I wrote a colorfully-named post years ago called Onboarding vs. Waterboarding, which detailed out some of the general principles around onboarding new employees that our companies have used over the years. A few weeks back, one of our clients and fellow CEOs of a Series C Ed:Tech company asked me for tips on onboarding senior executives, and some of what I said varied from or built on that earlier post. Here are a few of the themes we riffed on: Special thanks to my friend Amir for inspiring this post!
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Entrepreneurship
What Does Great Look Like in a Chief People Officer?
This is the second post in the series…. the first one When to hire your first Chief People Officer is here). While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything…
When to Hire Your First Chief People Officer
(Post 1 of 4 in the series of Scaling CPO’s) In most startups, the HR function starts out as tactical, because you have to get people hired and paid, and while you might have a founder or early-stage employee who can do these things, often these tasks are frequently outsourced to a PEO. As the company grows, it probably in-sources payroll and benefits, hires a recruiter, and maybe has an HR Manager who handles the function. Depending on the number of roles you see being filled, the degree of specialization, or a host of other factors, an in-house team to handle the tactical aspects of HR makes a lot of sense. But at some point you may need to hire…
How I engage with the Chief Privacy Officer
Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief Privacy Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling. There are a few high-quality ways I’ve typically spent the most time or gotten the most value out of Chief Privacy Officers over the years. Part of it may have to do with the business we were in at Return Path (and now, Bolster), but part of it is understanding what the Chief Privacy Officer needs from the business and working with them in that arena. For example, I found it helpful to work with the Chief Privacy Officer to…
Signs your Chief Privacy Officer isn’t Scaling
This is the third post in the series. The first one When to hire your first CPO is here and What does Great Look Like in a CPO is here). Chief Privacy Officers who aren’t scaling well past the startup stage are the ones who typically have the following characteristics and you should look for some of these telltale signs. First, if your Chief Privacy Officer looks at you sideways when you ask for a strategy or even a mitigation plan for a breach, then you might have a bigger problem than the fact that you don’t have a plan. While we like to talk about things like Privacy by Design and using data protection as an offensive strategic weapon,…
What Does Great look Like in a Chief Privacy Officer?
(This is the second post in the series… the first one When to Hire your first Chief Privacy Officer is here) Most Chief Privacy Officers are fairly specialized, often coming from a legal or law enforcement background, but regardless of background I’ve found that ideal startup Chief Privacy Officers do three things particularly well. First, a great Chief Privacy Officer will work to create educated evangelists inside the company. Our Privacy team at Return Path, under Dennis Dayman’s leadership, had a lot of experience and industry certifications, but that experience was not something only for regulators and other companies, or only bragging rights within their team. They also took the time to make sure others in the company, especially in…
When to Hire a Chief Privacy Officer
(Post 1 of 4 in the series of Scaling CPO’s) Most startups don’t have a Chief Privacy Officer and just rely on outside advice from external counsel or a privacy consultant. In Startup CXO our Chief Privacy Officer from Return Path, Dennis Dayman, strongly advocates for privacy to be baked into a startup at the very beginning. Some startups probably don’t have any help in this area at all but given the importance of privacy and security issues today that’s a mistake. If your startup doesn’t start life with a Chief Privacy Officer you’ll have to heed some warning signs and here are some I’ve picked up over the years. First, you’ll know it’s time to hire a Chief Privacy…
Daily Bolster Weeks 1 and 2 recap
We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications. Episode 1: 3 Tips to Scale Your Culture with Nick Mehta Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many?…
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…
How I engage with the CCO
Post 4 of 4 in the series of Scaling CMO’s- the other posts are, When to Hire your First Chief Customer Officer, What does Great Look like in a Chief Customer Officer and Signs your Chief Customer Officer isn’t Scaling. You can engage with each person on the executive team one-on-one to understand what their issues and challenges are, but I’ve found that engaging with the CCO offsite with customers is far more productive and leads to a better understanding of the service organization than any other meeting time. I have typically spent the most time with or gotten the most value out of CCOs over the years doing the following. In person at “Canary in the Coal Mine” customers….
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…