Episode Thumbnail
Episode 19  |  40:41 min

Krista Anderson-Copperman (Board Director): When To Add Customer Success Managers

Episode 19  |  40:41 min  |  03.08.2021

Krista Anderson-Copperman (Board Director): When To Add Customer Success Managers

00:00
00:00
This is a podcast episode titled, Krista Anderson-Copperman (Board Director): When To Add Customer Success Managers . The summary for this episode is: <p><span style="color: rgb(0, 0, 0); background-color: transparent;">Krista Anderson-Copperman has led two customer support teams through successful IPOs, first at Salesforce and then at Okta. At both companies, she was instrumental in building the SaaS playbook for customer success. Tune in and find out what Krista has to say about that and her time as Board Director at Drift and Advisor at Gainsight.</span></p>
Takeaway 1 | 01:45 MIN
Krista's journey from Salesforce to Okta
Takeaway 2 | 01:40 MIN
What it was like to be at Salesforce at the beginning of the subscription economy
Takeaway 3 | 02:13 MIN
The first Customer Success Managers
Takeaway 4 | 01:33 MIN
Companies should add Customer Success Managers before they think
Takeaway 5 | 02:29 MIN
Leading teams at Okta
Takeaway 6 | 03:14 MIN
The role of company culture
Takeaway 7 | 01:46 MIN
How to get internal buy in
Takeaway 8 | 04:20 MIN
Leading Salesforce and Okta through their IPOs
Takeaway 9 | 01:56 MIN
Why you should conduct customer and employee sentiment surveys
Takeaway 10 | 02:23 MIN
Is the customer always right?
Takeaway 11 | 02:10 MIN
Advising Gainsight and Drift on product messaging
Takeaway 12 | 00:55 MIN
Saying yes to a board seat
Takeaway 13 | 02:09 MIN
How to advance in your career
Takeaway 14 | 01:30 MIN
Favorite source of content
Takeaway 15 | 01:04 MIN
Best piece of advice

Krista Anderson-Copperman has led two customer support teams through successful IPOs, first at Salesforce and then at Okta. At both companies, she was instrumental in building the SaaS playbook for customer success. But are your customers always right? Tune in and find out what Krista has to say about that and her time as Board Director at Drift and Advisor at Gainsight.  


Key Takeaways:

[1:30] Krista talks about her journey starting at Salesforce and then moving to Okta.

[3:48] Krista talks about what it was like being at Salesforce at the beginning of the subscription economy and how she helped the customers realize the value delivered between renewals and their benefits.

[5:43] How did the idea of customer success managers come about?

[8:16] Companies should be adding customer success before they think. What are some signals, or when is the right time, or how should a founder know?

[10:08] What drew Krista to Okta?

[12:59] Krista talks about the love of customers’ company culture, instilling it across the organization, and getting buy-in on these principles across the company.

[16:24] Did Krista have any challenges getting anyone on the same page as she was on the importance of transparency with her customers?

[17:48] How does Krista get people on board? What did she do internally to get people to buy into what she thought was best?

[20:27] Krista talks about her first-hand experience during both of her IPOs, at Salesforce and Okta.

[25:02] How does Krista advise founders and CEOs to take the temperature of culture as they go through hyper-growth phases?

[27:09] Is the customer always right?

[29:49] Customer success is like inside sales.

[30:38] Krista talks about her role at Gainsight and the wisdom that she took with her from all her years at Salesforce and Okta and how it applies to Gainsight.

[32:58] What drew Krista to Drift?

[34:18] Krista shares tips for the listeners on how to navigate becoming more senior and taking on more responsibility.

[36:40] Rapid fire questions.


Guest Thumbnail
Krista Anderson-Copperman
Board Director at Drift, Advisor at Gainsight
Krista has spent her career in senior leadership roles building Salesforce and Okta, two of the most successful, hyper growth SaaS companies in the market today. She is an experienced Customer Executive, Advisor and Board Director with 20+ years delivering superior levels of adoption, growth and retention in enterprise SaaS.
Follow Krista on LinkedIn

Speaker 1: Welcome to the OV BUILD Podcast, Building to Boss. I'm inaudible an investor here at OpenView. This month we're releasing a special mini series with female leaders in the enterprise SaaS industry who know the path to leadership is challenging, but aren't willing to let that stop them from building something great. Today we hear from Krista Anderson- Copperman, chief customer officer and board director. Krista began her career at Salesforce where she stayed for 13 years and helped build the industry SaaS playbook for customer success, renewals and growth. She led the support team through its IPO in 2004 and grew the company from a 100 to over 13, 000 employees. She then joined Okta as their chief customer officer, and saw the company grow from 20 million to 580 million, and led another customer team through their IPO in 2017. And now she's an advisor at Gainsight and Drift. In today's episode, we unpack how Salesforce established the role of customer success managers, how to build company culture, and advice she gives startup CEOs about whether the customer's always right, all of that more in this episode of the BUILD mini series, Building to Boss. Let's dive in with Krista Anderson- Copperman. Krista, thank you for joining us on the BUILD podcast miniseries, Building to Boss. I'm excited to chat with you about all things customer success, company culture, women in tech and beyond. So maybe to start, tell us a little bit about your journey? You spent over a decade at Salesforce and then moved to Okta.

Krista Anderson-C: Yeah, so my journey has been unique in that I've spent a lot of time at two different companies versus time at multiple companies, arguably very good companies. I spent 13 years to start at Salesforce. I joined there around 5 million in revenue, stayed for 13 years, left around three and a half billion and 13, 000 employees. So it was quite a journey. It was my first role out of school, so not something that I can say I really appreciated at the time until at least halfway through it. Certainly looking back on it now it kind of makes me laugh of how naive I was in terms of what we were doing and creating a category in cloud. We were really the first cloud company. There's some contenders, there's some disagreement on who was first us or NetSuite. Yeah so 13 years there and a variety of different customer facing roles. I ran support. I ran CSMs, and then I ran basically the full customer experience post sales customer experience, so professional services, education, CSM account management, renewals all of that for the enterprise for a few years, and then for the commercial business unit, which is SMB at Salesforce in my last year there. I left there about seven years ago, just I needed 13 years is a long time at a company, and I was kind of in need of a new landscape. And also I had learned so much there. At three and a half billion, to move the ship or to change some things, it takes a long time at a company like that of that size. And I was excited to take a lot of the learnings and things that we did really well, and then things that maybe we were a little late on, or that we didn't do well and do them right at the next company. So I'd worked with Todd and Freddy at Salesforce. So it was pretty easy transition for me to move over to Okta and build that customer function. I joined for about 20 million. I left at about just south of 600 million.

Speaker 1: Wow.

Krista Anderson-C: Yeah, yeah, and built the team from about 20 people to 400. So it was really fun. I mean, two phenomenal experiences, and then two phenomenal companies.

Speaker 1: Couldn't agree more, and I'd love to start with Salesforce if that's okay with you. What was it like being at Salesforce at the beginning of the subscription economy? In the subscription economy, you're delivering so much value between renewals, but how do you help the customers realize that and see the benefits?

Krista Anderson-C: Yeah, I mean, that's kind of the theme of one of the things I wanted to do better. So early and this is funny, I was looking at my resume yesterday or the day before, and kept looking through the history and just refreshing it, and there was a bullet on there that said, achieved an 84% renewal rate or something like that, which made me laugh because an 84% renewal rate in the current world would be horrific. Right? But that was I mean, those were very early days of cloud adoption, and so people were still very hesitant, and early days at Salesforce we didn't understand what it was going to take to make a customer renew right? It was very different than set it and forget it. And so we were a little late to, a little later than I think we would have liked to this idea of CSMs, and that was born out of okay our renewal rates are not where we want them to be. What do we need to do again it was pretty simple. We needed to guide our customers throughout their journey with us and make sure that A, they were getting up and running and using it which that still stands today for SMB and enterprise and then B, make sure that they understood all the value that we were delivering in that duration of their contract. So I think at that point in time, Salesforce was maybe we were on a monthly release schedule, or maybe it was three times a year, I can't remember. But that's a lot of technology for organizations to absorb in either one of those release cadences, and so really figuring out how to educate customers on what was happening in those releases, and more importantly, what was important to them. Because what's important to one customer, like the important to the other, was the big driver for customer success. We were just a little late to it. Obviously it all worked out fine.

Speaker 1: Right. Right. It did. And you just touched on it for a second, but how did the idea of customer success managers come about? It's my understanding, it actually originated in Salesforce.

Krista Anderson-C: Yeah, it did. It was just what we recognized that we weren't in a traditional model with account managers where you're going to sell them one piece of technology, and they're going to buy the hardware software and do with it what they will, and then you're going to go sell them another one. It was very much so okay, how do we make these customers successful, because if they are not using that technology, then they're not going to renew, and they're certainly not going to buy anything else from us. And so it was as simple as that. We took we pulled some pieces from the Siebel TAM methodology. inaudible they're talking about and then it morphed into the CSM, as you know. There's a lot of things that have evolved in CSM world, but the name is pretty much still the same.

Speaker 1: Yeah, no, well now it's kind of like table stakes, right?

Krista Anderson-C: Yep, very much so, and that's one thing that I mean, I spend a lot of time right now talking to founders and CEOs. And the question that they're always asking is like, " When do I invest? And what's the right time? And, yeah, I know, I need support. And I know I need some CSMs. So what should they be doing? And when do I invest in a chief customer officer?" And my answer is always, it's earlier than you think. And what I say is you think about, there's kind of three legs of the stool for building a long term, enduring company. And the first one is obviously new logos. Investors are very focused on new logos, your CRO, or whoever's doing sales is going to be very, very focused on new logos. And that's kind of historically where people's mindset has been. And this is shifting much more, but the second piece of it, I think there's much I should say, there's much broader recognition of this now than there even was two or three years ago, but the second leg of that stool is install base growth, right? So you've got these new logos, and then how are those new logos growing? And then the third piece of it is, what are the renewals doing, and how am I really driving my team to 120% net retention? And if you don't invest in customer success, or CSMs or inaudible customers, or whatever it is, early on those two legs of the stool meaning install base, upsell, cross sell, and then the renewal are going to be more and more difficult. Again, for long term growth, you need those things to be like a third, a third, third, when you're looking at your revenue and your financials.

Speaker 1: And I want to take a second to go back to something you just said, with companies that you're working with, you said that they almost always should be adding customer success before they think.

Krista Anderson-C: Yeah.

Speaker 1: What are some signals, or like, when is the right time, or how should a founder know if there's any advice you can give on that?

Krista Anderson-C: Yeah, I mean, assuming we're talking about enterprise companies, it's whatever your contract duration is. Often you'll start month to month, but let's say you've established product market fit, you're north of 20 million, something like that. It's right around then. And really the way you have to think about it is okay, how many customers do I have up and running on my service? What are their contract lengths? And what's the lift to get them initially successful? Who's going to do that? And then what's the lift to keep them successful? And depending on the technology, it's really different. If I look at Drift, and some of their customers are really focused on their marketing campaigns. So they need somebody from Drift to work with them pretty regularly as their marketing campaigns change, right? But then you have technology like Okta, where you're going to say, " Okay, maybe you don't need someone on a monthly basis with that sort of involvement and expertise. But what you do need is Okta's releasing monthly." And so you're going to want to understand what it is they're releasing, and how it applies to you, and what you should or shouldn't do with that technology. So that was a really long way of saying once you start to get into the enterprise, and you recognize the need to not only get them up and running, but to help them continue to use features and functions on your platforms, that's when you do it. That's often around that 10 million mark. And it could be earlier could be later depending on the company, the product, who your customers are, they're giant enterprise customers, but that tends to be the average, I would say.

Speaker 1: Got it. That's super helpful. And we're actually going to come back because you just brought up Drift inaudible the companies you're working with today. So we'll come back to some of that stuff later. But I want to make sure we talk about the next part of your career that was obviously very important. Okta. So would love to hear you're at Salesforce over 13 years and then what drew you to Okta?

Krista Anderson-C: Sort of been really lucky in where I've landed. I went to Salesforce right out of school. Didn't understand what was going on there. I certainly understood the cloud and the value that Okta brought to the customers and the need because we saw it in Salesforce. But I never had really imagined that Okta would be as big as they are today. I remember having a conversation early on with Todd and saying, " Krista, our stock's going to trend at$ 80 one day," and I was like, " No it's not. You're crazy." Here we are. I haven't looked at it. I think it's in the 150, 160 range now, I don't know. Anyway so yeah I didn't necessarily know what I was getting into again in terms of how successful that company would be, but I went there, I worked with Todd, I had worked with Freddy. I went there as Chief Customer Officer to build this function for them. I think it was 17 million, so a little bit greater than that 10 million that I referenced, but we were again were a little bit late to hiring CSMs. We had really focused on the support team, and the support team and the education team were this hybrid what would now be professional services, education support in CSM. So everybody was playing a little bit of a different role across those four functions, but we called it all support. It was time to build those four functions separately with the appropriate expertise in each one. So I mean it's hard to sum up six years of work, but really built that team, and the first thing I was focused on was CSMs, because we didn't have them, and bringing enterprise CSMs to the table to help our largest customers at the time through the technology I mean a lot of these customers and this is true for any technology out there, a lot of them it's their first time on cloud, so they don't know how to manage in cloud, or your technology is a piece of a bigger transformation, often I say this in air quotes because digital transformation, because that can mean so many different things. We needed somebody to help guide our customers through that, our early adopters through that. So early days I was really focused on building that CSM team, and then I started to work on education, professional services, and then renewals right around the 100 million mark is when... renewals were always important, but where it became extraordinarily important and a really big focus of ours.

Speaker 1: Yeah makes a ton of sense, and I have to tell you because you're going to love this, Okta today is trading at 282.

Krista Anderson-C: You know what I mean? Yes.

Speaker 1: It's incredible yeah.

Krista Anderson-C: Yeah it really is.

Speaker 1: So okay continuing on Okta, talk about the love your customers company culture, and instilling that across the organization, and even more importantly getting buy- in on these principles across the company. Would love to hear about what you learned that worked, that didn't work.

Krista Anderson-C: Yeah I mean it's one of the reasons I went to Okta is both Todd and Freddy they had the Salesforce DNA, and so they knew how important it was, and they thought maybe they were a little bit early to hire a CCO. Turns out they weren't. But one of the things that, one of the reasons why I came because there was clearly a founder team that understood the importance of this, and understood it as a competitive differentiator, and were 100% willing to invest in it. So that made my job really easy. But what early days it was my first week I think I had started, and there was a inaudible is what it was called, seven years ago. It was this big fireworks that was circulating the internet. It was a really great immersive experience for me because I was day three and I was sitting with the executive team in a true crisis for a company, any SaaS company, but particularly one who was managing IDs using passwords. It gave me a really great sense of across the executives I was working with in product and engineering and marketing who really embodied this love our customers mindset, and who I needed to help get there. What I mean by that is for me, and Okta's really good at this today but for me love our customers the first thing is transparency, ultimate transparency with your customers, certainly up front in the sales cycle on what's going to be required for you to get up and running and be successful. I think a lot of SaaS companies who are transitioning from SMB to enterprise there's this friction and they're a little afraid to tell their customers, " Hey now you've got to purchase services, and now you have these education offerings and all of these things." But remember that that's the way that enterprise buys. That's what they expect, and so that transition will be a lot easier than you think. But so transparency, in pre sales, that's extraordinarily important so that customers know what to expect, and that's where you establish trust. But really, where relationships are often solidified is where things go wrong. So that could be they go wrong in your professional services engagement, or in this example that I'm using, things are just going wrong on the internet, and it's impacting the service that we're delivering to customers. So in that scenario, you want to be as transparent as possible with your customers. You want to tell them exactly what's happening, what you know, what you're doing about it, when you're going to update them next. Sitting in a room on day four at Okta with those executives again product, engineering, marketing, sales and myself, it was really clear who was on board with that transparency and who wasn't. That's something that I always say to people when they ask. " How do I really instill this culture," and I say the first thing that you have to do is it comes from the top, and you have to look at your executive team, and a great lens to look at it through is this transparency lens. How much are we telling them up front on what it's going to take to get them successful, and then what are we going to tell them in a crisis? The answers to those two questions are a great litmus test of where people are and where the work needs to be done.

Speaker 1: Yeah you got to see it on day four like you said, live. So if there wasn't anybody immediately bought in, did you have any challenges getting anyone on the same page as you on the importance of transparency with your customers, and if you did, how did you get them to realize that it was really important?

Krista Anderson-C: Yes there were definitely challenges, and I think the challenges, this is conflict in the workplace 101, but they were all coming from a good place, and a fair place. It wasn't that anybody wanted to hide things from the customers or be dishonest or what not. It was balancing things like security risk, because inaudible was a security issue on the internet at large. So how much can we tell our customers without giving potential hackers more information, right? So there was this balance, there is I think in any of these situations a balance of the information that customers want, because they want 1000% transparency. They want to talk to the developers who are working on the issue, and what you can expose externally.

Speaker 1: Yep.

Krista Anderson-C: That wasn't the answer to your question. What was your question?

Speaker 1: My question was you faced some people that well it is a bit of an answer right because there's always going to be a tension of how much can we share, and what do we need to share, where do we meet in the middle? My question was really around if you bump up against someone that just disagrees with you but because you're the one representing the customer and something does need to be shared in this example maybe, how do you get them on board? What do you do internally to I guess get people to buy into what you think is best?

Krista Anderson-C: Yeah I mean at this point the bar has been set in many cases, and Salesforce is a great example. They put everything out there in terms of performance, trust, reliability. I think it's called trust. salesforce. com. At that point in time, I could just say, " Listen, I know I come from Salesforce, and I know it's a really different company, however, they are known for their maniacal and fanatical customers, and this is one big piece of it, because things are going to go wrong, and that's how people are going to judge you." So it was easy for me in that respect, and I think that example is even easier now for people. It's a great starting point, but it's easy because there are so many examples of companies who are operating at that level of transparency. Again Okta's a great example. If there's an issue on their service, we will turn their stoplight red and say, " Yes we know we have an issue" seconds later, right?

Speaker 1: Yep.

Krista Anderson-C: Then they're going to say, " Here's what we believe the issue is" assuming there's no security risk for other reason that would make it worse by sharing information, and here's where we're going to update you. Then once the thing is resolved, their commitment, I think it's 24 hours, might be it's 48 hours to get customers a root cause analysis and to publish that and say, " Here's what happened." So there's so many examples of that transparency out there today that I don't think that would be hard for individuals to get buy- in across their company with. I think the harder thing is the day to day actions and how finance, how does love our customers apply to finance when a customer is behind on their bill, things like that, you know what I mean? Getting some real mind share around you don't send threatening emails. That's not who we are, threatening emails meaning, " We're going to cut your service off" right-

Speaker 1: Right.

Krista Anderson-C: ...or at least figuring out a way to deliver that message in a really customer friendly tone where it's not harsh, you know what I mean?

Speaker 1: Make a ton of sense and it's like you mean better than anybody, but once you lose the trust of the customer of if you ever damage the trust of the customer, I have to imagine that's really hard to rebuild if at all possible.

Krista Anderson-C: Yes and especially when things go wrong, and they will, technologies that are scaling and growing at the rate of certainly larger portfolio companies.

Speaker 1: Yeah and so shifting gears here a little bit, you've been a part of two incredibly successful IPOs, Salesforce obviously in 2004, Okta in 2017, but you were at very different points in your career, and of course they're very different companies, so would love to just hear a little bit about your firsthand experience during both of those IPOs.

Krista Anderson-C: Yeah I mean they're fun. They're fun. inaudible, you're going to make some money hopefully. They're a lot of fun, but I will say if both Salesforce and Okta they were a lot of fun, but they're also very serious, and they're also, it's also one day in your life, your life as a company when this big event is happening. So at both companies, we probably two years in advance if not earlier certainly from a leadership and executive perspective were talking about all the controls and regulatory things, finance, audit, yeah all that was going on. We're making sure we had the systems right, but really talking about culturally what it was going to mean for our employees and our customers to go public. The big guiding principle in both places was it's just a day. It's just an event. It's like when you turn 16 and you get your driver's license. That's not it. Life is not over. You have this whole life to live beyond that. So we're going to celebrate this day, but if we're really about building a long term iconic company, then we have to be ready for it, and we have to operate like we're a public company in advance of it, and then recognize we're going to celebrate, then we're going to continue on business as usual with our work. So that's the first thing, and that was really, really strong at both companies. We talked about that a lot, and it all hands or whatever now is probably in Slack channels a question would come up. That was always the answer is yes we're excited, but we're building a long term, iconic company, and that is just one day in our history, which leads me to the second piece of it, which is around culture. That in of itself, that idea of it's one day is certainly a cultural aspect of going public, but when you think about the makeup of a company going public and the employees specifically, you have the early employees who got you from zero to 20 or whatever it is, or zero to 50, then you have your recent hires, people who've been with you in the last 18 months or so, and then you have this future of what is it that you're going to operate, how do you believe you will operate as a public company, and what has to change about your culture. If you run your culture a little bit loose then you're probably going to have to tighten certain things up, right, and really taking a look at those things and recognizing that those are three distinct groups of employees, one being in the future and bringing that first group of employees, the ones who are with you early days who had really broad remits and their remits are probably narrowing a bit, really helping them understand why that's important, and the work that you're doing is important, and working with this new it's often called inaudible. If you look on Glassdoor, you'll hear it called that all the time, but this new group of employees who have been at larger companies and bringing those two together because often they're going to feel like they don't understand each other. That's a really, really important piece of going public is that cultural component, and then helping those two groups understand this is what it's going to look like in the future. These things about who we are are probably going to have to change a little bit. I'm trying to think of a specific example with Okta. I can't really think of a specific example at either one of them except they revolve around alcohol meaning with almost every startup has a Kegerator or whatever. Some of the behaviors around that, those really early employees might be attached to, and those employees who just joined you are like, " Yeah whatever." The future, some of those things that maybe used to happen aren't maybe going to be able to happen, you know what I mean? It's not like there was anything tragic or awful that ever happened, but that's a pretty widely applicable example is the Kegerator in the startup, you know what I mean?

Speaker 1: Totally. So how did you measure or if you did whether the culture and the values that you guys had held dear pre IPO especially between those different subcategories we just talked about of employees joining at very different phases of the company held through the IPO and beyond, and then also on top of that, how do you advise founders and CEOs to take the temperature of cultures they go through hyper growth phases, and maybe right the ship that needs to be righted?

Krista Anderson-C: Yeah I think it's really important to do both employee and customer sentiment surveys because they will reflect upon each other, and what I mean by that is there's a ton of technologies out there where you can run employee surveys, and often companies do it once a year which is not great. That's going to give you a benchmark against the prior year, but when you're growing at the rate that many of these companies are, that information is irrelevant by the time you get it. So whether it's monthly a couple questions or quarterly five to 10 questions, really understanding what's important to your culture and then asking about that, and understanding employee sentiment on a very regular basis, and it doesn't have to be overengineered. It can be really simple like I said a few questions, you will be able to get ahead of any, you can't say ahead because that's a rear view mirror, but you will be able to recognize any significant cultural shifts much earlier than you ever would with feet on the street, ears to the ground with your executive team and your people teams. So that's the first thing. The second thing is customer sentiment. Customer sentiment is a reflection of your employees right, their interactions of your employees. Again, this isn't something that should be done annually. I'm a big fan of doing this in cohorts. So if your business is monthly cohorts, customers who joined in this month, and then customers who joined in the next month or quarters, whatever duration you choose, measure that customer sentiment. In the first quarter after they purchase, how was your sales process? Were expectations properly set? Did you get up and run, really simple questions like that, and then obviously always leave room for comments, and you will start to see your employee culture reflected back at you and your values reflected back at you and what your customers are saying and how they're scoring you.

Speaker 1: I never thought of it like that that it is a mirror of exactly how you're treating your customers. Then I guess when talking to CEOs of startups, do you tell them the customer's always right? Is the customer always right?

Krista Anderson-C: No, absolutely not. Maybe you shouldn't publish it. No I'm kidding. You should. I stand by that because if you think about what it took you to get your first real meaningful contract, and then what it took for you to take that one customer to 20 customers, you probably did some pretty unnatural things whether it was back flips in the sales cycle or really changing your technology on the backend on the fly to meet the customer's needs, whatever it was, that has to change as you scale, right? You can't continue to do that. You do that at a certain point until you get the what I call seat at the big kid's table. Then you have to shift how you're thinking about your sales processes, and how you're managing customer expectations with the technology because you're going to have to move away from that custom work, and we're going to do whatever it is to get the customer. That's the first piece of it because early on, your sales people are going to say, " Yeah sure, whatever you want. Yes we can do that. Yes we can. Yes we can." That's going to have to shift to, " No we can't, but here's what we can do," which leads to the second point to where the customer isn't always right. Customers will often and especially going from on- prem to cloud, they will purchase the technology because they want to go to the cloud, but they want to repeat their business processes. Your team is going to want to say to them and particularly if it was that early team, " Okay yes. We can do that." But the reason that they are going from on- prem to cloud is they want to take advantage of the innovation that the cloud offers, and the speed and agility the cloud offers. If they're just repeating the exact same processes they had on- prem, and you're saying yes to that, you're doing the customer a disservice. In that scenario, that is where you should say, " No Mr. And Mrs. Customer, sorry, here's how I think you should think about doing it. Here's how other customers like you have done it," and to really reengineer whatever process it is that they are working through. In order to do that, this goes back to one of your earlier questions, in order to do that and to do it well, you have to invest in customer success resources, and you have to invest in pretty senior resources who can have that conversation with a customer that says, " No, I know you think that's the right way to do it, but it's actually not."

Speaker 1: It all comes back to invest in customer success early on.

Krista Anderson-C: It does. Yep it does. One of the things that we haven't touched on is customer success as inside sales. We talked about it a little bit on the three legs of the stool, but when you think about that second leg which is install base grows, if you have a CSM team who is active in your customer base and they have meaningful relationships with your customers, they're going to become your best source of leads by far on any campaign you're running, or anything the inside sales can do. So I mean if you need a reason, that's the reason.

Speaker 1: I want to make sure we move over to what you're doing now post Okta because it's really cool. I want to make sure we have time to talk about it. So you're now an advisor at Gainsight, you have been for a few years. Would love to hear a little bit of the work you're doing with them, problems you help them tackle, and maybe any I'm sure lots, but any of the wisdom you took with you from your years at Salesforce and Okta and how it applies to them.

Krista Anderson-C: Oh gosh, that last part of it, it's a big question. Yeah I've been an advisor at Gainsight for quite some time for obvious reasons given what they do and what I did in my time at Okta, but for them, it was primarily product and messaging, questions like" We're looking to get into this piece of the business. What do you think? Does this message resonate with someone like yourself? Do you think it'll resonate with a CRO," that kind of stuff. With Drift, it's been really fun because it's much broader. I certainly talk about everything customer success, and we've gone really, really deep on some of their customer success opportunities and challenges which is fun and easy for me. But we're also talking about broader things and bigger things. One example I think that every company again high growth company struggles with is talent. The talent that's going to get you from zero to 50 million is not often the talent that's going to get you from 50 to 250 or to 500 whatever it is. Kind of helping the executive team talk through and I talk about this not just with Drift, I talk about it with a lot of CEOs and founders, but yes you should expect this. What you're feeling is normal and okay. You should expect it. As a CEO and co- founder, it's going to be more difficult for you than probably anyone else in the company because you're extraordinarily loyal to those people. So really talking them through the psychology of it a little bit, and then just the practicality of, " Okay, here's what you're going to need." You got to think about talent. You always have to think about what you're going to need 18 to 24 months from now, not what you need in six months. By the time you hire them get them on board, you're going to be 12 months into it.

Speaker 1: Yeah you're in a bit of a hole.

Krista Anderson-C: Yeah exactly. So that's just one example. I spend a fair amount of time with them thinking about messaging, pricing and packaging, what markets they should go to next, thinking about their product and what really resonates from a messaging perspective depending on what buyer they're targeting, so it's fun. It's fun for me. I can bounce ideas off, and I don't have to do any PowerPoints or any Excel spreadsheets.

Speaker 1: That's always a bonus for everyone.

Krista Anderson-C: Yes, yes it is.

Speaker 1: I'm sure there's a ton of different boards you could have joined. I'm sure you're asked a lot of time to be advisors for various companies. What drew you to Drift? Why'd you say yes to Drift?

Krista Anderson-C: I said yes to Drift because I really liked the people for starters. That's one of my number one criteria. I'm going to invest my time here, I want to like the people that I'm spending the time with because it's different than an operator role, and you have to be able to have that kind of rapport and relationship with them where you're having a little bit of fun, and you can build trust and establish trust. So that's the first thing, but the second thing is Drift is a really unique company. A lot of people it's similar to Okta in that a lot of people think that they're just chat in the way that people thought Okta was just SSO. But there is so much more behind their solution in terms of targeting who the buyer is, and who your most valuable leads or prospects are, that it's just incredibly interesting technology to me. That's also really familiar landscape for me the CRO as a buyer because that's where we started at Salesforce. We were doing inaudible and so we were selling into VP of sales or CRO.

Speaker 1: Yep, and now I'd be remiss if I didn't ask this question. You've had a long career in enterprise, and would love for you to give our audience some tips as it relates to women owning their positions of power at work. Any kinds of tips for the listeners on how to navigate becoming more senior, taking on more responsibility?

Krista Anderson-C: Yeah I mean I think the biggest thing, and I say this to everyone is speak up. It's obvious right, but what I mean by that is there are very few unique ideas in this world. The credit I mean think about it, you're in a meeting and you say something, and somebody else is always, " Yeah I thought about that," and then you riff off each other. I mean it's pretty rare that it's, " Oh wow. I've never thought about it that way." That's the rarity right? So we shouldn't be afraid to speak up because nine times out of 10 what we're thinking, somebody else is also thinking, so that's the first thing, is speak your mind. There are very few unique ideas, and you don't need to be scared of it. The other thing that I tell people is really understand what motivates you, and don't be shy about it, which goes along the lines of speak up. But for some people it's relevance. They want to be relevant to their peers, or for writers for example, they want to be relevant outside of the company. For some people it's power, and having other people look at them and say, " Yeah that person can make decisions, and that person is leading," that's what motivates people. For some people, it's money. If I'm making financial security and making X amount of dollars, any of those things are perfectly okay and very normal answers, and clearly answers that apply to me, and that's why I'm so familiar with them. But really understanding what motivates you is the most critical thing in your career because for example if you're chasing power but it doesn't actually motivate you, you're not going to get where you want to be. So you really have to understand what is it that keeps you going, and what's not your North Star but from a career perspective and a work perspective what keeps you engaged. I think if you follow that, you will for the most part, I'd like to say always, but there's never 100%, but you will be pretty fulfilled with what you're doing. It's not necessarily the work. It is the what's the motivation behind doing the work.

Speaker 1: Yep. Speak up, figure out what drives you. I'm taking notes for my own career. So last few questions. We're going to do some rapid fire get to know Krista. Favorite source of content.

Krista Anderson-C: My favorite source of content, I read the Wall Street Journal. I read, I get two emails that I really like. One is theSkimm which is a really lighthearted take on what's happening in the world today, but it keeps you up- to- date. Then the other one is The Week which is the opposite. It's not the lighthearted take. It's more of here's what's happening in the world today. Then it's a lot more editorial I would say opinions that are bringing together the big picture that you're not going to get in the piece articles that you get in a lot of media. Then I spend 30 to 40 minutes in the car every day and I listen to NPR, and I listen to Bloomberg. I do listen, despite where I lean politically, I listen to both Fox and CNN. The reason I do that, yeah my daughter is five and she made some really funny comment recently about listening to Fox News. I was like, " No, no, no, no, no." The reason I do so is because I feel like you need, and this applies at work, right, you have to understand both perspectives, the extremes of both perspectives when there's any sort of disagreement or conflict, and know that the truth or the answer to the solution or whatever is somewhere in the middle. From a media perspective, I actually very purposefully do that because it's interesting to me to see what they're... I mean some days they're not even reporting on the same stuff right? So you can figure out what's relevant, what's important, and what's just craziness.

Speaker 1: Both sides of the table.

Krista Anderson-C: Yes.

Speaker 1: Last question, best piece of advice you've gotten?

Krista Anderson-C: Best piece of advice I've gotten professionally is nobody was ever promoted for being last person standing at the bar. To be clear, that was not because I was always the last person standing at the bar. It was because Salesforce is a very social culture, and it's a very sales like culture. I'm a pretty significant introvert, so that culture was hard for me because I felt like I needed to participate. It's hard for me, but I spent 13 years so obviously not that hard, but I felt like I needed to participate in that to a certain extent in order to stay informed. There's the likeability, sociability factor, but I really struggled because I always felt like, " This is a four hour endeavor on any given inaudible" you know what I mean? I remember talking to I can't if it's HR or it was my leader at the time, I can't remember, but that's what they said to me. They're like, " Just go have a drink and then leave."

Speaker 1: That's incredible. Yeah you don't need to be last man standing.

Krista Anderson-C: No, and it's so obviously but for me, it really it was freedom for me, and I think especially for women, we have this I mean it's scientifically proven that we have a need to be liked more, many women, not all. That was playing a big role in my I would say happiness factor at work. Once I was able to let that go with that little piece of advice, it was very empowering.

Speaker 1: I want to be a part of it. I don't want to miss anything, but man, four hour happy hours, it's a lot. It's draining, at least for me. I'm similar in that way. Krista, this has been incredible. Thank you so much for giving some time and coming on to Building to Boss. We really appreciate it, and I've really enjoyed the conversation.

Krista Anderson-C: Yeah thank you. I have too. It's been fun.

Speaker 1: Thanks for listening to this episode of the OV BUILD podcast, Building to Boss. We hope you learned as much as we did. We'd love to hear what you think about the show. Please leave us a review on Apple Podcast and subscribe to stay up- to- date with all the new episodes. If you're looking for more OpenView content, follow me, inaudible on Twitter at inaudible. See you next time here at OV BUILD.

More Episodes

Jürgen Spangl (Atlassian): Is Innovation Overrated?

Jürgen Spangl (Atlassian): Better Meetings = Better Collaboration

Astha Malik (Zendesk & VTEX): Recruiting For Product Marketing

Astha Malik (Zendesk & VTEX): Product Marketing 101

Pelin Kenez & Naman Khan (Zeplin): Design Delivery is Everything

Lauren Schuman (Mailchimp & Mural): Celebrate The Upgrade