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The Journey

The Journey

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

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Articles

The Journey: #78: CS Is Not Set It and Forget It

Jul 21, 2026

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4 min read

The Journey: #78: CS Is Not Set It and Forget It

Here's the thing about building a great customer success program: everyone wants credit for building it, and almost nobody wants to keep checking if it still works. Leaders love to point at the process they stood up two years ago like it's a trophy on a shelf, conveniently ignoring that headcount changed, the tools changed, the customer base changed, and the process definitely did not keep up with any of it. And let's be honest, auditing your own org is not fun, because it means admitting that something you built might need to change, or worse, admitting you haven't actually looked closely enough in a while to know one way or the other.

The Journey: #77: Onboarding Isn't a Phase, It's a Subscription.

Jul 14, 2026

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5 min read

The Journey: #77: Onboarding Isn't a Phase, It's a Subscription.

Every CS org has this ritual and you know exactly what I'm talking about. Account goes red, everyone swarms, you hop on a call, you pull up the health score, someone promises a save plan, and you have the same conversation you've had a hundred times before with a hundred different logos. And then nothing changes. The account gets a little better, everyone pats themselves on the back, and six months later it's red again and you're back in the same room having the same conversation like it's Groundhog Day.I ran this playbook for years, genuinely believing I was doing the work, before I finally figured out the problem was never the conversation. It was everything I assumed going into it.

The Journey: #76: The Meetings We Stopped Having

Jul 7, 2026

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4 min read

The Journey: #76: The Meetings We Stopped Having

In 2012, if I told my boss I was getting on a train to see a customer, the answer was "good, go." No business case. No approval chain. No "is this really necessary." It was the job. Somewhere between then and now, that stopped being true. And I don't think enough of us have clocked what we lost when it did.

The Journey: #75 The Brightest Red Flag

Jun 16, 2026

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5 min read

The Journey: #75 The Brightest Red Flag

I'm a researcher by nature. Before I make a big decision, I go deep. So when I was evaluating a new role, I came prepared. I asked over 200 questions covering business metrics, customer management philosophy, product innovation, growth strategy. I had seen the data and done the work. Yet I still walked into the wrong situation. Not because I was careless. Because I was asking the right questions about everything except the one thing that actually mattered.

The Journey: #74 It's Better to Know the Truth

Jun 9, 2026

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5 min read

The Journey: #74 It's Better to Know the Truth

Most renewal processes are built around the company's comfort, not the customer's reality. We set the timeline that works for us, schedule the calls that fit our calendar, and walk into those conversations armed with slides, talking points, and a whole lot of optimism. Somewhere in all of that, we forget to actually ask the customer what's going on. That's not a renewal process, that's a performance. And we can already guess how it ends.

The Journey: #73 Stop Blaming Sales

Jun 2, 2026

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4 min read

The Journey: #73 Stop Blaming Sales

Don't hate the player. Hate the game. CS teams have turned blaming AEs into a team sport. The deal closes, the commission gets paid, and suddenly CS is inheriting a customer that was never going to work, muttering under their breath about how Sales ruined everything ... again. But here's what I actually believe after 14+ years of watching this play out: the AE is not the villain. The process is. And until we're willing to say that out loud, we're going to keep solving the wrong problem.

The Journey: #72 This Is Not Customer Success

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.

The Journey: #71 The Influence in the Room

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.

The Journey: #70 Product Ideas to Prioritize and Punt

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.

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The Journey

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

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