What You Read The Most In 2024
My Top 5 Hello Operator posts from this year and what I learned from writing them
A little more than a year ago, I moved my writing to
.Then I gave it a name.
From the beginning, I wanted Hello Operator to stand for practical, honest thinking about what it takes to build, lead, and grow in my two worlds of B2B software and private equity. I also wanted it to connect me with people wrestling with the same questions I face at work. Questions about growth, strategy, hiring, leadership, and how to simplify the challenges that come with pushing a business beyond where it’s gone before.
What I didn’t expect was how much that writing would sharpen my thinking. Each post forced me to slow down, wrestle with my thoughts and feelings, nail down what I actually wanted to say, and pare it all back to something worth sharing with others. That process has made me a better operator and (maybe) even a better person. (You can ask my wife if that last part is true or not.)
These are my five most-read posts from the past year.
Whether you’ve read them already or not, maybe they’ll spark something new for you too.
1. What CEOs Should Expect from Their Sales Leader: Part 1
Hiring the right sales leader can make or break your business. But here’s the catch: what you need depends on where your company is. This post lays out the three phases of sales leadership (figuring it out, fixing it up, and scaling it up) and how to avoid the costly mistake of picking the wrong person for the job. Part 2 coming soon.
2. How CEOs Should Think About Growth
CEOs don’t need to do everything; they need to do the right thing. I broke down the three growth levers that CEOs should focus on—building pipeline, closing better, and keeping customers—and how to figure out which one deserves your focus. Growth is simple, but it’s not easy. Are you bold enough to pick just one lever and go all-in?
3. Fake It While You Make It
Ever feel like your sales pitch just isn’t landing the way it should? Same here. That’s why I ran a little experiment with one of my portfolio companies, using AI to pressure-test our talk tracks before we ever put them in front of a prospect. The process was eye-opening. It turns out a few small tweaks can make your pitch a whole lot better. If you’re not stress-testing your messaging, you might be leaving results on the table. This is my playbook on how to do it - and a step-by-step guide to one of the most no-brainer AI use cases out there today.
4. Stop Overthinking Your Strategy
Small companies love to overthink strategy. But here’s the thing: strategy isn’t a map; it’s a muscle. This essay explores why copying big-company planning habits is probably slowing you down - and why quick, iterative experiments are the real path forward for most emerging businesses. If you’ve been stuck in planning purgatory, this will give you the permission you need to simplify and start moving.
5. Simplifiers and Complicators
Some people answer questions, solve problems, and get things done. Others just muddy the waters. This post is a personal gut check: are you cutting through the noise or just adding to it? A little clarity goes a long way - in work and in life.
As I think about 2025, I’m excited to keep building on what Hello Operator can be. Writing this thing into existence has been one of the most rewarding parts of my year, and I’m thankful for the thousands of you out there that read my stuff, share it with others, and occasionally reach out to let me know what hits home. I appreciate all of it.
If you’ve enjoyed these posts, find them useful, or think you might someday, it would mean a lot if you hit subscribe and come along for the ride in 2025.
It’s free and always will be.
Cheers to another great year ahead. Thanks again for reading.