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CS Insights
Let me tell you what I really think about Customer Success.
Come along as I share my thoughts and advice on all things Customer Success and Leadership. Browse through webinars, podcasts, articles and more to get my perspective on CS and beyond.
The Journey: #33 Flip the Risk
I remember my first CSM role when the business really started to scale. Suddenly, “risk” became the centerpiece of every conversation. At...
6 days ago2 min read
The Journey: #32 The Missing Mindreader
For as long as I can remember, I’ve been ambitious. Every job I’ve ever had came with a built-in, personal side project: designing the...
Aug 103 min read
The Journey: #31 Product Perception Penalty
In Customer Success, we spend a lot of time talking about value realization. But over the years, I’ve come to realize something just as...
Aug 103 min read
The Journey: #30 Renewals by Design
Let’s get one thing straight: Renewals don’t just happen. They’re not a due date. Not a Salesforce stage. Not a task on your CSM’s...
Jul 273 min read
The Journey: #29 The Research Edge
When I started my first role in Customer Success, I thought I had it all figured out. I had been a power user of the product.I knew the...
Jul 223 min read
The Journey: #28 Personalized ≠ Customized
There was a time in my career when I believed that “wow” moments came from building everything from scratch. Every onboarding flow. Every...
Jul 143 min read
The Journey: #27 The CSM Success Code
When I first stepped into CS leadership, I found myself managing a high-performing, high-engagement team full of hungry, driven CSMs. ...
Jul 63 min read
The Journey: #26 Face Time Matters
A few years ago, I was logging 200,000 miles a year. Great for my Delta status. Brutal on my body, marriage, and sanity. But completely...
Jun 302 min read
The Journey: #25 $2M, Ain't It
For years, we’ve been haunted by a number. Not a retention target. Not a CSAT score. Not even NRR. I’m talking about the mythical $2...
Jun 223 min read
The Journey: #24 So Long, Scaries
It used to hit me like clockwork. Sunday. 3:00 PM. That slow build of dread. The “Sunday Scaries” creeping in like a fog. But one Sunday,...
Jun 152 min read
The Journey: #23 All Systems Go
When I started my career as a CSM, everything felt manageable. I had a book of business, a list of clear priorities, a schedule that I...
Jun 83 min read
The Journey: #22 Rev Rec Needed
When I first got into Customer Success, my team didn’t own a dollar. No renewals. No expansions. No upsells. Just pure, value-driven...
May 312 min read
The Journey: #21 The Early Arrival
I’ll never forget one of my earliest wake-up calls in Customer Success. We were onboarding a string of new customers who were wildly...
May 262 min read
The Journey: #20 The Interview Upgrade
When I interviewed for my first Customer Success role back in June 2012, after several conversations with various stakeholders, I made it...
May 182 min read
The Journey: #19 The Difficult Departure
When I joined this particular company a few years ago, there wasn’t much in place. No team, no structure, no clear strategy. Just a blank...
May 112 min read
The Journey: #18 Status Quo Syndrome
Over the years, I’ve learned what questions to ask during the interview process to set myself up for success. I got clear on what I...
May 53 min read
The Journey: #17 The Land Grab
One of the quiet games happening inside every growing company is the "land grab." Leaders fight to take over more teams. More revenue....
Apr 272 min read
The Journey: #16 Swing and a Miss
There’s a first time for everything. I’ll never forget my first board meeting as a new VP when I was presented with my first-ever...
Apr 202 min read
The Journey: #15 Unseen, Unsaid, Unknown
I used to think I was that manager—the one everyone trusted. The cool boss. Like how Regina George's mom thought she was the "Cool Mom"....
Apr 133 min read
The Journey: #14 The Automated Advantage
When I started my Customer Success journey, we didn’t have AI. Heck, we barely had folders we could find. No centralized hub. No...
Apr 62 min read
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