OP #294: Mastering the CMO-PE Relationship & More

Author

Darren Herman
April 15, 2025

Happy Tuesday OP Community!

Apologies for not sending the OP last week but April is/will be a super busy month. I've been traveling 3 out of the last 4 weeks for work, dance-competition filled weekends (yay Dance Dads! 💃), and a crunched schedule has unfortunately put a dent in the OPs that I usually send out.

Recent Adventures & Upcoming Events

Last week was packed! Started at the Bain Capital CEO Conference in New York and then zipped over to the Imaginarium B2B Summit on my way back to Massachusetts to speak about the relationship between CMOs and Private Equity. More insights on that conversation below.

Coming up before we know it: The Silicon Alley Golf & Pickleball Invitational on May 5 in Ardsley, NY. We've got an incredible group of folks signed up (130+) with only a few golf and schmoozer tickets remaining – pickleball is completely sold out! 🏌️‍♂️ 🥒

All excess funds from this year's event will be donated to the Sandy Hook Promise, an organization created to help educate and empower youth and adults to prevent violence in schools, homes, and communities. If you haven't signed up yet, you can do so here – but hurry, there's not much time left.

Speaking of signing up and winning, an Operating Partner community member came in third place in the Tremont School raffle! This is the second year in a row that someone from our community has won something from the raffle. Congratulations! 🎉

What's Caught My Attention Recently

⌚ Content and Commerce: My friend writes an incredible weekly watch & commerce letter. If you're into Seiko and associated brands (Laurel, Credor, etc.), this newsletter is a must-read. As a marketer, I love the content + commerce philosophy he's embraced, and his execution is stellar. Check out his website, Provenance Watches, where you'll notice the photography is exceptional. Again, as both a marketer and e-commerce practitioner, these visual details make a huge difference – those who invest in quality photography usually win out.

🎓 CEO Masterclass: OP community member, friend, and media/commerce executive Richard Jalichandra just released a 30-Day CEO Playbook. It's an awesome (though lengthy - 2hrs+) YouTube video delivering 20+ years of CEO lessons. I've listened to most of it and found it genuinely insightful and actionable. Hope you do too! Even if you are not a CEO, this video is relevant to all executives and those striving to be one.

📊 History of Programmatic Ads: Digital advertising pioneer and serial entrepreneur Brian O'Kelley has returned to blogging with some incredible content lately. I naturally gravitate to his writing about the birth of programmatic advertising – which is where I met Brian and got to work alongside him and his teams as one of our partners at Varick Media Management. His look back at the industry's evolution is fascinating reading for anyone in our space.

💡 CEO Mindset. Fascinating interview between Nido Qubein, President of High Point University and David King, Labcorp (ex) Chairman & CEO. I watched this and was very impressed with David, especially when he talks about Power vs. Influence. Lots of great lessons in this video as well, as, great interviewing by Nido.

Thank you for reading the OP today. As you can see, it's lighter than usual on OP Links (links to articles) as I've not had much time to consume content over the past week or two.

Be well, do good.

Darren

Imaginarium Recap: What Makes a Great PE CMO?

A few months ago, I ran into Scott Stedman —founder of The Imaginarium , a B2B growth org focused on ABM—while picking up groceries at Roche Bros. in our hometown. One of those classic “we should grab breakfast” moments turned into an actual breakfast. And over eggs and coffee at our local dinette, Scott shared more about Imaginarium and the Summit he was hosting for current and future B2B CMOs.

The Summit overlapped with Bain Capital's CEO Summit (more on that in a future post), but I managed to carve out a couple of hours on the way back from New York to join the crew in the Berkshires at Mass MOCA. Dan Rosenberg , founder of Octane11 —and an old friend from his MediaMath days—led a lunchtime fireside chat with me on what it takes to succeed as a CMO in Private Equity.

Here are the key takeaways I shared:

1. Know the outcome—and the levers that get you there. Too many marketers still celebrate impressions, reach, and clicks. That’s activity, not impact. Great PE CMOs tie everything back to tangible results—like revenue from a key segment—and they work relentlessly to get there.

2. Move with speed. We wear sneakers around here. That’s not just a metaphor. If our timeline to 3x EBITDA is five to seven years, every quarter counts. The best CMOs know how to move fast and build processes, governance, and partnerships that can scale just as quickly.

3. Use data to unlock creativity. The myth that data kills creativity? Not buying it. When you deeply understand performance, customer segments, and behavioral insights, you can be more creative. You know where to push, when to hold back, and how to tell better stories.

4. Embrace alternative playbooks. We’re often going head-to-head with giants—10x the people, 10x the budget. So rinse-and-repeat playbooks from bigger orgs don’t always cut it. We love CMOs who have zigged where others zagged. The ones who’ve built scrappy, smart, high-impact marketing with constraints baked in.

It was a great session, made even better by the setting (if you haven’t been to Mass MOCA, go) and the company—shoutout to Scott, Dan, and the rest of the Imaginarium crew. It was also a bonus seeing longtime friends Gayle Meyers and Andrew Bloom in the crowd.

**the post originally appeared as a LinkedIn post. Rarely does this happen. Usually, I take content from my OP newsletter and then adapt it to LinkedIn.

Jobs In and Around The Portfolio

As of writing this OP, there are over 4,855 opportunities across the Bain Capital private equity portfolio. You can view and apply to them here.

If mid-market Private Equity is not your thing, here are a few others:

Random AI Tip: Selecting New Watch Bands

I wanted to share a total game-changer I've discovered for solving one of the most frustrating parts of watch collecting - finding the perfect strap! 🕰️ If you work in e-commerce, or any related field, keep reading as this is applicable to the future of commerce.

As many of you know from my previous newsletters, I've been on a journey back to analog timepieces (check out OP #292 for the full story). While building my collection, I've run into that classic dilemma: how do you visualize what a new strap will actually look like on your watch without seeing it in person?

The Watch Strap Visualization Problem 🤔

We've all been there - staring at endless options online:

  • Thousands of strap varieties

  • Every material imaginable (leather, NATO, rubber, etc.)

  • Endless color combinations

  • Different textures and finishes

Without seeing them on your specific watch, it's basically a guessing game.

ChatGPT: Your Personal Watch Stylist 🤖

Here’s my exact process to how I use ChatGPT to help me style my watches. For the AI experts in the OP community, feel free to reach out if I’m doing anything wrong or ways to make this process better.

Step 1: Teach ChatGPT about your watch

Upload a clear photo of your watch to ChatGPT. Don't have it yet? No problem - just find a good product image online. Google Image search and/or Instagram are your friends. Heck, just ask ChatGPT. This becomes your visual foundation.

Step 2: Ask for curated recommendations

I simply ask: "Can you recommend 5 alternative watch strap ideas for this watch?" I even point it toward specific strap retailers I love (Handdn is my go-to but I have others as well).

ChatGPT then delivers personalized suggestions with mini-explanations for each choice. For example, with my Seiko Alpinist SBCJ031 Titanium HAQ, it suggested a "Beige Suede Leather Watch Strap - Adds a soft, casual touch that pairs well with the cream dial."

Step 3: See it before you buy it!

The magic moment: ask ChatGPT to visualize the recommendation. My exact prompt: "Can you show me what the Beige Suede Leather Watch Strap would look like on this watch? Can you please render a picture?"

The result? A stunningly accurate visualization of how that strap would transform my watch. See above.

The Future of Shopping Is Here

After seeing the render, I immediately purchased that beige suede strap and couldn't be more excited for it to arrive. The confidence of knowing exactly how it'll look on my watch? Priceless.

I can easily see this as a component to the future of shopping - trying before buying in the digital space. It's transformed how I approach watch customization, and I suspect it'll do the same for you. But this is applicable far and beyond just the watch/strap idea. I imagine this is useful and applicable across e-commerce.

What watch are you looking to refresh with a new strap? Drop me a comment and let me know if you try this method! ⌚💬

Thank you for reading and subscribing to this week’s OP letter. Feel free to always reach out with any questions and feedback.

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