Category

Leadership

Signs your CBDO isn’t scaling

(This is the third post in the series… The first one When to Hire your first CBDO is here, and What does Great Look Like in a CBDO is here). The metrics for understanding whether or not your CBDO is scaling differs from other functions like Sales, People Ops, Customer Service, and Finance because throughout the scaling process the CBDO team is likely to be small. So how do you know if your CBDO is scaling if they’re essentially the same size regardless of what the rest of your company is doing? I have found that CBDOs who aren’t scaling well past the startup stage are the ones who typically operate in the following ways. First, a CBDO who isn’t scaling is…

Fighting Confirmation Bias

I was mentoring a first time founder the other day who asked me, “How do you know what advice to follow and what advice not to follow?” (For the record, it’s a little ”meta” to answer that question!). I talked about looking for patterns and common themes in the advice from others and exercising judgment about how to pick and choose from competing pieces of advice. But then he asked me how I fight confirmation bias when I’m exercising judgment and incoming advice. Fighting confirmation bias is both incredibly important and incredibly difficult, and I’d never articulated my thoughts on that before, so I thought I’d do that here. The way you have to train yourself to fight confirmation bias…

What Does Great Look Like in a Chief Business Development Officer?

(This is the second post in the series….the first one When to hire your first CBDO is here) One of the tricky things about finding a great CBDO is that the role is fairly nuanced and there’s not a degree a person can get in “business development.” So you’re left with searching for someone based partially on experience, reputation, and alignment with your company culture and goals. But over the course of my career I have figured our what “great” looks like for the CBDO and I’m confident that what worked for us at Return Path and Bolster will work for any startup. First, a great CBDO should have a good balance of the three core components Ken Takahashi outlined…

Family vs. Team?

I used to describe our culture and our employees and our leaders at Return Path as a family. That was a mistake. It was just plain wrong. It served us well in some respects, but it bit us in the ass on others. Great groupings of people at work are teams, not families. You can have a highly functional family. But you don’t have high performing families. Work teams need to be high performing. Here’s what I mean. The family metaphor worked well at Return Path around the principles of caring for people and lifting each other up. Those elements of a culture are absolutely critical. I don’t regret them for a minute. But the downside of that metaphor is…

When it’s Time to Hire Your First Chief Business Development Officer

(Post 1 of 4 in the series of Scaling CPDO’s). For most startups the idea of hiring a CBDO is a pipedream, it’s a role that only global corporations have, right? After all, strategic partnerships and M&A are rare events for a startup and can be handled by the founder/CEO, or potentially by someone in Sales.  If a startup is partner or channel heavy, those areas may be the focus of the Sales team in general.  Or, if there is sporadic M&A activity that can be handled by external advisors or bankers. So how do you know when it’s time to hire your first CBDO? You know it’s time to hire a CBDO when you are spending too much of…

Camera On, Mic On

At my last company, we used to occasionally attend a giant meeting at one of the large ISPs — Microsoft, Yahoo, and the like — and it always annoyed me to be presenting to or engaging in a discussion with a room full of a dozen people and having all of them there with their laptops open, clearly distracted and doing other work. I’m increasingly finding annoyance with the Zoom equivalent, which is being in a meeting or attending a presentation, but turning off your mic and camera. It’s impossible to know as the person leading the meeting or speaking if you’re actually there. And if you’re there, if you’re paying attention. And how many times in a meeting can…

You’ve Seen One, You’ve Seen One

Like all CEOs and VCs, I’m a big believer in the power of pattern matching. I just wrote a whole blog post about the limits of pattern matching after hearing the quote above at a board meeting recently. But then a little alarm rang in the back of my head, and realized that I wrote about the value and limitations of pattern matching here years ago with an even better quote from my father-in-law: When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra. So rather that rewrite that entire post, I thought I’d just add onto it a bit here with a current example in my head about executive recruiting and…

Should CEOs wade into Politics, Part III (From Tim Porthouse)

I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject. Your Leadership Game: “No Comment.” Should you speak up about news events/ politics? Most of the time,…

Everything vs. Anything

I heard two great lines recently applied to CEOs that are thought provoking when you look at them together: You have to care about everything more than anything and You can do anything you want but not everything you want Being a CEO means you are accountable for everything that happens in your organization. That’s why you have to care about everything. People. Product. Customers. Cash flow. Hiring. Firing. Board. Fundraising. Marketing. Sales. Etc. You can never afford not to care about something in your business, and even if there’s a particular item you’re more focused on at a given point in time, you can never get to a place where you care about any one particular thing more than…

Measure Twice, Cut Once

The old carpenter’s axiom of being extra careful to plan before executing is something not enough executives take to heart in business. Just like cutting a piece of wood a little too long, sometimes you execute in ways that can be modified on the fly; but other times, just like the cases where you cut a piece of wood too short, you can’t. And of course, in business, sometimes it’s somewhere in between. Some examples: It’s an interesting question as to whether or not this axiom conflicts with the startup mentality of moving quickly and with agility. I don’t think it does, although in the startup ecosystem, a lot of fixed decisioning has moved to variable, which means you may…

You Don’t Need a CRO

One of the most common things early stage CEOs say to me once they find product-market fit and make a few sales is “I need a CRO.” The answer is almost always, “no, you don’t.” A couple years ago I wrote about the evolution of enterprise selling organizations in this post. Reading that is a good place to start this topic. Go ahead…I’ll still be here when you come back. Welcome back! So in the early days of a company, it’s all “selling on whiteboard.” The need that early stage CEOs have that prompts them to tell me they need a CRO is simple the need to have help selling. What the CEO really needs is a couple of very…