We want to hit 110% NRR. That’s the dream, that’s the goal. It’s not going to happen immediately, but that’s what we’re working towards.

The same number from different teams, but founders that are thinking the same way.

110% NRR has become the round target number for a particular class of founder and leader.

It’s exciting to be in the room for these conversations.

Why 110%? Why now?

No one’s getting strong-armed into this by a board or investors, not yet anyway.

The founders and the leaders that have said this to me are doing the math themselves. Money isn’t cheap anymore, so they’re looking to their own revenue for growth.

This 110% number came up in conversations with teams that are doing $1M ARR pushing to $10M. Those doing $10M ARR pushing to $50M or even $100M.

Both groups seem to have come to the conclusion that their existing customer base is the highest leverage path to their next milestone.

Robin Leathers ran the model on this: with the same $20M of S&M spend, a multiplication-first company — one that diverts a chunk of spend into retention and expansion — produces 83% more net-new ARR than an acquisition-first one. Same dollars in. $5M more ARR out the door. Same year.

The enterprise value math may be the bigger point. If you’re looking to sell or be acquired, revenue multiples go from 4.1x to 11.7x, depending on your NRR.

What founders think moves NRR

Here’s where I may get myself in a little bit of trouble.

NPS doesn’t move NRR. CSAT does not move NRR. CS headcount generally does not move it either. Relationships are important, but I’m not sure they matter as much or in the way many teams think they do.

What moves net revenue retention is product value delivered repeatedly to the right customer at the right moment in their life cycle.

Duh, right?

How this is measured is the tricky bit. Through no fault of their own, most customer success and post-sales teams are given qualitative tools and data. They’re given so much tooling and so much data, in fact, that the teams that I speak with often tell me that they feel overwhelmed by it all.

And so a lot of teams end up guessing, having more meetings, and reacting to the customers that make the most noise in the last QBR or through support channels.

What really moves it

Two things move your net revenue retention, and they’re connected:

1. Segmentation by goal, not just by size. Every customer comes to your product for a reason. What are they trying to accomplish, and how well are you solving for it?

2. Distance between signal and action. This is the most underrated and underappreciated. The longer the gap between the signal that says “this customer is disengaging” and when “we did something about it”, the less likely your action lands well. We’re all guilty of sitting on signals like usage drops, feature abandonment, and sentiment shifts for a little bit too long before doing anything about it.

Teams pushing NRR above 110% have shortened the loop:

1. Get the data.

2. Understand what it means.

3. Know what action to take.

4. Take the action.

5. Keep going.

The trick isn’t to get more data. It’s to make the data you already have so easy to act on that your team doesn’t have to interpret it. They spend more time moving and doing.

The head of RevOps at a $30 million ARR company recently told me his job is to help his team “spend less time thinking and more time doing.” He’s getting that done by providing his teams with signals and next best actions.

The stack that supports it

It’s not a sexy list:

• A CRM that carries real context like call recordings, transcripts, deal history, and as many notes as the sales team can bear to put in.

• Clean, usable, healthy data flowing through a CDP like Segment or RudderStack.

• A signal system surfacing engagement changes in real time, not in monthly or weekly health score reviews.

• A communication layer to reach your customers, which would include tools like loops, Intercom, HubSpot. Take your pick.

• Slack for alerts because a human still has to act.

The tools are all out there, and it doesn’t take much effort (or budget) to make this work.

What to do next week

Build a list of your top 10 to 20 accounts. Do an 80/20 sort, picking the lens that matters most to your business, like revenue, strategic value, or referral influence.

For each account, see if they:

• Expanded

• Contracted

• Churned

Now look at as much data as you can to learn what happened in the 30 to 60 days before the change. Are there any behaviors in your product data that you can tease out? Anything in your relationship or qualitative data that came ahead of the outcome?

Those are the signals to set up alerts for. That’s where a 110%+ NRR starts.

The math

Do you know your current NRR? If not, here’s the formula:

NRR = (Starting MRR + Expansion + Reactivation − Contraction − Churn) / Starting MRR

Run it for last quarter. Are you above 100, below 100, or not sure yet?

Reply or DM if I can help with it. Or if you’d like to brainstorm the tech stack and workflow side of things.

TTFN,

Peter

This was a bit of an urgent buy, something I wanted us to have sooner than later. Sales was friendly, accessible, smooth, and matched my urgency really well.

Signed an agreement, made a payment, and then it felt like I hit a wall.

You’ve probably felt this same thing before. Frustration and even confusion about what just happened, what went wrong.

It even got to the point where I considered canceling the agreement. But instead of doing that, I thought, why not reflect on this a little bit more and try to learn something from the situation?

So here they are:

Three ways to completely ruin your sales handoff to customer success

1. Do not match your customer’s urgency. If your customer is keen and ready to go, ignore it. Tell them you can meet next week if you have time. After all, you’re busy and your calendar fills up fast.

2. Surprise your customer with unexpected contracts and new teammates to meet. Just because heaps of well-established SaaS businesses let customers enter a credit card and click purchase doesn’t mean that you have to do that (even though it looks like customers can do that). And when asked about it, make sure that you bring in legal.

3. Don’t clarify who is responsible for fulfillment. Say things like “That’s not my job” and don’t offer a name of someone who can help. If really pressed on things, send links to onboarding documentation.

Making handoff an opportunity to squash buyer’s remorse

I seriously considered going back on this agreement. That’s how much I was questioning my decision to buy this particular tool.

A great friend who happens to be a great salesman reminds me often that “time kills all deals.” That rule applies even after the ink has dried.

So if instead you want to run a better business:

• you can match urgency

• you can have a clear process where appropriate

• with a real person owning your customers’ success.

This is one of those little areas of improvement that can have an outsized impact on recurring revenue businesses.

1. Match their urgency. Not every customer is in a rush, but when they are, match their urgency. Shorten that time to value, help them hit activation milestones and the outcomes that they’re chasing.
   

2. Be easy to buy from. The companies I most enjoy being a customer of are the companies that are crystal clear about how to buy from them and how to keep working with them.
   
   We haven’t worked with Fletch, but I know exactly what I’d get if we did.
   

3. Make it clear who’s involved and why. If a customer meets your criteria for high-touch customer success, make sure they know who they’re going to work with and what that relationship looks like.
   
   It’s nice knowing who I should reach out to or where I should look for answers to my questions.

No more dropped relationships

If you’ve ever done sales, if you’ve ever built a business, you’ve done this. I certainly have. There’s no perfect process for this, and sometimes tools don’t make it easy.

But hopefully, by looking at what bad sales-to-success handoffs can look like, it will make it easier to make them better.

Now off you go, write out your sales-to-success process so your next customer can see just how easy it is to buy from you.

Peter

“[F]ocusing on the next move, rather than how you got here in the first place, opens you up to a lot of possibilities.”

Shane Parrish writes to more than 1 million people every week. Geez.

In his latest book, Clear Thinking, he’s teaching about how to make better decisions. This is one quote from early in the book, but it’s stuck with me because every day in business we’re making decisions about what comes next.

Those decisions are often weighed down by what came before.

Thanks for being here with me. These emails are hand-written and AI spell-checked.

Hopefully they read kind of like a friend at a bar is sharing something he’s been noodling on before and after having had a few sips of beer.

These aren’t meant to be deep dives, but they often spark ideas that lead me off to explore some topics in more depth.

If there’s anything you read here that’s helpful, wrong, strange, you’d like to hear more about, or is just straight ridiculous, please hit reply and let me know. Or leave a comment.

Appreciate you.

Learn the lessons, keep moving

If we only thought about where we’re standing right now and what our next best move is, without ever considering our past decisions and how they’ve impacted us, I don’t think we’d be very successful.

"It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent."

~Charlie Munger

Our ability to make good decisions now rests a lot on having had skin in the game. Learning what works and what doesn’t work in certain situations. Making stupid moves. Getting beat up, but standing back up.

Goals and next best moves

I’m writing in the context of building a business. Understanding what we want that business to be is critical when thinking about our next best moves.

Goals are like flags planted somewhere off in the distance. Maybe you call it your North Star or your OKR. Whatever it is, it’s how you orient what comes next.

The next best move should put you closer to that flag. Or it should set you up so that two, three, four moves down the track you can make huge gains.

Having the confidence to make the move

I love the Charlie Munger quote because it’s such a great razor for decision-making. “Is this stupid?” is a pretty funny question to ask about any decision.

Decisions can be stupid for a number of reasons. Trying to do something too big, may be stupid. Trying to do something you just can’t do, may be stupid.

When we’re thinking about the next best move, we need to look at what we’re capable of, stretch it a bit, and have the confidence to make it happen.

Sunk costs and pushing on

About six months ago, we made a decision to sponsor a conference that was set to take place in October 2026. We just found out that the business behind the conference has gone out of business.

Not just gone out of business, but gone into receivership. Potentially taking our money with it.

Now it sucks to lose money for seemingly no good reason. And my first reaction was to go into scramble mode, try to claw it back. But thankfully, little Shane Parrish was sitting on my shoulder telling me to focus on the next move instead.

There is still hope that we get our money back or that the sponsorship is parlayed into a different event. But as of today, it’s a sunk cost. And the more time I spend dwelling on that, the less time I spend doing the work to grow the business.

Wrapping up

Like anything in life, running a business boils down to a series of decisions. It’s important to know how we got where we are right now. To learn from good and bad decisions we’ve already made.

That’s how we know if what we’re about to do is stupid. Ha.

It seems like a simple quote: “[F]ocusing on the next move, rather than how you got here in the first place, opens you up to a lot of possibilities.”

But if you look at where you’re standing today and you look up, you’ll realize that the possibilities are endless, and that’s pretty dope.

To your next move,

Peter

Don’t just maintain activity and output with fewer headcount, do more.

I used to read that as a question of discipline. It makes sense that way:

Ruthless efficiency and getting sh^t done for 8 straight hours results in greater output, more work done.

But what sounds like a question of discipline is more a matter of framing.

Fewer people, greater output is a coverage frame

When a support team, success team, marketing team loses headcount without losing any of the responsibility or “OKRs”, they’re being asked to cover the same surface area with fewer resources.

Be everywhere, just thinner.

What if it’s a leverage frame instead?

Smaller teams have smaller surface area. There’s only so much work that can get done. When the work thins, it’s still the same amount of work, just spread across objectives.

And that’s what teams try to do. Cover the same area. That means being at all the events, on the same platforms, in the same discussions, across the same channels…

It’s a garbage way to work.

What if the answer isn’t to try to cover as much surface area, but to cover only what compounds?

One frame increases outputs without burnout

A coverage frame on the “do more with less” requirement means throwing a bunch of balls in the air and trying to catch them all, frantically dashing from here to there grabbing like someone in those flying money booths at a conference.

You’ll get a few wins, but you’ll leave a ton of value sitting on the ground.

A leverage frame changes that. It’s like going into that flying money booth knowing that all you need to do is grab the $100 notes to make a big score.

Here in Australia, the money has different sizes and colors. A $100 note is the only green bill. For my fellow Americans in the US, tough luck eh?

Reframing customer success

Not enough teams are tiering their customers. Playing favorites. Whether your company has a CS team or not, you’re spending some time on it.

If you’re currently operating like all paying customers are created equal, they all deserve to be treated that way and to feel like they’re special — you’re in the coverage frame.

That means you’ll spend hours helping the $500 ACV customer while the $50,000 ACV customer quietly plans their exit. It’s not deliberate or negligent. It’s just how it works when every customer that makes noise (the small ones make more noise) gets attention and care.

Shifting to the leverage frame puts value front and center. Customers are tiered. The sparse resources you have are focused on Tiers 1 and 2, because that’s where your real revenue base lives.

You sort out how to manage and keep happy your Tiers 1 and 2. You build systems that see your NRR go up, even while making do with less.

What the leverage frame looks like in practice

If anyone in an org is responsible for looking after paying customers, the leverage frame looks like this:

- Tier all customers based on value

- Be realistic about how much capacity and time can be spent on each Tier

- Use manual processes to learn how to manage Tier 1

- Build systems that leverage your learnings with Tier 1

- When NRR is going up even with a small team, look to Tier 2

The 80/20 rule applies to everyone and that means you can get a lot of value from focusing on the 20% that drives 80% of revenue.

Heck, for a lot of companies the math gets into the ridiculous, like 95/5 or 98/2. Look after the denominator and things will be ok.

You don’t need tough math to start doing this. It can be done by looking at the top 10-20 customers that pay the most, that use your product the most, that you value the most. Find them, write them down, and make a plan to engage with them.

Measure the impact on NRR and GRR. If you see positive movement, do more of that and then think about how to scale it with tooling, process, or people.

The answer isn’t always to do more

That’s the biggest fallacy of work. Doing more gets you more. True sometimes, but not always.

What always works is finding the highest points of leverage and exploiting them. If you have customers paying you, your best customers are your highest points of leverage.

Don’t forget about the rest of your customers, but do optimize your work and your focus for the few that really make your business a business. Go from there. Don’t complicate things that can be simple.

Ok, </rant> from me.

If you find yourself feeling spread thin trying to hit revenue targets, maybe it’s not the workload that needs rethinking. Maybe it’s the frame.

Au revoir, y’all.

Peter

Twice lately I’ve been reminded that showing up again and again is how you show up at the right time.

Young Oly (Oh-lee) Hickman is growing up to be a steelhead fisherman. In this Patagonia Films short he’s just caught a gorgeous steelhead trout. He’s tired. He says he needs a nap.

But first, his dad asks, how did you catch it?

“Sometimes the worst cast can catch the best fish.”

Oly’s dad is a steelhead fishing guide. His job is to help others stay calm, cast flies, and catch fish. He’s taught his son well. And I reckon there’s a lesson for anyone looking to land a big fish.

Or a customer.

Troy Munson is an entrepreneur and account executive. He shares his approach to selling and outreach.

One of his key principles, shared a month or so ago, is to send a message today, not when it’s perfect.

So much of selling - like landing a fish - comes down to timing and showing up.

Maybe the fly Oly tied wasn’t exactly right. Or the email you sent didn’t have a crystal clear CTA. But if it lands in front of the right person at the right time with just enough to catch their attention, it works.

Sometimes the worst cast does catch the best fish. All it takes is showing up where the best fish swim and throwing a cast.

The next time you struggle to nail the perfect message for an amazing prospect, write something hand crafted and hit send. If it lands, amazing. If not, find another prospect and hit send again.

Scott Galloway said this recently on the Diary of a CEO podcast. He and the host were talking about how AI has not taken over everything as predicted.

Why hasn’t AI taken over? Galloway thinks the answer is biology.

I agree. We want to connect with one another. That desire to connect also confuses us and often makes us look in the wrong direction for signals that affect our business.

Humans want humans (sometimes)

When I hear “humans want to deal with humans” or “people just want to talk to other people” I kind of translate that to “relationships matter the most.”

That’s how we’re taught to build customer-centric companies. Focus on building better, stronger relationships with fellow humans.

But biology is messier than that. It’s more than how we relate to others. We can say lots of nice things, but it’s what we do that’s more telling than what we say.

“Actions speak louder than words” is true.

So why do we spend so much time listening, reading, analyzing all the things we say to one another and how we say it? Shouldn’t we watch more closely what everyone does?

We want to feel like we’re connecting with and speaking with a human. But sometimes, as someone whose job it is to re-sell a recurring revenue product, we may be better off watching how customers behave than giving every call transcript to ChatGPT.

Not enough ethnography

Ethnography is observing what people do in context. The in-real-life version is like sitting in a restaurant, listening to people order milkshakes.

The digital version can be watching someone over the shoulder as they use your product. Or maybe you’re using heatmap tools like Hotjar, or product analytics like Posthog, or screenshares over Zoom, etc.

Ethnography gains real weight when you combine what you see with what people are thinking. If you can find someone to use your product and think out loud honestly, you’re in customer research nirvana.

Right now, that kind of ethnography doesn’t scale well:

• You can recruit some customers to observe and listen to, but it won’t be many.

• You can get lots of feedback, but without real usage behaviors attached you’re operating on trust.

• You can watch lots of session recordings, but without the thought process narration you’re not sure why anything is happening.

Most teams default to feedback in the form of support tickets, reviews, and call recordings because “relationships matter most” and we like to believe what people say to us.

If we look at what really indicates happiness and attachment, a real relationship, words matter but actions matter more. More teams need more ethnography.

Paying lip service to behavior

I’ve been looking at a lot of Customer Success Manager (CSM) job openings lately. There are NRR targets. GRR targets. Lists of tools like a CRM, outreach, scheduling, and BI dashboards.

Many of the listings also mention “monitoring usage,” but there’s never a tool or ‘how’ listed.

CSMs are given an NRR target of 110%+ and told to use the “human to human” tools.

By not listing any analytics tools in these job descriptions, companies are setting a trap for new CSMs.

Optimizing for what you can see

What happens when you ask someone to monitor usage without giving them a way to see it?

They optimize for what they can see and measure. Touchpoints, meetings, NPS, sentiment analysis, gut feel, and even “osmosis.”

It’s relationship theater. It’s not laziness. The data either isn’t shared, or it’s buried in some dashboard that’s hard to decipher.

That’s how CSMs become relationship managers instead of revenue managers. They have easier access to what customers say than what they do.

Ethnography by way of analytics

Real customer-centricity isn’t just about listening to people. It’s about understanding how customers really behave and use a product.

That’s the real biology Galloway was pointing at, even if he didn’t call it that way. We need to understand how people feel (based on what they tell us), but we also need to understand how they behave.

To do that you can use tools like Hotjar and Posthog and Full Story (and Accoil, ahem). If you sell B2C, watch individuals. If you sell B2B, watch individuals and accounts.

Start with the usage patterns. Then enrich those patterns with what customers say, customer segments and industries.

When you start by observing behavior, you have a real sense of where customers get value before they tell you what they feel good about. If the two don’t align, default to what they’re doing over what they’re saying.

The challenge

“Monitor usage” shows up in a lot of CSM job descriptions, but leadership doesn’t resource it. They wrote it down. They know it matters. Given the conversations we have with post-sales teams, they often aren’t building the path to actually do it.

If you believe usage drives retention, resource it. Give your CS team event-level visibility, link it to segment and industry and tier, and let them see. You’ll learn one of two things. Either you were right, and you’ll unlock something real. Or you were wrong, and you can stop writing it in job descriptions. Both outcomes beat the current state.

Galloway said everything reverse engineers to biology. Humans want humans. But humans also do things. If you’re not watching what they do, you’re not actually paying attention and you’re missing lots of opportunities to grow your business.

To monitoring usage,

Peter

PS: This whole thing sounds a bit like I’m accusing you or someone else of doing things wrong. I think we’re all like water: we find the path of least resistance and follow it. If that’s defaulting to call recordings and sentiment reviews, that’s not wrong but it is missing an important half of the picture.

At the end of his quest, he talks about how he’s not going to stop traveling, but it will be different. During the quest, he traveled to new places so he could finish the quest. Choosing where to go was easy.

Have I been there already? Yes or No. If no, go there.

Now that the quest was over, he was “free to choose… and freedom seemed overwhelming.”

Similarly, the freedom to run almost any kind of marketing or growth or success campaign is overwhelming and paralyzing.

1 — Pick a destination

Chris had a long list of destinations, you could say, but the one I’ll use to tie this back to work is visiting all the countries in the world.

I’ve been thinking recently a lot about how to keep customers happier for longer. It’s one of the main reasons we started Accoil - help teams keep customers happy (and paying).

When we work with teams to build new workflows, it always starts with finding the right problem or opportunity to solve for.

Knowing what we want to accomplish makes it easy to start. If you lose too many customers each month, the goal could be to shrink that number. If too many people sign up but never buy a product, onboarding may need a fix.

Pick a number to improve and start moving towards it. Make it a meaningful, high-impact, important number.

2 — Define the constraints

The more countries Chris visited, the simpler his agenda got. Every time he ticked another country off the list, he had fewer to choose from next time.

When doing any work to keep more customers happier longer, there are a lot of ways to approach it. But if you list out all the things that you can’t do — like spend millions with a budget of $0 — you’ll start to see all the things you can try.

• Your audience is your customer base. Even if you have a ton of customers, it’s a small list in the grand scheme of it.

• Everyone is emailing, messaging, calling, advertising, and otherwise competing for customers’ attention, so you get only a little of it.

• Your work has to be valuable to customers and to your company.

• You probably have limited tools, limited budget, and limited people to try stuff.

Write down all the constraints. It’s freeing. If it helps, draw it out like world map and start crossing off the boxes you’ve already tried or simply can’t do.

3 — Start with one thing

I’ve done a lot of sales calls and worked with a lot of teams. There’s this thing that happens when people don’t pick a destination and define their constraints:

They realize they “can do all of it” and the freedom to choose gets immediately overwhelming.

Here’s what this looks like on a call: we’ll narrow in on a need to get more enterprise customers using a key feature. We’ll work out an approach… and then someone asks about doing the same for another customer segment, and another, and another.

It’s like there’s this “We can do all the things!” frenzy that happens. If nobody stops it and brings the focus back to the one thing we all already agreed is top priority, the freedom to choose makes it too hard to… choose.

So start with one thing that is a priority for the business. For so many teams, fixing even one thing can have an enormous impact on revenue and company health.

Off you go

Chris had the luxury of someone else making his list for him. 193 countries are all that exist, so it’s hard to change scope.

You may feel like “where do I even start?!” so maybe the best place to start is to pick one thing to improve, list out the ways you can and can’t do that, and then start.

To doing more things,

Peter

PS: I wonder if Chris quietly hopes for another country to be born so he can find one more way to continue his quest. Even for one more trip.

PPS: Always remember, you can just do things.

“Nothing is original,” says author Austin Kleon in his must-read Steal Like an Artist. It’s important for Success teams to remember this.

All other GTM teams steal constantly, as well they should. Sales tactics make their way through company after company. Marketing watches the competition and campaigns can look oddly familiar.

There are Success teams doing fun stuff. But so many of the conversations I have with CS teams are about the stock standard stuff:

• Run a QBR

• Respond to tickets

• Have a pre-renewal playbook XX days before renewal

Or for companies without dedicated CS teams, it can be more about simply trying to be there when customers need you most.

There is so much useable data

Working with customers, you have first-party data with clear links to people and their companies. Pre-sales teams dream of attribution like this:

• Chat

• Email

• Surveys

• Community

• Call recordings

• Support tickets

• Product usage (at account- and user-level)

When it’s a registered customer, most of these touchpoints are directly attributable to a user and an account. You can use these to trigger workflows.

Combine the signals

Just like pre-sales teams pull together combinations of prospect activity to create more effective campaigns, CS can do the same.

But customer data is directly traceable to users and accounts, so it’s really good stuff to work with.

Some combos to look for:

• Email / Support / Call data + product usage — flag positive or negative sentiment and compare it with account- and user-level product usage

• Product usage + in-app upgrade interest — high usage combined with power users checking out the upgrade path

• Support ticket volume + consumption % — increasing support volume about new use cases combined with high % of consumption (tokens, credits, etc.)

What signals do you have that you can combine to make some meaningful workflows? This is when you start to run, compared to the somewhat simple workflows from yesterday.

This is where you can get creative.

AI and whatnot

If reading the list of signals feels overwhelming, maybe it’s time to hire some new teammates. Agents. Skills. CoWork.

Agentic workflows unlock capacity whether you build them in-house or hire them from a company like Attention.com. Once you point agents at the data, you can start to scale beyond your current headcount.

How to do that is beyond this note. You’re probably experimenting with AI a lot, so consider adding some customer-focused workflows to your next build.

AI runs on data and you have heaps of high-quality, first-party data to get creative with in service of increasing customer LTV, dropping dreaded churn, and growing your company’s revenue foundation.

Start.

If you’re doing the stock standard customer success work or haven’t started yet, just do it. Pick one customer segment, one signal, and do something creative to keep them happy.

Off you go,
Peter

And while building that data layer is internal, the next steps run straight into your customers where it all starts to get real. Yeehaw.

Go-to-market gets all the love on the socials. Look at LinkedIn for longer than a sneeze and you’ll see systems-maxxing everywhere.

Workflows and enrichment and tooling all leading towards pipeline. Sales. And that’s where it stops.

Thankfully, with our constraints in mind and our customers at the center of our attention, we can build cool sh*t just like the GTM teams.

In fact, because those constraints narrow the options of what we can build it’s actually easier to get started and it forces real creative thinking.

Signals and systems

With your data layer ready, you have signals you can use to trigger fun new workflows aimed not at landing new deals, but at keeping customers happier for longer.

You’re now building for metrics like Net Revenue Retention (NRR), Gross Revenue Retention (GRR), and churn 👻.

This is valuable work if you like the idea of growing your business without needing to constantly chase new logos.

It’ll impress investors. It’ll impress acquirers. It’ll help you sleep better.

Start simple

Pick one or two signals to start with. Build hypotheses around them. Dream up ways to prove your hypothesis right (or wrong).

Pick something quantitative and/or qualitative. Doesn’t matter so long as it’s clear that the purpose of this work is to:

• Help customer get more value from your product

• Increase the LTV of select customers

• Give your business real revenue momentum

Signals can be things like:

• Product engagement dropping

• Big new account isn’t hitting activation thresholds fast enough

• Your Buyer Champion told you she’s leaving for another company

Not all customers are created equal

Once you choose your signals, tier your customers. Prioritize them by value to the bottom line and the continuity of your business.

Almost everyone stumbles at this at least once. I’ve done it countless times — spent too much time on $20/month customers while a $2,000/month customer slips away. Tier your customers so you spend more time for now on the most valuable.

When you’re deliberate about working on your most valuable customers first (Tiers 1 & 2), you will get to build systems for every size customer. That’s because when the big $$ customer base is more stable, you have the freedom to work on the more volatile little ones (Tiers 3 & 4).

Assign owners and let them cook

Don’t let a committee run this. Assign each Tier 1 & 2 account to a someone. Let them cook up ways to solve the problems.

Then give them the space to run experiments, monitor results, and feed that back to the rest of the team so the whole system can get better.

Capture what works and what doesn’t work. With AI now it’s getting easier to build this institutional memory so your system almost self-improves. That’s an entirely different topic, though.

The outcomes of the walking stage

For now, this is still the walking stage. We’re after learnings we can amplify later.

Plays can and probably should be run by hand. Let the humans take the signals, come up with the plans, email and message customers directly.

Get more than one positive outcome from the system before thinking about upping the pace. Running feels good until you realize you just ran a half-marathon in the wrong direction.

The drawing above is a bit simple, but it can be all you need to start building retention muscle. If you know you want to start keeping customers longer, but aren’t sure where to start, hit reply and we’ll jam on it together.

Next up, things get complicated quickly when you start to run. It’s wicked exciting.

In Customers We Trust,

Peter

This is a continuation of that idea, working through how to start dealing with those constraints creatively and effectively.

In other words, this is about turning the hard parts of keeping customers happy into undeniably valuable and fun work. Today let’s explore how to get started.

And hey. Thanks for being here.

Spreadsheets are still the number one thing I come across when I ask people to show me how they prioritize their customer work. There are more teams running retention work from Google Sheets than Gainsight*.

*At least among the companies I speak with.

Here’s what that looks like in practice, maybe you’ll see yourself in this story:

A founder recently showed me the spreadsheet his team built to track their biggest customers’ health scores. It was beautiful.

Everyone in the company can open this Google Sheet, look up a customer, see which features they use or don’t use, and see a High / Medium / Low risk score.

This same company uses Vitally, a customer success platform.

“Why are you still maintaining this spreadsheet if you’re paying for Vitally?" I asked.

“The team trusts it.”

I shared this story with a friend who helps Saas companies turn their CS practice into a revenue center. “That’s crazy common,” he said.

Signals you can see and trust

Building a spreadsheet isn’t a workaround or a failure of any customer success platform (CSP). It’s the team choosing signals they can see and watching them somewhere they trust.

Having a data point or a signal isn’t enough. It has to be something you know is right and it has to come from a source that you know isn’t going to massage it.

The first thing any team turning their attention to retention needs to put in place is a set of signals the team actually uses. For many that’s a spreadsheet. For a lot that’s a CSP.

But for now, let’s think about how to just get going.

Retention work is not a sprint (yet)

So the first thing to look at when you’re ready to work on keeping customers happier for longer is the signals you have.

This it the Crawl step. There’s not experimentation or real action yet.

People (me) skip this and move to trying new things with customers too quickly. Experiments are great, but with a finite set of companies to experiment on, they can be costly if done wrong. Bad experiments cost customers, which costs money (Constraint #1).

Get your data in order. I’m a fan of quantifiable data, so I default to things like product usage patterns, call recording analysis over lots of calls, etc. Data should be a mix of quantitative and qualitative to get a sense of what’s really happening and what customers say is the reason.

Observe your data. Boring, yup. Can AI do it, kinda. One day AI will be able to tease out all the meaningful patterns in our data, but for now us humans have some weird edge. We spot things and we can pair the quant and the qual together in ways that are just… human. Watch your data. Play with it. Take a walk and think about it. Patterns will surface.

Don’t do dashboards yet. That’s too abstract.

Build the picture before running the play

The team that built the spreadsheet, they had to see what was happening before they started running any retention or expansion plays. Smart. When looking at the spreadsheet, I could see that they know what normal vs bad vs good looks like.

You have to observe your data for a bit to get to that point. But it doesn’t have to take forever and most teams — your teams too if you have product analytics running and a call recording tool — can get this done in a week if there’s good historical data on hand.

Define the period of time you’re going to watch your data. Start building a picture of what behaviors and patterns lead to good outcomes and bad. This is a baseline to work from. It’s kind of the starting line.

Data sources to start with:

• Product analytics — if you’re already tracking it, great. If not, start. It’s free with tools like Posthog and Accoil. You can see how people really use your products, not just what they say they’ll do.

• Call recordings — a lot of CRMs have them baked in and there are plenty standalone options like Granola, Fireflies, Spinach. If you’ve been using one for a while, find the customer calls and start analyzing with Claude or whatever LLM is hot right now. If you don’t have call recordings, get a tool and start calling customers.
  
  A cool new tool for reviewing what customers are saying:

  https://useformat.ai/
  

• Surveys and whatnot — my least favorite data, but if you have NPS or feedback questionnaires or G2 reviews, parse those too.

• Customer data — from billing to entitlements to seat count or consumption, learn about your customers in relation to everything above.

Spreadsheeting is pretty easy now with AI, so you don’t have to build a thing of beauty like the team above did. Bring everything together and start to watch it. You’ll see things and go “ooh!”

It won’t take long to start walking

After getting your data in order, you get to be creative. Pick a signal and decide what you’re going to do with it.

And after some simple signal + action experiments, you can start to build systems across your book of business.

Crawling isn’t a downgrade, it’s the foundation

The team who built the spreadsheet aren’t behind the times. They’re setting the foundation for making their CSP and other tools do better work for them.

The more I think about how valuable current customers really are to a business, the more exciting this work gets. Yeah there are contraints, but without them it’s hard to know where to start.

So, set the foundation and let’s build from there. More thoughts soon on how to get up to pace walking and then running.

Peace,

Peter

It’s about building a SaaS and building revenue foundations that make a business last longer without always having to grow at all costs.

If you A) forgot why you signed up for this or B) just don’t want another email, it’s easy to unsubscribe. No hard feelings if you want to opt out.

Listen to customer success leaders and you’ll hear it over and over again:

Post-sales needs to be more proactive, less reactive

Post-sales being onboarding, customer success, and account management.

Ask what “proactive” means in practice and you hit a wall. The frameworks are too high level. There are no workflows. There’s no guidance on how to become this mythical thing: The Proactive Customer Success Team.

The problem isn’t that people don’t want to be proactive. It’s that nobody is explaining what proactivity looks like when you’re operating under a different set of constraints from every other customers-facing revenue role in the business.*

*This is not just about customer success. It’s about anyone doing the work to help customers get value from a product. Call the role whatever you want.

Success is not like sales and marketing, despite being close to customers and responsible for revenue numbers.

Understanding those constraints is where real solutions start. Where teams can get proactive and start owning more revenue.

The four constraints of customer success

Success teams have it harder than most people realize. It’s not a free-for-all like marketing and sales and growth.

If you work in success or do success-like work, see if these resonate.

1 — Your addressable market is finite and revenue-attached

Most marketing and sales teams have a gigantic total addressable market (TAM). That’s the fun part of those roles. For most B2B businesses, there is a big market out there.

Marketing gets to target the whole TAM. Sales gets to work through a pipeline of those who put their hands up, a list that keeps growing if marketing does its job well.

Success manages a fixed set of paying customers on any given day. Every one of those customers represents real, recurring revenue. Success does not get endless opportunities to test and trial — you can’t iterate your way through a list of customers like you would through market experiments.

2 — Success competes for a sliver of the attention

Hopefully your customer base is growing. But even if it is, your audience as a Success role is already a subset of a subset of the market. Within that you only get a tiny fraction of their time, energy, and focus.

Customers juggle your tool alongside everything else. That’s other vendors, internal initiatives, competing priorities, and buyers remorse.

It’s not ok to demand more of their time and attention just because you want to test something. When a marketing test doesn’t work, marketing tries again to get new dollars.

When a success initiative flops, customers stop paying and real revenue bleeds out the door.

3 — Your mission is to be a value maximizer for everyone

Yes, you’re job is to help customers get value your app they just bought. But your job is also to make sure your company harvests as much value as possible from each customer, too.

You're there to make sure customers realize more value from your products than they’ve investing in time, money, effort and emotion. That’s not just an operational goal — it shapes every decision you make.

Yes other teams build the products and promote the products with the promise of delivering value. But only the people charged with making sure that value is delivered (and understood and FELT) feel the pressure to keep everyone happy.

4 — Customer success functions are chronically under-resourced

Understaffed, under-funded, under-tooled. That’s not a bug in most orgs. It’s structural.

And I’m sure any team could argue the same, from product to marketing to leadership. But success teams seem to feel this more than others.

I think one reason is that when success does its job well, either nothing happens or there are incremental gains.

The silver lining on any constraint

These constraints don’t apply just to companies with big customer success teams. Every SaaS company operates within them, whether it’s a formal function or not.

Constraints like these aren’t obstacles to work around. They are the way, as Ryan Holiday says.

Agree with them or not, these are the foundations for how success teams get creative and become proactive.

Sales and marketing teams can chase proactivity with experimentation and volume. They get reps. Success has to be different — by understanding what’s actually possible within these realities.

I’m filled with hope by recent in-person conversations about this. More and more companies are taking success roles more seriously. That doesn’t mean success roles get any more headcount or funding. But it means teams are starting to think creatively about the role.

And that’s what I’d like to explore over the next days. It start with a Crawl. Walk. Run. approach to signals and experimentation. All with the goal of increasing the value of your current customers and building a rock-solid revenue foundation for a healthy business.

TTFN people,

Peter

The Mavericks (Mavs) are a good team. They’re talented individuals mostly who often gel and make magic happen. When things are going well, sales are stacking up, and the mood is high, the Mavs are a force.

When things get rough, though, and the sales gong is quiet for too long, the team starts to crack. I noticed that the root of the bad mood is usually one of two people:

1. The Rotten Apple — the one that spoils the bunch

2. The Less Talented Teammate — nobody is perfect and some people just shouldn’t have key roles

The Mavs’ Rotten Apple seems to wait for things to complain about. The moment a KPI turns down, blame starts to fly. Comments like “Why can’t you just make this little change?! It’s so obvious!” are pointed at everyone but Rotten.

In slow times, the Less Talented Teammate goes from being a fun guy to have around (he’s fun, enthusiastic, eager) to the perceived cause for the dip. And sometimes he is the cause of the dip. Then Rotten and the rest of the teammates pile on the blame. Less Talented’s position demands skill and talent above his God-given gifts. Harsh, for sure. Nobody’s perfect. Sometimes it’s just true that someone has less talent.

When these two people are allowed to pull down an entire team, the team suffers together. Teams should ride the peaks and valleys together, but teams need coaches and leaders to step in at those low moments to pull them back to the top.

Neither Rotten of Less Talented are company execs or leadership. What I don’t understand is how unwilling the company leaders are to do anything about this negative influence.

The leaders have brought this up with me, so I’m not even pushing some outsider opinion. When I question why they’re still on the team, I hear reasons like “When he’s on, he’s on” and “He’s friends with Dave-o… and I don’t want to upset Dave-o.”

I’m grateful to not have any Rottens or Less Talented Teammates. It’s our job as company leaders to make sure we don’t have them on the team and if we find ourselves with one of them, we do something about it. For the good of the team and the good of the company.

Peter

(421 / 500)

Instead of asking people to take baby steps, what if we give them lots of opportunities to take micro-steps.

What’s a micro step? Let’s compare:

• A baby step is a 2-minute demo

• Micro step? 10-second demo

Another?

• Baby step = enter your email for access

• Micro step = see it now

So much of marketing comes down to exposure, frequency, recognition. It’s the rule of 7. As much as I hate to admit it, us humans have the attention span of a chatbot. Show me. Show me again. Show me again. Etc.

Micro-steps should be valuable and show me something that makes me go 🤔. But they don’t have to show me entirely new, amazing, earthquaking things.

As a business owner and marketer, the micro-step has to get the prospect one tiny step closer. That’s the whole job.

Peter

(171 / 500)

Imagine this: you get paid to do your job. As part of doing your job, you’re allowed to record yourself doing the work.

You take that recording and share it on YouTube where your work is amplified to the max -- no surprise, given Youtube’s 2 billion+ monthly logged-in users.

I listen to a bunch of different music, but when I’m working it’s usually some form of lofi or this (recently new to me) house DJ-who-plays-a-coffee-house mix.

There are a few YouTube channels I go back to because the algo shows them to me. But for the most part, it’s a random collection of channel like MAIN KID above:

Low subscribers > > > Massive relative reach

These DJs have cracked the distribution code. And it’s all a 5x-win.

The café owner is happy. Customers have cool, live music. The DJ shares his work. YouTube gets long listen times. Viewers get to work with something nice in their ears.

Quick rant. Anyone else bothered by the little twist knob flicky thing DJs do? Like, dude, whatcha doin’ there? What does that little knob do, because I noticed nothing.</rant>

This model is amazing. Do your work. Share your work. Grow your reach. LinkedIn’s 2022 Global Talent Trends report showed that people who regularly shared their work or insights publicly saw up to a 10x increase in profile views and job opportunities. 10x!

Show your work + Distribution is the play here and I love it.

What’s the lesson here?

As user-generated content (UGC) takes hold on platforms like LinkedIn, I think the lesson is to experiment with more open and honest “Show Your Work” style content.

There are lots of benefits of this. Here are three I see:

1. We like buying from people we like. The Edelman Trust Barometer (2022) reports that nearly 60% of consumers say they are more likely to purchase from brands (or people) that share transparent, relatable content.

2. Trust and transparency. We like to feel like we know people. When you listen to a podcast, do you feel like you know the hosts really well? They’re not friends, but you know a lot about them and you trust them, right?

3. Feedback loops and fast iteration. Sharing work publicly creates tighter feedback looks. I don’t know about the quality of feedback, but it’ll be fast and probably directionally accurate.

Instead of obsessing over the right content and full content plans, I reckon faster production with more “Live DJ” vibes will continue to capture eyeballs and grow not just personal brand, but company brand and awareness.

Peter

(439 / 500)

In it, the author shares insights from 100s of interviews with people who are healthier, wealthier, and maybe wiser than him. All to discover what wealth really is.

Regardless of what wisdom is shared, it’s a remarkable observation that becomes the central theme of the book:

None of the people interviewed, even the ultra wealthy ones, talk about money.

And it occurred to me that when we interview customers and do sales discovery calls, we’re looking for people to say the “right things” and behave the right ways.

We — or at least I — have never considered to look in the negative space for insights. What aren’t our customers saying and talking about and doing?

What isn’t there is harder to spot than all the obvious things that are. Tools like Gong record our calls and tell us everything that was said. Even how many times and with what kind of sentiment.

But it does not tell us what we didn’t talk about. It doesn’t tell us what 9/10 people didn’t talk about.

Like the author of this book, we need to be open to seeing the things that don’t come up; the things that aren’t obvious.

What aren’t our customers talking about? If the things they don’t mention overlap with the things we offer, we could be in big trouble.

Peter

(282 / 500)

PS: This one is Sahil Bloom’s Five Types of Wealth. It’s one of the best I’ve read yet.

There’s this idea that work is allowed to occupy some of our time as long as it’s not too much of our time.

An extension of that thinking is that nights and weekends are off limits.

Some of the most successful and happy (emphasis on happy here) people I know work a lot. They work nights. They work weekends.

They also sit and have family dinners. They go on dates with their spouse. They do the school run and watch soccer games or swim meets. They exercise. They read.

They do all these things. And in part, they can fit a lot of it into their busy schedule because they work some nights and some weekends.

In fact, I can think of a handful of close friends who spend a bit of time each Sunday night planning their work and personal week. Some even do this with their partner so the family unit is aligned.

It’s work, but it’s in service of making it all fit.

Work does not have to fit into a box. It especially does not have to fit into a box someone else gives you.

Want to work this weekend? Hope you do. Want to take a call at 11pm? Hope you do.

I believe in getting sleep and looking after the important parts of life. But I don’t believe that there is a time and place where each part has to fit.

Get to work,

Peter

(258 / 500)

“Where do you want these plants,” my wife said as she drew a line across the grass with a long yellow tape measure.

We’ve had these plants, little conifers in pots, for months and she desperately wants to get them in the ground.

“How are we going to water them,” I ask like a dutiful husband, fully expecting to dig the holes, plant the plants.

Let’s stop there and do the obligatory pivot to a business analogy.

In this analogy plants are products or features. The more we add (the more we plant), the more we need to water and care for and nurture and promote and spend time with.

These “little conifers in pots” are only going into the ground because we own them and my wife hates (HATES) to let a good plant go.

We do this with our Saas products, too. Features we want to see. UI changes we’ve long wanted to happen. Maybe we don’t have a reason for doing the work other than the fact that we had the idea. And it’s a precious idea, of course.

So we do the work. We build the features. We plant the plants. We add one more thing to our product and systems.

And then shit falls apart because there are just too many things we need to do now. The burden of care for “little conifers” now in the ground is bigger than we thought it would be.

This puts the whole system at risk. We have only so many resources, people, time, money to spend on each thing we build and plant.

Be careful to plant or build the things that add value AND that you can sustain.

Peter

(303 / 500)

“When I say something, people believe me.”

I thought the practice of BS online countdown timers was done and gone, but turns out it’s not. Even at big, seemingly reputable companies.

Discounting is a terrible way to run a business. Putting that aside, I understand why discounts are used and I also understand how time pressure helps nudge people towards making a buying decision.

But here’s a thing that happened almost all week. This is from a Saas company:

• I got an email telling me that if I upgrade to an annual plan by close-of-business Wednesday, I get 25% off.

• Then I visit the product page to login on Thursday and get a banner telling me that the sale is still on. So it wasn’t Wednesday, but Thursday that the deal ends?

• Friday, I again login and now the deadline is for late Friday. Wait, what?

Scarcity and time pressure work to convince people that now is the time to buy. But when those same people are shown the same “scarce” and “time sensitive” offer day after day, the opposite happens:

They now have almost no incentive to buy.

Far from making me jump at the chance to save a few bucks on this subscription, I’m now wondering if I should stick around or not. Not because I’m better than this kind of discount marketing. But because I don’t know if A) it’ll be cheaper tomorrow and B) the product is as good as I thought, if they’re practically begging me to give them some money.

If you run a discount, do what you say you’re going to do. Stick to the discounted rate for the time you said. Otherwise you burn trust and probably end up losing more than you could ever gain from heavily discounted sales.

Peter

(318 / 500)

Talk to more customers.

A teammate recently gave me reason to rethink that tunnel vision advice.

There are people you and I work with whose opinion and point of view we haven’t asked for yet.

What does marketing think of the product? How does your superstar support person use it? When was the last time sales logged in?

The curse of knowledge makes us all forget how we learned to use our own products. We’re too close and in getting too close we lose perspective.

Talking to more customers isn’t always easy.

I wish 100 customers—some happy, some wicked pissed off about something—were always waiting to share their perspective on our product. But they aren’t. We have to ask them. Beg and bribe even (who hasn’t given away a pair of dope calf socks just to get someone on a call?).

Why not talk to the people close to you who aren’t yet close to the product?

New hires. Different departments. Different teams, regions, divisions. Everyone in your company (even if it’s a team of two) has a different point of view on the product.

I was reminded of this recently when a teammate shared some product feedback and a use case to go with it. Us founders have obsessed over this product for years. New teammates bring fresh eyes and a perspective that can almost always shine a light on something we hadn’t noticed or thought of before.

Ask your teammates to use your product and share their experience. What felt easy or hard? What stopped them from doing what they set out to do? How would they use it in their role?

Even simple little questions and suggestions can be gold. And it’s easier to ask someone close by than to beg and bribe. No matter how nice the socks.

Peter

(315 / 500)

In that time hunting for a shortcut, I could have been done with this one job. And now I don’t have a shortcut and I don’t have a finished list.

Do the work required. Learn what is required. Then pay someone else to build that system.

Peter

(86 / 500)