in the wild, marinate with clients. GTM motions take time to figure out. Brands take time to build unless you have billions to throw at the problem. Bread takes time to rise.  Patience is a really useful tool when people on your team or board get itchy for success and you need to calm them down and keep them focused. Impatience, on the…

What does Great Look like in a Chief Customer Officer?

(This is the second post in the series… the first one When to Hire your first Chief Customer Officer is here) I mentioned in an earlier post that few startups begin with a full-time Chief Customer Officer and the likely scenario is to promote someone from within the service organization to that role. It’s possible that the person who takes on the CCO role will be ideal for the job, but often startups end up searching for someone outside the organization to lead the customer success team. Either way, promoting from within or hiring from outside, there are several telltale characteristics that great Chief Customer Officers share, and there are three things they do particularly well. First, the CCO is…

When to Hire a Chief Customer Officer

(Post 1 of 4 in the series of Scaling CCOs) Very few startups start life with a Chief Customer Officer, even though customers are the lifeblood of every startup; instead, you’ll likely start your customer service organization with a “jack of all trades” account manager position. You’ll have one person who handles all customer issues from basic support all the way through to true customer success. Sometimes these functions will be handled by the product team but most often they are handled by a customer service team.  Specialized roles and multiple teams (e.g, support vs. professional services) with their own managers can emerge quickly in the life of a startup and these roles will usually come before a full-time CCO,…

Book Short: Must-Read for CXOs

Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, by Sarah E. Brown, is an amazing book – and one that fits really well with our Startup Revolution series, in particular our book Startup CXO. I kept thinking as I was reading it that it was the other side of the proverbial coin…that Startup CXO was about the details of each executive job in a company…but Sarah’s book is about the things common to ALL executive jobs – how to get them, how to succeed at them, essentially how to BE an executive. I read it front to back in a single day one weekend and loved it. Some of the most insightful…

Signs Your CMO Isn’t Scaling

(This is the third post in the series… The first one When to Hire your first CMO is here, and What does Great Look Like in a CMO is here).  In Startup CXO I wrote that I always think that the French Fry Theory can be applied to many things, usually other food items. The French Fry Theory is the idea that you always have room to eat one more fry and in my case I always do. But the same idea applies to marketing because you can always do “one more thing.” One more press release. One more piece of collateral. One more page on the corporate web site. One more newsletter. Trade show. Webinar. Research study. Ad. Search…

The quest for diversity in Tech leadership is stalling. Here’s why.

There’s been a growing cry for tech companies to add diversity to their leadership teams and boards, and for good reason. Those two groups are the most influential decision making bodies inside companies, and it’s been well documented that diverse teams, however you define diversity — diversity of demographics, thoughts, professional experience, lived experience — make better decisions.  Gender, racial, and ethnic representation in executive teams and in board rooms are not new topics.  There’s been a steady drumbeat of them over the last decade, punctuated by some big newsworthy moments like the revelations about Harvey Weinstein and the tragic murder of George Floyd.   It’s also true that in people-focused organizations, and most tech companies claim to be just that,…

What Does Great Look Like in a CMO?

(This is the second post in the series… the first one When to Hire your first Chief Marketing Officer is here). Whether you have someone in your company that can level up to greatness or you need to bring in a CMO, the characteristics and skills of a great CMO you should aspire to include some of the following. A great CMO understands that the marketing budget starts with drivers and business results and works backwards in a modular way to spend, not the other way around. Yes, they will get some resources but rather than spend that money to fill in the gaps on their team to make the Marketing function strong or powerful, they’ll look at the business…

When to Hire a Chief Marketing Officer

(Post 1 of 4 in the series of Scaling CMOs) Unlike some of the other teams in a startup, the marketing function often has a few people carrying out various tasks and you’ll find that there is at least a medium sized and quite busy marketing department—even at the earliest startup stages. You could operate this way for quite some time and it’s common to have a marketing team with multiple mid-level leaders well before there is a seasoned leader at the helm.  One of those leaders may be a VP of Marketing and, depending on the nature of the company, that VP is likely someone with a specialized area of focus within marketing (brand, digital, event, etc.) who has…

How to engage with Your CRO

(Post 4 of 4 in the series on Scaling CROs – other posts are, When to Hire your First Chief Revenue Officer, What Does Great Look like in a Chief Revenue Officer and Signs your Chief Revenue Officer isn’t Scaling) Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent. One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events.  Particularly if you’re a B2B company that engages with…