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I’m sure y’all probably know (or have guessed) that I’m a perfectionist. Not just that, but the worst kind of perfectionist: the kind to whom a half-assed effort (or even a rough first draft) is actually physically painful, to the point that my brain would rather do nothing than something that’s not beautiful or profound or at least marginally useful.
Which brings us to my other crippling fear: that the stuff I love doing doesn’t add anything of worth to the universe. You know that part of imposter syndrome that tells you that not only do you not know what you’re doing, but everyone around you is humoring you because they don’t want to hurt your feelings about you not knowing what you’re doing? Yeah, that’s the voice in my head all the time.
Combine those things, and it’s easy to see how I burn myself out and end up with long stretches of silence in the newsletter. I almost skipped this week’s Roundup, because my kids have been sick and there’s just been so much going on in my personal life that the last week has been a monster, tearing up my schedule. I knew I’d only be able to work on this issue briefly, and the ugly thought that it’s not going to be useful to anybody because of that whispered just skip it, no one will read it anyway into my ear.
But! Then I remembered this piece from Anil Dash that I read earlier this week: Launch it 3 times, about how if you have a product or an idea and it’s not gaining traction or you’re struggling, you really just have to rework and recommit:
But if you’re moving with conviction, and you’ve created something meaningful, and if you’re serving a real community that you have a deep understanding of, then it may be the case that you simply need to try again. If you are not moving with conviction to create something meaningful for a real community, then you don’t need to do it three times, because you don’t even need to do it once.
So many of the creators and innovators that inspire me most often end up working on their best ideas for years or even decades, iterating and revisiting those ideas with an almost-obsessive passion. Most of the time, they’re doing it because of a combination of their own personal mission and the deep belief that what they’re doing is going to help change people’s lives for the better. For those kinds of people, one of the things I want most is to ensure that they don’t give up before their ideas have had a full and fair chance to succeed, even if that means that sometimes you have to try, try again.
This was very helpful advice for me today, seeing as I feel like I’ve relaunched this newsletter about a dozen times, and sometimes1 that feels like failure.
So. This is me, trying, trying again, and doing the thing half-assed. Rather than apologize for that (as is my instinct), instead I’m going to thank you again for reading and being so patient and cool. Y’all rock.
News from Around Supportlandia
Alice in Wonderland (if Wonderland had layoffs)
SaaStr’s Jason Lemkin recently published a piece noting that Customer Support hiring declined by 65% from 2023 to 2025.2 He theorizes (reasonably) that AI is the culprit, as companies restructure their Support teams to automate basic work and provide premium human support.
And while I don’t think he’s entirely wrong, I don’t think he’s entirely right, either.
Why? Well, for starters, that time frame just happens to coincide with the worst layoffs Tech has seen in 22 years. The reasons for that are numerous, but this means that, during the same period, more CX professionals were competing in a shrinking market for fewer roles than ever before. In that kind of environment, of course Support hiring declined drastically.
But the second factor here actually does involve AI: not so much what AI can do in reality, but companies’ perception of what AI can do.
Y’all remember when Klarna announced back in 2024 how awesome their chatbot was and how it was doing the work of 700 agents, then just a year later admitted that its “pursuit of cost-cutting in customer service, fueled by advancements in artificial intelligence, has gone too far” because the support the chatbot was providing was low quality and customers wanted to speak to humans?3
For a short while, Klarna found itself in a strange wonderland, then realized it was actually a dream and woke up. I think a lot of companies were (and some still are) in that same wonderland. Whether their wake-up call is as harsh and as public as Klarna’s remains to be seen, but — for their sake and ours too — I hope it comes sooner rather than later.
And Now for Some Good News
Caitlin Sills joined Notion as an AI QA Analyst.
Derek Nielsen joined GitLab as a Senior Customer Success Architect.
Erica Clayton joined Forethought as Head of Partnerships.
Alexander Lavoie was promoted to Principal Customer Success Manager at Red Panda Data.
Andee Silverman earned certifications for all 5 Responsible AI courses from All Tech is Human.
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Read, Watch, and Listen
Read
Jen Weaver does some very cool work in the CX world, and if you’re not reading her newsletter, The Customer Snapshot, well, you should be (especially if you like this newsletter, Jen’s is a quicker read but with very similar vibes)! (It also has a shiny new format — love to see creativity at work!)
Jacob Baadsgaard wrote an excellent piece on the cruelty of being nice.
Bee Gagliardi posited that shadow CX is about to become a massive problem.
Miranda Green wrote about how laid-off journalists are turning to platforms like Substack to try to make a living, and Leah Garden wrote about how that’s increasingly impractical (and both point out why this is dangerous to our democracy).
Wired’s Molly Taft wrote about how Big Tech’s claims about generative AI’s positive impact on the environment are sketchy as hell.
Watch
Jess Cervellon says no money, no honey (and I agree with her).
Gabriela Passeri spoke with Support Stack about how AutoDS actually helped Fin understand their product.
Listen
Andrea Townsend spoke with The CX Files about the critical need to retrain frontline agents on AI, so they become AI enablers (rather than replacing them with AI). Host Ben Foden calls it a must-listen, and I concur!
Upcoming Events
Success, Support, & Ops Leaders Dinner NYC
February 23 at Grandma's Home, NYC, NY. Hosted by Women of Customer Success. Request invite here.
Austin Chapter - Leaders Dinner
February 24 at Juliet Italian Kitchen-Barton Springs, Austin, TX. Hosted by Women of Customer Success. Request invite here.
Customer Success Summit Austin
February 24-25 at Hilton Austin, Austin, TX. Hosted by Customer Success Collective. Get tickets here.
Contact Centre Strategies Summit
February 24-25 at the Old Mill Toronto Hotel, Toronto, ON. Hosted by Strategy Institute. Get tickets here.
CS and Revenue Leaders in Boston
February 25 at 5:30pm ET at OnRamp Office, Boston, MA. Hosted by OnRamp and MGMT Boston. Register here.
Marketplace Risk Austin Conference 2026
February 25 at the Dell Jewish Community Center, Austin, TX. Hosted by Marketplace Risk. Get tickets here.
Building Customer Success from Scratch in an Early-Stage Startup
February 26 at 11am ET. Online event hosted by Customer Success Collective. Register here.
Scaling Customer Success Without Losing Impact
February 26 at Dovetail, Sydney, AUS. Hosted by Women of Customer Success. Register here.
How to Start a Career in Community Management
February 28 at 11:00am ET. Online event hosted by CMX by Bevy. RSVP here.
Find these events and many more in the Events directory at Support Human Resources!
1 Oh, who am I kidding, usually.
2 Hat tip to Neil Smith for getting this on my radar.
That's it for this week! If you have items for the Roundup you'd like to submit, you can do so at [email protected], but be sure to check out the Roundup FAQs first.
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