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 🤝

Hi, I’m Angeline, VP of Customer Success turned Founder & CEO of CS RevSpeak. I help CS leaders turn messy, high-pressure realities into scalable systems that drive retention and growth.

𝗠𝘆 𝗝𝗼𝘂𝗿𝗻𝗲𝘆 𝗦𝗼 𝗙𝗮𝗿
With 𝗼𝘃𝗲𝗿 𝟭𝟳 𝘆𝗲𝗮𝗿𝘀 𝗶𝗻 𝗕𝟮𝗕 𝗦𝗮𝗮𝗦 (𝟭𝟭 𝗼𝗳 𝘁𝗵𝗼𝘀𝗲 𝗶𝗻 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽), I’ve had the privilege of guiding Customer Success through every stage, from pre-seed startups to growth stage.

Starting as an individual contributor, I’ve walked the path from managing small teams to overseeing entire departments, leading Customer Success, Managed Services and Customer Support functions. Working across four different startups over the last decade has shown me what CS looks like at every stage of growth and given me insight into the unique challenges and opportunities each phase brings.

𝗛𝗼𝘄 𝗜 𝗦𝘂𝗽𝗽𝗼𝗿𝘁 𝗖𝗦 𝗟𝗲𝗮𝗱𝗲𝗿𝘀
My mission when I built CS RevSpeak is simple: help Customer Success leaders lead with clarity, build high-performing teams, design scalable operating models, and confidently communicate the impact of Customer Success.

Through 𝟭:𝟭 𝗰𝗼𝗮𝗰𝗵𝗶𝗻𝗴, 𝗰𝗼𝗻𝘀𝘂𝗹𝘁𝗶𝗻𝗴 𝗮𝗻𝗱 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 𝗴𝗿𝗼𝘂𝗽 𝗽𝗿𝗼𝗴𝗿𝗮𝗺𝘀, I help leaders:
  • Navigate tough team decisions (performance, role clarity, exits)
  • Build high-performance cultures rooted in accountability and trust
  • Strengthen team structure, operating rhythm, and leadership presence
  • Lead their team with clarity through performance, role design, accountability and change without losing trust or culture

I’m here to share what I’ve learned and continue to grow alongside this evolving industry. Let’s connect if you’re interested in talking CS, leadership or just swapping insights on building teams for growth!

For free content and practical resources, 𝘀𝗶𝗴𝗻 𝘂𝗽 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗖𝗦 𝗥𝗲𝘃𝗦𝗽𝗲𝗮𝗸 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: https://csrevspeak.com/newsletter/

𝗔𝗻𝗱 𝘄𝗵𝗲𝗻 𝘆𝗼𝘂’𝗿𝗲 𝗿𝗲𝗮𝗱𝘆 𝘁𝗼 𝗲𝘅𝗽𝗹𝗼𝗿𝗲 𝗺𝗼𝗿𝗲, 𝘆𝗼𝘂 𝗰𝗮𝗻 𝗳𝗶𝗻𝗱 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴 𝗮𝘁 𝗵𝘁𝘁𝗽𝘀://𝗰𝘀𝗿𝗲𝘃𝘀𝗽𝗲𝗮𝗸.𝗰𝗼𝗺/.

Angeline Gavino

I’ve been the Founding CSM twice.
So I say this with respect: 𝗙𝗼𝘂𝗻𝗱𝗶𝗻𝗴 𝗖𝗦𝗠𝘀 𝗮𝗿𝗲 𝗮 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝗯𝗿𝗲𝗲𝗱.

You’re not “either” strategic or executional. You have to be both.

You’re building the plane while flying it in a season that’s equal parts messy and rewarding.

One week it’s onboarding and first value.
The next it's resetting expectations after the handoff, saving a renewal, and building basic visibility with whatever data exists right now (which is never as clean as you want it to be).

The job is hard for one reason:
𝗬𝗼𝘂’𝗿𝗲 𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱 𝘁𝗼 𝗱𝗲𝗹𝗶𝘃𝗲𝗿 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀 𝗻𝗼𝘄 𝘄𝗵𝗶𝗹𝗲 𝗱𝗲𝘀𝗶𝗴𝗻𝗶𝗻𝗴 𝗮 𝘀𝘆𝘀𝘁𝗲𝗺 𝘁𝗵𝗮𝘁 𝗺𝗮𝗸𝗲𝘀 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀 𝗿𝗲𝗽𝗲𝗮𝘁𝗮𝗯𝗹𝗲 𝗹𝗮𝘁𝗲𝗿.

There isn’t a built-in playbook.
There isn’t a bench of CS leaders to learn from internally.
There’s never enough budget.
And half the time, people don’t really understand what CS is supposed to do yet.

Most days, it’s just you trying to turn pattern recognition into process.
That’s why this role can feel heavy, even when you love it.

Looking back, what I wish I had more of wasn’t “tips.”
Most best practices floating around don’t apply to early-stage CS anyway.

I wish I had a true partner to pressure-test decisions with, help me pick the right priorities, and turn what was working into something repeatable before it turned into burnout.

If you’re a Founding CSM in that seat right now and want a thought partner while you build, that’s the work I do in 1:1 leadership coaching.

Not theory. Not generic playbooks.
Real-time support on the decisions that shape your CS motion.

If you want to explore it, let's talk. I’ll drop a link in the comments to book a quick consult.

I help CS leaders & startup founders fix strategy & execution to turn Customer Success into a growth engine | Customer Success Coach & Consultant | 🚀 Top 100 CS Strategists 2025 | Top 25 CS Influencer 2024

We built a directory of 40+ AI startups (and growing!) made specifically for Customer Success.

I’s been so exciting to watch how many companies are building for this space right now.

There’s real momentum:
tools that help teams automate the busywork, surface insights faster, support customers more proactively, and scale outcomes without scaling headcount.

At the same time, it can be overwhelming.
If you’re exploring AI for CS, the hard part is sorting through the noise and figuring out what’s actually relevant to your workflows.

So we made it easy.

Here’s what you’ll get in the directory:
✅ 40+ CS-relevant AI startups (and counting)
✅ Grouped by the jobs they solve (automation, insights, ops, enablement, revenue)
✅ Quick notes on each company’s mission + what makes them unique (beyond the marketing positioning)
✅ Practical evaluation details where available like integrations, compliance/security posture, and pricing/packaging signals

It also gives me a way to spotlight these founders and teams who are building with a real mission to help CS become more efficient and deliver better customer experiences.

👉 Comment “𝗗𝗜𝗥𝗘𝗖𝗧𝗢𝗥𝗬” and I’ll DM you the list.

And if you’re a founder building an AI product for Customer Success and want to be included, submit here: https://lnkd.in/e-GkurMU

I’ve had a lot of people tell me lately that I’m “lucky” to be able to leave my full-time job.

The truth is, luck had nothing to do with it.

This “overnight” move was built in slow motion.

It was early mornings before work.
Late nights after work.
Weekends when it would’ve been easier to rest.

It was posting when nobody was paying attention.
Recording podcast episodes when I had zero energy left.
Saying no to things that didn’t match the mission.
Staying consistent when the results were quiet.

It was betting on myself while still carrying a whole other job.

And most of all, it was choosing discomfort on purpose.

Entrepreneurship gets romanticized as freedom.

But the truth is: you earn the freedom first.
Through reps. Through risk. Through restraint. Through showing up when it’s inconvenient.

So yes, I’m grateful.

But I’m not “lucky.”

I’m prepared.

And if you’re watching someone make a big leap and thinking, “must be nice...” 
I promise you: there was a season before the leap where it was just work.

Quiet. Unseen. Relentless work.

That season counts.

_________________________________________

Hi, I’m Angeline 👋
I left my VP of Customer Success role to build CS RevSpeak full-time, where I coach CS leaders navigating retention pressure, growth expectations, and the messy reality between strategy and execution.

If you like grounded takes on CS, leadership, and building a career that actually fits your life, join my free newsletter. Link in profile.

Your CSMs are doing a ton of work.
The problem is it’s not landing as value.

They’re running calls, chasing adoption, coordinating internally, building relationships, putting out fires.

But customers don’t renew because your team worked hard.

They renew when they can clearly say: “𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗰𝗵𝗮𝗻𝗴𝗲𝗱 𝗶𝗻 𝗼𝘂𝗿 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗯𝗲𝗰𝗮𝘂𝘀𝗲 𝗼𝗳 𝘁𝗵𝗶𝘀.”

And most CS orgs don’t have a consistent way to get there.

So the CSM ends up doing everything 𝘦𝘹𝘤𝘦𝘱𝘵 the thing that protects renewal: capturing outcomes, building proof, and making the value story easy for the customer to repeat internally.

That’s when you hear the painful renewal language:

“We like you but we need to cut spend.”
“We didn’t really get ROI.”
“We can’t justify this right now.”

The team did the work.
The value never got operationalized into proof.

A value realization motion is what turns activity into something defensible:
→ align expected outcomes early
→ define what “proof” looks like while you can still influence it
→ track signals as you go so you’re not scrambling at QBR time
→ translate usage into impact a CFO will care about
→ build a narrative the champion can carry without you in the room

That’s exactly what I built the 𝗩𝗮𝗹𝘂𝗲 𝗥𝗲𝗮𝗹𝗶𝘇𝗮𝘁𝗶𝗼𝗻 𝗙𝗿𝗮𝗺𝗲𝘄𝗼𝗿𝗸 (𝗩𝗥𝗙) online course for.

It’s a self-paced online certification for CS leaders who are accountable for outcomes and need consistency at scale.

It standardizes how your team defines value, tracks progress, and communicates impact so renewals don’t hinge on last-minute storytelling.

Interested? Check out the details at csrevspeak.com/vrf.

The only relationship metric that matters in Customer Success: would they defend you when budgets tighten?

Because “they like us” is easy to say when things are stable.

The real test shows up when:
→ a CFO starts scrutinizing every line item
→ leadership changes and priorities shift
→ procurement is pushing for cuts
→ a competitor shows up with a cheaper option

In those moments, rapport doesn’t protect you.

What protects you is whether the customer can confidently say (without you in the room):

✅ We need this.
✅ Here’s what it changed for us.
✅ Replacing it would create real disruption.
✅ This is worth the spend.

This is where “healthy” accounts surprise-churn.
Everything looks okay: meetings happen, usage is decent, sentiment is positive.

But if the value isn’t clear, repeatable, and shared across more than one person, you’re not safe.

In today’s CS RevSpeak newsletter, I break down a simple Customer Relationship Strength Meter you can use to move beyond gut feel and actually assess how defended an account is (and what to do when it’s not).

📩 𝗧𝗵𝗲 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗥𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽 𝗦𝘁𝗿𝗲𝗻𝗴𝘁𝗵 𝗠𝗲𝘁𝗲𝗿 drops at 10 AM ET. 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘃𝗶𝗮 𝘁𝗵𝗲 𝗹𝗶𝗻𝗸 𝗶𝗻 𝗺𝘆 𝗽𝗿𝗼𝗳𝗶𝗹𝗲 𝘁𝗼 𝗴𝗲𝘁 𝗶𝘁 𝘀𝘁𝗿𝗮𝗶𝗴𝗵𝘁 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗶𝗻𝗯𝗼𝘅.

My webinar on the one-slide value review with ChurnZero sparked more questions than we could squeeze into the Q&A. 

So I'm dedicating an episode of the CS RevSpeak podcast to tackle your questions around exec conversations, complex accounts and missed goals. 

Because this is where the one-slide approach gets real.

It’s easy to tell a clean value story when the account is healthy and the wins are obvious.

It’s harder when:
❌ the sponsor isn’t showing up
❌ the customer has 5 stakeholders with 5 different definitions of “success”
❌ the outcomes aren’t landing (yet)
❌ and you’re walking into a room where everyone’s quietly wondering, “Is this spend worth it?”

In this episode, I break down what to do when you’re off track, how to earn exec attention in messy accounts, and how to talk about risk without losing trust or momentum.

If you’re trying to run exec-level value conversations that actually build renewal confidence (especially when things aren’t perfect), this one will help.

🎧 Listen now: 𝗖𝗦 𝗥𝗲𝘃𝗦𝗽𝗲𝗮𝗸 – 𝗧𝗵𝗲 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗥𝗲𝘃𝗲𝗻𝘂𝗲-𝗗𝗿𝗶𝘃𝗲𝗻 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗟𝗲𝗮𝗱𝗲𝗿 (Spotify, Apple, or wherever you listen)

P.S. Missed the live webinar? I’ll drop the ChurnZero replay link in the comments.

Okay, I am genuinely excited about this.
And if you are investing in growing as a CS leader this year, this is for you.

The VIP waitlist for my signature program 𝗟𝗲𝗮𝗱 𝘁𝗼 𝗦𝗰𝗮𝗹𝗲 (𝗟𝟮𝗦): 𝗧𝗵𝗲 𝗖𝗦 𝗔𝗿𝗰𝗵𝗶𝘁𝗲𝗰𝘁𝘂𝗿𝗲 𝗣𝗿𝗼𝗴𝗿𝗮𝗺 is officially open.

And VIPs get 30% off! 🎉

Over the last few months, a lot of you have reached out about 1:1 coaching.

Some of you are ready for that level of support.
But the budget just is not there right now.

A lot of you are already invested in learning and growth.
You read my newsletter. 
You listen to my podcast. 
You join my webinars & masterclasses. 
You want to do Customer Success better.

But you do not need more ideas.

You need something you can actually implement inside your org.

So I built this.

𝗟𝗲𝗮𝗱 𝘁𝗼 𝗦𝗰𝗮𝗹𝗲 (𝗟𝟮𝗦): 𝗧𝗵𝗲 𝗖𝗦 𝗔𝗿𝗰𝗵𝗶𝘁𝗲𝗰𝘁𝘂𝗿𝗲 𝗣𝗿𝗼𝗴𝗿𝗮𝗺 is a 12-week, hands-on implementation cohort for CS leaders building or rebuilding their CS org with a clear operating model behind retention and expansion.

This is not another course.
It is not 1:1 coaching either.

It is a structured cohort where you get the same strategic depth and frameworks, plus hands-on guidance, with a program built for execution.

Inside L2S, you will:
✅ Build a scalable CS operating model you can run consistently
✅ Apply everything inside your actual org
✅ Work through the core layers of CS strategy so you stop guessing what to fix next
✅ Leave with a plan you can present with confidence and execute on

This is for:
→ Founding CSMs building from scratch
→ Newly promoted CS leaders
→ Heads, Directors, and Managers scaling beyond the scrappy early stage
→ VPs inheriting messy systems and high expectations
→ Startup CS leaders navigating growth with no internal enablement

Here's what you get for joining the VIP waitlist:
💰 30% off enrollment
💻 Early access before we open publicly
⏰ Priority for limited seats, plus VIP-only bonuses

Want to learn more? Visit: csrevspeak.com/l2s

P.S. I only run L2S twice a year. If you miss this round, the next one is a long wait.

I’ve said this before and I’ll say it again:
𝗬𝗼𝘂𝗿 𝗿𝗲𝗻𝗲𝘄𝗮𝗹 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆 𝗶𝘀 𝗻𝗼𝘁 𝘆𝗼𝘂𝗿 𝗿𝗲𝘁𝗲𝗻𝘁𝗶𝗼𝗻 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆.

You need both.

Because they solve two different jobs.

𝗥𝗲𝘁𝗲𝗻𝘁𝗶𝗼𝗻 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆 is the work that earns the renewal:
→ adoption that leads to outcomes
→ momentum after onboarding
→ multi-threaded relationships
→ value that’s real in the customer’s day-to-day

No retention motion = nothing to renew. Period.

𝗥𝗲𝗻𝗲𝘄𝗮𝗹 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆 is the work that converts that retention effort into a decision:
→ pulling the year’s progress into a clear “here’s what changed” narrative
→ aligning the right stakeholders before the decision room shows up
→ naming what’s at risk early enough to fix it
→ framing the next phase so renewal feels like forward progress, not status quo

I usually go deep on retention because it’s the front-loaded work that makes everything easier later.

But if you’re heading into renewal conversations, you also need a plan for how to lead that decision.

That’s what I break down in today’s CS RevSpeak newsletter: 𝗧𝗵𝗲 𝗩𝗮𝗹𝘂𝗲-𝗙𝗶𝗿𝘀𝘁 𝗥𝗲𝗻𝗲𝘄𝗮𝗹 𝗖𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸.

If you own renewals or support a team that does, and you want your team to walk into those conversations feeling more in control and more confident even when things aren’t perfect, this is for you.

📩 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿 𝗱𝗿𝗼𝗽𝘀 𝗮𝘁 𝟭𝟬 𝗔𝗠 𝗘𝗧. 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘃𝗶𝗮 𝘁𝗵𝗲 𝗹𝗶𝗻𝗸 𝗶𝗻 𝗺𝘆 𝗽𝗿𝗼𝗳𝗶𝗹𝗲 𝘁𝗼 𝗴𝗲𝘁 𝗶𝘁 𝘀𝘁𝗿𝗮𝗶𝗴𝗵𝘁 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗶𝗻𝗯𝗼𝘅.

“Do more with less” is one of the most dangerous phrases in Customer Success.

CS leaders already know how to be scrappy. 
Most of us have been operating in constraint for years.

The danger is how the mandate gets interpreted:
𝗸𝗲𝗲𝗽 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀, 𝘄𝗶𝘁𝗵 𝗳𝗲𝘄𝗲𝗿 𝗽𝗲𝗼𝗽𝗹𝗲, 𝘄𝗶𝘁𝗵𝗼𝘂𝘁 𝗰𝗵𝗮𝗻𝗴𝗶𝗻𝗴 𝘁𝗵𝗲 𝘀𝘆𝘀𝘁𝗲𝗺.

Because CS isn’t linear. 
You can stretch portfolios for a quarter but the cracks show up in the same places every time: proactive work gets crowded out, value proof becomes last-minute, and risk doesn’t get seen until it’s expensive to fix.

And then the real kicker: when your best people burn out, you’re suddenly doing 𝘦𝘷𝘦𝘯 𝘮𝘰𝘳𝘦 with 𝘦𝘷𝘦𝘯 𝘭𝘦𝘴𝘴.

“Less” only works when you build leverage.

Not more hustle. Better design.

✅ Clear segmentation and service levels.
✅ A digital motion that carries the journey without a human pushing every step.
✅ Triggers that tell your team where to intervene and what “good” looks like when they do.
✅ A way to capture value continuously so renewals aren’t rebuilt from scratch.

In this environment, CS leaders can’t just absorb the mandate.
We have to rebuild the operating model so the team can be consistent under pressure.

That’s the real upgrade: not doing more.
Designing CS so outcomes hold even when capacity doesn’t.

_________________________________________

Hi, I’m Angeline 👋 I talk about 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀, 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 and 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽. I’ve built CS orgs in scrappy startups and high-growth scale-ups and I share what I’ve learned (𝘢𝘯𝘥 𝘶𝘯𝘭𝘦𝘢𝘳𝘯𝘦𝘥). 
Want it in your inbox? 𝗦𝗶𝗴𝗻 𝘂𝗽 𝗳𝗼𝗿 𝗺𝘆 𝗳𝗿𝗲𝗲 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿. [Link in profile]

A lot of CS teams own renewals now. That means you’re owning negotiation too.
And if we’re being honest, most CS orgs were never trained for that part.

So what happens?

CSMs negotiate under pressure and without guardrails.

Then the customer says:
“We need a discount.”
“Can you throw in more support?”
“Procurement needs justification.”

…and the default move becomes concessions.

That’s how CS quietly trains customers to repeat the same play every cycle:
push back → escalate → get more.

That’s the compounding risk most companies underestimate.

Because in Customer Success, you’re not just negotiating a price.
You’re negotiating the operating model your team has to deliver for the next term.

So the worst outcome isn’t losing a renewal.

It’s renewing on terms that:
→ erode margin you can’t get back next cycle
→ expand support expectations your team can’t sustainably deliver
→ create “special case” precedents the rest of the portfolio will ask for
→ and the account churns anyway.

That’s self-inflicted delivery debt.

If CS is going to own renewals, negotiation needs the same discipline Sales has baked in: BATNA.
𝗕𝗔𝗧𝗡𝗔 = 𝗕𝗲𝘀𝘁 𝗔𝗹𝘁𝗲𝗿𝗻𝗮𝘁𝗶𝘃𝗲 𝗧𝗼 𝗮 𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝘁𝗲𝗱 𝗔𝗴𝗿𝗲𝗲𝗺𝗲𝗻𝘁.

In executive terms: your negotiating position.
The alternatives you’re prepared to offer, the boundaries you will protect, and the trades you require so the agreement stays executable.

In today’s newsletter, I break down how to apply BATNA specifically to CS-led renewals, including how to define walk-to options, walk-away boundaries, and a trade list so negotiations stay value-led and your operating model stays intact.

📩 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿 𝗱𝗿𝗼𝗽𝘀 𝗮𝘁 𝟭𝟬 𝗔𝗠 𝗘𝗧. 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘃𝗶𝗮 𝘁𝗵𝗲 𝗹𝗶𝗻𝗸 𝗶𝗻 𝗺𝘆 𝗽𝗿𝗼𝗳𝗶𝗹𝗲 𝘁𝗼 𝗴𝗲𝘁 𝗶𝘁 𝘀𝘁𝗿𝗮𝗶𝗴𝗵𝘁 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗶𝗻𝗯𝗼𝘅.

Have you ever questioned a decision your company made and thought: 𝘵𝘩𝘢𝘵 𝘪𝘴 𝘢𝘣𝘴𝘰𝘭𝘶𝘵𝘦𝘭𝘺 𝘵𝘩𝘦 𝘸𝘳𝘰𝘯𝘨 𝘮𝘰𝘷𝘦?

I have. And I was sure leadership was making the wrong call.

From where I sat, it was obvious.
I could see the downstream impact.
I could see what customers would feel.
I could see the risk.

Then I got into leadership rooms.
And I realized decisions are rarely about what’s “best” in isolation.
They're about tradeoffs.

Because leadership is holding pieces you usually don’t see from the outside:

→ what’s happening with runway and revenue
→ what other teams are committing to (and what has to give)
→ what risks are unacceptable right now
→ what’s realistically possible with current capacity
→ what needs to be sequenced, not solved all at once

It doesn’t mean leadership always gets it right.
But it does mean a lot of decisions have context you don’t have access to.

So before you assume it’s a bad call, ask:
What might they know that I don’t?
What constraint are they optimizing for?
What risk are they trying to prevent?

You don’t have to agree with every decision.
But if you want to influence it, you have to understand what it’s solving for.

In CS, this shows up every time you’re trying to influence Product, Sales, or Finance.

Walking in with “this is hurting customers” is true 𝘣𝘶𝘵 𝘪𝘵’𝘴 𝘯𝘰𝘵 𝘦𝘯𝘰𝘶𝘨𝘩.
Influence comes when you can also bring:

1️⃣ the constraint (capacity, roadmap, margin, timing)
2️⃣ the tradeoff (what we stop or delay)
3️⃣ the alternative (the smallest change that protects outcomes)

That’s how you turn customer insight into executive action.

_________________________________________

Hi, I’m Angeline 👋 I talk about 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀, 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 and 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽. I’ve built CS orgs in scrappy startups and high-growth scale-ups and I share what I’ve learned (𝘢𝘯𝘥 𝘶𝘯𝘭𝘦𝘢𝘳𝘯𝘦𝘥).
Want it in your inbox? 𝗦𝗶𝗴𝗻 𝘂𝗽 𝗳𝗼𝗿 𝗺𝘆 𝗳𝗿𝗲𝗲 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿. [Link in profile]

One of the hardest parts of CS leadership is making high-stakes decisions in isolation.

Especially because the decisions you’re carrying aren’t small.

They’re the ones that impact retention and revenue.
They affect team morale and capacity.
They shape how CS is perceived at the exec table.

And most days, you’re making them with:
incomplete data, shifting priorities, and a calendar that doesn’t leave room to think.

You’re stuck choosing between tradeoffs like:
→ Do we protect margin or save the logo?
→ Do we stay customer-first or push for expansion?
→ Do we invest in process or keep firefighting?
→ Do we escalate now or wait and risk being late?
→ Do we hire, redesign, or re-segment when headcount isn’t coming?

That’s why so many CS leaders feel mentally exhausted, even when they’re performing.

You’re not just leading a team.
You’re carrying ambiguity.

And the longer you carry it alone, the easier it is to second-guess yourself, default to safe decisions, or stay in reactive mode.

This is exactly where coaching helps.

A thought partner who can help you:
✅ pressure-test the decision before it becomes a problem
✅ clarify tradeoffs and pick the right priority
✅ build an operating rhythm that creates traction
✅ show up with more confidence in exec and renewal conversations
✅ stop feeling like you have to figure everything out in your head first

If you’re a CS leader navigating a high-stakes season and you want support, let’s talk.

I offer a free consult call where we’ll walk through what you’re carrying and whether 1:1 leadership coaching is the right next step. I’ll drop the link in the comments.

There’s a gazillion things on a CS leader’s plate these days.
And everything is “urgent.” That is the problem.

“Do more with less” is the baseline.
Digital CS and 1:many expectations keep rising.
Revenue accountability is louder than ever.
And now the AI mandate is on everyone’s roadmap, whether you asked for it or not.

It is a lot.

And it is easy to get distracted by the next shiny thing:
a new tool, a new motion, a new dashboard, a new playbook, a new “AI initiative.”

But here’s the coaching reminder I come back to every time:
Do not lose the plot.

Customer Success still comes back to the same fundamentals:
𝗛𝗲𝗹𝗽 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿𝘀 𝗮𝗰𝗵𝗶𝗲𝘃𝗲 𝗿𝗲𝗮𝗹 𝘃𝗮𝗹𝘂𝗲 𝗶𝗻 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝘀𝗼 𝘁𝗵𝗲𝘆 𝗿𝗲𝗻𝗲𝘄 𝗮𝗻𝗱 𝗴𝗿𝗼𝘄 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂.

If you do not have that foundation, everything else becomes noise.

Digital CS will not save you if value is unclear.
Revenue accountability will feel unfair if the motion is undefined.
AI will not fix a broken system. It will just automate the chaos.

So if you are feeling pulled in 10 directions, here is the move:
Stop chasing initiatives and build the CS Operating System underneath them.

That is exactly what we do inside Lead to Scale (L2S): The CS Architecture Program.
We take the fundamentals and turn them into a system you can actually run, even when the market keeps changing.

VIP waitlist is open with:
💰 30% off
💻 Early access before we open publicly
⏰ Priority on limited seats, plus VIP-only bonuses

If you are investing in yourself as a CS leader this year, do it with structure and support.
Visit csrevspeak.com/l2s for more details.

Most SaaS products assume a baseline level of technical ability.
But when customers aren’t technical, CS becomes the workaround and the cost-to-serve climbs fast.

What usually happens next is predictable:

Implementation quietly turns into “CS does the setup.”
Enablement becomes “CS answers questions.”
And scaling becomes “hire more people to do the same work.”

That’s a motion design problem. And at volume, non-technical customers need a different setup + enablement system.

If you want to serve non-technical customers effectively and protect margin, the goal isn’t less support.

It’s different support.

Support that guides setup, builds capability, and keeps momentum moving without turning CS into the default doer.

The scalable fix isn’t just “make them self-serve.”
It’s redesigning implementation + enablement so customers feel guided without CS doing the work.

That usually comes down to a few levers:
→ simplifying the path to first value
→ making support conditional instead of default
→ tightening what customers must own vs what CS guides
→ building enablement that keeps progress moving after go-live

When you get this right, time-to-value stays predictable, customers feel supported, and your CS team stays focused on outcomes instead of configuration work.

I break this down in today’s CS RevSpeak newsletter: 𝗪𝗵𝗲𝗻 𝗬𝗼𝘂𝗿 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿𝘀 𝗔𝗿𝗲𝗻’𝘁 𝗧𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹: 𝗛𝗼𝘄 𝘁𝗼 𝗚𝘂𝗶𝗱𝗲 𝗦𝗲𝘁𝘂𝗽 𝗮𝗻𝗱 𝗘𝗻𝗮𝗯𝗹𝗲 𝗮𝘁 𝗦𝗰𝗮𝗹𝗲.

📩 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿 𝗱𝗿𝗼𝗽𝘀 𝗮𝘁 𝟭𝟬 𝗔𝗠 𝗘𝗧. 𝗦𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘃𝗶𝗮 𝘁𝗵𝗲 𝗹𝗶𝗻𝗸 𝗶𝗻 𝗺𝘆 𝗽𝗿𝗼𝗳𝗶𝗹𝗲 𝘁𝗼 𝗴𝗲𝘁 𝗶𝘁 𝘀𝘁𝗿𝗮𝗶𝗴𝗵𝘁 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗶𝗻𝗯𝗼𝘅.

I worked with a leader whose language did more damage than they realized.

Condescending questions.
Accusatory phrasing.
Comments that assumed intent instead of asking for context.

Most of it was subtle enough to deny.
But consistent enough to erode trust.

Over time, the impact was clear:
→ People stopped speaking up
→ Initiative turned into hesitation
→ Confidence turned into self-protection

Not because the team wasn’t capable.
But because the language made everything feel unsafe.

As leaders, we should know:
Language isn’t neutral.
Tone isn’t cosmetic.
Words don’t just communicate information.
They signal power, trust, and intent.

Great leaders choose language that:
✔️ invites clarity instead of defensiveness
✔️ assumes positive intent before assigning blame
✔️ separates outcomes from identity
✔️ corrects without diminishing

You can address issues without making people feel small.
You can hold high standards without sounding accusatory.
You can be direct without being demeaning.

Leadership shows up in the words you reach for under pressure.
That’s when people are listening the most.

And they’ll remember how you made them feel long after they forget what you said.

_________________________________________

Hi, I’m Angeline 👋 I talk about 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀, 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 and 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽. I’ve built CS orgs in scrappy startups and high-growth scale-ups and I share what I’ve learned (𝘢𝘯𝘥 𝘶𝘯𝘭𝘦𝘢𝘳𝘯𝘦𝘥). 
Want it in your inbox? 𝗦𝗶𝗴𝗻 𝘂𝗽 𝗳𝗼𝗿 𝗺𝘆 𝗳𝗿𝗲𝗲 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿. [Link in profile]

Entrepreneurship isn’t for everyone.
And that’s not a hot take. It’s just reality.

Some people genuinely want a steady salary.
Clear scope.
A team to plug into.
A role they can crush, then log off and be fully present in the rest of their life.

There’s nothing wrong with that.

In fact, it’s underrated.

Because entrepreneurship comes with a different trade:

Freedom, yes.
But also uncertainty.

More autonomy, yes.
But also more responsibility than you expect.

You don’t just “do the work.”
You create the work. You sell it. You deliver it. You improve it. You repeat it.
And you do it while managing your own nervous system.

Some people thrive in that.
Some people don’t want it.
Both are valid.

The point isn’t to chase entrepreneurship because it looks impressive online.

The point is to choose what fits the life you want:

→ Do you want predictability or possibility?
→ Do you want clear lanes or wide-open terrain?
→ Do you want to build inside someone else’s vision or carry the weight of your own?

Neither path is “better.”
But pretending there’s only one “right” path is how people end up miserable.

For me, entrepreneurship is the season I’m in.
Not because it’s glamorous, but because it’s the right container for the work I want to do and the life I want to build.

If you’re choosing the salaried path, I respect it.
If you’re choosing the entrepreneurial path, I respect that too.

Just make sure it’s your choice.

_________________________________________

Hi, I’m Angeline 👋
I’ve been the founding CSM, the team lead, the VP of CS, and everything in between.

Now I’m building CS RevSpeak full-time and coaching CS leaders who are navigating retention pressure, growth expectations, and the messy reality between “strategy” and execution.

If you like grounded takes on CS, leadership, and building careers that actually fit your life, join my free newsletter. Link in profile.

Here’s a shocker: more Customer Success budget does not mean higher NRR.

In fact, NRR decreased for 75% of software companies even as nearly 60% increased Customer Success spending.

Most companies did the “right” thing.
They invested more in post-sales.
And still watched retention and expansion get worse.

So what is that telling us?

A lot of “extra CS spend” goes into activity, not architecture.

You get more touches, but not clearer segmentation.
More meetings, but not a tighter operating cadence.
More playbooks, but no agreement on what gets used when.
More data, but no forecasting model leaders trust.
More headcount, but the same ambiguity about ownership and priorities.

The system gets busier.
But it does not get more predictable.

If this stat feels uncomfortably familiar, I would start here:

→ Do we have one operating model for retention and expansion, or a collection of best efforts?
→ Can the whole org run engagement motions and value realization consistently?
→ Can we forecast renewals and expansion with confidence, or are we constantly surprised?

This is the shift CS leaders are being asked to make right now:
Less “more CS.” More “better system.”

If you want help building that system, this is exactly what we do inside Lead to Scale (L2S): The CS Architecture Program.

It is a 12-week implementation program where you build your CS Operating System across segmentation, engagement motions, value realization, data and forecasting, and operating cadence.

VIP waitlist is open with 30% off and early access before we open publicly.

Want to learn more? Visit: csrevspeak.com/l2s

Buying AI before redesigning the motion is like buying a Ferrari for a road full of potholes.

You’ll move faster, sure.
But you won’t get where you want to go.

AI is not a strategy. It’s an accelerator.
It will scale whatever you already have, good or bad.

So if your CS motion is unclear, inconsistent, or improvisational, AI won’t fix that.
It will simply make inconsistency happen at scale.

Before you plug in AI, you need to do the boring work first:

𝟭) 𝗗𝗲𝘀𝗶𝗴𝗻 𝘁𝗵𝗲 𝗺𝗼𝘁𝗶𝗼𝗻 𝘆𝗼𝘂 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝘄𝗮𝗻𝘁 𝘁𝗼 𝘀𝗰𝗮𝗹𝗲
What does “good” look like in onboarding, risk, renewals, expansions?
What are the moments that matter, and what should happen when they occur?

𝟮) 𝗦𝘁𝗮𝗻𝗱𝗮𝗿𝗱𝗶𝘇𝗲 𝗯𝗲𝗳𝗼𝗿𝗲 𝘆𝗼𝘂 𝗮𝘂𝘁𝗼𝗺𝗮𝘁𝗲
If every CSM runs the workflow differently, AI has nothing stable to augment.
Define the minimum viable playbook. Set the inputs, outputs, and “done” criteria.

𝟯) 𝗚𝗲𝘁 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗼𝗼𝗹 𝘀𝗲𝗹𝗲𝗰𝘁𝗶𝗼𝗻
Tool decisions should be downstream of operating model decisions.
Be explicit about:
→ what decisions humans must own
→ what can be automated safely
→ what data is the source of truth
→ what the escalation path is when the signal is messy

Then AI becomes powerful because it reinforces what you’ve already made consistent.

It takes a motion your team can run and helps it run the same way, every time, at scale.

That’s why the teams actually getting AI ROI did the unglamorous work first: 𝗱𝗲𝘀𝗶𝗴𝗻 𝘁𝗵𝗲 𝗺𝗼𝘁𝗶𝗼𝗻 → 𝘀𝘁𝗮𝗻𝗱𝗮𝗿𝗱𝗶𝘇𝗲 𝘁𝗵𝗲 𝗽𝗹𝗮𝘆𝗯𝗼𝗼𝗸 → 𝗮𝗽𝗽𝗹𝘆 𝗔𝗜.

_________________________________________

Hi, I’m Angeline 👋 I talk about 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀, 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 and 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽. I’ve built CS orgs in scrappy startups and high-growth scale-ups and I share what I’ve learned (𝘢𝘯𝘥 𝘶𝘯𝘭𝘦𝘢𝘳𝘯𝘦𝘥).
Want it in your inbox? 𝗦𝗶𝗴𝗻 𝘂𝗽 𝗳𝗼𝗿 𝗺𝘆 𝗳𝗿𝗲𝗲 𝗻𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿. [Link in profile]

If you are holding the whole post-sales motion together with sheer effort, read this.

A lot of CS leaders are carrying more than anyone can see from the outside.
Escalations. Renewals. Expansion pressure. Internal misalignment. A calendar full of “urgent.”

And when the system is unclear, 𝗬𝗢𝗨 become the system.

You hold the context in your head.
You decide priorities in real time.
You patch gaps across Sales, Product, and Support.
You keep things moving through willpower.

But that is not scalable. And it is exhausting.

The transformation in L2S is not “more frameworks.”

It is that you stop holding everything in your head.

You build a CS Operating System you can actually run, one block at a time, with clarity and consistency.

What usually changes on the other side:
✅ You can explain your CS strategy clearly and present it internally with confidence
✅ Your team runs one consistent motion instead of everyone improvising
✅ Value is easier to communicate because you have a structure for it
✅ Risk surfaces earlier, which takes pressure off renewals
✅ Your week feels calmer because you have an operating rhythm you can rely on

If you are ready to build the system behind retention and expansion, this is what we do inside Lead to Scale (L2S): The CS Architecture Program.

Enrollment opens soon. If this has been resonating, join the VIP waitlist for first access and 30% off.
I run L2S twice a year, and I keep it hands-on, so seats go quickly.

Visit csrevspeak.com/l2s for more details.

Every new growth stage breaks your CS motion.

What worked at 20 customers stops working at 200.
What worked as a team of one becomes chaos at five.

And no one hands you a roadmap.

So you end up making high-stakes decisions based on urgency and opinions instead of stage and strategy.

Questions like:
❓ When do I push for more headcount and how do I justify it?
❓ When should we specialize roles and what comes first?
❓ Is it time for CS Ops or do we need a clearer model first?
❓ How do we segment customers as volume and complexity grows?
❓ What should be automated, what stays high-touch, and what is the right mix?

These are real questions CS leaders face as the org matures.

And there is no universal playbook.

But there is a right answer for your stage, your product, and your customer base.

That is why I created Lead2Scale (L2S): The CS Architecture Program.

L2S is a 12-week implementation program for CS leaders building or rebuilding their CS org with intention.

This is not a passive course.
You are building your CS Operating System with live support, structure, and accountability.

You will leave with a CS org design that fits your product, customers, and business goals.
Plus the confidence to execute it.

If you are:
✅ the founding CSM building the foundation
✅ a CS leader scaling beyond the scrappy early stage
✅ inheriting messy systems and unclear ownership
This is for you.

Seats are limited because this is hands-on and I only run it twice a year.
Sign up for the VIP wailtist to get 30% off and early access.

For more details, visit: csrevspeak.com/l2s

taplio

The Battle

Jeremy Donaldson 🤝

Angeline Gavino

Followers

Posts

Engagements

Likes

Performance ScoreAngeline Gavino's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Jeremy Donaldson 🤝

Angeline Gavino

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Angeline Gavino's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreAngeline Gavino's LinkedIn Performance