CX Insights

CX Insights Episode 2: “Evolution of customer success organization” with Sara Masson

Sara Masson is a Director of Customer Success at Loopio Inc.

CX Insights is a new online show where Customer Experience leaders and experts share insights and expertise to uplevel our CX game.

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Sara is an innovative Customer Success professional who’s passionate about customer focus, creative campaigns, and organized project planning.

Here are some of the highlights from this episode:

  • Evolution of customer success organization
  • Customer Journey
  • Customer Retention
  • Customer Health Score
  • Scaling Customer Success Team


Hello, and welcome to the show. Our guest for today’s episode is Sara Masson, director of customer success at loopio. Sara. Welcome to the show.

Thank you. I’m excited to be here.

Awesome. Sara, tell us a little bit about yourself.

So my name is Sara and I, as you mentioned, am the director of customer success at loopio where I joined about four and a half, almost five years ago. And when I joined, we were a really small team. So I joined. As employee 10, we were in a small coworking space and we’re now about 140 people. Our customer success team has grown pretty considerably over the last few years. And it’s been really exciting to see that evolution before that I was at a different Canadian tech company wave.

And at wave I, again, joined pretty early. I was in the early twenties employee size and I was there probably till we were the eighties in terms of number of people. And I really did focus on driving customer engagement, totally different models, freemium models. So you can understand the scale and the methods of engagement.

Completely different, but a lot of the same philosophies in terms of trying to drive better adoption across the platform, trying to drive. Expansion in a very different way, but upselling from freemium to paid products, as well as retention. So getting those customers coming back again, the model is very different, but a lot of those philosophies were the same.

So that’s a little bit about me and my journey in tech. Awesome. And you know, it’s  and it tell us a little bit about Loopio. So Loopio.  sounds like an RFP software company and, you know, tell us, tell us kind of what you guys do and how do you solve customer’s problems. Absolutely at . We have a software that helps people respond to RFPs, RFI security, questionnaires.

And I’m not sure if you’ve ever answered one before, but they are a paid.  to have all of these questions are super tactical. The answers are really important, will influence whether or not you win the deal, but they’ll also influence your commitment to that organization. Once they become a customer, often it’s a blocker in the sales cycle and it requires a ton of expertise from across the organization.

So what’s interesting is people really hate responding to RSPs, which means that I get to work with some of the best customers in the world because they are so excited when they discover that it’s a solution out there. So absolutely love it. Absolutely love our customer base. , but yeah, RSPs are a pain.

And speaking about customer base.  are you guys targeting enterprise, or mid market SMB? All of the above. What, what kind of customer segments are you looking at? It’s a great question. All of the above.  RFPs,  pain everywhere. So we work with fortune 500 companies. We work with really small emerging tech companies.

And of course, we want to make sure that we design the journey and to design the elements to accommodate each of those segments needs. So I’ve mentioned I joined. Very very early in Loopio’s journey. We actually now have three customer success teams dedicated to each of those specific groups and to make sure that we’re really taking care of their needs and their realities.

Absolutely. Sara and you know, you’ve been with Loopio here for some time. You’ve seen the evolution of the company on one hand. As well as you’ve seen the evolution of customer success organization, on the other hand, in terms of sort of strategy, the operational work,  you know, the tech stack,

how has it been to be part of that evolution, right. From start where, you know, the product may have not been that much mature as it is today.  customers that were just sort of getting used to the product and,  you were, you were kind of dropped in or you dropped in and said, okay, here’s how we’re going to do this.

And the evolution from that point to now,  how has it, how has it been that journey? It’s been incredible.  In the tech space. I know it’s rare to be at a company for almost five years, but every single day has been so exciting, so interesting because when I joined. I was the first dedicated customer success manager and our processes when it came to customer success were really, I, I came in and I think our CEO had written two email templates, maybe three, and we had one and that was customer six hasn’t loopio yet.

And that worked. We, we were really small. Our customer needs one, all that complex. We really didn’t have any enterprise customers who had really sophisticated needs, but. I was so excited to basically walk into a blank slate and have so much opportunity to create everything. The health scores, the journeys, to just understand our customers and dig into personas and influence even the product at that early stage of a company.

And as you can imagine, our team is much more robust at this point in time and things are. A little bit better defined, but I would say we’re still really growing at a very, very accelerated pace, which means we are reinventing ourselves all the time. And that has been my biggest lesson when it comes to customer success.

And probably when it comes to any role in tech. Is that if you want to join a really, really innovative, fast growing exciting company, you need to be willing to reinvent yourself and you need to make sure that you have no ego attached to anything you’ve done in the past. Because if you’re, if you’re holding onto history, then you’re quickly going to become history.

I love it. Solid points there, Sara, you know,  when, when someone has to start. In a new company in customer success. What’s a good first place to start. Is it customers like the customer segments type of customers, etcetera, personas. Or is it the product? Like what’s our go to market? How do we serve customers?

What problems do we solve for them uniquely? Or is it more like, Hey, I want to look at the whole customer journey. Like, wait, what’s a good starting point for someone to start thinking about here. Here’s how we’re going to start. And then after that, I’m going to scale. I am a big believer and this will depend on the stage of the company.

So if you are joining a company that is really large and really established, and they don’t have a customer success practice in place, you’re going to do things quite differently because you probably have more resources. You have more spend,  you can hire multiple teams and individuals to do a lot of things concurrently.

So I’m going to speak to this from the lens of someone who’s joining a younger tech company and really has that wonderful blank slate situation. And I would say you want to start with. A really iterative process where you are willing to learn and experiment and document as you go. You never want somebody to come in who is either super process oriented and not willing to experiment.

And they just want to write down, you know, a 50 page document on this is customer success at our organization without experiment digging and iterating and playing with things. But you also don’t want somebody who is very. Fly by the seat of their pants. I’m just going to go, go, go. And I’m not going to write down anything and I’m not going to, you know, document anything for the next person who comes along.

You need a good combination. And so I think that that iterative process is really, really important. And for me, that iterative process comes from the customer. So you start with the customer, you work with it that learn about their needs, learn about the state of the company. Do you have any data or insights into what they’re doing?

If not, maybe that’s okay. Maybe some conversations can help, still expose a whole bunch of information. You’re going to want to learn about the product and how it fits into their world. So what is in your customer’s tech stack? What is their world look like? How often should they actually be logging in.

and you want to learn about the industry, but for me, it all really does start with speaking to the customer, learning about the customer. And then once you start to understand their needs, you want to be very, very iterative, even. As simple as, Hey, I’ve spoken to our customers. I’ve had the same conversation three times.

So now I’m going to write an email template to help prompt this conversation and see if this is problematic anywhere else in our customer base. I’m not going to send that email to the whole customer base because even if your customer base is really, really small. Yep. You’re you’re losing your opportunity to iterate.

And this probably comes from the fact that I, I started in a much more scale based organization. So I really did learn a ton, but the value of those AB tests and those iterations, even if your customer base is 15, people send the email template to two people, see what the responses are like, and then iterate.

And eventually you’ll end up with a really strong journey, but I wouldn’t try to over-engineer and define your whole customer journey at a tiny tech company in your first 90 days. Totally. And Sarah, as we learn more about the customers and let’s say me experiment innovate, iterate on a tiny section of customers, then we go to more customers.

It sounds like that’s a logical approach. I like that a lot. Was there a. Difficult,  lesson that you learned, something that, you know, really surprised you, was it like it was super difficult to digest and it was hard to overcome or hard to understand. Oh gosh, there’s so many different lessons to learn.

I would say, like, you’re never done.  if you think you’re done you’re wrong.  so we, for example, started documenting the primary reasons that our customers were leaving. So we have great retention, but if customers were leaving, we really wanted to know why. And you would think, okay, you’ll document that you’ll learn.

You have a great process in place. Let’s say M and a really, really common mergers and acquisitions. It is one of the fundamentally hardest things to combat because if you have a really small organization and they are acquired by a larger parent organization, They don’t have so much sway. So how do you help them retain your software in that kind of situation?

It’s really hard. That ended up being one of our common reasons for a customer leaving.  Which is positive. It’s a really good indication. Laura customer has now been acquired by another organization. So your customer has to leave your software because the larger organization is using a different platform, et cetera.

Exactly. And so it’s a good thing because it means that, you know, a lot of our customers are really sticky and they’re not leaving unless they’re being forced to leave, but we still wanted to combat that. And so we did a ton of research. We came up with a full merger and acquisition playbook, as soon as the customer goes through an M and a, and not in every situation, obviously, but in a lot of situations, we actually, as we evolved, managed to turn those mergers and acquisitions into really exciting expansion, potential into those larger apparent organizations.

So we built this MNA playbook,  didn’t entirely solve the problem, but made a ton of headway and then. Are turned to disappear. You still have to look. And there’s always a number two problem to be solved.   even when things are humming along nicely, you need to look and say, okay, well now what’s the opportunity that I’m not seeing, because if, if I’m hitting all my targets, those targets are just increased.

So I need to really look around and say, what is working today? What are the problems of today that I’m solving and what are my next three problems, but I’m going to have to be tasked to solve and how can I start planning to solve them now? I think that’s the biggest lesson is you’re never done. Yes.

Focus on solving the biggest problems, but you’re always going to need visibility into the ones that are coming down the pipe.  📍 I totally agree with that. And that makes so much sense to start looking at the problem, solving that problem. Prioritizing bad. And yeah, MNA seems to be an interesting quality because it affects the whole industry, especially when we are in a dynamic environment like right now.

So,  yeah, I think, I think many companies would be able to learn from this playbook of having M and a as a scenario for customer success and turning that from short-term into expansion. So that was, that was super valuable.  as you scaled up customer success, Of course there were processes to be defined and all of that.

And of course the other part of that is automation and the platform, or maybe a collection of platforms. Tell us a little bit about the collection of platforms that you might be using at Lucio and kind of how you guys scaled up. Absolutely when I started and we were in our early stages, we were really, and we still are a very Google heavy company.

So Google tablets stored. Oh gosh. I think by the end we had about 40 email templates. We used in different scenarios. The goal was very much so semi-automation so not. Send these blindly, but here’s the template. It’s a great starting point, iterate, evolve, and make it really customed to this customer. Well, one thing you mentioned, semi-automated so interesting area because how do you make that call?

Like, Hey, I want to go full automation. I want to go zero automation. I’m going to go semi. I’m going to dip my toes a little bit. See what works. How do you make that call? Like many things in customer success. I think that your answer will depend on your team. So for example, at wave, we had half a million customers.

I had no options, full automation is the only path that made it. 80 cents at all. At Loopio, when I joined, we had around a hundred customers. Oh, totally different scale. We obviously have a significantly larger customer base now where semi-automation does make sense. Yeah. But in some ways, you’re going to be forced by your customer base and your monetization model.

There is a number where you just have no toys and you have to go full automation. And I would say if you have a customer book per person that is over a thousand people, your hands are tied, you’re going full automation. And one more angle there is do the customers who are receiving your communication.

Let’s say whether the communications automated via templates via your platform versus handwritten. I E you’re actually typing up those emails. Can customers tell like, Oh, this is a machine generated synthetic email. I don’t know if I should actually respond to this, or if this is important versus, this is, this email has been written for me.

What has been sort of your,  sort of view on that space?  do customers, can customers tell in the first place it’s a fantastic question. I, I think email writing is a lost art, and I think that if you write a really thoughtful well-crafted email, You can write it in such a way that they can’t tell that said, I do think that if you have a full automated journey, They pick up pretty quickly because you lose that personalized element.

But if you are really thoughtful about the triggers to your journey, and if you are really, really careful about making sure that people are receiving the most important information for them, and especially if you’re able to customize it, which a lot of automation tools will let you do. And then when you sit down to write it, I always coach people to think of someone who they love speaking to.

Everyone, all customers are fantastic. We love absolutely each and every one of our customers, but there’s some people you’ve just loved speaking to it prints up your day. And when I sit down to write an email, I always actually type them ones in a minute. So I won’t say, Hey. Dash dash dash dash, dash. I’ll actually type somebody’s name into it and I’ll write the email draft to them.

And then if you remove their name very often the warmth and the emotion and the caring and just the level of tailoring shines through no matter who’s getting it. So that’s my top tip. If you want your emails to really feel like they’re written to a person is write them to a person. I love that that’s amping up your EEQ high so that you get the caring, the warm.

And the understanding that a customer deserves. I love it.  Sarah, I think I very nicely backtrack or sidetracked the original,  automation stack questions. Why don’t we go back there? So automation stack for your customer success organization. Oh, gosh. Okay. Let’s go back full circle. So when it comes to automation, like I said, when we started very Google heavy, we still do use the Google G suite pretty heavily, but everything was in drive and even our health score.

I remember spending hours pouring over the six health templates, trying to build in formulas and see lookups probably three weeks just. Heads down in Excel. I am not an Excel person, but it shouldn’t work. And we asked our development team to write a simple script so that once a month they would pull an export from our system and we’d load it into this Excel template.

Have the customer health score for every single customer. And then look at all the customers who had had a shift in score by over three. So it was a score out of 10. If they shifted dramatically one way or another month over month, you would escalate and use these email templates to follow up with them.

And when we were tiny, this worked and it’s scaled shockingly far. I think I was Illumio for about two years before we evolved from that. And I think that’s a good thing because by the time we bought a software, we knew exactly what we needed. A lot of teams will come in and buy a software with no idea what they’re actually solving.

Customer success is hard to scale. Put a software in there. let’s buy it. They’ll solve our problems for us. I don’t believe in silver bullets, software solutions. I think you need to know what you’re actually solving and have some good insights. And so we were really well prepared when we purchased, we did purchase Gainsight and.

Because we already had so much in place. We knew exactly what we needed to prioritize with our implementation. So if you’re familiar with Gainsight, we prioritize to help score because we already had a health score and we wanted better insights faster than once a month. And we prioritize call faction, which essentially replaced all of this manual pulling and email lists.

So we were doing once a month and helped us semi-automate that. So again, we had the templates, they were a starting point, but then we would customize. Got it. And are you guys also pulling in telemetry from your product and kind of, what, what are you guys using for telemetry? So we aren’t using anything there where we’re Gainsight heavy.

we use gong, which is one of my favorite softwares. It is. I said, I don’t believe in silver bullet solutions is B fastest value software. I think I’ve ever experienced because. There’s no training. There’s no ramp time. It just automatically starts recording your customer success team calls and giving them really actionable coaching.

If you go into the insights. So things like, are they asking questions often enough? Are they being patient with us during calls? And I found that the CSM to spend a lot of time in gong, looking at those insights, they accelerate ramp and grow at a much faster pace because they have real time insights into exactly how they’re doing.

So gong is one that I would say if you’re looking for a software, but you’re not ready for a customer success full software, yet huge value, especially if you can connect it to your sales team. And then you have the full journey in call format. We also use text expander, which is just really simple macros so that you can plug them in anywhere.

and vineyard, which has been huge for us. I mentioned that we have those three customer segments and I think. A disservice, a lot of people due to the SMB segment in particular is they think that you have to go full automation. And they think that the only way to manage an SMB team is to give them a fully automated journey or a pool based customer success team, where they don’t actually get a dedicated CSM and to manage everything at scale.

So people tend to evolve to all or nothing like it’s all scale or it’s all, One-to-one and we have used video to really beautifully marry some of those scale things like webinars with really creative options, like doing our version of the QBR. We call it a partnership review via video so that they’re still getting those really personal deep insights, but it scales at a much more effective rate than trying to actually book calls for all of those customers.

that’s interesting. So you have, so for some customers, SMB customers, You guys are looking at, recording the videos and then sending it asynchronously to them. The customer sees that says thumbs up, thumbs down, or like it, or, Hey, let’s have a conversation or what have you. Oh, that is super interesting.

And is that a, is that something that you do for a section of the customer population or is that for all of your SMB customers? Like how does that work? So it’s for the SMB customers in particular, we’re not doing that same model for a mid-market or our enterprise customers, but I find it that it’s much more.

In acknowledgement, not only of our CFMs time, but also over SMB customers time, they’re often wearing multiple hats. They’re juggling multiple pro projects. They don’t necessarily have 30, 45 minutes to book a call. And if you’re juggling a lot of projects, the fires come up. So. Booking and rebooking rebooking.

These calls it’s a headache, but they want to know what’s happening in the solution. So if the CSM can record a five minute video and send it to them and get them all those same insights and they get all the same value, they would have over a call that was 30 minutes, but took an extra 15 minutes to book and then reschedule and then book and then reschedule.

Both teams end up saving a whole pilot time, but they’re getting the exact same quality of insights. And then if they have questions, if the goals are misaligned, we can always book a follow-up call. But for, I would say 70% of them, we actually accomplished that same level of alignment just through that personalized video.

Outstanding. I love it. And that’s a great way to scale a customer success, especially when you’re trying to do that pervasively across SMB and some of the other segments as well. Awesome. And so, Sarah, what’s the, you know, as we sort of start to wrap up here, you know, if you were to share one piece of advice for the listener on customer success, what would that be?

My one piece of advice for the listener would be to constantly listen to your customer base and be open to evolving your journey. Based on their evolving needs. We’ve seen this last year, the world has changed dramatically. Your customers might not want to do video calls from home when they have kids in the background, they might want to do more things via email things that worked really really well.

Eight months ago might not work today. And the. Most important thing is just to be willing to iterate, evolve and let go of your ego when it comes to anything you’ve done in the past and keep your eyes towards the future. And if you’re doing that, if you’re listening to your customers, then you’ll be set up for success.

Sara, this was outstanding. Thank you so much for being part of the shell.  for folks to follow you, what’s a good way to connect with you, Twitter or LinkedIn. LinkedIn is usually best. You can find me there it is. Sara Masson. I’m happy to connect with any of you and answer any questions anyone has, especially around scaling a customer success team and the right elements for the right stage in the journey.

So our amazing director of customer success of Loopio, thank you so much for being on the show. Super valuable. Appreciate it. Thank you so much for having me have a great day, everyone.