Mastering Customer Success in Transformational Times ft. Andrea Bumstead

Randy Likas (00:02.52)
Change is the only constant, but navigating through transformational times is rarely straightforward, especially when it comes to ensuring customer success. Shifts in market dynamics, rebranding initiatives, and evolving go-to-market strategies can create a ripple effect across organizations, testing the resilience and adaptability of customer success teams. Hello, everyone. Welcome to the Revenue Lounge podcast. I am your host, Randy Likus. And in this episode, we’ll explore how leaders can master the art of steering their teams and customers through periods of change.

From maintaining team morale and ensuring alignment across functions to leveraging data and technology will impact the strategies and frameworks that empower customer success leaders to not just survive but thrive during transformational times. And joining me today is Andrea Bumstead. Andrea is a recognized expert in customer success strategies for SaaS technology companies known for turning satisfied customers into loyal advocates, spearheading collaborative customer initiatives, and building high performance teams that deliver exceptional results. Andrea excels at

bringing out the best in people while driving measurable business value. As a thought leader in customer success, Andrea is an active member of Women in Revenue and Pavilion and is a sought after speaker sharing her insights on driving business growth through customer-centric strategies and exceptional team leadership. Andrea, thanks so much for joining us today.

Andrea Bumstead (01:17.689)
No problem. Thanks for having me, Randy.

Randy Likas (01:20.502)
Yeah, I’m looking forward to the conversation. So Andrew, I usually like to start these and just maybe have you walk us through a little bit about your background and your career journey.

Andrea Bumstead (01:29.915)
Sure, so I can’t believe it, but I’m actually coming up close to 20 years of experience all in the post sales side. So I started in marketing. I then was an account executive for a number of years, and then I transitioned to customer success. And in my last three roles, I’ve been responsible for major transformations of customer success organizations. First at Procore when Procore was entering the Canadian market for the first time.

I founded the customer success team and built that from four people to over 30 people across five functions. Then moving to revenue.io as a vice president of customer success, I transformed their customer success organization as they moved from a single product focus to a platform company. And then third, and most recently at KindSight as vice president of customer success, I transformed their customer success.

organization on the heels of two acquisitions. yeah, lots of transformation in my past three roles, but it’s been an exciting ride.

Randy Likas (02:33.112)
Yeah.

Randy Likas (02:37.418)
That’s fantastic. So what I would love to do is maybe let’s get granular on and maybe give us an example of one of the big transformational initiatives or projects that you’ve worked on or that you’ve led. And how has that sort of impacted the customer success strategy at the organization?

Andrea Bumstead (02:55.737)
Yeah, so let me talk a little bit about the last customer success transformation that I did at KindSight. So KindSight started as an SMB focused business. They had two major acquisitions, one of which was an enterprise platform. And so they tasked me with bringing these two very different things together, an SMB motion and an enterprise motion and rebuilding the customer success team.

while launching a brand new integrated platform, which integrated this SMB solution and the enterprise solution. So this was no, this is no small task, I’ll have to say. And that SMB business had been entrenched in market for quite a while. The teams are pretty comfortable in what they were doing. And likewise on the enterprise business side, they had their own motions, which were quite different. So,

I’d say it was exciting, very challenging. And one of the core things is the people, right? There’s the transformation of the business, but then the people aspect is so important and maintaining team morale during this major transformation was both challenging, but extremely important.

Randy Likas (04:20.302)
Yeah. So in that example you provided, there’s any transformational initiative has inherent in it is a lot of change, right? And leading that change, both from, I guess, your internal stakeholders and partners that you work with in the organization, but also the change on the client side as well. Can you maybe talk about how do you effectively manage that change? Or maybe give us some recommendations for as someone’s going through a transformational initiative like that.

Like what are some best ways to manage change?

Andrea Bumstead (04:52.625)
Yeah, it’s a really good question. mean, first change is hard. No one really likes change, even if it’s good change. So let me talk about internal and then I’ll talk about external. But on the internal side, yeah, the change, even though it might be exciting, there’s a new vision, we’re bringing these companies together. It’s very exciting. The change is difficult. And so I strive for transparency, first and foremost.

with my teams and the broader teams talking about why we’re making the change, getting them excited about the vision, where we’re going as an organization, but then also bringing them along with me on the change. We all have to go through the change together. And just because I’m a leader in the organization doesn’t mean that I have all the answers or even sometimes that I know what I’m doing, right? Because these are big things that we’re trying to do.

And it requires more than just, you know, me as a leader orchestrating this. It requires the other leaders. It requires all the individual contributors on the teams. We’re so much smarter together. And so first I strive for transparency, but also empathy. Change is hard and I’m going through the change with my team. And certainly as I made major changes at KindSight, there were days when

you know, in team meetings, I approached them and I was like, look, this is hard stuff. This is really hard. I get how you’re feeling. I get that this is really uncomfortable. I get that it feels uncertain and maybe even a little bit chaotic. And really establishing that for me as a leader, it’s my job to make these hard decisions and to basically go on the journey with them on this change. I’m with them 100 % of the way. So that transparency and empathy.

go a long way. Do you want to comment or I can adjust the second part of your question? Yeah, so you had asked about change on the external side. So there’s internal change, which is very uncomfortable and difficult. Then there’s a change for the customers. When you’re changing a go-to-market strategy, this impacts customers. It changes everything from how they think about your brand and your solution to the platform that they purchase to the value that they’re going to receive.

Randy Likas (06:50.446)
No, no, keep going,

Andrea Bumstead (07:15.089)
And so keeping in mind that as an organization fundamentally changes its go-to-market strategy, like after an acquisition, this impacts customers and makes them feel uncertain. That can impact at retention. So you need to be very intentional about how change is rolled out to the market and involving customers and getting their feedback along the way. Not all changes are good. Sometimes the changes that as an organization we think are good,

are not good for customers. I’ll give one example of this, which is we did a rebranding and we changed the colors of the platform. We love them. We thought they were great. Our customers immediately said that they didn’t love them. In fact, some of them didn’t meet the accessibility standards and we needed to go back and then revise that. So without that feedback loop from customers, we would have just kept going.

But that feedback from customers and pivoting was really important.

Randy Likas (08:18.648)
Yeah, what I love about what you said about sort of going through the change and having empathy, you said something which is like, I don’t necessarily have all the answers, right? And I think that builds credibility, that you’re in it with them, right? And you’re figuring out, we’re all kind of figuring it out together. And so I really like that comment. I have a question for you on the external side. So obviously, you know,

retention and renewals is very important. But as you’re going through a change like that where you’re bringing sort of three organizations together, do the metrics change at all as part of that? Or is it still being held to the same goals and metrics, even though you’re introducing a lot of variance here with your clients?

Andrea Bumstead (09:07.665)
So if I understand your question as like, do the metrics change when you change the go-to-market strategy and how you’re measuring the business?

Randy Likas (09:15.726)
Do you get any relief from the retention number knowing that there’s going to be some upsetting of the apple cart as you manage some of this change?

Andrea Bumstead (09:29.561)
The short answer is no. You don’t get any relief, right? The business is still a business. You’re still looking to make a profit. The gross revenue retention, net revenue retention, your NPS and your CSAT scores, those are all the same. I wish I could say that you get relief. I always say that when you’re going through change, wouldn’t it be nice if you could just land the plane, make the change, and take off again? But that’s not what happens.

What happens is that the business keeps going. You are flying the plane and making changes to the plane as you’re flying it. And so those metrics are still really important. In fact, they become more important to monitor because the changes are going to impact things. If they start impacting things negatively, you need to know that. Maybe you need to pivot or maybe it’s just a short sort of period in time and it will rebound.

But if you’re not watching those metrics, you don’t know when and if you should pivot.

Randy Likas (10:33.666)
Now, going back to the internal side of things, I think what you talked about before is like leading with empathy and being a little bit vulnerable is a lot of times in terms of like the people that maybe are part of the success organization and maybe report up through you. What about your peers? What about your CRO or your VP of sales, your VP of marketing? They’re in the strategy and the change with you. Sometimes people are resistant to that, right? And there’s differing opinions.

Can you maybe talk about how do you bring your peers along with that change and some recommendations on that?

Andrea Bumstead (11:08.271)
Yeah, absolutely. Bringing peers along is extremely important. And in fact, I’d say that they’re your first team and your team is your second team. Meaning that you need to collaborate really closely at the peer level and with the other executives in the organization. Change doesn’t happen in a vacuum. And in fact, silo change will fail, right? If I made changes just on the customer success side,

with nothing changing on the sales or marketing product side, I will fail. Likewise, if sales makes the change on their side and doesn’t involve me, that’s going to fail. We’re all connected. The go-to-market journey is extremely connected. And so I’m very intentional about collaborating with my peers, running things by them, strategy, getting their feedback.

Randy Likas (11:39.534)
Yep. Yep.

Randy Likas (11:47.939)
Yeah.

Andrea Bumstead (12:01.153)
I’m talking about how it impacts their team and their go to market motions. Meaning, I’ll just give an example, but when I change the customer journey, that impacts how we sell to customers. We need to set the right expectations of what they would expect on the post sales side. So their implementation, their onboarding, their relationship with their customer success manager. If I change that and sales doesn’t know,

We’re communicating the wrong message. We’re setting the wrong expectations. So it’s all connected. I collaborate very closely with my other leaders, meeting with them very frequently throughout the process.

Randy Likas (12:40.366)
Yeah, think one of the, we see it very often where the different functions that make up GoToMarket oftentimes are working in silos and maybe sometimes have different metrics, right? And I think what’s, this change, this transformation actually brings an opportunity to then break down those silos and get on the same sort of sheet of music here. And so that, I think that’s really interesting.

I have a very tactical question for you because you mentioned something earlier about you had the SMB business and then you had the enterprise business. There’s a big trend right now happening around optimizing the resources by segment and SMB maybe moving more of like a digital channel as opposed to having that direct human relationship. What have you seen in that area and is part of the change transformation that you made? Was that part of your strategy or?

how do you align your resources to the different segments?

Andrea Bumstead (13:44.015)
love this question and I also don’t love this question, Randy, because the SMB segment is really hard to manage. And as a leader, I always say that

Randy Likas (13:46.368)
Yeah.

Andrea Bumstead (13:55.677)
There’s two really difficult segments actually. There’s SMB and there’s enterprise. And they’re both challenging for different reasons. My love is everything in between. All of those sort of mid-market customers are your easiest customers to sort of manage, to create customer journeys against, etc. But SMB and enterprise each bring very unique challenges. On the SMB side, the challenge is that these customers have not paid a lot of money.

Right? So one, their investment is lower, both in terms of the capital investment they made, the actual dollars that they paid, but it’s also lower in terms of they have less skin in the game. Right? So it’s easier for them to drop the solution. They also probably came in in a high velocity sale, meaning the sale, it didn’t take a long time. They didn’t have to go through a rigorous decision making process. Maybe one person saw the product

demo and thought I like this and they bought it. And so they’re harder customers to retain and they’re harder customers to onboard because they didn’t pay a lot of money. You can very easily burn through the revenue that they paid you just in terms of touch points with the customer through the onboarding, the customer success manager, the more touch points you have with a human, the more you burn through the revenue that they gave you in the first place. And so

Yes, you absolutely need to incorporate the right level of tech touch. I think this is where automation really comes in an AI and that’s certainly a hot topic in customer success right now. But I can honestly say that I don’t think anyone’s truly figured this out. How to have a high volume of SMB customers make them

profitable for the business, still onboard them and give them a great customer experience with the right level of tech touch and human touch. I told you this is a meaty question and it’s one of my least favorites because it’s the most challenging.

Randy Likas (16:07.97)
Yeah, we could probably spend a whole, for 30 minutes just talking about that, right? So as you go through a transformational change like this, is there a framework that you use, that you kind of follow, and what makes up that framework?

Andrea Bumstead (16:23.001)
Yeah, this is a really good question. And it’s interesting because in the past week, my answer has actually changed. So the framework that I’ve used in my past three roles, I’ve actually just recently taken a course with Winning by Design called Revenue Architecture. That changed my framework. It wasn’t that I didn’t have a great framework before, but now that I actually have some models and some data,

and a way of thinking about making transformational changes, there’s some additional things that I would definitely incorporate. So let me give you a couple of examples. But the first thing I would look at more closely is data before jumping into any major change and not just the data and the customer success organization, but the data across the go-to-market motion, meaning how many leads are we getting in from sales? What are they converting at?

How many wins are we getting at? How much are we discounting on the customer success side? What are the conversion rates there? Are we holding on to customers? Are we churning? Are we expanding? And where are the areas of challenge as well as areas of opportunity? I would look at the whole thing to start, to know exactly where to focus. I think the dangers when you’re in a customer success leader being asked to transform an organization,

is you want to change everything all at once. Right? Everything needs changing. And you try and change sort of as many things as possible in a short a period of time. I would approach things a little bit differently now and I would use data to know exactly where to change things that would give me the highest return. So for instance, on the sales side, if win rates are great, so leads are great, conversions are great,

You know, you’re getting lots of deals in the door, but you’re discounting to get them in the door. That’s problematic because on the post-sale side, it’s really hard to get a customer back to where they should actually be paying. Increasing their price over time can only usually happen in small increments. So that’s problematic. Another example is you could have great win rates, conversion rates, everything’s going great on the sales side.

Andrea Bumstead (18:44.997)
but those deals are not actually a good fit. They’re not actually the right ICP, right? And so then those customers churn. That’s also problematic. And so you can see how things are interrelated and looking at the entire sort of journey, the entire go-to-market motion is really important. I can’t increase net revenue retention by 2 % if we’re closing bad deals. That’s not going to happen.

Likewise, if we don’t have a great onboarding process, that’s also not going to happen. I think oftentimes we look at the end metric, the NRR and the GRR, without looking at all the metrics that came before that.

Randy Likas (19:28.366)
I want to dig in a little bit on the data piece because it’s so important. And unfortunately, I think it’s very rare we see an organization who says, data is great. Most organizations have bad data, or they’ve got data that lives in disparate systems. So curious, as you went through this transformation, did you have a source of truth? And how reliable was it? Or did you have to go across several different systems to sort of

Andrea Bumstead (19:39.441)
Yes.

Randy Likas (19:57.442)
collate all this data to make decisions.

Andrea Bumstead (20:00.579)
Yeah, that’s a really good question. Yes, different organizations have different sort of levels of data, cleanliness around data, rigors of data, even the data that they’re capturing. I’d say this, use the data that you have to the best of your ability and then intentionally capture the data that you need going forward. That’s the best that you really can do.

working with a rev ops person and across the organization is great, just to help collect as much data as possible. But at the end of the day, if you don’t have the data, you don’t have the data. So use what you’ve got and then going forward, capture what you need.

Randy Likas (20:47.938)
Yeah. think, so in sort of preparation for this podcast, I had listened to one that you did not too long ago. And there was something you said that really resonated with me, which was like, if you’re at 70 % of the strategy, good enough, right? Keep going. how does the saying go? Like, the enemy of perfection is, or the enemy of success is perfection, right? Like, you can’t have it all figured out.

as it relates back to data, you’re never going to have perfect data. Use what you have. Make the decisions on that. Any comments on that sort of idea of if you’re 70%, you’re good enough?

Andrea Bumstead (21:31.953)
Yeah, it’s interesting. So I love the 70 % rule. It’s not my rule. I went to see a speaker early in my career and she said that. She was like, look, stop trying to be 100 % sure of anything. You’re never 100 % sure. If you’re 100 % sure, you’ve already missed the boat. She was like, 70 % is where it’s at. If you’re 70 % sure of something, then you commit 110 % to making sure that it’s successful.

And then if it’s not working, you pivot. She was like, it’s just that simple. And so I really use this in all areas of my life. If it’s like, should we go on vacation? I don’t know. You know, like, And you start doing all your research and your homework and digging in. And it’s like, look, if you’re 70 % sure that this is where you want to go on vacation, you’ve got the funds, makes sense, great. Book your ticket.

And then do your research, commit 110 % to making sure that you have a great vacation. It’s the same with business. We’re never 100 % sure of a decision. In fact, you really shouldn’t be 100 % in a decision when you roll it out to your team. You need buy-in from other people. Like I said, I don’t have all of the answers. If I’m 100 % sure of the vision or the strategy or what we’re doing, nobody is going to buy-in because they’d be like, Andrea has all the answers. She’s doing it.

If I’m 70 % sure, then I’m saying, look, I think that this is the right approach based on this data, based on these things. What do you think? Let’s get a little closer to 100%. We don’t need to get to 100%, but let me just get your buy-in, get your feedback, take you on the journey, then let’s commit. And then it’s 110 % effort to really get there, to we’re 110 % committed.

Randy Likas (23:27.96)
Yep. Yep.

Andrea Bumstead (23:29.681)
We’re gonna make this successful, we’ll pivot along the way. I think that’s the best way to really approach anything in life. You can use it for dating if you want. You’re never 100 % sure by the time you get to 100 % sure that person’s dating someone else.

Randy Likas (23:38.124)
Yeah.

Randy Likas (23:45.39)
Yeah, yeah, absolutely. OK, so getting back to the transformational initiative that you spoke about before, inevitably, things are not going to go perfect. There’s going to be things that go wrong. to your point, you’ve got to pivot. Let’s talk about some lessons learned. Like, with the benefit of being hindsight, what were some of the lessons that you learned from that transformational effort?

Andrea Bumstead (24:06.005)
my gosh, so many, so many lessons learned, right? Because things don’t go perfectly and it does require buy-in across the organization. Gosh, would say, know, I’ve, one, let me just say it’s really important to reflect on the lessons learned. Reflecting on the lessons learned is the important piece because it’s the willingness to go back and say, okay, what went well? What didn’t go well? What would I do differently?

I would definitely say, as I mentioned, I would incorporate more data into the decisions that I make. I think it’s challenging sometimes as a leader because you can get pressure to make decisions really quickly, to act really quickly before you really know the direction that you need to go. And so in hindsight, I would listen more to what the frontline teams were saying. I would have listened more to customers.

and I would have gathered data and analyzed that better as best as I could before jumping in and making changes. It’s not to say that the changes that I made weren’t the right ones. It just means that I could have been more intentional and we probably could have created less chaos along the way if I had a little bit more structure.

Randy Likas (25:28.214)
Before we wrap up the transformation, I’ve got a couple of questions for you that are things that we’re seeing in trends. I’d love to get your opinion on it. But what have we not talked about as it relates to managing big transformational projects that maybe I should have asked you about or we didn’t talk about yet?

Andrea Bumstead (25:47.633)
Gosh, what haven’t we talked about? We covered a lot of ground. We talked about people and the importance of people. We talked about some of the strategy. We talked about collaborating with other functional leaders and how important that is. We talked about the change management process, leading with empathy and transparency. So we covered a lot. I would say one thing we maybe didn’t talk a lot about is executives and boards.

Right? So change and transformation almost always starts at the executive or the board level. What they’re seeing, what they think the strategy should be based on the data and the information that they have and where they want to take the company. That’s extremely important. It’s always really important to know exactly what is that vision that the board has, that the executive team has, where are they getting their information from, what’s the vision behind it.

It’s really interesting, but one of the things that I would look at a little bit more carefully or closely going into another organization is the board deck. And the reason I look at the board deck more carefully is I would actually count the number of slides in the board deck that are on acquisition and new business, how many are on marketing and how many are on customer success. Almost always,

there are less than half the number of slides on customer success as acquisition. And yet customer success grows and net revenue retention is the lifeline of the business. That’s where the profit and the value is going to come from the long-term growth of the company. And so if there are half the number of slides on customer success as acquisition,

that immediately tells me that there is a bias towards acquisition in the organization and that they have not looked at the full go-to-market motion.

Randy Likas (27:51.778)
That is a fantastic insight. think that’s really interesting. Anything else?

Andrea Bumstead (27:58.883)
No, my gosh, we’ve covered so much, including my 70 % rule. no, I think maybe, I know you were gonna ask me about what I’ve read recently, which I’m, it’s funny, I was trying to think of, know, what would I share? I would say there’s two books that I’ve read more than once in my career, which is very rare, I very rarely read something more than once. And as they relate to customer success and transformation.

Randy Likas (28:09.24)
Yeah, I’ve got a few, yeah, yeah.

Andrea Bumstead (28:28.529)
One is the Customer Success Professionals Handbook and the other is the Seven Pillars of Customer Success. Both of these are great. And then if you’re not a big reader or if you like to read and you like a little bit more, I highly recommend the Revenue Architecture course by Winning by Design. Phenomenal course. I wish that it existed earlier in my career because there’s no

There’s no degree or schooling that really prepares you to be a leader in a go-to-market function. And I would say this course is as close as you can get to providing that level of academic sort of rigor that’s really important to have, especially when looking at data and models and strategy across an organization. So highly recommend those two books and the course.

Randy Likas (29:24.686)
Yeah, one of the things that I love about revenue architecture, and it actually is going to be related to one of my other questions, is the focus on the right side of the bow tie. Because at 100 % percent, because, and that leads to sort of my off topic question I had for you. So like right now, most, not all of course, most SaaS organizations are struggling to build pipelines.

Andrea Bumstead (29:35.588)
Yes, yes.

Randy Likas (29:52.962)
right, in meeting numbers. And so when that happens, it means that we got to protect everything that we have, right, as much as we can. And so there has been this big focus right now on customer success, investing in customer success, to protect that revenue and make sure we don’t lose it. But can we expand, right? Because it’s so much cheaper to expand with your existing customers than bring in a new one.

Are you seeing the same thing as you talk to other leaders? It’s sort of a similar sentiment or similar trend.

Andrea Bumstead (30:30.651)
Yes and no. mean, yes, I absolutely agree that it’s important, especially in today’s economy, sort of the market for SaaS companies. It’s extremely important to grow your existing customers. Your returns over time are so much greater. Am I seeing it reflected in the other organizations or like SaaS companies today? No, no, not really, which is interesting.

And that’s where I saying, like, I would look at the board deck and see how many slides are on acquisition versus retention. But, and in other leaders, yeah, I think that the leaders sort of know it, but I’m not sure that we’ve embraced it, if that makes sense. Meaning, like, I still see a lot of organizations focused on acquisition.

Randy Likas (31:27.16)
Yeah.

Andrea Bumstead (31:27.925)
And I also see a lot of organizations cutting their resources on the customer success side. That is the worst thing that you can do as an organization right now is put your resources on acquisition instead of your customers. Put your resources on your customers, scale back on acquisition because the long-term growth will come out of the customer. So to answer your question, yes, 100 % agree. Do I see it reflected in the market? Not exactly.

Randy Likas (31:33.57)
Yeah.

Randy Likas (31:58.195)
And why do you think that is? Like any hypothesis in terms of why that is?

Andrea Bumstead (32:06.321)
I don’t know. So it is a really interesting question. I do wonder, and this is just, it’s my opinion, nothing more, but I do wonder if it’s still a bit of the hangover of on-premise type solutions. Meaning we’ve always, as businesses, been focused on the left side of the bow tie, on acquisitions, right? For years and years and years, it was about getting customers in the door for any type of business.

SaaS turns that on its head where it says, yes, get your customers in the door, but you really need to focus on growing them, which is the right side of the bow tie. I think we’re still wrapping our heads around the right side of the bow tie and have it completely adapted to the fact that that’s a priority. I think there’s still the sort of legacy mentality that new customers is where it’s at. That’s how you sustain your business, which is not true.

Randy Likas (33:05.198)
Yeah. OK, next question is around sort of the increasing number of people that are involved in a buying decision, right, as we call sort of buying committees or buying groups. And sales engages with so many different people as part of the process to land a deal. Sales reps are notoriously bad at capturing all those different people and putting them into a system. And so the deal gets sold.

you know, it’s handed off over to CS and CS is like, all right, who’s most important on the account, who are the influence? And oftentimes what happens is once it goes, once the deal is done and it goes to an implementation, like all of those influential people kind of go away and it’s delegated down to like an administrator of the client side that manages the tool. And the CSM gets stuck sort of at that level and talking to that person. And you know, they’ve got

weekly or bi-weekly standing meetings to talk to that person. But yet, when it comes to delivering value to and outcomes that the company’s trying to achieve, why they bought the software, it’s hard to engage those other stakeholders. Sometimes they don’t even know who they are because, again, the sales reps didn’t capture them. But if you’re trying to look at expanding business, if you’re moving over a point solution, you’re trying to sell a platform, you need those other people involved.

Andrea Bumstead (34:17.606)
Yes.

Randy Likas (34:33.302)
So what recommendations do you give for people that are kind of in that scenario? And how does a CSM think of it as a renewal committee or an expansion committee? Any thoughts there?

Andrea Bumstead (34:48.665)
Yeah, this is, I mean, this is kind of the age old problem, right? Is that transition from sales to CS. And I like to think of the customer like an egg, like a hard boiled egg, right? Where you’re holding onto a hard boiled egg. As you pass the egg from team to team and from person to person, you want to maintain the egg intact, right? With the shell on, right? With the white inside and the yolk in the middle. But what happens is you start losing pieces of the shell and then you start losing pieces of the white.

And then all of a sudden you get to the end and all you’re holding is the yolk. Well, that’s really problematic to your point because who are you going to sell to? Who are you going to expand to? You know, you’re left holding one champion and that champion leaves the organization and all of a sudden the customer churns. So as much as you can keep the egg whole, as you pass it from team to team, the better. And I’m not just talking about, you know,

the AE to the CSM or the AE to the onboarding team. I’m talking about from the BDR to the AE from the AE to the onboarding manager from the onboarding manager to the CSM from the CSM to the renewals rep. If you have one the account manager, whoever it is, you have to keep your egg whole. And in fact, you need to be adding to the egg as you transition right and not taking away from the egg and so capturing information about the customer.

in one place like Salesforce is extremely important. And obviously the larger the customer, if it’s a strategic or enterprise customer, the more important that is. An SMB customer, if you can capture even the bare bones in a high velocity sale of who the key stakeholders are and why they purchased the solution, that’s great. That’s probably good enough. But when you get to an enterprise customer, you need to know the map.

right in that organization who made the decision, who are the supporting functions, who’s the executive sponsor, what are the other departments that maybe you haven’t expanded in today that you could expand into. All of that information is extremely important. You need to increase the rigor around what you capture. Now luckily the sales process is always slower in those types of deals and so you have more time to capture that but the more that you can capture

Andrea Bumstead (37:14.297)
the better because to your point, it has a direct impact on retention at the end of the day. The more you can keep that egg whole, the better.

Randy Likas (37:23.596)
Yeah. Yeah. Now, what you had said about trying to keep it in one system of record and capturing it in, say, Salesforce, that is the goal, right? I think that’s what everybody wants to do. But man, it’s just really hard to do, right? People just don’t do it. And so how do you change that? is it incentive behavior? Is it you have to have the leadership from the top, which is like, this is the way that we do it? Because so many organizations like

In theory, that’s what they want to do, but in practice, you look at it and it’s just not there. So what are your thoughts there?

Andrea Bumstead (38:00.079)
Yeah, it’s always a challenge because look, if you ask an AE what the favorite part of their job is, they’re not going to tell you it’s putting notes in a Salesforce. Likewise, if you ask a CSM what is their favorite part of their job, they’re not gonna say it’s putting notes in a Salesforce. Nobody likes to put notes into Salesforce. And I think this is where AI can really help us. So things like Gong that basically will capture a call, the relevant sort of point of that call,

Randy Likas (38:06.88)
No. Right.

Andrea Bumstead (38:29.263)
the next steps, perfectly imperfect. AI can help us greatly in this area, right? Taking notes on calls, getting those directly into Salesforce, super important. Any way that we can save time for individual contributors and leverage AI is amazing here. Even ChatGPT, know, if you’ve got nothing else, you’ve got ChatGPT, throw your notes, whatever you have in there.

Get Chat GPT to spit something out and put that into Salesforce is super key. And then to your point, how do you kind of, you don’t want to police it, but how do you motivate people? How do you ensure that this actually happens? Some of the things you can do is just saying it’s not moving. This opportunity doesn’t move to the next stage unless these things are entered into Salesforce. Likewise on the customer success side and that handoff from sales to customer success.

you cannot move this customer to onboarding without these details filled in. You can, you know, add incentives around that, whether it’s recognition, rewards, whatever it is. I have rewarded, you know, top note takers in the past because it’s important. It makes the difference. Now, having said that, you…

Let’s just talk about the opposite for one second because in every organization, there’s the person who creates meticulous notes that are so long and their full sentence paragraphs, right? There’s always at least one. You got to incent the person the other way. Bullet points, super brief, right? Because they’re spending too much time on their notes. We don’t need full sentences. We need high impact bullet

Randy Likas (40:09.996)
Yeah. Yeah. Yeah.

Andrea Bumstead (40:22.513)
that communicate relevant details.

Randy Likas (40:25.57)
Yeah, I think the point on technology, the technologies has gotten so good to this point that if you’re not, if you don’t leverage it and you’re still asking your rep to do it manually, like you’re missing a huge opportunity, a huge efficiency, like, because reps don’t want to add the data, CSMs don’t add the data. They shouldn’t have to, right? It’s gotten to the point where you can capture it. And, you know, I think AI is only going to enhance that. So listen, I,

I could talk to you probably for another 30 minutes. I really enjoyed this conversation. Unfortunately, we are running out of time. I do want to ask you a couple of questions on our lightning round here. And we already talked a little bit about your favorite book, so we can skip that. But I’ll ask you two questions. So as a CS leader, what’s the favorite part of your job?

Andrea Bumstead (41:12.401)
Yes, hands down the people. Just love my team, love working with people. I mean, you have to love working with people. I think both customers and your team, yeah, hands down, best part of the job.

Randy Likas (41:30.252)
Yeah. Now there’s a flip side to that question, right, which is least favorite. Or sometimes I ask the question, say, what’s really hard about your job?

Andrea Bumstead (41:37.891)
Yeah, least favorite, so I don’t love pulling data. I don’t mind analyzing the data, but I don’t love pulling it together from different sources and trying to figure out whether it’s true. And yeah, not my favorite. So if someone helps me get the data, I’m more than happy to analyze it and ask the right questions, but don’t ask me to get the data.

Randy Likas (42:01.422)
Great. Last question. What advice would you give somebody who is maybe a little bit more junior in their career who would like to be a leader sometime? What skill sets might they acquire or just general advice?

Andrea Bumstead (42:18.597)
sure. Yeah. mean, bottom line is you can do it. I mean, it’s so funny, but I think, you know, there’s all the slogans and all the sayings that like you can do it, right? But you really can. Like you are the orchestrator of your career. And so don’t wait around for others to get you there. They won’t, right? They just, they don’t. And so it really is your responsibility. Attack it with intention.

Right? But it’s absolutely doable. And on the customer success side, there’s so many resources. There’s everything from books to groups that you can join to, you know, just talking to people and networking. Like it’s, it’s possible.

Randy Likas (43:04.322)
Yeah, yeah, I think you just do it and you take ownership of your own career, right? Ask for advice, look for mentors, people are willing to help, but that’s fantastic. So listen, I wanna wrap things up. So, Andrew, I just wanna say thank you very much. I thought this was a really insightful conversation. I appreciate your time. I know our listeners will enjoy the episode as well. So with that, that’s another episode of the Revenue Lounge. Thank you everyone for joining us.

Andrea Bumstead (43:28.817)
Thanks for having me.

Randy Likas (43:29.879)
Of course, bye.

Andrea Bumstead (43:31.857)
Bye.