ALPS In Brief Podcast - Episode 88: The Value and Community of Bar Partnerships ft. Bob Paolini of VT
In this mini episode of ALPS In Brief, our Bar & Affinity Partner Strategist Rio Peterson sits down with Bob Paolini, Executive Director at the...
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Rio Laine, Director of Strategic Partnerships
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Posted on December 17, 2025
Transcript:
Hi everyone. I'm Rio Laine, the Director of Strategic Partnerships at ALPS Insurance. Welcome to our latest installment of the Alps In Brief Podcast. I am joined today by our Chief Financial Officer, Sara Smith, and she is also the president of the Montana Society of CPAs.
Her theme for her term as president is connection, which is a value that runs through both her leadership and her life. So at ALPS, Sara helps guide a growing company that's redefining what it means to lead with purpose. And when she's not leading finance teams, she's often on a mountain bike trail somewhere in Montana. So exploring new terrain, both literally and figuratively.
So thank you so much for joining us, Sara.
Sara Smith:
Thanks, Rio. Thanks for having me.
Rio Laine:
Yeah, it's a pleasure. I'm happy we got this chance to sit down and chat about all the exciting things you have going on, and I'm really looking forward to our discussion.
Sara Smith:
Yeah, me too.
Rio Laine:
Yeah.
So okay, let's start with your story, the beginning. What first drew you to accounting and being a CPA?
Sara Smith:
That's a great question.
When I was in high school, I took accounting and they taught the class with a packet, right? And it had the balance sheet and income statement and all the journal entries. And it was such a neat and clean process, and I really enjoyed that. But when I went to college, I thought, "I am much too exciting to be an accountant. I have way more things that I would like to do and this seems really boring." So I went the long way. I got my undergraduate in marketing and management and got my MBA, and then discovered accounting and pursued my CPA after that.
Rio Laine:
Oh, awesome. And did you kind of revisit that love of that kind of order and the balance sheet and all the nice orderly parts of it?
Sara Smith:
Yeah. I think the thing ... There's a misconception about accounting that it is very black and white. And in reality, it's really messy and it has a lot of shades of gray, which make it much more challenging than it looks on paper.
Rio Laine:
Yeah. Oh, interesting.
So before joining ALPS, you spent a lot of time working for a variety of companies, including Target and Montana Rail Link. So I'm very curious, can you tell us a little bit about that path and what eventually led you to ALPS?
Sara Smith:
Absolutely.
So I was an intern at Target when I went to college here at the University of Montana. It was such a fun internship. I mean, we just basically ran around that store and did whatever we wanted. And I thought, "Oh, well, if this is how the work turns out, then I want to join this team." And there weren't a lot of good job prospects when I graduated from college, so I moved to Colorado with Target and went through their store management training program, which was a lot of hands-on management, which was great. I really enjoyed it.
It wasn't long into that process though that I realized that this was not for me. Retail was not going to be a long-term career. And I utilized their program to pay for graduate school and I went and got into my MBA program.
So I did that for a couple of years, and then 9/11 happened and decided to move back to Montana; and had a friend of a friend that worked at Montana Rail Link and got in the accounting department there. And I didn't love it, to be honest. It was not my favorite place, mainly because of culture.
Rio Laine:
Yeah.
Sara Smith:
And so my advisor suggested that I try ALPS, and I've been there 22 years.
Rio Laine:
Wow. Yeah, it's true. I mean, culture is such an important part of a workplace.
And so in terms of ALPS, I mean, obviously the culture was appealing, but also is there anything else that made you feel like it was the right fit?
Sara Smith:
Yeah. I came in in a strange part of time in ALPS' history. They were on this really kind of creepy second floor and the doors were closed all the time, and it wasn't actually a very welcoming type atmosphere. And so I really found solace in the accounting department. They liked to have fun, they played jokes on each other. There was just a lot of laughing.
Rio Laine:
Mm-hmm.
Sara Smith:
And so that's something that I really, really enjoyed.
Rio Laine:
Yeah. Oh, that's awesome.
And I mean, there's still a lot of laughing at ALPS, which is really nice. I mean, now we're on a different floor and it's much more open and nice, so ...
Sara Smith:
Yes.
Rio Laine:
Oh, that's awesome. Well, we're obviously very happy that you're part of the ALPS team.
Sara Smith:
Thanks.
Rio Laine:
And you're a really important part of it. I mean, really, you literally make the numbers work, so ...
All right. So let's shift our focus a little bit and talk about the idea of connection and how that plays into your kind of leadership philosophy. You know, you made connection the central theme of your leadership this year kind of personally, but also at the Montana Society of CPAs. So I'm curious to know what inspired you to make that your theme?
Sara Smith:
So there were three things that actually fed into that. First was just from an organizational perspective, people weren't coming to things in person, right?
Rio Laine:
Oh yeah.
Sara Smith:
They were choosing the online option. And then my guess is they were likely multitasking, right?
Rio Laine:
Yes.
Sara Smith:
And so they're missing that opportunity to connect in person.
And then the second thing is the people that did come, you would go to a table and they'd all be on their phones. Right?
Rio Laine:
Oh yeah.
Sara Smith:
And so that is also very challenging. It's hard to connect when you literally have your nose in your device.
And then earlier this year, I was on a flight, and I had a woman sitting next to me and she started to talk to me. And I just wasn't sure if I was going to take the bait, if I was in that place to have that sort of conversation on a plane, and I ultimately decided, "Yes." And we had such a rich conversation and had a lot of connections about a lot of different things that I didn't anticipate, and I actually went and had coffee with her a few months later after she got back from her travels.
Rio Laine:
Oh, really?
Sara Smith:
And so if I had not said yes to that, I wouldn't have formed that new connection. And so that really has just stuck with me, right? You got to say yes in order to engage.
Rio Laine:
Yeah, absolutely. I love that.
I love that you made a new friend on the plane too-
Sara Smith:
Right?
Rio Laine:
... Because yeah, you never know sometimes.
Sara Smith:
Yeah.
Rio Laine:
I travel a lot and you're like, "Am I going to have this conversation?"
Sara Smith:
Yeah. Right. Exactly.
Rio Laine:
Yeah, yeah. I'm happy you did. That's pretty amazing.
So it sounds like kind of your approach to connection is the idea that it not necessarily comes from doing more, but from being present and kind of saying yes to that. So I mean, what does that mean for you in practice as a leader, but as a person? I mean, aside from saying yes to airplane conversations. Yeah.
Sara Smith:
Yes.
I think that one of the most important things is just not being distracted. And whether that means you put your phone away, you turn it off, you put it someplace where you can't access it, I think that's step number one.
Rio Laine:
Hmm.
Sara Smith:
And then you really intently listen with your whole person and try to understand what that person is really saying to you. I think those are the two things that I really try to take into practice. And it can be hard some days.
Rio Laine:
Yeah. So unplugging and active listening.
Sara Smith:
Yes.
Rio Laine:
Yeah. Both of which, yes, are definitely difficult, especially we live in a time when we're so tied to our devices and we're just expected to be available every second of every day, and yeah, that's a difficult thing to accomplish. So it's ... Yeah, kudos for making that a priority.
Sara Smith:
Right?
Rio Laine:
Yeah.
So in your role as kind of CFO for ALPS, how does that idea of connection show up in how you lead and make decisions?
Sara Smith:
Right. So I think one of the pieces of my job that is really important is building trust, right? You have to trust the numbers, you have to trust what the data that we're looking at is saying, and just the overall data set that you're looking at. And in order to get comfortable with the numbers, you have to be comfortable with the person, right? And you have to have that trust.
Rio Laine:
Yeah.
Sara Smith:
So I think building and establishing strong relationships with the people that I work with is the number one way to build that trust and connection.
Rio Laine:
Mm-hmm. Yeah, absolutely. And I mean, that is a really, really good point. If you don't trust the person, you're not so sure about those numbers.
Sara Smith:
Right?
Rio Laine:
Yeah. And when you're growing, the numbers are really important, so ...
Sara Smith:
Mm-hmm.
Rio Laine:
Yeah.
Oh, that's pretty awesome. I love how that kind of plays such an important role in your life, but also your leadership. Yeah, that's pretty great.
So let's kind of shift again. I want to transition a little bit and talk about growth and how connection kind of plays into that as well.
So ALPS has been growing pretty rapidly over the last few years, and growth can sometimes make it really hard to stay connected, particularly as we have more remote staff like myself and things move faster and change quickly. But it sounds like obviously for you connection is part of that formula for sustainable growth. And so in terms of kind of ALPs, what does sustainable growth mean to you, like financially and culturally?
Sara Smith:
Well, I think at the core of our business is we have to be financially stable and sound in order to pay claims and make sure that our insureds are in a safe place, right?
Rio Laine:
Mm-hmm.
Sara Smith:
And so I think that is at the foremost thought all the time is, are we financially stable, are we growing responsibly to help grow that base, and are we in it in the long term, right? I'm a big believer in long-term thinking, not short-term gains.
Rio Laine:
Yes.
Sara Smith:
And so in order to be sustainable, you have to think more long-term.
Rio Laine:
Yeah. And I love that. I mean, I've come from companies that have been in kind of hyper growth, they've grown very, very quickly, and it does tend to be quite shortsighted and really come at the cost of the people who are doing the work.
Sara Smith:
Correct.
Rio Laine:
And it makes me really happy to hear that we're thinking about it in terms of, is this sustainable for the long term? Because I think that's when you really find success, in that balance between financial success, building revenue, but also people success and culturally and having a strong company.
Sara Smith:
Absolutely.
Rio Laine:
Yeah.
So how do you and kind of the larger leadership team at ALPS keep that sense of connection alive as the company grows?
Sara Smith:
Yes. So I think the senior leadership team, we've been through some ups and downs, and so we have a really good, solid understanding of who we are and how we interact. We have a dedicated Teams channel that we joke and talk on, and that helps form that sense of connection, especially when people are traveling so much. It's hard, right? We're not always in the office together at the same time.
Rio Laine:
Yeah.
Sara Smith:
So that's great. And I think that also transcends down as well, right? Having just connection with your teams and building those cross-functional relationships is really important.
Rio Laine:
Yeah. Yeah, absolutely. And it's definitely difficult when everyone's on the go all the time and trying to stay connected to that central hub.
What's one kind of practice or habit that you think ALPS has embraced that's kind of maintaining that strong connected culture?
Sara Smith:
Yeah. I think there's probably different things in different departments that help kind of foster their own identity and culture, but overall holistically, I think that ALPS does a Coffee Talk every two weeks and that helps bring all the information together. We get to understand our employees a little bit better. We have an Employee Spotlight, we get to learn more about each other. And I think that only helps build that kind of connection.
Rio Laine:
Yeah. Yeah, absolutely. Yeah, I'm a big fan of the Coffee Talk too, especially when we do the Employee Spotlight, getting to see everyone's pictures of their pets and their family and the fun stuff they do.
Sara Smith:
Right?
Rio Laine:
Yeah. Yeah, absolutely. I think that's a really good thing that we do. Yeah.
So as a finance leader, how do you see connection influencing business outcomes, whether is it through collaboration, innovation, decision making?
Sara Smith:
I think it's everything.
Rio Laine:
Yeah.
Sara Smith:
I think the one misconception about finance is that we don't know what's going on in the business, but we know everything that's going on in the business. We have to. We have to understand the drivers and the levers that are bringing the numbers into focus and telling a story. So I think that collaboration between departments to get the story behind the numbers is really, really important. And so I think that's where we really serve our purpose, is storytelling among the different groups.
Rio Laine:
Yeah. And I find that misconception so interesting, because I mean ... I don't know, I'm a big true crime aficionado, but if you want to understand what happened, you look at the numbers, you look at the money.
Sara Smith:
That's correct.
Rio Laine:
What are they spending the money on?
Sara Smith:
Right.
Rio Laine:
That's how you know what's going on. So yeah, I would think that you'd know all the things that are going on.
Sara Smith:
That's right. You got to follow the pennies.
Rio Laine:
Yeah. Yeah, exactly.
Awesome. So okay, let's kind of shift our focus and talk a little bit more about your personal life and how you spend your free time.
Sara Smith:
Hmm.
Rio Laine:
So you've mentioned that you love to get out in nature and you love to hop on your mountain bike and sometimes be completely off grid. So how does that help you kind of reconnect with what's important? Like how does that help you connect with, I guess, the things that are important in your life?
Sara Smith:
Right, right.
Rio Laine:
Yeah.
Sara Smith:
Well, so part of the mountain biking pieces that I've done is bike packing, right? Where you go in the woods and the only thing you have to do that day is ride your bike. You have to get from point A to point B without crashing, keeping yourself hydrated and fed, and not have any animal encounters. But that's all you have to do, right? That is your job for the day. And that really puts things into focus and simplifies your outcome.
And so that, I have really appreciated because it really ... I mean, you could die out there, right? So you get hyper focused on what you need to do today and nothing else really matters at that point.
Rio Laine:
Yeah. And I guess that's a really good time to kind of put down your phone and to be focused, and to practice that kind of active paying attention and being aware of where you are in your surroundings.
Do you feel like that experience kind of teaches you anything in terms of leadership or how you approach it?
Sara Smith:
Oh, absolutely. I feel like there are lessons to be learned every time you do something like that.
As an example, this one trip I did this summer, we found ourselves lost.
Rio Laine:
Yeah.
Sara Smith:
And not really lost, but we had three different mapping devices. We had already gone 20 miles, we had to go 20 more, and what the trail was telling us, it just didn't sit right. It didn't seem right, right? And so one of the big decisions was what to do. "What do we do?" Right? "There's no one we can ask. We have no cell service. We are out in the woods."
And I think trying to make a decision collectively, and when that can't be done, just making a decision and sticking to it and doing it. Because inaction is also a decision and one that doesn't generally work out very well.
Rio Laine:
Yeah, yeah, absolutely. And especially if you're in the middle of the woods.
Sara Smith:
Yes. Exactly.
Rio Laine:
Yeah.
So it sounds like kind of mountain biking teaches a lot about obstacles and trusting your instincts and maybe builds confidence?
Sara Smith:
Absolutely.
Rio Laine:
Yeah.
Sara Smith:
Absolutely.
Rio Laine:
Yeah.
What was it that first drew you to mountain biking? Like how did you first decide, "I'm going to get on a bike and do this?"
Sara Smith:
Well, I grew up in rural Montana and I didn't have any friends that lived anywhere near me, and so the only way to get anywhere was to get on a bike. I had to ride three miles to see my closest friend.
And then as I got older, my brother and I shared a car, which also was not awesome, and so I could either ride the bus, which was not very cool when you were 16 years old, or I could ride my bike to school. And so I just started riding my bike and I haven't looked back.
Rio Laine:
Nice. Oh, that's awesome. That's awesome.
Whereabouts have you gone mountain biking? Is there one place that really stands out to you that was your favorite?
Sara Smith:
Oh boy. They're all so different.
There's a trail in Beartooth called the Line Creek Plateau, and you start riding at 10,000 feet and there's no trees.
Rio Laine:
Oh, wow.
Sara Smith:
And so it feels like you're riding on the moon. It's like all tundra.
Rio Laine:
Yeah.
Sara Smith:
The first time we did it, there wasn't much of a trail, and so the wisdom was, "Stay right. You'll know the end when you get there."
Rio Laine:
Yeah.
Sara Smith:
And so it felt very kind of mystical in this journey.
Rio Laine:
Yeah.
Sara Smith:
And then it drops to about 3000 feet in very short miles.
Rio Laine:
Oh, wow. Wow.
Sara Smith:
So it's a great ride. It's one of my favorites.
Rio Laine:
Yeah. Oh, that's awesome.
I love that kind of idea of like the mystical journey. It kind of sounds like your leadership journey too, right?
Sara Smith:
Right.
Rio Laine:
Like just moving through the world, like, "This is mystical, crazy times." Yeah.
Sara Smith:
Exactly.
Rio Laine:
So speaking of kind of like the leadership journey and lessons in leadership and life, you've held many leadership roles in that span; finance, kind of strategy. So I want to kind of talk a little bit about what you've learned along the way and really what you see for the profession ahead, I mean in terms of CPAs.
So I think my first question would be, how has your view of leadership evolved over time?
Sara Smith:
Yeah, boy. I think that ... That's a great question. And I think about how much you learn from people that you work for and other leaders. And so you take some of that in yourself about either what to do or what not to do.
Rio Laine:
Yes.
Sara Smith:
So that's been a big journey.
And I think as a young person, I thought, "Oh, you eventually figure it all out, right? You got it." And as you get older, you realize you never will have it ever and that the pursuit is constant.
Rio Laine:
Yeah.
Sara Smith:
You're continually growing and evolving as you go along.
Rio Laine:
Yeah, which is kind of a beautiful thing about life. I mean, it'd be kind of boring if you got to a point and you're like, "I have this all figured out. I don't have to think anymore."
Sara Smith:
It's probably just so much easier, but ...
Rio Laine:
Yeah, but it's-
Sara Smith:
[inaudible 00:18:00].
Rio Laine:
Yeah, but it's kind of fun that you don't. Yeah.
So kind of along that lines then, what advice would you give to leaders, especially maybe in a data driven or finance role?
Sara Smith:
Yeah. I think that when you look back at your life and you think about all the things that you've learned, most of that learning has come from making a mistake. And so giving yourself some grace when you do make a mistake. Just don't make the same mistake again, but really be willing to take a look at yourself, why you did it, and then how do you evolve to make it so it doesn't happen again?
Rio Laine:
Yeah. Yeah, that kind of personal accountability is really important.
Sara Smith:
Yes.
Rio Laine:
I think it's also something that's very difficult for a lot of people too. It can be a humbling experience to learn that you're not perfect and that you have to improve some stuff. Yeah.
Sara Smith:
Yes.
Rio Laine:
Yeah, that's really good advice. Yeah.
As the president of the Montana Society of CPAs, what do you hope to accomplish under your term this year, kind of in terms of connection?
Sara Smith:
Yeah. It's so hard because when you start this ... My presidency is only a year, and so you wonder how much you can actually get done. But then I also go back to my experience on the airplane and how just one small interaction can make a big difference.
Rio Laine:
Hmm.
Sara Smith:
And so I think that my challenge to our group is, "What kind of connection can you make? Can you make one connection this year that's new or different? How do you engage?" And my hope is by next year at our annual meeting, we have more people there, and more people talking to each other and I see less phones out.
Rio Laine:
Yeah. Yeah, absolutely. That's a good goal. It's a good goal to have.
And I know they say ... Well, a lot of professions are evolving quickly, but the accounting profession is definitely one.
Sara Smith:
Mm-hmm.
Rio Laine:
You know, technology, automation, new expectations. How do you think connection can help the profession stay resilient and human?
Sara Smith:
Yeah. Well, I think the one thing is, I was just at a conference with a bunch of other CFOs and there is a lot of hesitancy to allow an AI bot to tell us what the numbers look like, right?
Rio Laine:
Hmm. Mm-hmm.
Sara Smith:
And it's that fundamental question about trust again.
Rio Laine:
Yeah.
Sara Smith:
How do you get trust from something that's not alive and real, and how do you trust that number? And that's going to take some time, and you're going to have to have not accuracy of 60%, but accuracy of 100%. And we're just not there yet, but we're going to get there eventually. And so I think it's still continuing to build that trust one day and one person at a time.
Rio Laine:
Yeah. Yeah. Agreed. And also, I mean, AI can't even figure out how many fingers a human has. So I feel like it probably shouldn't be trusted to run the numbers just yet.
Sara Smith:
Not yet.
Rio Laine:
It'll get there, but yeah, not quite yet.
Sara Smith:
Yeah. Not yet.
Rio Laine:
Yeah.
So what is one piece of advice that you would give your younger self starting out as a CPA? What would that be?
Sara Smith:
Yeah. I think, again, I would come back to just being open to learning constantly and then not being so hard on yourself when you do mess up, right? I think early in my career, I took things really personally, and that's not ever going to work out well.
Rio Laine:
Yeah.
Sara Smith:
You have to forgive yourself once in a while when you screw up and just give yourself some grace.
Rio Laine:
Yeah. Yeah, I think that's really good advice. We could all use a little more grace from ourselves. You're your own worst critic, they say, so ...
Sara Smith:
Absolutely.
Rio Laine:
Yeah.
All right. So we've got just a couple more minutes. I'm going to wrap it up with one more question kind of tying into your theme of connection for this year. So how do you plan to make space for more connection in your own life this year?
Sara Smith:
Yes. You know, it would not be great if I set that theme and then I didn't do anything myself.
Rio Laine:
Yeah.
Sara Smith:
So a couple of things that I've been working on is just when I am going to conferences or meeting new people is being the one that says hello first.
Rio Laine:
Yeah.
Sara Smith:
Right? Which is hard for me.
Rio Laine:
It's hard.
Sara Smith:
I'm not a super extroverted person. And so taking that first step is one that's hard, but really important that I do it.
I've been reaching out to old friends that I haven't talked to for a long time, and that's been really fun to reconnect with them; and just having really good, deep conversations about hard things, I think is really important.
Rio Laine:
No, that's fantastic. And it is really hard to be the first person to say hello. For myself, I have a very public facing job and, yeah, it is difficult. You're just like, "Oh."
But it's nice to remember that everybody is probably feeling that way-
Sara Smith:
Exactly. It's so true.
Rio Laine:
... And they're so thankful that somebody did it.
Sara Smith:
Yes.
Rio Laine:
So it's good work to be doing.
Sara Smith:
Yes.
Rio Laine:
Yeah.
Awesome. Well, Sara, thank you so much for sharing your time and your insights. I'm really, really happy that we got to sit down and have this conversation, and it's really impressive how you've shown that connection isn't just a personal goal, it can be a leadership philosophy and a business advantage really. So yeah, I mean, I think from the trails of Montana to the boardroom, your message definitely reminds us that slowing down and being present often leads to the strongest momentum.
So yeah, thank you so much for joining me today.
Sara Smith:
Thank you, Rio. I enjoyed our conversation.
Rio Laine:
Yeah.
All right. And that's a wrap, folks. Thank you so much for joining us on this installment of the ALPs In Brief Podcast. We will see you again for the next round.
(Music).
Rio is the Director of Strategic Partnerships at ALPS. In her role she works to build flourishing relationships with legal associations across the United States, and works passionately to educate lawyers on the importance of using technology and data to build better practices and drive the legal industry forward. She is a regular speaker at bar events across the country delivering compelling CLE and other educational content that engages her audience with the information being presented. Rio lives on Vancouver Island in Canada.
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