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We Started Out Friends featuring Reagan Helms

Released on MAY 23, 2025

20 years ago, American Idol winner, Kelly Clarkson, blanketed the airwaves with Since U Been Gone. The song explores the aftermath of a now-ended relationship. While break-up songs often express longing, regret, and sadness, Since U Been Gone is a realization of how much better things are now. It also expresses the feeling of finally recognizing red flags that have been in plain sight for a while.

These feelings are not exclusive to romantic relationships. People get emotionally connected to software they use at work all the time. And sometimes, they start rethinking their commitment, especially when the relationship feels one-sided. Reagan Helms has led Support at Planning Center for 15 years and during his last appearance on the show during Season 2, he compared his relationship with his support platform to marriage. But recently, that relationship soured and he’s moving on.

  • Warning Signs in SaaS
  • The Migration Dilemma
  • Vetting New Solutions
  • AI That Actually Works
  • Preparing for Change

Connect with Reagan on LinkedIn

Music courtesy of Big Red Horse

Transcript

Rob Dwyer (00:02.034)
Hey, we're back for another episode of Next In Queue and we're back with another returning guest. Back on the show after a two plus year hiatus, Reagan Helms. Reagan, how are you?

Reagan Helms (00:16.814)
Good Rob, good to be back. That's surprising that it was two years ago, but.

Rob Dwyer (00:22.64)
almost two and a half, that's how long it's been. And so when I talked to you the first time, you were at the same company, but in a different role. You keep moving up. You started at Planning Center as the first support person that they had. And what are you doing today there?

Reagan Helms (00:42.11)
I am the Vice President of Customer Experience. So I report directly to the CEO and I have people under me that manage the different arms of that side of the company.

Rob Dwyer (00:54.28)
Look how far you've come, like 15 years and you've been rocking and rolling ever since you got there. Last year, I read that your organization responded to nearly 150,000 support tickets. That's pretty incredible.

Reagan Helms (00:56.92)
So.

Reagan Helms (01:00.557)
Yeah.

Reagan Helms (01:16.526)
Yes, yeah, we have a lot of customers and a lot of different products. So yeah, not necessarily a bad thing in relation to how many people use our software. That was a pretty small amount of people.

Rob Dwyer (01:22.803)
Yeah.

Rob Dwyer (01:30.11)
Yeah, absolutely. So when you joined the show almost two and a half years ago, I distinctly remember you comparing your relationship with your support platform to a marriage. Today, I wanna talk about divorce. So you are actually in the...

Reagan Helms (01:47.744)
Yes.

Reagan Helms (01:53.642)
All right, looks good. I'm ready.

Rob Dwyer (02:00.026)
in flight as it were in kind of moving away from the platform that you've been using for I think probably more than a decade, right?

Reagan Helms (02:10.306)
Yeah, we started using the platform, which we're intentionally not trying to, you know, besmirch anybody's name necessarily on your podcast. but we started using our support platform, our help desk about six months after I came on at the company. So it's been about 15 years, 14 that we've been using this, this software.

Rob Dwyer (02:31.518)
It's a long time. So you made it past the seven year itch. But apparently, they're... Okay, well, that's good to know. Let's talk about some of the early warning signs. Maybe some of the things that kind of popped up along the way that made you think, maybe, maybe this marriage won't last forever. What were some of the things that jumped out to you?

Reagan Helms (02:35.327)
Yeah, think things started getting itchy around that time, but

Reagan Helms (02:59.886)
I think acquisition is always a telltale sign that things might be going a way that is contrary to what you're used to as a customer. Under new management is always a can be troubling. I think we saw support really decline. So, you we used to be able to get on a chat with agents, get response times similar to ours.

when we wrote into their support. and then, think rep turnover is another one, you know, especially, more enterprise organization. You always get a sales rep. mean, I've had probably 10, you know, about one a year, if not, less frequently than that, that they're turning over. and those are frustrating because it's like, I don't want to invest anymore of my time to get to know you.

I don't really need to know you. I know what I need to do. I've been using the software for a long time. those were some of the signs. And then I think obviously like features that have existed for a really long time or that you know don't work as well and they just haven't been addressed. Or when you ask about them again, they're just like, yeah, well, you know, send it up as a feature request or we'll let you know. We'll talk to our product team about it. And then features that you don't think are necessary.

are coming out, right? Because again, with that acquisition and things, they're trying to please investors with AI solutions or things that don't actually work for their real life customers.

Rob Dwyer (04:38.3)
It strikes me that it has to be particularly frustrating for you as someone who's involved in support and has really built a career around support. And this is the primary platform through which you deliver to feel like you're not getting the same kind of support for that software that you use to deliver. Can you tell me a little bit about that?

Reagan Helms (05:05.76)
Yeah, I mean, it's frustrating when you're paying six figures for any software and you don't get good support for it, you know. So we've had a recent interaction with them that took about three weeks to hear back from them on as to why a particular feature or solution wasn't working. so yeah, I mean, I, you know, I have, I have pretty high standards for my team and what I expect them to be able to do, but I don't.

I try to not let those be unreasonable standards for other people, but I think any software where you're that amount of money and waiting that long to hear back is pretty unacceptable.

Rob Dwyer (05:46.622)
Yeah, certainly it's going to lead to you maybe looking elsewhere. So as you start to see those signs, you just brought up how much you're spending. Like How much is cost a factor? Or is it simply my expectations exist because of the cost? do you have you

Reagan Helms (06:13.121)
Yeah.

Rob Dwyer (06:15.418)
looked at other options simply because they might be less expensive?

Reagan Helms (06:20.406)
Yeah, that's a good question. mean, on one hand, you know, we have 50 agents or 50 people in the CX department that use that software. So it's going to be a high sticker value regardless of where you go. But I do think it makes you question what are we actually getting for this amount of money and being CX minded.

the customer experience is a big part of that conversation. I don't think it's necessarily even that when you're factoring in costs that you should just factor in what you're paying that software, but also factor in what it takes to move, right? What dependencies you have on the software that you're currently doing and how much manpower you've invested in that.

yourself or as a company and how much manpower you're going to lose, productivity you're going to lose in learning a new system or even in building out a new system. So the sticker price was definitely something that made us scratch our heads and make us start looking at other places. typically, well, not always, but you typically get what you pay for. So if you're looking at cheaper solutions, it's typically because they aren't as full bodied as what you're

you're currently on if you're paying a lot of money.

Rob Dwyer (07:39.944)
Yeah, there is definitely just like a car, right? There is a difference in the features that are available, the fit and the finish that you can expect, the difference between kind of the lower tier brands versus the luxury brands. That said, the ideal situation is they've got four wheels, an engine, and a steering wheel. Get you where you need to go. The question is,

Reagan Helms (07:52.472)
Mm-hmm.

Rob Dwyer (08:09.626)
What's that journey like when I'm traveling and I may be willing to pay for more? Maybe I need more room. So you've got 50 agents. That's a pretty decent amount of people. Maybe I need more room than a lower cost option might be able to support. So I think those are all really good points. But you bring up something else, which I think is what keeps a lot of incumbents in place.

Reagan Helms (08:16.248)
next.

Rob Dwyer (08:36.702)
And that's the headache that is coming with migrating. And whether it's a help desk solution or a CCAS solution or really any platform that you are using in your business that a lot of people use in one way or another, there's a migration effort and there's a training effort. So let's talk about, and they both go hand in hand, but let's talk about the migration.

piece. Tell me a little bit about kind of what you expect as a lift when you make this migration. Like what is that going to cost you productivity? How many people are going to be involved in?

Reagan Helms (09:21.014)
Yeah. Well, that was the primary thing that kept us from looking for a long time is that we're like, we've been with this company for over a decade. We've got internal tools that we've built. We've got internal integrations that we've built. We've got integrations on integrations with other things that we have going on in the company, our entire bug process, our feature request process, our QR QA process. Everything is married to this system. Right. And so it was just kind of a non-starter.

for a very long time of like, we could never do that because X, Y, and Z. And I think that once we had kind of broken the seal as it were on this conversation and moved past that initial block of we could never because we started listing out, you know, what do we actually have to solve? What do we actually depend on for this provider?

to do versus what can we just move from somewhere else? Because if using, if you've built a lot of integrations, then you just change where the API is pointing and where it's piping data, especially things like Zapier. And as we started listing out those dependencies, we realized that a lot of the things that we thought we were relying on our help desk for, we had either built something ourselves because it was unreliable or,

that it wasn't as big of a lift as we thought it would be to move those things. It's kind of like a car. I like the car analogy a little better than the marriage analogy, just because I think my wife might listen to this episode. So let's stick with the car analogy. it's like when you've had a car for a long time, like, well, at least I don't have a car payment. You're like, yeah, but you also don't have a reliable vehicle.

You know, like if my brother in New York said, I need you out here next week to help me with a funeral or something, I don't trust that I can take my car to get there. know, that it's not gonna break down in Milwaukee as I'm trying to get there. Or that the stereo doesn't work. You know, I remember my first car, it's like so old, it has a tape deck. And eventually it just, you have to get one of those tape things that you stick in there that, you know, connects to your iPod.

Reagan Helms (11:44.556)
and then eventually eats that tape and you can't get the tape out, you know? It's one of those things where it's like, well, I've just learned to live with this for a long time. It's a little inconvenient, but at least I have a car, you know? And I think that the real question is, do you want a not, do you feel like you deserve a car that can get you from point A to point B on the continent? Let's just say not just going to the grocery store, but on the continent without fear of not being able to get there? Or do you want a car that you can...

be comfortable and have some AC and have some tunes to listen to while you go there, wouldn't that be nice? And so I think that once you break that initial seal of what other cars are out there, you can start to figure out what do I actually want in a car and not just does this car transport me around in different places. I mean, you could use...

I talked about this in our last episode too. You could use Gmail for a ticketing system. It's not going to do a great job, but at least it's free, you know, or at least, you know, you're paying just, you're already paying it for it in your business plan. That's not the best solution for, you're going to lose productivity in other places by, by popping out with that, you know.

Rob Dwyer (12:44.52)
Yeah.

Rob Dwyer (13:01.66)
Reagan, you have perhaps unknowingly made me feel a little bit old in comparison to you when you're talking about this device that you plug into the tape deck. Because when I was plugging in a device to the tape deck, same thing. It was connected to a Discman, not to an iPod.

Reagan Helms (13:26.164)
right. There you go. I had one of those too. And you had to have the Discman that had the anti-shock thing so that it didn't get through. Yeah.

Rob Dwyer (13:33.916)
Yeah, absolutely. Joe, I got to ask, what was this first car? What was your?

Reagan Helms (13:40.43)
Oh man, I had a 1992 Ford Explorer. I paid $1,500 for it. It was the same week that I got my first job. It was parked right outside the building that I was working in. And I felt so proud that I could drop, just pay for it outright. And I paid for that car every month for five years in random.

Rob Dwyer (13:44.514)
Mmm.

Reagan Helms (14:08.91)
fees, whether that was a $200 clinking sound or a $2,000 transmission skip, it was fantastic.

Rob Dwyer (14:18.734)
I had an 86 Cavalier that had a droopy headliner. That was great. Yeah. Yeah. Yeah.

Reagan Helms (14:23.598)
Oh yes, the glue just kind of goes away and then eventually it rips like a pirate ship and you know it's hanging in your face. Yeah, I had a lot of friends that had those too.

Rob Dwyer (14:30.942)
But it had aftermarket American Racing rims on it. you know, zoom, zoom. That's what I did in my Cavalier. OK, so.

Reagan Helms (14:38.327)
Nice.

Rob Dwyer (14:45.392)
You've gone through this effort of recognizing, hey, maybe I can look at some other stuff out there. And so I imagine you went through a process of going, we'll just keep the analogy going, going to different car lots and checking out what was available. Talk to me about that vetting process. And in particular, I'd like to know like,

How much time did you spend on websites? How much time did you spend talking to maybe peers and other organizations that are using different solutions? And how many demos did you sit through? What was that like?

Reagan Helms (15:29.056)
Yeah. Switching back to the other analogy, it was less like a car shopping and more like the cheating boyfriend meme where I had a competitor that I had been looking at for a little while and going, maybe someday that would be so nice to be able to switch to that. So I didn't do a ton of shopping around. mean, outside of, you know, I think someone in my role.

Rob Dwyer (15:39.144)
Ha

Rob Dwyer (15:46.706)
Ha ha!

Reagan Helms (15:57.248)
you're always kind of looking at what what's everybody else doing, what solutions are they coming up with. So, you know, there's some leaders in the space that I have. I love their I talked about this on our last episode to like help scale. I love their blog. I love their content. I wasn't sure that they would be a good solution for what we were doing at scale for a few different reasons. So there's not that was one example of like something like I don't really think I want to go with that. Right. There's some things that

just kind of ask you, if you're curious and you're just kind of always looking around at what's out there and available, there are solutions that present themselves or that you go, obviously we could never do that because this is how we do it over here. So there was really one competitor that I was kind of serious about and that I had seen other people talking about moving to that just seemed more in line with what our needs were as far as flexibility.

as far as where they're implementing AI, the places that I see them doing that, and the people that are joining the company that I see, either through an acquisition or through just LinkedIn. That I'm like, oh, I actually respect that person in the space as a thought leader or as an expert in AI.

And so the fact that they're joining the company leads me to believe that company is going places with those types of solutions, as opposed to the one that we were with just piping out AI pipe dreams to people at an enterprise level at a giant keynote. And then, you know, you go to hook it up and it doesn't actually work or do what they say it's going to do. so that was one part of it. As far as like the time invested, that's still ongoing. So, you know, we

We went through the initial demo process, talking to a rep, seeing they had a meeting with us to get info about what solutions were we looking for in their software. And then they gave us a running demo a week later in an hour long meeting about here's what it could do based on what your requests were. But that just ultimately left us with more, just more questions of how do you set that up or what happens with that.

Reagan Helms (18:13.548)
Right now, I would say we've probably invested probably 120 hours or so between me and my ops guy. And we probably have the next two months at least to kind of go as far as getting things moving ready and coming up with internal solutions to some of the hanging problems that are left over. Like for example,

in our old help desk, we're hosting documentation with them. Moving forward, we'll probably just be hosting documentation on our own, right? So that's a whole other moving piece that ultimately is probably a lot easier because we don't have to like port it over one to one, but it's also harder and like, okay, well now we have to host ourselves and I have to have these internal conversations with the head of our design team or the head of our marketing team who hosts our...

our main domain or marketing site, you know. So just those types of things, I think.

Rob Dwyer (19:10.942)
It makes me wonder how much re-imagining of how you support and the structure of things you went through. mean, obviously you talked about going through these dependencies, but here's a situation where you're like, okay, but this thing we're going to have to do differently. And I wonder how many different things did you go, well that will be different.

And it could potentially be better if we stop doing it the old way and start doing it.

Reagan Helms (19:47.278)
Totally. I'd say we're up to probably 10. 10 things that I've found in this new system that either I had a solution for in the old system that was janky. And again, we lived in that old system for 15 years. So some of those things, was like there just wasn't a feature for that or there was and it just didn't do it quite the way we wanted to. So we built our own solution for that problem.

in the new system, you know, and again, it's kind of moving houses. We've got three analogies going on, but they're all kind of related. You typically when you're getting divorced, you need a new car, you need a new house as well, but maybe not a new one, maybe a used one, but that so in moving houses, you know, you can't just be like your floor plan is going to be different. your kitchen is going to look different. your bedrooms are going to be in different places, different sizes, closets. So it's like

Rob Dwyer (20:27.528)
Yeah, all related.

Reagan Helms (20:46.926)
What things do we have and where will they fit in this new place? And also what things do we not need anymore because we have this new place, right? And I help customers with this all the time because we have a similar thing where we have customers moving from another solution to us and being able to have that conversation of like, hey, you don't have to keep doing things the way that you were doing them in this old place. You can reinvent the way that you do things or.

cut a lot of the things that you were doing. So let me just give you an example. In our old system, we kind of work from an open inbox process on our support team. And so in the old system, one of the concerns is like, hey, if somebody's out sick or has to step away for a longer amount of time than just an ordinary lunch, we don't want their tickets to go stale. We prioritize reply time.

on our team. And so we built this whole automation system of, know, when the ticket is X minutes old, add this tag to it. And when the automation runs again in an hour, I'm sure that people who know, they can fill in the context of what system I'm moving from. But automations only run every hour. So first hour that it runs, add this tag to it. Second hour that it runs,

remove the tag from it and kick it back to the inbox for other people to be able to see it. In the new system, they're just like, you can just say, I'm out of the office now and any replies to tickets that are in your inbox get sent back to the inbox automatically. So it's like, I don't need any solution for that anymore. In fact, they have an API where I can hook it into Rippling, which is our out of office stuff. And so I can just set their schedule.

based on them logging their time off with their manager, which is what I would prefer. Right. So I don't have, can make, I can not only not do something, I can optimize it so that it's easier for our team without having to do a log things in two places, you know? So those are some examples of things that like, just, life's going to be so much easier when you move. It's just paying for it now.

Rob Dwyer (22:43.484)
Yeah.

Rob Dwyer (22:50.94)
It's always nice when you can simplify existing processes that are tangential to really the central thing that you're doing. And I love that you're going to be able to just move those tickets to Next in Queue with someone else. So I love that you brought up AI and

Reagan Helms (23:10.062)
Thank you.

Rob Dwyer (23:19.58)
It's interesting to me that you talk about a solution implementing AI in places you go, well, that just doesn't make sense to me. And another solution implementing AI in places where you're like, yes, I like this. And I think this is something where lots of companies hear, we have AI in our solution. And that's pretty much every solution these days.

how it's implemented makes a huge impact on whether or not it's usable for your organization. I'd love if you could illustrate some examples of kind of the flavor of AI that you go, okay, great, but that doesn't help me. And a flavor of AI that you're excited about being able to utilize.

Reagan Helms (24:08.386)
Yeah. Well, I think when most people, I think the developer joke is most AI is just if-then statements, right? Which we've kind of had in place for a long time. if you, if you know where to look. So I think that a lot of, a lot of the AI I'm talking about really is just better if-then statements. So in the old solution,

they're wanting to charge us to even turn on those if-then statements. And it's gonna be anywhere from an increase of 50 to 100 % of what we're already paying them. Yeah, significant. And this new system, they just give us those for free because they're like, well, that's just a feature we give to all of our customers. So again, just difference in how you're thinking about a thing. The if-then statements I'm talking about are like, for example, you can create rules that are

for like heightened language, right? Swearing, triple exclamation points, just string recognition. But then you can apply tags to those tickets that either notify the manager automatically or just CC the manager automatically so that they can get a report of those later or do more significant things, send them to a particular agent or a success team instead of the support team, that type of stuff.

And again, that used to be available in our old system. You could do string recognition. And I'm sure there were for many reasons it broke at an enterprise level. You can't do string recognition on 500 strings for a single trigger. But instead, they're like, well, you can just have an AI agent automatically reading all of your tickets and then making decisions for you based on this black box that we've designed from all the customer.

research that we've done. And I'm like, that's not what I want. What I want is to be able to customize the rules for me. And I want to be able to do that because that's what a help desk should do, not because I'm paying you an extra 50K a year for that. And so, um, so That's just one, one example of like the AI I'm talking about. think the other one is like AI that can, um,

Reagan Helms (26:24.936)
That's obviously like LLM type stuff, recognizing things, helping agents write better, writing according to a particular style guide, doing QA. like, you know, tagging tickets for managers to look at or flagging particularly problematic.

interactions, depending on either your reply times that you set up or the number of back and forths that you recommend or any of those types of things. Again, it's kind of just keeping your ear to the ground and seeing what are other, how are other people implementing these things? And also are they putting them behind another pain wall that I then have to add? or are they just giving this to everybody because they believe in the solution that much that it's just in their bottom line and not, you know,

extra.

Rob Dwyer (27:14.022)
Yeah. I love that you brought up just because I had this conversation actually earlier today with someone else and it's thinking about in particular customer facing AI and some of this autonomous action that a lot of companies are touting as this is the real value add that we can just automate these things. And I do believe

that there is probably some value in that, but it does take away accountability. And you mentioned the black box. And I think that is the part that a lot of us really worry about is when the AI does something that you go, whoa, whoa, whoa, that's not the right process. It's really difficult to understand what the decision making was.

Reagan Helms (28:02.798)
Thank

Rob Dwyer (28:10.33)
If I'm using robotic process automation, kind of that then that you're talking about, it's pretty easy for me to identify where in that flow things went wrong so that I can go in and just fix it.

Reagan Helms (28:20.524)
Mm-hmm.

Reagan Helms (28:23.875)
Yeah.

Rob Dwyer (28:25.042)
But AI is a little bit different. And the fix is not as black and white. And it's hard for me as a leader in an organization to know what I need to do to fix it when it does go rogue. that is, I'm not a doom-sayer or anything like this. I believe that AI is

Reagan Helms (28:43.437)
Yeah.

Rob Dwyer (28:54.12)
going to make significant impact in our industry. But I do think it's important for people to think about exactly that. Like, who's making this decision? What data has this been trained on? And how do I know that that aligns with my brand and how we would handle things in an ideal situation?

Reagan Helms (29:10.285)
Yeah.

Reagan Helms (29:15.532)
Yeah, and think everybody's solution for that is different. know, we all in the early days heard the horror stories of Canadian Airlines and, you know, Ford selling a guy a truck for a dollar, these types of things where it's just, you know, you get what I said earlier, you get what you pay for. If you are deciding I'm laying off a bunch of people and I'm just throwing an AI bot in front of customers, there are going to be consequences to that decision.

So I don't feel bad for those large companies having to pay out those lawsuits for those types of things. And similarly, I, and this is again, going back to the decision to leave, is that I think that there's, everybody has their own responsibility in this space for what do you want your customers to feel like. And in the old solution, it's using a term that I hate in the industry, I wish we would get rid of it, or at least I feel like,

the spirit behind it I think we should get rid of, which is like the term of ticket deflection, right? Here's how many tickets you can deflect with this AI bot that out of the box is trained on, you know, six billion customer interactions that we've had or whatever. I, as a customer, always know when I'm being deflected. And I have never once liked it. Like, because typically as a, now as a early millennial,

you know, I'm going to typically look for self-help before I even reach out to support. And so the fact that I have to then do, to pull out a John Mulaney bit, the robot test of like, have you actually done all these things that you say that you're doing, you know, is frustrating because like now I have to invest even more work before I can even prove that like I deserve to be here and deserve to be talking to your team and have a human on the line because I can't do this myself.

is frustrating. like, I'm not a big fan of that term or companies that prioritize that philosophy, right? And that's what seems to be the, the principles thing that's causing a lot of that disturbance in this space is that like, you know, customers know when they're being deflected, they don't really trust it. They just want to talk to a person. I think that there are more holistic ways to implement AI.

Reagan Helms (31:34.902)
in a flow to make it more efficient without having to like either let the customer know that they're being deflected. So as an example, you know, you could have a customer create a ticket and it, AI writes the response, but the agent proofreads it and sends it and ties their name to it. Right. And that's kind of how we're approaching things as a company is that we're saying it doesn't really matter how the work is getting done. As long as there's a person owning the work being done. Right. So the agent would be attaching their name to the ticket. I don't care if they

If they type that out, you know, I mean, it gets to an efficiency standpoint, right? Of like, you could write that out in a Shakespearean quill, make a picture of it, have AI transcribe it and then type it for you and then send it. That's no different than just cutting out all that first step and having AI type out a response for you in accordance with your guidelines, with the answer. And the agent goes, I've read that. That's the right answer. I'm going to click send, you know?

Um, it to me, and I think to the customer as well. So, um, again, it's just kind of a never on an AI topic and not a divorce slash car shopping slash moving topic. But I think that like, it's important to get, to get back to those analogies. It's important to tie yourself to something that you. You're in charge of your brand, right? And you're in charge of your customers and your team. And so you need to tie yourself to a company that.

Rob Dwyer (32:51.643)
Hmm.

Reagan Helms (32:56.29)
believes the things that you believe and is implementing them in ways that you want to see them implemented. And so again, just going back to those AI solutions, I think that that's the difference in those stances between those two companies.

Rob Dwyer (33:09.882)
You've given me a fantastic idea for a new solution, and that is Shakespearean support. And I don't think people appreciate Shakespeare as much as they should. And I think it would be great if not only were the solutions in a Shakespearean tone, but I think it'd be even better if they were. You could even.

Reagan Helms (33:12.535)
Okay.

Reagan Helms (33:27.586)
Thank you.

Rob Dwyer (33:37.744)
automate this with a robotic arm, like use the quill, put it on paper, and then mail it out to them. Go full on old school. Have it delivered by horseback. That way they will know that you really, truly care.

Reagan Helms (33:54.988)
That town crier stands outside your door. Yeah. You know, in that case, Rob, I think the three week reply time would have been an acceptable amount of time in that case. Yeah.

Rob Dwyer (33:57.66)
Mm-hmm.

Rob Dwyer (34:03.228)
Yeah, your SLAs definitely are going to have to change if you're going to go that route. So look for Shakespearean Support at a SaaS provider near you in the coming future. I'm predicting it now. I want to talk about really just one last thing before we wrap up, because we've identified some of these pain points.

We've identified at least how you went about vetting, and I know that you've been thoughtful in how this will move forward and what it's going to take. But I'm curious, what about this is keeping you up at night right now?

Reagan Helms (34:53.196)
Honestly, the thing that keeps me up at night right now is the excitement that I have. Right? I, I feel like the, my agents and my managers, they're going to have new solutions to problems that they've had for a long time. I feel like it's definitely, it's that feeling of like moving, you know, you're like, I get, this is my last night in the

old house. And if we're going to go back to the breakup analogy, once you decide this, I hate this, I don't like this, you get like so you're it. Everything is a problem, right? You're like, I've always disliked that about you. I've always felt like you do that to me. And now you I see it, I see you that to me. And so I think that like, there's just that excitement of like, change and hope.

Rob Dwyer (35:40.683)
Mm-hmm.

Reagan Helms (35:49.9)
like that there's like a solution that can get better. There's obviously like the, a little bit of anxiety in the sense that, I was just telling someone today, you don't want to rock the boat too much. You don't want to upend 50 people's day-to-day workflow. But again, you have to balance what parts of this have to change right now, and then what parts of this can change gradually over time.

because there are some things that are just going to be different. Like there's no, there's no one-to-one comparison. And actually, if you're starting with like a one-to-one comparison, you're just going to build a jankier system in this new way and then have to unspool it rather than just go, you know what? We just don't do that anymore. Okay guys, like we log our time off in Rippling, which is where we log it anyway. And I'm just going to magically bring it over into this new system for you.

Rob Dwyer (36:38.504)
Mm.

Reagan Helms (36:46.368)
If you wanted to set something in this new system, that's fine too. But most of the time off requests that you put are already in Rippling, so those will just come in automatically.

You we don't have to, you don't have to have a Q quarterback anymore or a backup person that watches out for you when you're out or all these things that we've built on our side. just have, we just, the system handles that for us, you know? So that, that part is gone. And how much more do we save by not having to have a person police these things or watch these things or, you know, appointed a person to do these things. So, that's the thing that I think is keeping me up at night right now is just all the ideas and excitement. And then also.

the prioritization of what things should happen first. Again, kind of like moving, you know, like we can't pack the kitchen up until we're ready to eat off of paper plates and order pizza, which we don't have enough money to do for an entire week. So you got to do that three days before, you know, you're doing like the beginning with the end in mind and backtracking it to be like, first order of business is this, right? And I think that that's the

That's the zone that I'm in right now. It's just curving my enthusiasm to be like, live in this box right now. This box is just discovery and curiosity and then figuring out, okay, how do I organize this mishmash of things in my brain to be like an order of action items? And then we got to start implementing those action items or pointing people over those particular areas, you know, so.

Rob Dwyer (38:16.786)
I do think the moving analogy is actually pretty good, right? Because there's both packing up, which to your point, kitchen is one of the last things I'm gonna do. And then there's unpacking, which is also gonna go in a specific order. As someone who just moved right after our last conversation, just within a few months, I still remember this pretty vividly, right? There is...

Reagan Helms (38:24.174)
Yeah.

Rob Dwyer (38:44.966)
a long process and there's the stuff that's just like, yeah, we can go ahead and pack that up now. I'm not going to need that for the next month. And then there are the things where you're like, no, no, no, that's, that's actual moving day. That's when that gets packed away. And then even within the moving truck, right? You might, me, be strategic about where you put things inside the moving truck as to like, what's going to be at the back of the

Reagan Helms (39:00.162)
Yeah.

Rob Dwyer (39:14.526)
it's going to be able to come out first, because those are things that I'm going to need through the process of unloading, unpacking, and then the unpacking part again. There are going to be things that I'm just like, no, no, no, that can wait. And then there are those things that's like, no, first night, I need to have these things ready to go. I am sleeping on my bed tonight, so the bed's got to be set up. That's happening.

Reagan Helms (39:14.562)
Thank

Reagan Helms (39:35.33)
Yeah.

Yeah, and if you have things that just live in the garage until today, then did you ever really need them to begin with?

Rob Dwyer (39:46.14)
Look, I don't want to have that conversation. I moved to a place with a lot more storage, so I didn't have to think about that.

Reagan Helms (39:53.23)
There you go. All right. As long as you don't have things that you're like, yeah, I'll just throw that in the garage until I find somewhere for it to live. And it's still in your house two and a half years later, you know.

Rob Dwyer (40:02.002)
Look, Reagan, still, there are certain things that may go on the priority list. I still don't have my shelves the way I want in my office. So those that see these fun things behind me just know there are more in boxes that are just waiting for a place to live outside of the box. That's a thing and it's been two and a half years. So.

Reagan Helms (40:24.046)
There you go.

Reagan Helms (40:30.07)
Yep. They're nice. They're systemic. So that's nice. Yeah.

Rob Dwyer (40:31.452)
It happens. Yeah, priorities. Reagan, if someone wanted to get in touch with you, maybe because they want to ask about the cool solutions that you have at planning center, maybe they're actually thinking about moving from their platform and they want to hear about kind of in a deeper level what went into your head and what things get you excited about other options that are out there.

Is LinkedIn the best place for them to get in touch with you?

Reagan Helms (41:04.45)
Yeah, if you want the dirt, you can reach out to me on LinkedIn or on Support Driven if you're in that community. I'm in a few of the like CX adjacent Slack communities, typically just at Reagan, typically the only person with my name or at Reagan Helms. But yeah, on LinkedIn, I'm Reagan Helms. You feel free to send me message. I'm happy to talk to you about it.

Rob Dwyer (41:25.278)
Yeah, well, veterans of the show, you know what to do. You can absolutely go find the link to LinkedIn and talk to Reagan, send him a request, tell him you listened to him on Next in Queue. And everybody should know by now about Support Driven. If you don't, go check it out, particularly if you're a support professional or you're considering getting into that world.

Or if you just want to get advice from people who live in that world, that is absolutely the place to go. So, Reagan, thanks so much for joining me today.

Reagan Helms (42:01.666)
You're welcome, Rob. Thanks for having me back on.