The Journey

Real talk on Customer Success, revenue, and building a career you're proud of.

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Articles

May 26, 2026

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7 min read

The Journey: #72 This Is Not Customer Success

There is a version of Customer Success that looks really good on paper. It's the one where there are QBRs on the calendar, NPS surveys in the queue and clean customer journey with an Onboarding Manager, CSM, and AM all neatly in a row. There are bright green Health scores and even a renewal meeting scheduled 90 days out. It checks every box, and for a lot of organizations, that's exactly the problem. I've spent the last several years partnering with and consulting CS teams across the industry, and what I keep seeing is the same thing: programs that are built to look like Customer Success but aren't actually doing it. And I get it. I really do. Because I've built it and been there too.

May 12, 2026

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4 min read

The Journey: #71 The Influence in the Room

We spend so much time focused on the main point of contact, decision maker, exec sponsor and the economic buyer. You know ... the people who impact the contract. And that focus makes sense. Until it doesn't. Because the person who can quietly kill your deployment, poison your renewal, or advocate for your competitor might not be on your stakeholder map at all. See these folks aren't at the table, but they are in the room. You can't always see them, but they're there.

May 5, 2026

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5 min read

The Journey: #70 Product Ideas to Prioritize and Punt

Every CSM I know has a list. A long one. Feature requests, product ideas, enhancement asks, wishlist items that have been sitting in a spreadsheet since 2021. And most CSMs treat that list like a sacred document. Like their job is to carry it into every product meeting and fight until something gets built. I was that CSM. But when I became the leader, I understood the assignment, it was time to pick and prioritize. This is the issue that changed how I think about it.

Apr 28, 2026

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5 min read

The Journey: #69 It's Your Journey, Not Theirs

I have built beautiful customer journeys. They were color-coded, had exit and entrance criteria, and were generally stakeholder-approved. The kind that made folks nod and made new CS hires feel like they had a real playbook. And for years, I told myself customers just needed to follow the path. But they didn't and they weren't going to. And somewhere between my fifth leadership role and a team meeting I'll never forget, I finally stopped pretending otherwise.

Apr 21, 2026

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6 min read

The Journey: #68 Your Exec Sponsor Program Is a Lie

Every company I've ever worked with has an exec sponsor program. Or at least, they think they do. What most actually have is a name in a field inside their CSP, a quarterly touchpoint someone had to chase down to get scheduled, and a leader who shows up just long enough to say they were there. That's not a program. That's a checkbox with a title next to it. Real executive sponsorship isn't about showing up on schedule. It's about being genuinely accountable for someone else's success, whether or not it's on the calendar. And there's a big difference between those two things.

Apr 14, 2026

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9 min read

The Journey: #67 You Don't Have to (And Shouldn't) Automate Everything

Everyone has an automation story. A workflow they built, a sequence they set up, a trigger they configured to save their team hours every week. And honestly? A lot of those were the right calls. But somewhere along the way, automation stopped being a strategy and became the default. The question was never "should we automate this?" It was "what else can we automate?" And that shift, that subtle change in how we frame the problem, can cost us more than we realize.

Apr 7, 2026

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7 min read

The Journey: #66 You're Only New Once, So Make It Count

There's a short window when you start a new job where you can ask anything, push anywhere, and people will give you access and candor they'd never extend to someone who's been around longer.It's called being new. And most leaders waste it.They spend the first 90 days learning the internal landscape, building relationships with their team, sitting in on syncs, reviewing dashboards. All of that matters. But there's one thing that matters more.Getting directly in front of your customers.

Customer Success

Mar 31, 2026

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8 min read

The Journey: #65 You Don’t Have an ICP, You Have an IBP

Everyone loves talking about the Ideal Customer Profile (ICP). You know, the thing that's supposed to filter out the bad fits before they ever become your problem.Except for a lot of CS teams, it doesn't work that way. We get customers handed to us daily, and while they technically meet the criteria, we can see and feel the difference. We're all struggling.The problem isn't your execution; it's something much greater than that.