Within customer success, you’ll often hear people say “I’d love to scale my CS program and make it more proactive than reactive”, in fact, it’s probably something you’d like to do for your own organization.

In this article, I’ll discuss the three challenges most B2B CSM teams face when it comes to scaling, and share tips, tricks, and learnings for how to overcome them.

My name's Mike Lemire, and in this article, I'll discuss scaling customer success.

My background

This is my resumé in logo format.

Mike Lemire resumé in logo format

I actually started my career in the music industry working for Blue Note records. I myself am a musician I sing classical choral music and try to teach my kids piano and guitar when I have the opportunity to.

I love talking about customer success, but I also love talking about jazz, classical music, hip hop, soul, R&B, music from China, India, Africa. If you've got an interest in music, chances are I'd be happy to talk to you about it.

From there, I've moved on to working in ad agencies, working at Yahoo to help stand up our Yahoo India office. At HubSpot, I launched and ran our professional services program.

Before Toast, I most recently worked to launch the Customer Success Program at an early stage startup in Boston called Notarize and also lead the customer support team there.

At Toast, I was brought on to lead our restaurant success team which is essentially our customer success management team, and find a way to scale that which we were doing.

As you all know with COVID the impact on the restaurant community was profound at this time last year. So we had to say goodbye to a lot of our CSMs when that took place at which point I took over our education team and I'm now launching a new team that's just focused on proactive and scaling adoption of our product to our customers.

Customer success: proactive than reactive

One of the things I hear as I work with friends and colleagues around customer success is this phrase: "I'd love to scale my CS program and make it more proactive than reactive."

Chances are this is one of your missions or something you'd like to do.

What does scale mean to your organization?

One of the first things I talk about when talking about scale is making sure that you know what scale means to your organization because it's one of those relative terms that means a lot of different things to a lot of different people.

Making sure you know how comfortable you are, and what a definition of good looks like when it comes to have you actually scaled?

  • Does it mean your CSMs go from a book of business of 30 accounts to 100 accounts? Or,
  • Does it mean you can get rid of most of your CSM organization and have it all be tech touch as opposed to human touch?

First, I think that definition is something you need to make sure you're comfortable with, with your own organization.

The big three challenges

I'm going to frame this article around the three big challenges I see at different organizations, that I've personally faced, and in some instances still wrestling with. But that I've seen in other organizations I've worked at, or I've worked with friends and colleagues at as they launch their own customer success programs.

Those are:

  1. The difference between proactive and reactive work

The ability to scale each one of them is very different. What I've found is it's much easier to scale proactive work as you're beginning this type of engagement than it is to scale reactive work.

2. Scaling takes data to drive automation

Because duh, everyone is familiar with that. But the access to data takes infrastructure and partnership and that's where a lot of folks tend to fall down, they know they need that data but how do they actually get it? I'll talk a little bit about that.

3. Customer communication at scale is more than just emails

I think certainly, as we head into the 2020s, the old concepts of automation and scaling, which were very email-oriented and driven, aren't as effective anymore.

I think having customers in the hospitality industry, that is way amplified for our group. Restaurant owners are not sitting in front of their email inboxes all day. But I think the more we evolve as an industry, we're going to see fewer and fewer people wanting to engage with their software partnerships or vendors through just email.

I think there is still a role for humans and that's why I wanted you to think about the definition of scale.

The big three challenges for B2B CSM teams

You can scale proactive work much easier than reactive work

When I joined Toast, our CSMs were 100% reactive, spending a lot of time putting out fires from their customers, and the fires would come either directly to them from the customers up through the customer support team, or from the sales reps the customer had originally worked with coming through to them.

They had no ability to do any proactive work and it's tough to begin scaling reactive work and changing your install base's behavior to say, "I know you're used to having a very hand-holding relationship when you run into problems but now just use this self-help resource".

It's a path when it is tough to do that. It is much easier, to begin with saying, "Here's something new and additive for you and that is coming to you in a technical way or in a self-help way".

Before we even begin to experiment with any of that we need to give our CSMs the opportunity to take advantage of proactive time with our customers.

ID what is required of a CSM for reactive work vs. a support or care team. Then move it.

This is the first recommendation I have here, which is to ID what is required of a CSM for reactive work versus a support or care team then move it.

So often what I see is the CSM group can become an escape valve for the customer care team if it gets a little too hot, or the customers emotion rises. It's "Well they threatened to churn so it's it's going to the CSM", which is probably true, you want to keep an eye on retention, that's ultimately the primary metric the CSM is responsible for.

But I don't think all companies give enough credit or belief in the abilities of their support or customer care teams. The support teams can, in most cases that I've seen, handle tougher calls, tougher escalations within that organization.

If you give them similar tools in their arsenal that the CSMs have available to them, like credits for instance, with some protection on when they're able to deliver them, they can resolve more of those escalation issues than you might have guessed initially.

What is the work that really can be handled by the support team? And making sure it stays there to free up some time for the CSMs is really that first step so they can begin some of that proactive engagement themselves to figure out what's working, what can be automated, and what data is needed to take that action.

Dive in and make proactive work at least 10% of their month

Once that's done, you can dive in and make proactive work at least 10% of their goal.

If you're reading this in the middle of February, you're probably starting to think a little bit about your Q2 OKRs at this point, the goals for your group for Q2, now's the time.

If you can start having those conversations with your support team and setting that up and say in Q2 we're going to put 10% productivity on the heads of our CSMs.

Not all proactive work needs to be delivered via a QBR

What that proactive engagement looks like. So often, the well-trod playbook of the QBR is where we go, everyone knows how to build and deliver QBR, customers understand it. But it really isn't the best way to engage a customer proactively at every organization.

There are certainly enterprise customers who would expect that but if you're working with an SMB community, they don't all need that formal type of readout slide deck presentation. Most often, they want to know what features they're not taking advantage of that they could do better with, and how they compare to other users within the product.

That can be delivered in a much lighter format. That's where I'd start - think about what is the proactive work you want to drive with your customers and I'll talk a little bit about the metrics you can be in control of with that.

Documents proactive engagement differently so you can track it

Lastly is making sure you're documenting those proactive engagements within your CRM or whatever CSM piece of software your team uses to run their day-to-day.

Because we want to track the impact and efficacy of it and if they're just logging activities the exact same way they would from a reactive standpoint, you won't be able to measure how valuable this corrective work is so you can make decisions downstream on what data should be prioritized to take action on it.

Scale proactive work easier than reactive work

Scaling takes data to drive automation, data takes infrastructure and partnership

The next topic is the data itself and making sure we need data to drive automation and getting access to data takes infrastructure and partnerships internally.

Confirm what type of action you want to scale via automation

The first thing I want you to consider here is confirming what type of action you want to scale via automation.


Is it renewals?

Is that something where the touch and engagement with the customer are light enough where you could provide them with a "Here's your first year, here's your one year option for renewal, here's your two, multi-year option for renewal. This comes with an automatic 10% discount. This one comes with a no discount.", and take that first crack from a renewal standpoint?

Account changes

Is it account changes?

Is there work where we're handling the reactive nature? The customers are working with their CSMs on a regular basis for something that is fairly paperwork-oriented, that we can automate?

Product adoption

Or is it product adoption?

We want to drive product adoption because we believe that will increase retention, decrease the likelihood to see down-sells on specific features you may have as options within your software. Or it may just increase the likelihood for referrals, the more the customer is seeing benefit from the product.

There's a lot of impacts that can come from just focusing on product adoption. That's where we're focusing right now at Toast is making sure our customers are using to the fullest extent, the products they have.

Making sure you understand what type of data you want and need to take the action on the metrics you want to move.

The triggers need to be prescribed to the CSMs, then converted to automation

The next is making sure the triggers are prescriptive to your CSM, so you can then convert them into automation.

Lesson learned at Toast

We built the data around product adoption, we partnered with our product team to do that, and I gave my team Looker dashboards. So filter by your name, you can see your entire install base, you can see all of the adoptions to varying degrees on every feature customer by customer.

The team didn't really know what to do with that, "Okay, so I see this customer has a score of 50, this customer has a score of 70. When do I take action with the customer?"

Just giving them information or access to data isn't enough. I think you need to go one step further and be incredibly prescriptive and say "When a customer is experiencing this degree of adoption, that's unacceptable so you need to reach out to them".

We can move it from just access to data to if the data is below this threshold, automatically create a case just the same way they would potentially be working out of a reactive case or activity previously.

Proof of concept

Once you've done that, and you're able to verify that through the human outreach this proactive engagement is having the impact you would expect it to have on your customers or you hope it would have, then you have the proof of concept and you're able to scale that by handing that to potentially a marketing team, customer marketing team, or product marketing team.

Where they're thinking more about the resources they have to scale that. I'll talk about not just relying on email next but proof of concepting with your CSMs and then handing that over to automation.

This is not a CS-only job. You must get buy-in from product/ops teams

The last is the data automation and the infrastructure and partnership is not just a CS-only job. I think this is where a lot of folks within our industry can get frustrated or run into roadblocks is building out these data triggers alone.

Because they don't have easy access to the product usage, databases. If they do, they may not have the skillset on converting that database into an actionable case in Salesforce, for instance.

To begin this journey, you're going to really need to get buy-in from the product team to make sure they're instrumenting the tool in such a way that gives you the data points that are going to be valuable for a trigger standpoint.

From the operations team, or whoever manages the Salesforce instances, Salesforce admin, HubSpot CRM admin, Gainsight admin, because if it's just on the CS team alone, it'll be really difficult to get done because you don't have the correct access.

Making sure you're getting the data and making sure you're building the infrastructure alongside the partnerships across your larger organization.

Scaling takes data to drive automation, data takes infrastructure and partnership

Customer communication at scale is more than just emails

Scaled engagement doesn’t mean no human touch

I think so often when we hear customer success at scale, it's almost assumed the customers are no longer engaging on a regular basis with humans on your team, which shouldn't be the case.

I think there is an opportunity for human touch, it's just prioritizing the type of human touch that has the most impact for the customers that need that.

I talked about that proactive engagement and there may be instances as you go through those experiments on driving up your product adoption that the customer can get all the videos, emails, or SMS text messages in the world but a certain persona within your install base requires that human conversation and it makes a big difference to them.

So you could prioritize that and then some of the lighter work hand over to tech touch.

I'd encourage you as you're going through the experiments to identify:

  • What does require human touch?
  • Is it providing the value you would hope it to, to earn that human touch? And
  • What can go through tech touch?

Meet your customers in your product

I'm a big fan of meeting your customers in the product. This has been a game-changer for us in getting the in-product messaging to our customers for proactive engagement and our ability to scale.

Of course, we use tools like HubSpot and Marketo to drive traditional email campaigns and email automation to our customers. But more recently I've been using tools like Appcues and Pendo in our software to communicate to customers directly once they trigger an adoption threshold.

With those tools, we're able to provide either a click-by-click guide, here are the steps you need to take to increase that adoption or push an in-app video to them.

This is why I like to start with the human engagement first to experiment because we'll find talk tracks that work really well, we'll find that one rockstar CSM, who can get any customer to take the action, regardless of the concerns they have. And we'll record a video of them, put it into Pendo, push it to the customers that have hit that trigger that say they need that type of engagement from us. As well as testing SMS messages.

I would challenge you to try to find ways to get in the product. Those tools like I mentioned Pendo and Appcues have been really valuable for us to do that without requiring a ton of partnership from engineering and waiting on their sprint cycles to get that done.

Slack can work wonderfully… but beware the reactive

Slack can also be wonderful in engaging with customers and using that to recommend certain actions be taken with them. I like that because more so than in email or a phone call, your CSM can have five or six Slack conversations at the same time with customers.

Whereas for email, it's not as easy to do that or certainly not with the phone. But beware, if you hadn't taken the early step of giving the customers the path for their reactive needs that are working well, opening Slack up to your customers can cause a lot of internal frustration with your CSMs because now it's just a more direct path to them for all of their fire drills.

Slack does have that expectation of a faster response time than even email. Think about where your customers are spending their time.

For us, working with the restaurant industry, they're not using Slack. Restaurant owners are not spending their time there. But they are spending their time in our system and that's where we've seen Pendo present itself to be incredibly powerful for us.

Customer communication at scale is more than just emails

Next steps

I always like to as a good CSM, despite my poo-pooing of the QBR, close with next steps.

I encourage you to take an audit of the work your CSMs are doing, and see if there's any reactive work that can stay with the support team or can be solved by giving the customer the ability to self-serve, like making those account updates.

Confirm what actions you want to scale and make sure the data is in place that you can push to your CSMs to start. Probably where you're going to need to start is with your fellow leaders in product, make sure they’ve bought into the mission here, and then support you in instrumenting that data flow.

Next is to create a way for your CSMs to document their proactive work and push them to start in Q2. It won't be perfect, the focus on scaling, the focus on certainly proactive work, there can be a ton of paralysis by analysis until everything is perfect, and you have everything lined up exactly the way you expect it to.

A lot of this is let's get started and optimize. Get to a place where your CSMs can take action, and then start to optimize from there before you try to design the most perfect system.

Making sure those partnerships are strong internally, find what proactive work is doing well once you've launched that, and then turn on automation that's more than just an email.

If you don't have in-app messaging systems, I would encourage you to look at some of the options available to you today. If you're not using SMS and you think that's a better fit for your customers. If there is an opportunity to use Slack.

Think about different methods of communication over just email. Then track the impact of the scaled work and the proactive work on NPS, on adoption, on retention to make sure all the hard work you're putting in to develop this program allows you come budget season next Q4 to make a case for more infrastructure and more budget to support this as you're able to grow the books of business potentially for your CSMs.

Key summary of scaling customer success

Thank you.

Learn how to set up your own customer success function

Has this article opened your eyes to the possibility of building your own customer success function, we have the perfect course to help you position CS to a leadership team and establish a successful customer success operation.

Introducing... Building a Customer Success Team Certified |Masters.

By taking this course, you'll discover how to:

🔧 Leverage technology and automation to streamline customer success operations and improve efficiency.

🧑‍🎨 Sculpt out a strong CS function and learn for your business, including where CS slots into the client experience and why it’s an investment for the future.

🎨 Create effective customer onboarding processes and ensure a seamless transition from sales to customer success that sets the stage for long-term relationships.

🧱 Build a culture of continuous improvement by cultivating a mindset of learning and growth within your customer success team.