Ep#73: Maximizing Customer Lifetime Value: Strategies for Small and Medium-Sized Businesses ft. Kelsey Peterson (VP Customer Success, Ashby)

[00:00:02] Adil Saleh: Hey, greetings everybody. This is Adil from Hyperengage Podcast. I have Kelsey Peterson alongside me. She joined our podcast. Thank you very much, Kelsey, for taking the time. A bit of introduction about Kelsey. She was SVP at cross check back in the year. Currently she's a part of she's leading a customer success team as a VP at Ashby. She just joined the role a few months back. Kelsey, thank you very much for taking the time today for this talk. [00:00:36] Kelsey Peterson: Thank you for having me, Adil. Super excited to chat with that. [00:00:41] Adil Saleh: Love that. [00:00:42] Adil Saleh: So Ashley, having some sort of diverse experience ever since, you know, talking about you working as an early customer facing role back in the years when you started after your degree and then working at HubSpot for a good three years more in the enablement operations. Then all of this from the management side like you talked about project manager. I see you started for about two and a half years back in 2013. Could you walk us through along your journey? Talking about sales, talking about project management for good two years, then customer success at housepat that are more in the small to mid market segment. So how did it all turn out for you to shape your experiences, shape your career, and then how it all led to you keeping a VP role you joined just a couple of months back. So walk us through your entire journey, your lessons, your entire thought process and how it shaped you over the years. [00:01:59] Kelsey Peterson: Yeah, sure. So, as you mentioned, I started in the project management space and as a part of that role, we had external stakeholders and then, of course, some internal coordination. And I found that I most enjoyed the external piece right. Working with our end client. And so that kind of shifted me into a period of my career that was closer to consulting. And in that time, I had stayed in contact with HubSpot over a couple of years and they were building a new Portsmouth office and they were looking to start a customer success presence there. So I was really excited to be actually the first customer success manager in the Portsmouth office and then, as you mentioned, kind of shifted into enablement and our strategic partnerships. So it was a bit of a kind of a unique journey in that regard. And then I really enjoyed a lot of my customers and I stayed in touch with them. And so some years later, a customer that I had had five, six years prior reached out because she was a marketing leader at Crosschreck and she said, hey, have you thought about the HR tech landscape? Is this interesting to you? And so we had a series of conversations and that's sort of when I made the shift from customer success and sort of the go to marketing and sales experience over to the HR tech landscape. So helping folks with their hiring, I joined Crosstrek and then most recently, as you mentioned, I'm a part of the customer success team here at Ashby. [00:03:35] Adil Saleh: Incredible. Incredible. [00:03:36] Adil Saleh: So, in a nutshell, for about seven to ten years, you had a mix of sales, bit of product management and then customer successes. Cross check, then Ashley. So what is that one thing that you see very common? Sitting on a VP role, working with these people in the small to mid market segment that you see that is common, that's very challenging and some system needs to put in place to overcome it, or you find it challenging and then let us know how you address it. [00:04:17] Kelsey Peterson: Yeah, I would say the commonality across those various go to market functions and across SMB all the way through enterprise is really organizations not having a unified tech stack. And so I've seen this both in my consulting and brand side, if you will, just disparate data points across various solutions that are not connecting and talking to one another. And so that's something that I think HubSpot as a product does a really great job, being that single source of truth. And that's something Ashby does as well, that we've been really focusing on getting the information in one spot so that people are really empowered to make smart decisions. So I'd say if there's one magic wand that I could know a company does something well, I would feel really confident if they had a consolidated solution and were able to make sure that their data is really working for them. [00:05:12] Adil Saleh: Great. Very interesting. [00:05:14] Adil Saleh: Talking about your experiences Cross HQ. I see that you've been cross checked. I'm sorry, I see that you've been pretty much taking information from the install base and make sure it gets translated into the right team, which is the product team. So were you using any sort of technology or how that information gets translated? I'm trying to explore more of the cross functional components of customer success and this becomes very critical when you have your product features on the line and customers health is on the line. So how did you incorporate those operations when it comes to your role at cross check? [00:06:00] Kelsey Peterson: Yeah, I think there's a few ways to think about that. The first thing that I think is important is that all of the information is being collected. So we don't want to be in a world where it's up to the individual person to pass along feedback or not. We want to take all feedback for what it's worth and make sure it's being ingested in a centralized location. And then from there, the next piece is working with the product team to ensure that we understand the why of the ask. Right. So sometimes customers will, you know, I expect this to work. In this particular you're missing, if the CSM isn't collecting the context, then it's difficult for us to advocate internally. So we want to collect the information, we want to have the context, share it internally, and then from there, it tends to be a matter of prioritization. So if there is something already on their roadmap that we can pull forward to delight that customer, we absolutely will. If we find that the ask is maybe more of an edge case and not something that's going to serve our today customer and our future customer, then maybe we'll look into is there a creative solution so that we can achieve what the customer is trying to do? I've seen this done across companies through a variety of mediums. Product board, for example, is a solution where you can aggregate that data. I've also seen it within spreadsheets. I think the important piece is that you have the right context and the right information so that when you're having this collaboration, or even you could call it a negotiation with the product team, that you're fully informed in what you're presenting. [00:07:42] Adil Saleh: Very interesting. So you also talked about centralizing having a unified tech stack. And we encourage and we preach this a lot and we talk about this a lot as well, not just the tech stack but also the data. Just like you mentioned, all the information that's being taken from the customer lives in a central space where everybody could view it, access it, and take action if that's needed and if that team is relevant. [00:08:10] Adil Saleh: So now talking about post sales journey handoffs from sales to success onboarding, and then it gets translated to the product activities. The CSM or Account Manager, if that is an enterprise account, takes care of that account and sees that information, monitors it, maintains that account. So how does that entire journey used to work when you were at cross check as a VP for your let's talk about the mid size customers first. [00:08:47] Kelsey Peterson: Sure. [00:08:48] Adil Saleh: Hybrid sort of touch. [00:08:50] Kelsey Peterson: Yeah, so that's exactly right. Midsize for us was not full digital or tech touch. It wasn't necessarily the full enterprise pro services. It was sort of that middle territory. I think for us, making sure your customer is set up for success in implementation and Onboarding really is predicated upon a thoughtful sales cycle and making sure that you're collecting the right information. So I lose sleep over the idea of a customer starting their kickoff and the Onboarding or the CSM resource saying, okay, now tell me a little bit about why you bought. Right. Because that information has of course or hopefully been discovered. And so for us, there's a pretty refined sales CS transition document. And so that's a big piece of it is making sure we're collecting. Yes, we know that there are general reasons or value propositions for why somebody would buy a software, but what particularly is important to them and so we can make sure that we are in the Onboarding period expediting their set up with the features and functionality that most closely align with the goals that they've shared with us. And then it also requires some discipline around making sure we're staying in direct communication and aligned on the goals. Because particularly in this sort of macro climate, we are finding that goals are shifting and changing, especially in the hiring space. And so it's important for us to be fluid with the customer and to make sure that as their internal priorities change, that we are shifting how we support them from a customer success perspective. [00:10:28] Adil Saleh: Okay, that's amazing. I want to stick a little more with cross check because I've been on the both side of the table. I've been a customer, I've been an employee as well. So I've seen when I was running my own business, one of my employees went off, joined another company that was using cross check. So as a CEO, got that notification 982. I had some set of questions that I wanted to answer for that employer. This was quite seamless when it comes to customer experiences. [00:11:11] Adil Saleh: When it comes to your internal processes, CSOPs in the SMB segment mostly, how did you ensure the self serve model, like onboarding, seamless self served onboarding and then how you set up operations regarding making sure value realization and then increasing the LTV over the time of that customer. So what kind of strategies have you applied there? I'm just talking. [00:11:45] Kelsey Peterson: Yeah, well, first of all, I'm really glad you had a positive experience with the software. That's great to hear. For us. In the SMB segment, we did a lot of automation. So we have, for example, a landing page and we've done a bit of analysis on how folks like to learn. And it varies, as you can imagine, by audience, by segment. But oftentimes what we're calling chapter or bite sized information is most digestible for folks. So I want to know about this exact thing and I want to watch a two minute video about this. I actually don't want to sit through a 90 minutes onboarding training. And so that was something that we really worked on, was having a landing page accessible with surfacing various videos, depending upon the key onboarding steps for a customer so they could say absolutely. Could they go through the learning track and start at step one and go one through ten and be fully onboarded in a digital way? Yes. But could they also go and say, you know what, for me it's most important to have these custom surveys. Why don't I skip down to step six, for example? So that was something that we had been working on, was making sure we were offering the right amount of self serve information in a way that is digestible for end user. Because it's important from a customer empathy perspective to remember that your software that you're providing to somebody, they are not thinking about it the way that you are. Right? And so your job is to meet them where they are. So that was a big part of one of our later initiatives. [00:13:22] Adil Saleh: Okay, that's awesome. [00:13:25] Adil Saleh: So then moving on from Know, just this past year, you were also a part of Rev Room. So could you tell us more about your experience there? You're still a part of Know. What kind of community is that? Is that more of revenue leaders getting all, like, in a slack community of sources? [00:13:51] Kelsey Peterson: Yeah, that's the base of it. Jared Robin had reached out around connecting some go to market leaders, and it's a pretty intimate group right now. I think there are 50 or so of us who are like founding members. And then pretty quickly, we opened this, I think just last week, and there are several hundred folks on the waitlist and Jared is working through them. But the goal of the community is really to find a space for marketing sales CS leaders to get together, collaborate on shared challenges and opportunities. And it's a slack community. We have a roundtable that's weekly. We have coffee, chats, and then we've had a lot of async or kind of one off communication. I recently actually had a really interesting conversation with a sales leader in Revrim, and we were talking about the opportunity, especially in this climate, for expansion among existing customer base. And how can sales learn from CS so that they're servicing the right information, the right anecdotes in the sales cycle and setting customers up for success? And then also, how can CS learn from sales to be active listening and hearing opportunities for growth? So there's been some really cool I've only been in the community for, I think just a couple of months now, but there's been some really awesome collaboration because even though we're across different segments and we have different organizations, there's a lot of commonality among the challenges and opportunities that are before us. [00:15:27] Adil Saleh: Okay, that sounds good. Great. So is that only for folks that are listening? Is that only for the revenue leaders or GDM teams more often? [00:15:40] Kelsey Peterson: Yes. So right now I think it's VP up of go to market leaders. I think they have been talking about extending this out and having unique communities for different audiences. But that's the current v. One state. [00:15:57] Adil Saleh: Okay, cool. [00:15:58] Adil Saleh: So HB I heard it from a friend of mine quite a while back, and I was thinking that this is something that this can transform even not just the onboarding experience. Folks, I'm just talking about HP and sure, she just joined a couple of months as a VP and a little bit on HP. It's more of a core SaaS platform out of SF that's helping companies to helping companies with hiring processes. It's more of the people's team, more of that project. And thinking of her experience as cross check. Now she's the VP of HP. So now thinking of customers like Deal, you know, we've had leadership from Deal coming and sharing their story too, back when we started. So how does this product, HP is similar to cross check your previous experience as VP and what kind of challenges you've had up front. [00:17:05] Kelsey Peterson: Yeah, so I think it's very cool that you've had a speaker join from Deal actually started working with Ashby. I think what they were about 20 employees. And I think, if memory serves, they're like closing on 3000 now. So they're a really great example of a customer that's grown with us, or we've grown with them, rather. Yeah, so actually, I think it's in the HR tech landscape. It's a consolidated solution. So it's an applicant tracking system, a CRM scheduling for interviews, analytics, so it's all of this reliable data into a single source of truth. So that's the main core value that Ashby presents. And I would say from a CS perspective, I've been able to take a lot of the learnings from my time at cross check around, as I mentioned earlier, like servicing the right information at the right time and making sure that we're properly supporting different customer segments. I've been able to extrapolate a lot of that, which has been great, though I will say Ashby is really big on principled thinking. And so rather than, let's say, reasoning by analogy, like, oh, I've seen it done this way and that worked, really, like breaking things down to the fundamentals and reasoning through from there. So I've been able to take some playbooks that I already know, and then it's also been a unique opportunity to sort of unlearn pieces and really start from scratch, which has been exciting. [00:18:30] Adil Saleh: Absolutely. [00:18:31] Adil Saleh: So, I mean, I've been reading about HP as well. You kind of ensure and make sure people, your customers, invest in data. So how does data come into play when it comes to hiring in an SMB segment? Starting point is hunting a bright candidate. The biggest challenge for companies these days is to replace these recruiters. They cannot afford these recruiters. We spoke to Motive team. They had a local recruiter, they had a very big team in Pakistan, more than 300 people as a customer facing team. In Nashville as well, in San Francisco as well, they had local recruiters that helped them with qualifying the right candidates and all. So let's say if I'm a small business, my biggest thing is to get rid of these recruiters and hire my own people, my own team of people, like head of people HR team that can take care of the entire operation. Starting from hunting the right candidate, qualifying the right candidate, making sure we get the right communication, and get them scheduled for the interviews, get them through to the entire evaluation process. A lot of companies, even the tech companies for the technical roles, they have some assessments and all of that. So could you walk us through from an SMB perspective and especially this recruitment challenge? Because a lot of companies are now, even after COVID, they're trying to cut their costs, optimize their cost as much as they can as a startup, it becomes a very big challenge, hiring. So how does HP come into play? What is something that is different? Because we've seen a lot of tech platforms, a lot of tech companies over the years, more in the HR tech helping with hiring, but quite unfortunately, nobody has nailed it as of now. [00:20:30] Kelsey Peterson: Yes, I think the SMB space is pretty unique. And that's where actually, we started with a lot of we have a huge breadth of startup customers. And I think to your point, people are really trying to optimize and work with lean teams, particularly in this climate, particularly in the people team space. And so what Ashby is able to do is make sure that your candidates don't feel the scale of the experience. Right. So we are ultimately facilitating automated sequences and communication and scheduling, like you mentioned, so that you can deliver a consistently great candidate experience while not overworking the recruiting team. Right. The recruiting team is able to focus on the things that where they can add unique value and not necessarily have to be distracted by some of the rinse and repeat the coordinating of schedules, which there's quite a bit of admin time there. And Ashby is able to alleviate a lot of that. And then with the analytics piece, we're able to help inform hiring decisions and really understand breakdowns in the process. For example, like, okay, you mentioned a take home assessment. It looks like at this stage in this take home assessment, we are seeing a drop off. What can we do about that? How can we optimize there? So Ashby really helps support recruiting teams in that way so that they can be focusing on the questions that are super important, and we give them the data to help answer those rather than distracting them with some of the admin or the pieces that can be automated. [00:22:14] Adil Saleh: Cool. Interesting. [00:22:17] Adil Saleh: So, given the kind of technology, kind of skill set on the team you had back at Trust Check, what kind of team you have here at HP, how big is it? Only talking about post sales and how you have segmented your team based on the customer install base, of course, their size, their complexity, and just give us little details on the team formation here. [00:22:44] Kelsey Peterson: Yeah, sure. So our post sales like our Customer Success and Support team, I think there are about 20 of us at this juncture, and the team is broken out into like a high touch team, which is servicing predominantly our enterprise customers, maybe mid market. And then we have our scaled customer success team, where we've done a good bit more of the automation and a little bit of a digital onboarding approach. And then we have, of course, our customer support team, which is a highly technical team that is super well versed in the product itself. So that's kind of the three facets we have of customer success. And while generally you could see an enterprise customer in high touch and maybe mid market is sort of the line. We do have exceptions to your point based upon customer complexity. Right? So if we have a customer that is meaningfully using our analytics product, then we'll have them in high touch segment because we'll want to be working with them and iterating and providing best practices. So there are sort of exceptions to how we partition out, but generally those are our segments. [00:23:57] Adil Saleh: Okay. And talking about just the success alongside support and this digital model, I would say digital CS, so that is helping on growing the customer, the lifetime value, evolving their goals, just like same notion model, same figma model. So now you're just talking about digital touch. How is the growth going from some of the low paying customers? The goal is to make sure your startups become the small business, your small business become the mid market and then mid market becomes the enterprise. So you are growing the year by year. You're growing the lifetime value of your customer base, install base. So what kind of technologies you have in place? I'm sure it's just been a few months. I'm not going to throw a lot of questions, I'm sorry if I do. So what kind of technology is around to ensure that? Because that's only scalable when you put on tech stack that is getting you answers and getting you data and triggers that you can make it a scalable operation for a bigger install base. So how is that going at HP? [00:25:12] Kelsey Peterson: Yeah, so this predates me. So no credit to me on this, but the team has done a great job using Bento for Onboarding guidance. So it's an in app experience and I think Onboarding has been a really primary focus, onboarding implementation for the scaled team. I'm sure you're familiar, right. Typically we don't see depending upon the SaaS model, but you might not actually recoup money from a customer until twelve or 18 months into your lifecycle. Right? And so if you have a customer who's not up and running successfully in Onboarding and they churn at their renewal, you may have effectively paid them to use your software. So Onboarding is a huge emphasis for our team to make sure that folks are seeing success. And then we have various touch points kind of at natural inflection points later in the customer lifecycle. But I would say in my first couple of months here, bento has been extremely helpful both at saving the team a little bit of time for some of the rinse and repeat aspects, but also making sure that folks can dive in. And if they want to take 10 hours their first week and go through onboarding, that's available at their fingertips, which has been important to the team. [00:26:25] Adil Saleh: Okay, that sounds good. Just one last thing I wanted to explore more at Ashby since you just joined. What kind of training initiatives? Training and management initiatives you're taking for the team. And when it comes to customer education, I know you have a lot of open source knowledge base and training material during the onboarding stage to adoption. What kind of knowledge is that like outside the platform? Industry knowledge in terms of customer education and training and management for your internal teams, how Ashley is trying to invest into that segment of a business, which becomes very critical for when you want to get bigger as a business. Right now, you're at series AB. Now you're going moving towards post product market fit and then achieving these growth and success, scaling the operations. So having a little bit of foresight into a bigger team, bigger operations, bigger customer base, and then seen looking at your team training, management, investing in trainings and then customer education. So how does that come along with Ashby? [00:27:47] Kelsey Peterson: Yeah, so something that was very attractive to me about Ashby was our emphasis on the product. Both of our co founders have strong engineering backgrounds, which I think is a helpful profile in this space. And our product training is incredibly robust. So, for me, I had ten dedicated hour long sessions to get deep into their product. And that's for me in my role as a manager, right? Not as an IC. And so you can imagine the folks who are actually using their product day in and day out have really robust knowledge and training. And then I think, unique from that, there's this piece around the broader community. And so we just invested in a community hire. This is somebody who's actually been on our team, working mostly with the analytics product. And she has this recops background, which is hugely helpful because she has directly understood and experienced the pain points of our customers because she didn't have Ashby and she was facing some of these same challenges. And so we're making this investment in the community role. And that's a big piece. And then the last thing I'll mention here is the recops investment. We do have other folks on the team as well, because we think it's really important not just to know customer success, best practices that feels table stakes at this juncture, but to really truly understand the customer. And so that's why we've been really investing in folks that have been our end user. And even at times we have Ashby customers folks on people teams saying, hey, I would be interested in customer success and hand raising for those opportunities. So we don't take that lightly. We're super grateful for that. And so I would say the product investment, the understanding and the entrenchment in a broader community, and then our focus on recops are a few of the areas. And then, of course, you mentioned Ashby University, which is robust documentation. And then the next iteration of that is for us to ensure that we are serving up the right information and some maybe intent based ticketing and things like that, that's sort of, I think, the next generation of that for us. [00:30:03] Adil Saleh: I love that. I absolutely love that. Great. Right now, just before we set you free, I really appreciate that you worked out the time with us. I know it was hectic at the beginning. We had like, some disturbance and I really appreciate that. You've been pretty patient. [00:30:21] Adil Saleh: So now, talking about the hiring process inside HP, so what kind of roles you've had open? I see a lot of engineering roles. I see some of the customer facing role. A lot of folks listening to this, a lot of recruitment partners of ours listening to this. A lot of individuals that are moving, always moving and trying to get new, better opportunities. And what kind of roles you have open on your team when it comes to customer facing and what kind of skill set you guys are looking for? [00:30:57] Kelsey Peterson: Yeah, so right now we are looking on the CS team. We are both hiring for senior CSM as well as support. I think for us, I mentioned this, the product piece is really important. So we like to hire folks who are keen to really understand the product and have that true expertise. We are always opportunistically hiring engineers. They're the backbone, they are the product. And so it's important for us, we typically hire more senior engineers. That's a priority for Ashby. And so, yeah, I think we are also always keen to have conversations. I think you never know when somebody you might have a conversation and maybe there's not the exact role open, but later something will surface. So I think we're really open to that. And then I would say specifically, just to zoom back on CS. In particular, in addition to the product piece, we generally tend to hire for project ownership. So folks who have strong project experience and initiatives, like the things we've talked about, like scaling customer success, like taking this to the next level, my interest would be super piqued if I were to talk to somebody who has ideas around chat GPT and how that can help us as a next iteration. Right. So I think the product piece, the project ownership specific to CS, and then more broadly, we're always keen to have the conversations. I think we are a hiring company. We have an entire series on hiring excellence. So if you're keen to learn more about our ethos there, I would recommend tuning in to that webinar as. [00:32:45] Adil Saleh: Kelsey. [00:32:46] Adil Saleh: I mean, there are a lot of technologies after the evolution of Know HubSpot team, they have built their own chat widget inside the mailing systems for marketing, sales teams, support teams. Same goes for salesforce grammarly. So are you guys using any of those inside? [00:33:14] Kelsey Peterson: Yeah, it's a conversation. I felt like HubSpot chat GPT launched and I blinked and then I saw Dharmesh's post. It was incredible. It was so swift. I think for us, we're still having. Its early conversations, but it is something that's on my mind as we think about kind of akin to how Ashby is helping recruiting teams not need to distract themselves with scheduling and things like that. There are probably the equivalent pieces on the CS side that we can optimize so certainly always eager to have the conversation if there are ideas there and it's something that's on our list as. [00:33:52] Adil Saleh: Yes, and it's getting smart with every just got launched last week. Now these big CRMs like salesforce HubSpot, all these folks that have huge amount of data that they can train their own models and they can intersect those data points with Chatigree to make it enhance it, elevate the entire use cases and save even more time only for their customers. That's super powerful. I haven't checked GPT Four yet the very day it got opened just I guess three days back and we applied so let's see how soon we can get access to it. Exciting. [00:34:37] Kelsey Peterson: Fingers crossed for you. [00:34:40] Adil Saleh: Very exciting times. I'm not a tech background my CTO he's a core tech guy and I hear a lot of these and then I start researching and start getting knowledge around is just like Elon Musk says it can go dangerous. [00:35:01] Kelsey Peterson: I think so too. I'm trying to be very optimistic and I think it would be a mistake to there are competing opinions, right. Some folks are saying oh, that makes me nervous, I don't want to touch it. I think that's a mistake. I think we have to lean in. But I am curious to see even it's interesting to think imagine if someone listened to this interview maybe three years down the road how outdated the take on Chat GBT right now is. It's so wild, it's evolving. [00:35:30] Adil Saleh: So, yes, absolutely do check out human loop. There's a platform and they're helping with prompting on the Chat GPT engine GPT-3 and four engines. So they're helping small businesses with prompting with fine tuning the prompts to get the accurate data because this can become a challenge. So it's going to be a very disruptive platform and there are loads more coming in the space as well to make our efforts more optimized and we only focus on the high value task. Yes, exactly best we can automate. [00:36:16] Adil Saleh: Very exciting times, Kelsey, indeed for sure. I appreciate you taking the time today, it was real nice talking to you. Your background, your strong knowledge on the technology on the product and the way you are pretty much stick with the kind of technologies as a VP of customer success. Now previously cross check and then platform in a similar space, ashpeed so I wish you good luck with this role and I'm sure there's going to be good and bad days, but I'm sure you'll have a good smile on your face. [00:36:56] Kelsey Peterson: Appreciate that ideal. Thank you for having me and thanks for the chat. [00:37:00] Adil Saleh: Likewise. Have a good rest of your day. [00:37:02] Kelsey Peterson: You too. Take care.