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Episode #111 Mastering Customer Relations to Drive Strategic Growth ft. Reanna Dempsey (Unanet)

#updateai #customersuccess #saas #business

Reanna Dempsey, VP of CS at Unanet, joins our hosts, Josh Schachter, Jon Johnson, and Kristi Faltorusso, to explore how executive engagement, data management, and product adaptability have led to improved client retention rates. They also discuss her innovative approaches, including multithreading customer interactions. Reanna emphasizes the critical role of persistence and strategic involvement from internal executives to connect with key stakeholders, while also adding a lighter note, on enjoying Reese’s pumpkins. Plus, we’ll touch on the unexpected challenges Customer Success Managers (CSMs) face in securing CEO attention and provide actionable strategies for building long-term executive relationships.

Timestamps

0:00 – Preview, BS & Intros

8:53 – Stepping in to level up CS initiatives

12:29 – Customer feedback & internal data

15:40 – Service Levels for different customers

18:40 – Ongoing process of cultivating successful business partnerships

22:20 – Difficulties CSMs face in getting CEO attention 

25:20 – Strategies to get the executive buy-in to facilitate customer interactions

28:10 – Importance of multithreading approach

29:00 – Setting realistic expectations for executive relationship-building

31:27 – Communicating the importance of tracking & maintaining data

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Keywords:
How to keep your customers happy, customer success manager, customer support, customer success management, Customer Success Manager role, Customer Success Management, customer churn, customer success metrics, forecasting customer outcomes, revenue growth, customer satisfaction, fear in customer success, NRR (Net Revenue Retention), GRR (Gross Revenue Retention), customer loyalty, Customer Success Manager training, core responsibilities, preventive measures, customer feedback, holistic approach, market fit, strategic planning, leadership in customer success, sales and product alignment, churn problem solutions

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Quotes

  • “I was just at a conference, and it was like most enterprise companies have 230 software applications now. So it’s like, okay. So I’m one of 230 CSMs trying to get the attention of a CEO, that is a very difficult task.” — Reanna Dempsey

  • “Our CEO has said to me, “Hey, just tell me who you want me to call. I’ll call anybody. I’ll go visit anybody.”I think I’m at a company where customer success is not a department for us.” — Reanna Dempsey

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👉 Connect with the guest

Reanna Dempsey : https://www.linkedin.com/in/reanna-dempsey-9402076/

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Youtube: ⁠https://youtu.be/H6mnKkpU2lI?feature=shared⁠
Apple Podcast: ⁠https://apple.co/3dfWXmD⁠
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👉 Connect with hosts
Jon Johnson: ⁠https://www.linkedin.com/in/jonwilliamjohnson/⁠
Kristi Faltorusso: ⁠https://www.linkedin.com/in/kristiserrano/⁠
Josh Schachter: ⁠https://www.linkedin.com/in/jschachter/⁠

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👉 Past guests on The Unchurned Podcast include ⁠Nick Mehta (GainSight)⁠⁠Mike Molinet (Branch)⁠⁠Edward Chiu (Catalyst)⁠,⁠ Kristi Faltorusso (Client Success)⁠, and customer success leaders and CCOs from top companies like  ⁠Cloudflare⁠⁠Google⁠⁠ Totango⁠,⁠  Zoura⁠, ⁠Workday⁠⁠Zendesk⁠⁠Braze⁠⁠BMC Software⁠⁠Monday.com⁠, and best-selling authors like ⁠Geoffrey Moore⁠ and ⁠Kelly Leonard⁠.

 

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Reanna Dempsey:
It was the end of the road. No one above me would come in and, like, ever engage with customers, and I just I mean, I know that it’s hard to get jobs right now, but, like, I’d be looking for a company where I had that executive buy in all the way from the top, and that’s what I have. Our CEO has said to me, hey. Just tell me who you want me to call. I’ll call anybody. Like, he is so oh, yeah. I’ll go visit anybody because I think I’m at a company where customer success is not a department for us.

Reanna Dempsey:
It is truly something that, like, all of our executives take on. I mean, we’re bonused in, in a way that the whole company has bought into our customers being successful. The way that I explain it to our executive leaders, I’m like, I I asked our CEO. If a CSM from one of the software tools that we use wanted to meet with you, would that get your attention? He’s like, of course, it wouldn’t. Like, that’s that’s ridiculous.

Jon Johnson:
No. My favorite is everybody just said this as, like, we’re not typing on podcast.

Josh Schachter:
Hands up. Yep. Yep. Raise your hand raise raise your hand if you’re wearing pants,

Jon Johnson:
pants. They’re there’s layers. Pants.

Josh Schachter:
Oh, okay. Alright. They’re like some phabletics or something. They’re okay. You’re okay. Alright.

Jon Johnson:
They’re supportive. I have reasons to be supported, Josh.

Kristi Faltorusso:
He said Fabletics in a very condescending way.

Jon Johnson:
It’s a great brand, by the way.

Josh Schachter:
Like Fabletics. They got me they got me, and then and then they moved me to, like, full price, and I was like,

Jon Johnson:
I

Josh Schachter:
was used to the the the initial offer.

Kristi Faltorusso:
Is it amazing how brands will take care of new customers, but they won’t take care of existing customers?

Jon Johnson:
I feel like there’s a podcast episode about that we should dig into.

Josh Schachter:
Yeah. There’s a podcast for that. Well, hello, guys. Welcome. It’s been a while since we’ve all been on the show together. I am Josh Schachter.

Jon Johnson:
The energy is just

Josh Schachter:
Yeah. No.

Kristi Faltorusso:
It’s energying.

Josh Schachter:
We’ve got John and Christy, my cohost, and Rhianna Dempsey. Rhianna is the VP of customer success at Uninet, and we are so thrilled to have Rihanna on the show. Thank you for joining us today.

Reanna Dempsey:
This is officially my first podcast ever, guys. So this is a big deal. Oh. Really?

Kristi Faltorusso:
Oh, gosh. This is where you started?

Reanna Dempsey:
I did. I feel like I

Kristi Faltorusso:
feel like it’s

Reanna Dempsey:
all gonna be let downs after after this. That’s my feel. I hope so. Don’t share.

Jon Johnson:
Awesome. You know, the

Kristi Faltorusso:
It’s possible it’s either gonna be, like, this will be the high of your podcast career or the low of your podcast career.

Jon Johnson:
Every episode. There’s no middle. Yeah.

Kristi Faltorusso:
There’s no middle.

Jon Johnson:
Every episode is either the best or the worst in my experience.

Josh Schachter:
So true. There’s no middle ground. But

Jon Johnson:
that’s Usually,

Kristi Faltorusso:
the best one’s the ones when John isn’t here. Hey. Oh, just kidding.

Jon Johnson:
That’s Josh’s play.

Kristi Faltorusso:
John gets the most love of all of us. So anytime that anybody asks anybody about the podcast, oh, John’s my favorite. He’s the best.

Jon Johnson:
They’re just bigger.

Kristi Faltorusso:
Thoughts and opinions.

Reanna Dempsey:
That’s true.

Jon Johnson:
Follow followed by me. Okay.

Reanna Dempsey:
Now Nobody likes you, Jimmy.

Josh Schachter:
Nobody likes me. Nobody likes me. I am totally the Ed McMahon of this podcast for this series.

Jon Johnson:
We we should have had the first, like, three and a half minutes because I feel like we had a bit of a hot take on on Rhianna’s candy choice.

Josh Schachter:
I’m sorry. What’s her name?

Reanna Dempsey:
We did. Rhianna? Okay. That’s right. He got it. Josh, I got it right.

Jon Johnson:
I

Josh Schachter:
know, but you stumbled, and I’m just

Jon Johnson:
drawing attention to that. Oh my god. Thank you for that. What is your this is the time of year for you. Can can we reiterate what our candies are for the Halloween season as we approach? Rhianna, what did you what did you say or

Reanna Dempsey:
your comments? So I I have a struggle with all of these seasonal Reese’s. So for me, it would be and I think I said eggs. It doesn’t it’s the eggs, the trees, and the pumpkins. So that is really

Jon Johnson:
They’re all the same.

Reanna Dempsey:
Peanut butter to chocolate ratio. Just the egg. Yeah. Yeah. It’s just the egg. Yeah. So the pumpkins, the Reese’s pumpkins, my Kryptonite, and it is a struggle. Yep.

Jon Johnson:
Yeah. I’m not allowed to have peanut butter in my house because it’ll kill my daughter. And I

Reanna Dempsey:
Oh, that’s a good reason not to have

Jon Johnson:
it. Yeah. Yes. Not enough EpiPen’s in the world. No. But I love Reese’s, like, so much. Yes.

Kristi Faltorusso:
So when I do travel to a store, do you buy them and eat them in the car, like, privately? And, like, do you have, like, a lot of wrappers and you sit there and shame when you’re done?

Jon Johnson:
That actually is not far from the truth.

Kristi Faltorusso:
And it’s very specific visual.

Jon Johnson:
Literally. Yeah.

Josh Schachter:
That sounds like a

Jon Johnson:
personal anecdote. Go on travel when I go on my travel trips, when I at first, when I get on the plane, I’ll get the I get, you know, Reese’s peanut butter cups, and it’s heaven that I wash my

Josh Schachter:
hands. About Unanet.

Reanna Dempsey:
Great segue, Josh. Real real natural segue there. Yeah. Yeah. I’ve been calling you for a while. 2

Jon Johnson:
2 years of working with me.

Reanna Dempsey:
Uninet is, a company we focus on project based businesses. So we’ve got a lot of products that that really cater to project based businesses. Half of our business, roughly, is in the government contracting space. So we have financial systems and a CRM product and inventory and manufacturing solutions, lot of fun things. And then the other side is our AEC industry. So architecture, engineering, construction firms. And that space, same kind of model. We’ve got an ERP focusing on financials and project management, and then we have a CRM.

Reanna Dempsey:
And that is basically us in a nutshell. So I’ve been around sort of a really, I found it when I when I joined the company 5 years ago, founded by a female, like, 25 years ago, which you weren’t really hearing a lot of female founders in the financial ERP space. And she was sort of paving the way and has a really cool backstory, family built company, and she still serves on our board. So, really, really cool history of the company, and then we’re private equity backed now kind of in that hyper growth phase.

Josh Schachter:
So she came so so the PE shop came in in 2020. Who who’s the who’s the PE that,

Kristi Faltorusso:
you can call me? Jane

Josh Schachter:
Jane. John, stop typing. Wait. Hold on. Sorry. Sorry. John, I can still hear you typing.

Jon Johnson:
I don’t understand. I don’t understand. I don’t understand. It’s definitely

Josh Schachter:
you. Every time.

Reanna Dempsey:
We we saw it that time.

Josh Schachter:
This is what we deal with.

Reanna Dempsey:
Saw the hands. Yeah. Yeah.

Kristi Faltorusso:
I know.

Jon Johnson:
No. I just was looking

Josh Schachter:
up the PE firm that bought you. Just listen. Listen. You have 2 ears, one mouth.

Reanna Dempsey:
Oh, this is great. Smart checking. Equity? JMI equity. Cool.

Josh Schachter:
Good old JMI. Great. Yeah.

Reanna Dempsey:
Yes.

Josh Schachter:
And so so they bought it in 2020, and then you came into the organization to don’t do it, John. You came into the organization to, to build customer success.

Reanna Dempsey:
Yes. Yep. They

Josh Schachter:
True.

Reanna Dempsey:
They had customer success when I joined. It looks very different now than what it did, I would say. So, lots of changes. I would say, you know, CS was seen as kind of like a note taker. You know? Like, we were coming into the meeting and taking a lot of notes and then setting the next meeting, but not really driving strategy, definitely not thinking about driving growth within the accounts. Data was pretty disparate. Like, a lot of things that I think are pretty normal at the the stage that we sort of entered the picture. So lots of building and, you know, forming the team.

Reanna Dempsey:
I’m pretty proud because I think let me think. It’s at least 1, 2, 3, 4, 5. I think there’s 7 of my original team, like, still with me. Like, the major the people that I wanted to really make sure stayed, and that’s hard because it was a very different experience. And, of course, as you all know, we were in the office. So when I started in March of 2020, I was in the office for 3 weeks, and it was very much an in person feel. So to go from that over to fully remote, you know, PE kind of pace, it it’s it’s been a lot of change, and they’ve sort of weathered the storm and stuck with us, which is has been really great.

Josh Schachter:
And what is the team like? What did it look like then, and what does it look like now, the composition?

Reanna Dempsey:
Yeah. So it was I think I had maybe 12 people on the team when I joined, and I was when I joined, I was hired for the GovCon side of the business, and we only had an ERP then. And I think it was, like, the 2nd week on the job that my boss, like, dropped in a meeting. Oh, we want you to focus on the the other ERP product too. I was like, wait. This is first time hearing of this. I’ve I’ve since given him grief on that, many times. But now the team we’re almost 50 people, so right around 50.

Reanna Dempsey:
So, you know, we have a renewals team now. We have an ops team. We’ve got, you know, a GovCon and an AEC team and then some specific roles under those. So sort of, you know, ready for the next phase and and able to scale with the work structure that we have.

Josh Schachter:
Okay. Cool. So you come in 5 years ago ish, and you’ve got this 20 year old startup there at that time.

Reanna Dempsey:
Yep. Yep.

Josh Schachter:
And you are you are taking them to the next level on organizing and structuring their CS initiatives. What are the first three things that you do when you come in?

Reanna Dempsey:
Yep. So for I mean, first was obviously analyze the people, like, understanding who do I have, who do I think is has the right mentality to kinda get through this next phase, and and really clearly articulate what the role is today and what we expect the role to be in the near future. So kind of that road map for the the people. And I remember I it was pretty cheesy now that I’m thinking back, but it worked because we were only GovCon, and we laid out this this vision of, like, you know, we’re sort of, like, in, like, a a jet formation. And if you wanna, like, be on the team, we had this whole instead of getting on the bus, it was all about a jet because we were you know, lots of our customers are are military focused. It works for us. But I did have a few people early on just kind of opt out on, like, that doesn’t sound like the type of role that I want to do. You know, I get where we’re going, which is great.

Reanna Dempsey:
So I feel like getting that out of the way early was was was a good move. And then data would be the second big piece. I mean, data was it I remember when I joined, we were considering basically having 2 sources of truth for our team. And I was like, guys, we cannot do this. So, and I just to give you a very tactical example, the first escalation I had, I remember CSM came in. We’re sitting down because we’re still in person at the time, and they started telling me this situation going on with the customer. And so at first, I was like, hey. Can you just tell me what like, the name of the customer? Like, what’s their ARR kind of how long have they been a customer, some, like, very table stakes kind of data points, and they were like, oh, well, you know, the customer pays x amount per user per month.

Reanna Dempsey:
And I was like, okay. Well, how how many users is that? I’m literally, like, doing the math just to get to it’s because they didn’t even have access to that data, and I didn’t even realize it because it was, like, day 2 on the job. So I couldn’t even run a report back then myself. Now finance could, but it was this weird sort of wait. So we can’t even run a report to see what customers we have and sort of who’s, you know, at the upper end, and it it was fascinating. So there was a massive amount of sort of data, like, just accessibility, like, where’s the data gonna be and then clean up and then making sure the team had the reports that they needed to, you know, run their book of business in a way that that made sense. So, that was and I would say after that would just be industry knowledge because I was an outsider. So it was, like, the people, the data, and then just understanding the customers, who they are, why do they buy, what does their product do for them, you know, the value that they get, because I was definitely I still feel like I’m a total outsider 5 years in.

Reanna Dempsey:
I’m like, this whole government contracting world, I feel more comfortable with AEC. My father started a construction business 30 years ago that my husband works at now, and so I’m very familiar. I worked there for 2 years.

Josh Schachter:
Architecture, engineering, and construction?

Reanna Dempsey:
And construction. Yeah. Yeah. So much more, like, familiar with that side of the house. And I think, like, we built a house, so I worked with an architect. At least I understand what happens there, but the government contracting space was completely new to me. And so it’s been definitely learning, a lot over the past 5 years about the industry.

Kristi Faltorusso:
Yeah. Arianna, can I can I in instruct here for a question? You did your people analysis, data analysis, industry analysis. At what point when you entered the company did you spend time doing a deep dive on your customers?

Reanna Dempsey:
Well, I would say almost immediately. I mean, once I had the data to figure out who should I talk to, then I started I don’t wanna call it in a a formal listening tour, but just getting on the phone with as many customers as possible and just having conversations with them. Like, hey. I’m new here. Like, I could play the new card. So I would say during the 1st 90 days doing as many of those listening calls as I could and just asking them, like, what’s been your experience? What surprised you about working with us? Or, you know, just kind of asking the higher level questions and letting them talk. And it’s it did start to it started to also uncover some things that we should have been doing for them that we weren’t pretty early on. And we’ve been able to build like, one one very obvious thing I can think of is just certification in our product.

Reanna Dempsey:
So we have a certification now. We didn’t have that before. So, but I spent a lot of time the 1st 90 days, you know, just listening. And and every customer escalation I joined, I’m like, even if I couldn’t I don’t have the product expertise sometimes, but I had the I just wanna listen to what you’re saying and not do a lot of talking, and that was

Josh Schachter:
helpful. I like the new card.

Kristi Faltorusso:
The things that you were hearing from your customers versus your team about your customers? Because I’m always interested in hearing that. Right? Like, CS teams, like, oh, everything is great. They’re happy. They’re using the product, getting a sense of value. You speak to the customer. It’s a very different conversation. So how different was that from what you were getting from your team and the data versus what your customers were telling you early on?

Reanna Dempsey:
I think it was actually surprisingly very consistent. And I think with the GovCon product. Now with the CRM product, that has been a very different experience, and I think it’s because it’s a CRM adoption, though, a little bit harder that, like, if if if you want to get paid, you have to use the ERP. Right? Like, if you if you wanna get hands up. If you want to, submit expenses and and submit your time, like, you have to log in to the ERP. So adoption, not as hard, but on the CRM side, I think we would hear a lot of people that have been at the company for a long time because that was an acquisition we made, I think, in 2021 or 2022. I can’t even remember now. It’s all blending together.

Reanna Dempsey:
I think 2022. And, definitely a misalignment of, yes, some customers are incredibly happy, but there are a lot of product gaps that I don’t think we were paying attention to, and and we’re still in that process. I think CRM’s harder. There’s more, quite frankly, like, more CRMs out there, than there are, like, niche ERPs. Like, you know, we don’t we know who our competitors are, but CRMs are popping up every day. So we have to really stay in tune to, like, what is going to help our customers. I do think we’ve got a really good process now, but though I think I was surprised more by those conversations, on the CRM side. And it’s it wasn’t necessarily reality with what I was hearing.

Josh Schachter:
You’re working with big, big companies and companies that presumably are very buttoned up because of their size, but also because of the industry that you’re in. You mentioned GovCon and, you know, AEC architectural engineering construction companies. I know you’ve got folks like Accenture and General Dynamics and these other monster organizations that you work with. How does that impact the approach, the CS approach of your team?

Reanna Dempsey:
Yeah. We’ve so and and especially on the the AEC side, we didn’t have a lot of large customers 5 years ago, and now we do. So I think and same with like, we’ve just continued to go upmarket, and that is absolutely the model for enterprise customers is completely different from the rest of the business, and I think, you know, Christy, when you were talking about doing deep dives into customers early on, we were very much the all customers are created equal model. Like, that was we love all of our customers. They’re all and we do. Like, we still love all of our customers, but it’s just we cannot afford to give the same level of service to a customer that pays $1,000,000 a year as someone that pays 5,000. And that was actually a cultural shock to a few of my CSMs who are still here, but they were like, wait a minute. We’ve never thought about it that way.

Reanna Dempsey:
We’re like, it’s just it’s sort of, you know, logical when you think about it that way. So we’ve had to we have a a customer success engineer role that we had, but we we kinda doubled down on. So we, for our enterprise accounts, we absolutely make sure we have the c r the the CSM, which is definitely the the quarterback. They’re they need to know their customer. They need to know their executives, really be a partner in the relationship. But then when it comes to, like, diving deep into the product, we have our CSC team, and we have one of those assigned as well to all of our enterprise accounts. So they kind of have the expert on call, and we have the CSM. And then we have really I mean, we just have to have that executive engagement.

Reanna Dempsey:
It’s just dangerous when we don’t. Like, I mean, I’m sure all of you in your careers, it’s like you have these great relationships down at the director level, and they love us, and they’re doing great things. And then a new CFO comes in, and we’re not multithreaded. We don’t have the executive relationships. You’re immediately a risk even if you’ve done 5 years of, like, foundation laying, and you have a 100% adoption Yep. Without those additional relationships. So we’ve we’ve actually prioritized and, I don’t even know, like, quantitatively been able to report now on especially for enterprise and mid market, like, who are our customers, who are the execs, and when’s the last time we engaged with them. And, no, sending them an email does not count.

Reanna Dempsey:
Like, we also had to get out of that. Like, just because you send an email to an executive does not mean that they’re engaging with us. So we had to kinda take time to define what does that relationship and partnership look like when it’s done right. And we’re still working on that. That is a work in progress. I could give you a great real life example, the because it just happened. So Tuesday, we went to Dallas to meet with and, Josh, I just missed you. Remember, you were in Austin, and we were coming to Dallas.

Reanna Dempsey:
So one of our largest accounts, they’ve been with us for a long time, but they’ve also grown with us. So when they started, they were, I think, around 200,000,000. Now they’re approaching 500,000,000. So growing with them, it’s been really fun. Like, just to give you an example of them, they rented out Jerry World, like AT and T Stadium

Jon Johnson:
Mhmm.

Reanna Dempsey:
For their a 100 and 30th anniversary party. Like, this this is a an amazing company.

Jon Johnson:
They have a strong 3 year

Josh Schachter:
old they’ve been up?

Reanna Dempsey:
A 130 years. Yes. They’re an

Josh Schachter:
engineering firm.

Reanna Dempsey:
130 years. It does. Okay.

Josh Schachter:
I I

Reanna Dempsey:
could probably they probably want me to say their name on the podcast. I didn’t get their permission, so I won’t. However

Josh Schachter:
That’s fine.

Reanna Dempsey:
So, basically, sat down with them. We had 6 people from our side attend. We ended up we had 2, I would say, tactical meetings with some users while we were there getting feedback on product stuff that they had been asking for, talking through one of the new features that they had been piloting, seeing how it was going. So we had the tactical, but then the last session of the day was an executive meeting. We had 5 of their c level executives in the room with us, which I’m like, they’re busy. Like, they have a lot going on. But and I guess the culmination that’s a that’s been a 3 year partnership that my enterprise CSM has been cultivating. And it so it didn’t happen overnight, but the fact that their COO did a drop in during the day, he said, listen, guys.

Reanna Dempsey:
I’m on a project, so I have to you know, I can’t stay. But I just wanted to tell you how important this partnership is to us, and thank you for being here. And it was just, like, a a great testament. And then we had a we were only supposed to have an hour with those c levels. And, again, we had head of, like, business development, we had their chief strategy officer, we had their chief financial officer all sitting in this room, and we ended up going until 5:30 instead of 5. And then we ended up going to dinner with them as well. We had scheduled dinner. You know? So I think the fact that people show up and then they keep talking because it’s important to them and because they know, yes, we care about our product, but, like, if we don’t understand what your goals and your KPIs and what’s important to you, we we can’t do the other things with the product.

Reanna Dempsey:
Like, we have to have that as a base level of understanding. But then I think what we’ve done over the years is also reminded them of the value that we’ve brought to the partnership. And, like, hey. Remember when you asked for these 5 things? We’ve delivered 4 out of 5, and the 5th one, here’s the status and and the, you know, expected delivery time. So we had to constantly cycle back to remember why you bought, remember why we’re in this together, and then, you know, actually, you know, do what we say we’re going to do. Because if we didn’t do that, I doubt they would be showing up. So that’s what good looks like. That’s what we’re really trying to get to.

Josh Schachter:
Hey, everybody. It’s Josh. I’m taking a quick break from the podcast to tell you a bit about UpdateAI. I started UpdateAI to solve 2 major challenges for CS teams. The first is that we save CSMs 4 to 5 hours per week with our productivity through AI. Secondly, we give leaders a window into all the conversations across each account and the entire portfolio. So we help knowledge transfer, we help increase the coverage model of your CS teams, and we help you detect emerging patterns in what your customers are telling your CSMs across all the risks, product feedback, advocacy moments, and expansion opportunities. So come check us out at www.updateai.

Josh Schachter:
It’s completely free to sign up and trial.

Jon Johnson:
I wanna I wanna ask a quick question. Just this is a topic that I think a lot of people hear as CSMs. So little context, I am I’m still in I’m in IC, within my team, so I’m not in

Josh Schachter:
your business. An IC. Like, you’re it’s like a misnomer,

Jon Johnson:
old man. Nope. Only in your mind, Josh. It’s fine. Okay.

Josh Schachter:
In my mind, you’re a leader.

Reanna Dempsey:
But in

Jon Johnson:
a lot of folks a lot of folks that do hear this, like, hey. We need to get multithreaded. We need to have these executive conversations. We need to get these deep relationships. And you even just said this this kind of was a culmination of a couple years of work, you know, with your senior CSM. Like, I’d love to kinda understand your perspective as a leader on the responsibility of a CSM to build those executive love level conversations. That’s often where we get a lot of the hard work. It’s easy to work with the directors because we’re talking to them every day.

Jon Johnson:
We’re talking to the users. We’re in the weeds solving those problems. But it’s often most CSMs that don’t have that experience find it really hard to elevate those conversations. How do you, as a leader, kind of think of, empowering the team, and and where do you take on the ownership? And and what are some kind of recommendations that you might have for folks that are in this position where their bosses are saying, I need to get into the c suite. Get me in. How do you push back and be like, dude, you’re the c suite. Go reach out to them yourself.

Josh Schachter:
I had

Kristi Faltorusso:
to piggyback on that because, John, I was literally I just came off of mute because I was gonna ask that exact same well, something in that vein. But, Rhianna, when you respond to John’s question, if I could piggyback one more thing I’d love you to weave in there, how do you also set expectations around the timeline? You said your CSM had been working on that for 3 years to get to that place. You’ve got people in companies who are like, great. CSM, go build

Jon Johnson:
executive relationships,

Kristi Faltorusso:
expect a conversation. Yeah. Like, after one conversation that you’re going to have this really deep rooted relationship where you’re gonna be able to take this partnership from a dollar to $10,000,000. So how do you also manage the expectations internally with the broader organization around the timeline that is required to go and and build that?

Reanna Dempsey:
Fantastic questions, all of them. So I think

Jon Johnson:
I get a credit report. That’s

Reanna Dempsey:
John’s question was so insightful. No. Well, I’ll start with John’s side, though, because so I think I am in a very unique situation, and I’m well aware. We have so my chief customer officer, as he would say, that’s why I report to he reports to our CEO. He is not a White Tower, Ivory Tower leader in any way. So he’s the first person to say, okay. And Josh has met him. Like, he he couldn’t be more, like, accessible for our team.

Reanna Dempsey:
But I do think, like, there’s there’s a a certain point where if the CEO like, I always I the way that I explain it to our executive leaders of, like, I I asked our CEO, if a CSM from one of the software tools that we use wanted to meet with you. Would that get your attention? He’s like, of course, it wouldn’t. Like, that’s that’s ridiculous. And especially, I was just at a conference, and it was like most enterprise most enterprise companies have, like, 230 software applications now. So it’s like, okay. So I’m one of 230 CSMs trying to get the attention of a CEO or you know, that is is a very difficult task. So I think the first the first advice I would give is how can you equip your main POCs with what we, like, we call a 3rd party story? They could be like, give them example that listen. In your role, it’s really beneficial.

Reanna Dempsey:
Like, our best customers who have the best adoption, who are seeing growth using our software, like winning more deals, closing more profitable projects, whatever, you know, insert your value prop there. Like, we get the best results when our executives are talking to your executives, and here’s how. So it’s like you almost get because what I think we what I did early in my career as a CSM is I was trying to get the direct report, you know, the director or the the VP that I’m working with to get the c level engagement on their own and trying to drive it through them instead of saying, how would you feel if my chief customer officer or my CFO reached out to your CFO? But you have to have that executive buy in. And if you’re in a company where your executives will not and, by the way, I’ve been there too, and that sucks. And that is really freaking hard when you are I I never there is a place that I worked a a while back, and, like, I just didn’t get that air cover. Like, I was the I was the end of the road. No one above me would come in and, like, ever engage with customers, and I just I mean, I know that it’s hard to get jobs right now, but, like, I’d be looking for a company where I had that executive buy in all the way from the top, and that’s what I have. Our CEO has said to me, hey.

Reanna Dempsey:
Just tell me who you want me to call. I’ll call anybody. Like, he is so oh, yeah. I’ll go visit anybody because I think I’m at a company where customer success is not a department for us. It is truly something that, like, all of our executives take on. I mean, we’re bonused in, in a way that the whole company has bought into our customers being successful, and I think, like, that really helps because everyone all the way our head of product say like, I can get I can literally get anybody to call in any customer. And so I think that’s where but we’ve said to our CSMs, like, do what you can. Try to, again, work the angle of, hey.

Reanna Dempsey:
Our partnership is stronger when, you know, we have our executives talk to your executives. Are you open to that? Because if so, I will have so and so reach out. I do some of the outreach. I say I think our chief customer officer definitely when you add that c, it certainly helps get the attention of another c level executive. They just tend to like to talk to each other more than, again, a CSM when you have 231 software applications. It’s just it’s Yeah. And so yeah. So, Chrissy, I don’t know if that kind of answered your question, but it’s like that’s, you know, without that partnership at my exec level, I know we would not be as successful as we have been because we and and, again, it it helps.

Reanna Dempsey:
If you have a CSM that leaves or a CSM that switches roles within the organization, then we’re set up because we have more than one touch point even with on our team. Like, I feel like we always think about making sure you’re multithreaded on the customer side, but for us, it’s like Yeah. Most of our enterprise accounts have a product person that knows them well. They have a CSE. They have a CSM. They have an executive. They have me. I like and, actually, some people in support that end up, you know, talking to them, engaging with them.

Reanna Dempsey:
So that’s really what we’re trying to do is build the multithreading on both sides, and and it’s it does take that exec buy. And I don’t know how you do it otherwise. It would be really hard. I’m sure LinkedIn, like, reaching out in certain ways and trying to engage, but, like, it would be really hard for me without my execs, like, being in the trenches with us.

Jon Johnson:
Well, I also think there’s there’s this kind of realization that that a lot of us come to. Right? If if we have, you know, let’s say we have a 1000 customers or how many people we’re kinda working with, and the expectation is that every CSM is multithreaded with every executive, How how can our CEO be connected with a 1000 CEOs and have, like, a deep connection? So this isn’t to say you shouldn’t strive for those. Obviously, that’s where segmentation comes in

Reanna Dempsey:
and and kind of

Jon Johnson:
growth mindset. But the reality of, like, what multithreaded means is not every platform needs a CEO to CEO connect.

Reanna Dempsey:
Now That’s very true.

Jon Johnson:
Not to say you shouldn’t always look for, like, you know, opportunities to connect, but oftentimes, like, a lot of the power in those growth, like, it’s I forget what the the phrase is, but, like, most CEOs don’t care about things that are under $10,000,000 in in spend, right, depending on the size of the company. So, like, if you’re a CSM and somebody’s paying you $20,000, like, you will never get into the room with the CEO. So why as leaders are we pushing these stories to say, go we need to have executive connections. We need to have this. It’s almost like we need to look at the mirror ourselves and realize how important we are. Not to deme not to be diminutive, but to just to make sure that we we’re, like, fighting the right cause instead of trying to play in a field that, you know, we don’t have any space for.

Reanna Dempsey:
Well, and I was throwing the term CEO around a lot too, and you’re right, because you said something that we have made a big distinction, which is executive level contact. Like, for us, in the especially architects and engineering, in those types of practices, a lot of times, it’s a principle. Their type is just principle, but they are, like, driving

Jon Johnson:
the person

Reanna Dempsey:
in that company. We have I’m thinking of a couple VPs that we work with that we’re like, that is the executive. Like, it doesn’t need to be the CEO. It’s and that dude is the one or that gal is the one, like, driving that particular growth. We, like, literally label them in our system as such. So it’s like, don’t just look for the c level title. We have a way of flagging, hey. This is actually the person.

Reanna Dempsey:
Even though it might not look like their title says, they’re the person, they’re the one that we wanna be connected with. So it definitely and and we have different levels of that with our segments as well. Like, enterprise is one thing. Mid market is something different. SMB, certainly not the same expectation of, you know, knowing the the CEO and all those accounts. That would be impossible.

Josh Schachter:
Brianna, you mentioned labeling it in your system. So you guys have a a Power BI dashboard that you built, right, that that helps you track all these things? How do you get the team how do you create the operations and procedures around keeping that that data hygiene fresh?

Reanna Dempsey:
Oh, I think the isn’t that always the struggle? Like, how fresh is it when you’re manually inputting something? Like, story of our lives. No. I think it but, really, once we I feel like every time we ask a customer success team to do anything and, you know, everyone wants us to track 75 different data points, you know, manually. They just think that that’s all we have. You know, we can just go in and manually update fields all day. So whenever we’re asking the team to do something like this, it’s always starting with why is this important. So we actually frame up, like, how much are, like and we do. We have some talk.

Reanna Dempsey:
We pulled up a much better our retention is when we have executive relationships versus when we don’t. So, like, linking it back to NRG or our

Josh Schachter:
retreat. Wait. Wait. Wait. Wait. We’re gonna pause. We’re gonna pause so you can actually pull up the talking points because this is a talking podcast, and I feel like the talking points on this would be very compelling for people. That might even make the headline of the episode.

Reanna Dempsey:
Damn it. I need to find because this was years ago when we did it at Okay.

Josh Schachter:
You’ll fax it to us later.

Jon Johnson:
It’s fine. The headline’s definitely gonna be about peanut butter cups.

Reanna Dempsey:
I hope so. That would get a lot of attention. I will I will find it, but it was it was a very specific talking point that I used, and I will find it and send it. But, just let’s just say retention better retention better when executives are present. That that is that was, like, the highlight. So getting them to understand and then getting them to understand, like, how are we going to use

Josh Schachter:
Sorry. But is it the dashboard that that you’re that you’re putting this data in? What you’re what you’re inputting, is it just this is a person that we’ve spoken to, or this is a person that we went to a meeting with, or this is, like or are they qualifying, and labeling the like, the depth of their relationships? So a a good buddy of mine is, Ziv Pallet, and

Reanna Dempsey:
Oh, I listened to that one.

Josh Schachter:
Oh, yeah. I listened to that

Reanna Dempsey:
podcast episode. He was great.

Josh Schachter:
Yeah. Ziv’s awesome. And so, I mean, he’s built this amazing Looker dashboard. And if you ever wanna see it, like, Ziv is so proud and so boastful. Oh my god. Oh my god. He will show it off, like like, anybody that asks walks down the street. Hey, Ziv.

Josh Schachter:
Can I see your Looker dashboard? So, you know, anyways, he he he’s a good friend. So, he he asked his CSMs to, like, rate, you know, for each each of the stakeholders in the customer side. I think it’s, like, 1 through 5. Like, one is if I messaged this person, they would get back to me immediately. Or 2 is if I messaged this person, they’ll get back to me by the end of the day. 3 is by tomorrow. 4 is sometime this week. 5 is not at all.

Josh Schachter:
Like, literally down to that level. Do you have like, how are you at what what type of information are you asking from, of your CSOs?

Reanna Dempsey:
I love that idea, and I I would love to get to that level of maturity. So we basically, are they identifying system with the first step, which we had this year. This was sort of brand new where we’re like, we need to make sure because, again, you can’t just go by title. We wanted to be able to identify who were the right people even if it’s not c level that would qualify as executive.

Josh Schachter:
Right.

Reanna Dempsey:
From there, we build out reports. So for instance, for enterprise, we would expect that once every quarter. Now that I’m leaning towards 6 months, honestly, but we we once every quarter, we have some sort of engagement with an executive at each of our enterprise accounts. For mid market, it’s once a year.

Josh Schachter:
Yeah.

Reanna Dempsey:
So we’re saying annually, we would expect that we would have and that could we have all different activity types. So we the way we built the report is if it says CSR, EBR, or on-site meeting, or there’s a couple different it doesn’t count if it’s just like that person attended a webinar or that per again, we send an email to that person. And we don’t even count, did they email us back? That’s not engage you could be that could be a meaningless email that has nothing to do with the partnership. But I think that’s the next phase of I I do wonder how you keep that up to date because that whole state

Josh Schachter:
but Oh, there’s an app

Reanna Dempsey:
for that. Is outlooker? I

Josh Schachter:
No. No. No. It’s in your call.

Reanna Dempsey:
Updated AI. We’re trying, Josh. We’re trying. Listen. I

Josh Schachter:
I know. We’re working through the AI board review. I know. Yes. I know. I was asking about that.

Reanna Dempsey:
QBRs this week, and it’s I just want you to know it’s a talking just I’ll show you how I wove it in.

Josh Schachter:
No. No. I appreciate it. But by the way, like, so so we I I speak to I speak to hundreds of prospects. Right? No. I speak to thousands of prospects. My my pipeline is is huge. Right? Anyways Millions.

Josh Schachter:
No. No. But but Millions of prospects. Reanna is the only company that I’ve heard of so far that has a an AI board review, which I thought was super cool. Mhmm. Like, they actually have, like, assembled a group of leaders that go through, and they they have, like, a framework and a government governance and all this stuff. Like, it’s actually the most mature review of AI that I’ve seen from any companies. So kudos to you guys for for stepping that up.

Josh Schachter:
Okay. Anyways, our podcast producer, Manali, who I love, has asked us to please keep, a a finite number of of minutes on these recordings because it increases the the listenership and the lack of drop off on our episodes. Also, I think because we don’t pay her for more than that. So I

Jon Johnson:
think it’s more that we only have Meredith at 35 minutes of audio a week.

Josh Schachter:
Is that why she

Kristi Faltorusso:
tells me to cut down my episodes?

Josh Schachter:
Well, no. She just thinks she talk too much. So, she also does Christy’s, She’s So Sweet, which is an amazing podcast that I’ve made.

Jon Johnson:
Very kind, John.

Reanna Dempsey:
I have Davolph. I have Davolph.

Josh Schachter:
Yeah. Well, anything with Christy is amazing. So I guess that’s the abrupt end because now we’re at 36 minutes. Yes. Way to way to monologue our way out of here. Wow, Josh. That was

Jon Johnson:
worse than my opening.

Josh Schachter:
No. No. No. No. No. No. No. Everybody going around.

Josh Schachter:
This is like Heads up. This is this is meet the news. This is meet the press. Right? You all get the 30 seconds overage, right, while the producer is in the person’s ear saying get off the air. So, John, you first. You get your 30 seconds.

Jon Johnson:
What what? About happy Say goodbye. Monday. I love

Josh Schachter:
you. Okay. Christie?

Kristi Faltorusso:
Okay. Rana, thank you so much. I I’m gonna do a follow-up with you, though, because I do have some more questions on the executive engagement piece because I’ve done some analysis on the EBR, QBR process, and I wanna dig a little bit deeper with you since that’s something that you guys do. And it seems like it’s successful for you.

Josh Schachter:
Rhianna, give give a give one last gold nugget.

Reanna Dempsey:
Topics, Christy. So, yes, please. Let’s do that.

Josh Schachter:
Yeah. I love the topic too. So what’s the last golden nugget you can give give our our fans here, our raving fans, about executive stakeholdership?

Reanna Dempsey:
Executive stakeholdership. I would also say just don’t give up. I feel like sometimes you try to reach out to someone, and you’re like, well, I tried. There’s a lot of ways of of reaching out to people and use your your internal execs to help. That would probably be my golden nugget at this point and eat Reese’s, pumpkins.

Josh Schachter:
I think that Reese’s pumpkins. There you go. And I agree with you, by the way. Like like like, executives are not as, off putting or whatever as you think they might be. Right? They want they they wanna be engaged, so don’t be afraid to reach out. Like, it’s not they don’t bite. That’s that’s my last.

Reanna Dempsey:
But also don’t waste their time. Right? Have some good stuff to share with them. Because if you engage them and you waste their time, they’re never gonna talk to you again. So that’s that’s probably another podcast episode.

Josh Schachter:
Thanks, everybody. Have a great day.

Kristi Faltorusso:
Thanks, guys.

Reanna Dempsey:
See you, guys.