As we close the year, I’ve been thinking a lot about the choices that shape our careers; the bold ones and the quiet ones. And the truth is, for a long time, I made the quiet ones. The safe ones. The comfortable ones. The ones that didn’t require me to be seen too much or want too much. I spent years playing small. Act 1: Marketing: When growth felt effortless In my early career, Marketing Kristi, opportunity seemed to find me. Fresh out of college, I landed in advertising wi

For a long time, December looked the same for me every year. I’d sign off the day before Christmas Eve and disappear until somewhere between January 3rd and January 5th. No email. No Slack. No pretending I was “kind of around.” And honestly, it made complete sense. I host all the holidays. My house becomes the gathering place. There’s food to plan, people to take care of, traditions to keep alive, and a running list of things that somehow only exist during the last two weeks

One of the most common things I hear from Customer Success Managers is some version of this: “I didn’t want to hurt the relationship.” It usually comes up when we’re talking about a customer who didn’t renew. One that went quiet. One that felt “off” for months before the decision finally landed. Or when we know we need access to someone more senior, but the main point of contact is acting as a blocker. And every time I hear it, I know the story before it’s fully told. Because

When I started as a CSM back in 2012, I was convinced I had the best job on the planet. Enterprise accounts. Fortune 500 logos. Big budgets. Big expectations. A whole lot of white glove energy. And I took that “white glove” part very literally. I met with my customers weekly or bi-weekly. I ran every call. I coordinated every conversation. If they had feedback for Product, I was the messenger. If they escalated a ticket, I was the firefighter. If they were speaking at our cus

Every year tons of brands rush to release their industry trend reports, and while I save most and read some, I do so with a mix of excitement and skepticism. Let’s face it, some feel completely out of touch. I literally sit there wondering who fills out these surveys. And then there are some who feel aspirational. Like yes, in some alternate universe with unlimited budget and resources that could possibly be a reality. And then there are the few that hit so painfully close to

I was recently scrolling through LinkedIn and came across a post encouraging CSMs to ask more questions. At first, I barely paused. It felt harmless enough. But the more I sat with it, the more it bothered me. Do we actually need more questions? Or do we need better questions? Because if we just pile on more basic, surface level questions, we are not doing real discovery. We are filling the air with noise and still walking away without the insight we need to drive impact. Qua

Coaching is one of the hardest parts of leadership and I learned that the hard way. When I first moved from being an individual contributor to a leader, I thought coaching meant carrying my team. I believed my job was to have every answer, jump in at every sign of trouble, solve every problem, and of course, do it all faster and better. At least that was the story I was telling myself. In reality, all I did was exhaust myself and unintentionally signal to my team that I did n

I remember the first time I heard the acronym PIP, Performance Improvement Plan. And I genuinely believed it was exactly what the name suggested. A thoughtful, intentional path for a leader to help an employee improve. A chance to course-correct. A roadmap back to success. It sounded helpful. Clear. Goal-oriented. A tool for growth. Then I became a leader. And the first time I went to HR to terminate an employee, I was told, “Before we do that, you need to put them on a PIP.”

There’s a certain type of manager you meet early in your career who teaches you something important, not through their brilliance, but through their absence of it. In my first SaaS role, over five and a half years, I cycled through a handful of managers. All different. All memorable for different reasons. But one sticks out because she was genuinely lovely, warm, positive, thoughtful, the kind of leader who asked how your weekend was and actually cared about the answer. She w

Lately, I’ve been thinking about timing, not the “trust the universe” kind, but the real-world timing inside startups and scaleups that determines whether you move forward or stall out. After 13 years in SaaS, I’ve seen a consistent pattern: Companies rarely suffer because they make the wrong move. They suffer because they make the right move far too late. You see this everywhere: Waiting to hire Waiting to fire Waiting to buy the technology Waiting to invest in onboarding, e

Every Customer Success leader wants to talk about churn, forecasting, onboarding, product adoption… but there’s a quiet little monster living in the background that most teams aren’t paying enough attention to: Feature ideas. Not the ideas themselves, those are gold. The way we manage them, that’s the problem. Most companies have figured out how to collect requests: forms, spreadsheets, portals, Slack messages, emails with subject lines like “Quick thought”… even the occasion

There is a moment every Customer Success leader knows well. A moment that feels like your stomach drops through the floor. A CSM resigns. And the first thought that hits you is the one none of us says out loud: How the hell am I going to redistribute these accounts? Because let’s be honest with ourselves. Your team is already at capacity. You are already at capacity. And while you are trying to stay composed and strategic, everyone on your team is quietly thinking the exact s

I’ve coached hundreds of Customer Success Managers over the years. Different companies, different products, different regions, different markets. Yet the same pattern appears over and over again. CSMs do not feel empowered. They are not empowered to say no. They are not empowered to drive change. They are not empowered to raise red flags. They are not empowered to make tough decisions. They are not empowered to prioritize for their customers. They are not empowered to deviate

Here is a hard truth we do not talk about enough in Customer Success. Some of the customers we write off the fastest are the ones sitting on the biggest opportunities. I know. I know. It feels easier to focus on the shiny, well-funded, “textbook” expansion accounts. They show up to calls. They read your emails. They know what they want. But not every customer is that obvious. And honestly, thank goodness, because the obvious ones are only half the fun. The real magic lives in

When I first started in SaaS, Sales Kickoff (SKO) was this mysterious, high-energy event I wasn’t invited to. It was the Super Bowl of Sales, strategy, targets, enablement, and a whole lot of celebration. At my first company (where I spent nearly six years), SKO was exclusively for Sales. No Customer Success, no Services, no Support. Just the folks with quotas and commissions. So imagine my shock when, at my next company, I learned Customer Success was included. I thought, “W

I perform my best when I have a clear goal and a plan. I’m an executor. A rule follower. A do-the-work-and-get-it-done kind of person. When I was in college, I chased A’s. I remember graduating with a 3.98 GPA because of one single A- in a journalism class, and I was furious. I missed my goal. Still Summa Cum Laude, still an incredible GPA, but in my head… not the goal. During my senior year, I landed my first job before graduation. My professors told me that if I completed a

I love when data validates what many of us in Customer Success have been saying for years: customer-led growth is the engine of modern business performance. The latest Public Market Pulse Report from Certinia analyzed more than 4,000 public company earnings reports and the findings are a massive win for Customer Success. The data shows a clear pattern: companies that talk about Customer Success are creating more value, and the market is rewarding them for it. Let’s unpack wha

Some of you may not know this, but my daughter Adriana is actually my stepdaughter. When Anthony and I got together, she was just three years old. She only knows life with me and Anthony… and then with her mother. In our house, we’ve never used the word step. She is my daughter, and I am a mother. Period. But in the beginning, it was hard. Really hard. I was trying to find my place, what was appropriate, what wasn’t, how to show up as a parent without overstepping. I wanted t

Early in my career, I didn’t know the differences between large corporate companies, small independent companies, and startups. My priority after college was simple: get a job. Ideally something that matched my major (or at least sounded like it did). Check. After a few years working for a large publishing company, I decided to take a chance and join a small marketing agency, private and profitable. Then, I moved to a large public company. Then back to publishing. Then back t

When I saw the 2025 SuccessCoaching Top 25 Customer Success Influencers list drop, I had to take a second to breathe it in ... six years in a row. Six. Years. That’s wild. And honestly, it’s not something I ever expected when I started sharing my thoughts on Customer Success all those years ago. I didn’t set out to be an “influencer.” I set out to make an impact, to share what I was learning, to help others avoid some of the same mistakes I made, and to build a community wher