Jeremy Donaldson

Hello! My name is Jeremy Donaldson.

I am a Top 25 Customer Success Influencer and Leader with over 10 years of experience helping organizations solve their biggest challenge: Retaining and Growing customers.

I work to solve retention and growth by leading teams in 4 areas:

1) Serving my teams.  I work for them, not the other way around
2) Understanding my customers and their goals
3) Working collaboratively to build trust with our cross-functional partners
4) Using data to drive decision making

I have managed teams of up to 12 CSMs across multiple segments including digital CS, enterprise, and strategic accounts.

My teams have consistently delivered over 120% NRR, 95% GRR, 50+ NPS, and 70%+ product adoption all while growing $100+ million dollars in arr collectively.

I am the type of customer success leader who will serve our teams, challenge the status quo, and create revenue opportunities for our business. 

---

My "why" revolves around being there for his wife, 3 kids, and faith in Jesus.

Success to me looks like:

🔹 Transparency: Speak your mind
🔸 Authenticity: Be the real you
🔹 Vulnerability: Let people in
🔸 Conscious listener: Allow people to be heard
🔹 Celebrator: Show people they are valued
🔸 Giver: Always give more than you receive 

“When I stand before God at the end of my life, I would hope that I would not have a single bit of talent left, and could say, 'I used everything you gave me'." - Erma Bombeck

Fun facts:  I've traveled to where J.R.R. Tolkien found his inspiration for Rivendale in the Fellowship of the Ring (Lauterbrunnen, Switzerland).

Founder & CEO

CS in the Valley is on mission to serve customer success professionals in growing their businesses and careers.

- Career coaching for customer success managers
- Job seeker support
- Executive consulting for CS teams
- Customer Success technology optimization (Totango & Gainsight)

Jeremy Donaldson 🤝

Jan Young, MBA, CSPO, CSM

Project Manager

I help Heads of CS become VPs and get a seat at the Executive Table | Customer-Led Growth Advisor | 2X Top 25 CS Influencer | Top 50 CS Influencer | Top 50 Women Leaders in CS | Top 100 CS Strategist | Investor

Why do some CS leaders command executive respect, while others, despite strong results, keep fighting to be heard?

I've been in Tech for 20+ years and been through two exits as VP Client Services. Here's what I've learned:

✨ EVERYTHING has changed.

The speed. The AI transformation. The business models. The way we need to lead.

I see CS leaders working until midnight, delivering great results... and still getting told "we need to cut CS headcount."

Sound familiar?

The old playbooks stopped working.

AI is reshaping how we work, how we go to market, how we serve customers. Your 2023 playbook is irrelevant.

Today, you need SYSTEMS.

Here's what I know from coaching hundreds of CS leaders:

Those who break through have mastered The Modern CS Growth System, 4 pillars of executive impact:

💡 Modern Management & Change Leadership - Lead in the AI era  
💡 AI Fluency, Automation & Autonomy - Transform operations, pricing, GTM
💡 Business & Customer Economics - Speak profitability, not just retention  
💡 Repeatable Customer Revenue & Team Systems - Build scalable frameworks, not heroic firefighting  

This is a systematic approach to demonstrating executive-level impact in the language your fellow executives understand.

👉👉 This is what CS Business Leaders master. Not pieces. The whole system.

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WHO I WORK WITH

CS leaders who've built a department but aren't getting traction:

✔  You deliver strong results, but executives still see CS as a cost center
✔  You're excluded from strategic decisions where your insights would be valuable
✔  You’re told "do more with less" instead of getting resources
✔  You know modern CS should look different, but you're stuck in outdated frameworks

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HOW WE WORK TOGETHER

⚡️ CS BUSINESS LEADERSHIP ACCELERATOR - Master the 4 pillars and build the Modern CS Growth System specific to your goals/challenges through executive peer community + project-based frameworks + personalized coaching.  

🔗 https://go.stepupxchange.com/csbl-accelerator

📬 NEWSLETTER:  I publish a weekly newsletter on modern CS strategies

📧 DM me and I'll share which resources fit you

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RESULTS

✅ Become an award-winning executive
✅ Reposition your team as a strategic revenue driver
✅ Transition from firefighting to repeatable, scalable systems
✅ Innovate with AI to drive profitable customer revenue growth

The modern CS leaders who succeed aren't keeping up with change: They're leading it. 

-----
📬 Newsletter: janyoungcx.com/#newsletter  
📧 DM me: discuss your challenges  
🎯 Follow for daily insights

Founding Member

RevRoom is a trusted space where curious revenue leaders are collaborating on the future of B2B Go to Market alignment and GTM-Led-Growth.

I've been this CS leader. Sitting on the side of the road, looking at a map, trying to figure out where I went wrong.

Not because I didn't have data. Because I was watching for the wrong things.

I had NRR. Churn rate. Ticket deflection and resolution. "Health score."

But all of those metrics told me where I'd been. None of them told me where my customers were going.

And by the time I saw it, it was too late to change anything.

I was working with a CS leader recently who had the same problem. 
She knew every account's story. 
And that was the issue.

Everything felt like an anecdote. No pattern emerged. Just a series of one-offs.

The problem isn't the data. 
It's that we measure what's available instead of what actually matters.

Without knowing which stops matter and when you should get there, you won't know you're off track until you've arrived somewhere you didn't intend to go.

What most dashboards show:
→ NRR, churn rate, ticket volume, "health score"

What actually tells you if a customer is on track:
→ Are they doing what your best customers do at this stage?
→ Are they hitting the moments that move them toward their goal?
→ Are they progressing on time, or quietly falling behind?
→ Have they actually achieved what they came for?

Once you've defined those milestones, AI does the watching for you. It surfaces who's falling behind early, so you can act while there's still time.

Without that foundation, you're just watching the gas gauge on a car with no map.

Do you know what "on track" looks like for your customers at each stage?

📝 This week's newsletter walks through how to build the map.
🔗 [https://lnkd.in/gBrhN3As

 Want faster results and a room full of CS leaders building alongside you? 
🚀  Doors are open for the StepUpXchange CS Business Leadership Accelerator through the end of this week. 

→ It's a guided, project-based community where we build these systems together. 

→ DM me if that's your kind of room.

StepUpXchange
JanYoungCX

Customer Success Leadership Coach | Transforming CS Leaders into AI-First Business Leaders | Modern CS Strategy + AI + Systems | 3X Top 25 CS Influencer | Get weekly CS strategies: Subscribe to my newsletter

A promotion. A raise. A seat on the executive team.

Here's the shift that got Virginia there.

Her CS team was scaling fast. But the work wasn't.

→  Manual workarounds that couldn’t scale with the team
→  CSMs building custom reports instead of driving outcomes
→  High-growth accounts getting whatever time was left over

Virginia talked about it before. The stories made sense to her. But they didn't land.

Not because leadership didn't care. Because she wasn't communicating it in a way they could act on.

Stories without data are easy to dismiss. 

Virginia was in the first cohort of the StepUpXchange CS Business Leadership Accelerator. One of the pillars is Business Expertise. 

✅  And this is how she put it to work…

She stopped telling stories. She started doing the analysis. And showing the numbers.

She started small.

She reframed their manual work problem as operational efficiency and aligned it with the product roadmap. Now her CTO could act on it.

Then she went deeper.

She pulled Revenue and Cost to Serve by account. Analyzed segments. Found where the growth opportunities were, and where they could cut, to improve profitability.

But these weren't small changes. The stakes were real.

→ It meant retraining Sales on a new motion
→ It meant giving the board a different story about growth
→ It meant shifting the product roadmap to new segments

Virginia backed it up with detailed data. The data made it undeniable.

The results:

✅   Marketing and Sales doubled down on the highest-performing segments
✅   Engineering accelerated features for power users
✅   Onboarding got shorter. CAC dropped. NRR climbed.
✅   More advocates. More referrals.

Virginia's team moved from manual and reactive to strategic.

And something else changed too.

Now when she brings the data, it anchors the conversation. She earned a seat at the table by proving the business impact of the CS function.

Big results for the company. 
✨ And for Virginia: A promotion, a raise, and a seat on the executive team.

The steps that got her there:

1. Reframe the problem in terms leadership cares about (efficiency, profitability)
2. Back it with data the executive team can act on
3. Start small, prove it works, then go bigger

Nobody asks you to do this work. You just start doing it.
And somewhere in the doing, you find the data that changes the conversation.

This is Business Expertise in action, one of the three pillars of the Modern CS Growth System.

It's not about knowing more. It's about translating what you know into the language executives use to make decisions.

We work on this together in the StepUpXchange CS Business Leadership Accelerator.

I'm walking through the full system at the StepUpXchange NexGen CS Leadership Masterclass:
📆  Tuesday, Feb 24
🕘  9am PT / 12pm ET
👉  Register here: https://lnkd.in/gsETU8a2

📝  I'm writing about the cost of gap filling in my newsletter this Saturday.
👉  Get it here: https://lnkd.in/gBrhN3As

StepUpXchange
JanYoungCX

A lot can change in a year. Last spring, Nathan Spear was just starting to learn AI tools. Last week, John Gleeson held him up as an example for the entire CS community.

Nathan is a member of the StepUpXchange CS Business Leadership Accelerator and he’s in between roles. But that doesn’t keep him from building. 

His most recent creation:
An interactive resume website that shows how his achievements and experience will impact the hiring company’s customers and help them achieve their goals. 
-->  Hiring managers can even upload their JDs to see if Nathan is a match and how he will help their business.

✨  This is classic SHOW Don’t Tell. Modernized for age of AI.

It’s really cool.

It’s so cool, John Gleeson clicked the link and was inspired to write a LinkedIn post challenging CS leaders to stop talking about change and start building it. 

Nobody asked John to do that. Nathan's work just made him want to.

Now other CS pros are reaching out to Nathan for advice on how to build their own version of an interactive resume.

This isn't just a cool one-off project. Nathan's site connects everything we work on in the Accelerator:

Business Acumen: 
Shows how his work impacted past companies' bottom lines AND his clients'. Translated to how he can help yours.

Repeatable Customer Revenue Systems: 
Shows how he's driven expansion and renewals. Translated to how he can help yours.

AI Fluency: 
He literally shows it. And shares links to other projects so you know this isn't a fluke.


That's what happens when you're in a community of builders. You share ideas and use cases, your growth is accelerated, you build momentum you wouldn't find on your own.

What would it look like if you showed your value instead of explaining it?

👉 Nathan's interactive resume: https://lnkd.in/gM3HHnpn
👉 John's post:  https://lnkd.in/gJNVdKXx

If you want to learn more about the StepUpXchange CS Business Leadership Accelerator, I’ll share some info after my next Masterclass where I’ll be sharing the same Modern CS Growth System that Nathan has used to accelerate his growth.

👉 NexGen CS Leadership Masterclass, Feb 24:  https://lnkd.in/gsETU8a2

StepUpXchange
JanYoungCX

What if Preventing Churn is the Wrong Goal?

The idea that the primary job of Customer Success is to prevent churn is the single biggest reason why most CS teams are treated like a cost center.
 
It's a fundamentally reactive and flawed way to view your customers.

Look, I completely understand why this belief is so common. Churn is a terrifying, revenue-killing metric. 

Every executive and board member is watching it, so it makes perfect sense to build your entire strategy around stopping the bleeding.

But "preventing churn" is just playing defense. 

It defines success by the absence of a negative. 

True Customer Success isn't about preventing failure; it's about actively engineering your customer's victory. 

When you become essential to their business outcomes, churn becomes an afterthought because successful partners don't leave.

Instead of playing defense, you go on offense by architecting customer growth with a proven system. 

It's about defining what “success” means for your customer and then using leading indicators to guide them there, turning their progress into your revenue.

So let me ask you... do you want to continue playing defense, constantly fighting to justify your team's existence by pointing to the disasters you prevented? 

Or are you ready to go on offense, becoming a proven revenue driver by architecting the growth you actively create?

If you’re ready to transform your CS team from a defensive cost center into a proactive growth engine, come learn the systems that make it possible.

👉  Comment “Modern CS Growth System” or DM me and I’ll share the info.

StepUpXchange
JanYoungCX

We're at a crossroads in CS and most leaders don't see it yet.

AI has changed what's possible. We can analyze data we couldn't touch before. Automate work that used to take hours. See patterns we used to miss.

But when it's time to scale? Most CS leaders still go back to the same place: "I need to hire another person."

That instinct made sense in the old era. It's a trap in this one.

Because the leaders pulling ahead aren't asking for more headcount. 
👉  They're redesigning how their teams create value.

I've seen it firsthand. Accelerator members have had their teams cut by 60 to 75% and still scaled their programs with better results. 
Not by working harder. 
By building differently.

Here's the thing: 
Depending on your business stage, your CS team is contributing 70 to 95% of your company's bottom line.

But most CS leaders are still acting like they're in the engine room. 
 - Burnt out. 
 - Stretched thin. 
Working overtime on a function that drives the business without claiming the influence to match.

The ones in strategic conversations? 
--> They've moved to the captain's deck. 
-->  Not because they asked for a seat. 
Because they own the metric that matters most: Customer Revenue.

The gap isn't experience. It's a model.

In the StepUpXchange CS Business Leadership Accelerator, we build that model: the Modern CS Growth System.

It has three parts:

👉  Customer Revenue Expertise. 
Stop hoping customers renew. Build a system that earns it.

👉  Business Expertise. 
Walk into executive conversations without needing a translator.

👉  AI Fluency. 
Not another tool to figure out alone. A strategic layer that multiplies what your team already does.

When these three come together, you stop being a cost center and start doing what CS was always built to do: 
🚀  Drive the revenue that grows the business.

You've heard "stop being a cost center" before. What you haven't had is a system to make it real.

Will you keep negotiating for budget to execute your vision?
Or build a model that earns you the influence you've already worked for?

Join us for the next StepUpXchange NexGen CS Leadership Masterclass:
📌  How You Can Drive Growth & Exec Impact 
       Even if You're Not in the Boardroom
📆  Tuesday, Feb 24
🕘  9am PT / 12pm ET / 5pm UK

StepUpXchange
JanYoungCX

If you've ever found out about a pricing change, product pivot, or go-to-market shift in an all-hands meeting, along with everyone else, you know this feeling.

Sound familiar?

You're hitting your numbers. Building relationships. Retaining customers.
And you're still not in the room when the strategic decisions get made.

This is the C-Suite Impact Gap.

And Q1 2026 is when it matters most. AI is reshaping investor expectations, and companies are locking in strategic decisions right now about where to invest, where to cut, and which teams get influence.

I wrote about the four questions that determine whether CS leaders get heard in these conversations, and the system that connects them.

Question 1 is about why your insights get dismissed (even when you're right).

The other three? They're in the article below.

If you're tired of being excellent at execution but invisible in strategy, this one's for you.

🗞️ Read it below 👇

Quick Note: This article was first shared with my email community. If you want strategies and systems like this as they're released, join thousands of

Open article: Invisible in the C-Suite? How to Get Heard as a CS Leader  by Jan Young, MBA, CSPO, CSM • 7 min read

Invisible in the C-Suite? How to Get Heard as a CS Leader

I used to think being available for fires made me a good leader.

My calendar had gaps. On purpose. So when my team needed me, I could jump in. Save the account. Calm the customer. Be the one who fixed it.

I thought that was human-led leadership.

Turns out, it was the problem.

My team didn't have a system. They had me. And every time I stepped in, I reinforced that pattern.

React. Resolve. Repeat.

When I finally looked at the fires we kept fighting, they weren't random. The same types kept coming back, just wearing different client names.

Most CS fires come from 4 places:

1️⃣ Customers who weren't set up well from the start.

Onboarding focused on product features instead of business goals. Three months later, the customer doesn't see value. Now it's a save conversation that could have been prevented.

2️⃣ Handoffs that dropped context.

Sales promises something. Implementation interprets it differently. CS inherits a customer who expected something they're not getting. Nobody finds out until the customer is frustrated.

3️⃣ No early warning signals.

By the time someone raises a hand, the problem has been building for weeks. The customer has already made up their mind. Now you're in damage control instead of prevention.

4️⃣ Work your team does that isn't really theirs.

Features that don't exist or don't work the way the customer needs. Your CSMs become the manual workaround. That's not customer success. That's filling gaps for another team's roadmap.

When I started building systems to prevent these instead of just responding to them, things shifted.

Fewer escalations. My team focused on work that moved the needle. Customers trusted us more. Renewal and expansion rates went up.

You can't stay strategic if your team is stuck in firefighting mode. And being more available won't fix it. Building prevention will.

📝 This week's newsletter goes deeper and includes a quick 2x2 exercise to map your fires by frequency and control, so you know where to start.
🔗 in my profile

👉  Which of these 4 is eating most of your team's week?

StepUpXchange
JanYoungCX

If you've ever had a great idea for a CS tool and watched it die in a backlog, you know the feeling.

😣 That slow frustration of seeing exactly what your customers need, and having zero path to build it.

A renewal risk dashboard that updates in real time. An onboarding flow that adapts to each customer's tech stack. A health score calculator built around the metrics you actually care about.

All sitting in a ticket queue. Waiting on engineering. Going nowhere.

👉 Here's what most CS leaders don't realize yet:

💡 You already have everything you need to build those tools yourself.

Not because you've learned to code. Because you're closer to the customer than anyone else in your organization. You know which problems are worth solving and which ones are noise.

You know what customers actually struggle with. Which interventions move the needle. The gap between what executives say they want and what actually drives retention.

🧠 That knowledge is the strategy. AI is just the builder.

If you're a CS leader watching AI evolve and wondering how it actually applies to your work and your role, this is where it clicks.

I built an interactive CS assessment app in 4 hours with no coding background. Here's exactly how I did it, why building with AI is simpler than you think, and why your domain expertise is the unfair advantage that makes all of it work.

🗞️ Read it below 👇

If you want strategies like this hot off the press, join thousands of CS leaders at JanYoungCX.com/#newsletter - If you've ever had a great idea for a

Open article: That CS Tool You Wanted to Buy? How CS Leaders Are Building Them With AI Instead by Jan Young, MBA, CSPO, CSM • 7 min read

That CS Tool You Wanted to Buy? How CS Leaders Are Building Them With AI Instead

The best conferences don't just inform you. They change what you do on Monday morning.

I'm speaking at CS Summit NYC on March 10, and in my session we're going to reflect and take action. 
👉 CS Confessions: Vent, Share, Solve

Here's how it works...

By the time you get to me, you'll have spent the morning absorbing some seriously good content:
🔸  Customer data as strategy, 
🔸  Scaling CS without losing trust, 
🔸  Cross-functional alignment...

My session is where we stop, surface what hit home, and turn insight into ACTION.

We'll bring the real challenges to the table.  
Share with each other. 
And together we build an Action plan. 

Not "notes to revisit someday," but focused priorities you can act on now.

Then the afternoon shifts to AI in CS, and we'll go in primed. 

Because knowing WHAT to solve makes it a lot easier to figure out HOW AI can help you act faster and smarter.

Day Two continues that momentum. 
Every session, every conversation, every hallway connection becomes material for what you'll act on when you get back to your desk.

That's the point. 
Not just learning. 
Taking ACTION.

If you're in the NYC area, there's still time to register.
👉 https://lnkd.in/gpM7p6jA

What's one insight from your last conference that you actually turned into ACTION, and what made it stick?

Drop it in the comments. 
Let's build a resource thread right here.

So excited to partner with Customer Success Collective and Liza Shtilbans! 🚀

StepUpXchange
JanYoungCX

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