
Jenn 00:02
It's all personal to me. It's my baby, like I've sacrificed so much personally for this, and this has afforded me so much personally as well. And so the blend to me is just, it's just my time. And you know, whatever is the highest priority in the moment, gets my time.
Leah 00:19
Hi, thanks for being here. And welcome to Season Two of The Founder Mindset, brought to you by ATB. I'm Leah Sarich, your host, and I'm super excited to talk to more founders about the human experience of being an entrepreneur. In this podcast, we're digging into what it really feels like to build a company from nothing. I was a broadcaster for over 20 years. So, I've interviewed thousands of people, but entrepreneurs, not that many, and yet they have the best stories. They're solving big problems, and they're creating an incredible impact. But it is hard work. So, why would they do this? Let's find out.
Leah 01:06
Joining me in studio today is Jenn Hunter, co-founder and director of operations for PayShepherd, a contractor management platform for heavy industry. Hey, Jenn.
Jenn 01:14
Hey, Leah.
Leah 01:16
Thanks so much for doing this.
Jenn 01:17
Of course happy to.
Leah 01:19
So fun to have you in the studio. Let's go right back to the beginning, as we do with all of these conversations, how did you actually get into entrepreneurship?
Jenn 01:27
I wouldn't have thought that I would be an entrepreneur. It definitely wasn't something I thought about growing up. But it wasn't something I was exposed to a lot. But a colleague that I'd worked with for many years had, you know, left the company that we were both at, and he was starting something and he asked if my husband and I wanted to invest. And so I actually got to kick the can without taking a lot of risk. I still had a full-time job, I didn't have to, you know, lose that financial security for my family. But I was able to kind of join the hustle and see what that was like. And it was a really great stepping stone for me to actually take it on full-time, which I would consider kind of the real baby as PayShepherd.
Leah 02:01
Okay, cool. So, you dipped your toe in the water with this first operation? And how did you feel about it? Even from the get-go? What did it feel like to you?
Jenn 02:10
I mean, it felt really natural for me like the hustle, you kind of like picking up the evenings and weekends, it was like really exciting to have like that new problem to solve and that new thing to reach for, and have it be a bit my own, you know, you always do that at work. And that's kind of what, you know, he probably saw on me and having it be something that we were working at for ourselves was really awesome. And that's how we started PayShepherd as well. You know, we worked really hard for 12 months, and it was a small operating margin, the cash flow was really tight. Wes was always in the field managing labour, it was super challenging. It wasn't conducive to like going off and having families of our own and things like that. So, we used that money that we made in that company and seeded the next venture that we had, which was PayShepherd.
Leah 02:58
So, let's talk a little bit about PayShepherd, right? What is it?
Jenn 03:00
PayShepherd is a contractor management solution, and we really digitize the workflow between contractors and their clients. And we're experts at the relationship between clients and their contractors, and what good looks like and it automates the contract compliance. So, you know, anything from post award to invoices paid and the relationship is being managed and performance metrics and who's going to be awarded the next job. That whole lifecycle is, you know, without PayShepherd, there's like no data flow, there's really thumb wags of what good looks like and costs that are coming in and no visibility. And so PayShepherd solves that gap in the relationship but provides the opportunity for the source of the information and the source of the data to share it back and forth with the parties that need it. And it is really a shared data source. And so now both parties have access to that single source of record and a communication tool to manage that relationship.
Leah 04:00
So, did you identify that problem that you wanted to solve this idea of digitizing this industry right from the get go? Or was it something that you sort of came to realize over time?
Jenn 04:10
On my side, it was always a problem I had seen and lived painfully from the vendors experience. So, you know, there's a lot required of a vendor from their payroll, their billing, administration, reporting progress, their own performance that they need to report to their client. And when that's not going well, you could waste loads of hours, like sitting in the office. I remember, you know, being in the office, five extra hours, one day a week, after everyone had left just looking for, you know, some formula error or some like data entry problem, because the numbers just weren't making sense and it's super painful. And if that relationship is not going well, it can get quite hostile. It's like not a fun environment to be around. And so we really wanted to set out to solve that people could invest the time where they could add the most value, and not waste time creating data, manually checking for errors and eroding relationships, and really invest in the good value and the work that they could be doing.
Leah 05:14
Interesting, and you're in heavy industry. So, for people listening, like what is heavy industry, what do we mean by that?
Jenn 05:21
Anything that you can, you know, drive by or look at. Smokestacks, or pipelines, or big facilities that have a lot of operations, you know, they require that skilled trade force of, you know, boilermakers and pipe fitters and electricians and things like that. It's really the bedrock of our industry, and it's not going anywhere, it fuels a lot of the Canadian economy. And it's a really exciting place to be, you get to build something from the ground up and like see it go to operations, and it's just a really fun place to be when it's going well, and it can be really not a great place to be when it's not going well, or when the relationship is eroding.
Leah 05:59
So, what does that look like? What do you mean by that? Like, how bad can it get? Like, give me an example.
Jenn 06:04
Yeah, well, I mean, when you're kind of building something, and it's, you know, way back in the back 40, or, you know, in really small communities, most people have to travel in. And so you work all day with people who are on opposite sides of the contract and opposite sides of the, whatever incentives they're working at. But then you also go home to the camp and you sit across the table from one another, or you are, you know, eating at the same restaurants, or you're having people over for dinner, and like there's all these different facets of those relationships that you have to navigate. And so it's not always the easy thing to do the right thing.
Leah 06:48
Right. Oh, interesting. And so of course, when everything's digital, then that's just removed?
Jenn 06:47
It removes the subjectivity. And the difficult conversation of I need you to do this. And PayShepherd really allows it to be well, the technology found this and let's have a conversation about it, or the corporation requires this of me, and now I need to have a conversation with you about it, or for your contract, this is the expectations and this is what you're accountable to. And the system does all that. The data tells the system and the system is advising people how to handle it and how to, like manage those decisions. Yeah, so it doesn't need to be like a, he said, she said, or I think this is happening. You're coming, and you're having that dialogue with the data. We just heard a really great customer call just yesterday. And so a quote that that person had was, they feel indebted to PayShepherd. PayShepherd had helped them save like half a million dollars because they didn't have to go to litigation with a contractor, and they could come to that conversation with data. And he said, I never like to go to my CEO without data. And I always go to PayShepherd to get my data.
Leah 07:48
Whoa, how does that feel to hear that?
Jenn 07:51
It feels incredible. PayShepherd does a really great job at letting customers know where the value is happening. You know, the system, it has that like audit record, and we can report on that, and it's part of our analytics. And so we are already, you know, having a dialogue with the customer about the return or the value to the vendors and the value to the customer and the users. But to hear somebody talk about a value that we didn't even narrate or, you know, we didn't even know that it escalated to that point, that's really powerful. And that's part of the impact that PayShepherd is making that we don't even realize sometimes.
Leah 08:28
So, and this is founder, I mean, you're building this thing. And you're really hoping that it's going to solve these problems and make life easier. So, when you hear something like that, what does that mean to you personally?
Jenn 08:41
Personally, it feels so validating hearing that I just love that story. The customer is happy, you know, they're delighted, you know that they're going to be a returning customer, it feels really awesome. But for me, the most exciting thing is when we talk to prospects, and they know they have this problem, they're super problem where they know that they're not looking at things, they know there's issues happening. And when they hear that there's something that can help them solve that. There's just like this lightning in them, and like a bit of relief, that's a really big human impact. They work really hard, they're working 12 hours a day, and they're just getting, do they need to do two more hours of paperwork before they make it home to their families? And, you know, often in peak periods they're working more than seven days in a row, could be like 14-21 days in a row to like do a major turnaround or, you know, be part of that critical path on a capital project. And just being able to give them a little bit more time back, let them know that every single piece of data is being checked and it's compliant. And you know, they don't have to comb through pieces of paper or bank service boxes worth of invoices after and potentially deal with litigation. That's, you know, what we set out to do and it's funny because as founders, you talk about these things, really early on. Some of the things we haven't even developed to the product yet, but we hear the customer still needs them. So, it's very validating that we really understood the problem, you know, six years ago, and before we even set out to build the technology, and we wanted to solve it, then. And it's still a problem now. It's really validating to say, like, you're on the right path, kind of like a deja vu moment, you're like, Oh, I've been here before, I'm on the right path.
Leah 10:19
That's got to feel nice, to get that validation. Especially because as a founder, and I know this, I've talked to founders all the time, you know, it's an uphill battle, building a venture. You know, it's like, a few steps forward, and a whole bunch back, and a few steps forward, and a whole bunch back. But to get that little piece of validation, it's got to be instrumental.
Jenn 10:37
It's very interesting. I often describe it like a roller coaster, because even in those moments, and I'm, you know, talking about this really, like, you know, brightly here, but there's always like the, okay, that's the problem we need to solve, and how are we going to solve it, and like, you don't get a lot of time to celebrate those moments. And there's always a few other problems or items that you want to solve for in the background. So, it's never really like, you're just getting to enjoy it in the day, you can experience that super high and the super low. And so I always share with people like a piece of my advice is like, don't do it alone, have like co-founders, have a team around you. And like, you know, trusted advisors, because it can be a lonely journey, never putting work down, always taking it home with you, always thinking about something that's going on in the background, because there's always things to solve.
Leah 11:24
Of course, there's always a problem to solve. Yeah, no kidding. Can we talk a little bit more about heavy industry and women in heavy industry? Am I right to assume that there are fewer women in heavy industry?
Jenn 11:36
For sure, it's a male-dominated field, I've had a really amazing experience. Personally, I've had great mentors, that were women in heavy industry. I’ve had great mentors who were men in heavy industry, but it is harder to find us. And I think that it's changing now, I see a lot more women champions, women decision-makers, and that's really awesome for us. But not a lot of people know, the difference between dealing with a male champion or a male decision maker and a women decision maker, like what's important to them is different, how they're going to make decisions is different. And that's a little bit of a piece that I bring to the perspective for our team. And I don't know all of the different perspectives that there are, but at least there's a little bit of more of a diverse strategy session when we're dealing with different types of personas.
Leah 12:23
For sure. Is it important to you to be a part of that conversation and be leading some of that change?
Jenn 12:29
I've never had to fight for it yet, previous organizations or here, but I do, you know, work with people who have had to fight for it, and they appreciate it a lot more than I do, because it's such a different thing that they perceive at PayShepherd. So, I really value that. We really value like fast conversations. And so, you know, I'm not saying that I've never heard something that I didn't appreciate, or, you know, find a comment to be, you know, biased or things like that. But I just have a conversation right away and be like, what was the intention behind that? Do you realize how that might have come across? And I hope it helps just bring awareness to people as they speak to others and how things might come across too.
Leah 13:10
For sure. That's where it starts with awareness. Yeah. So exciting. Okay, so let's talk about you as a founder, and you're building this company. And let's talk about the fact that you're building this company alongside you're building your family. We were just walking in here. And I was like, and how many kids do you have again? And you have three kids?
Jenn 13:29
I do, well, I have four babies. So PayShepherd.
Leah 13:31
PayShepherd is one of them.
Jenn 13:33
Yeah, I mean, just that whole history, the first time that I became pregnant, my husband and I had been trying for a while, just since before we had founded PayShepherd. It took a while for us. And so we never knew when it was going to happen. We had to keep trying, because like we knew we wanted to have a family. And then we'd been off the ground, probably for about a year, you know, getting some traction. Working really hard at getting traction. And then I'm like, Oh, what do we do now? And I go and tell my co-founder, and it was such a difficult conversation for me to have. He's like, congratulations, so amazing. Like, didn't fase him whatsoever. And I'm like, already, like we're trucking on. We were still the founding team at that point when I had my first and so I could navigate everything between naps, evenings and weekends. And in fact, I was even still working part-time for income. So, I was like, totally skilled at using every little piece of time that I had, and I got to be home with the baby. That was an interesting one because a customer that we had had at that time, we had closed a contract with them for like six months, and we were waiting for them to make the first move to execute on the project. And the paperwork came in the day I was in the delivery room.
Leah 14:41
No, how did you manage that?
Jenn 14:44
I, you know, had a conversation with y husband, he's sitting in the hospital room across from me and I was like, oh shit. This just happened. So, you're gonna have to take time off for the baby. So, he just took paternity leave. And we just figured out how many weeks he needed to take and you know, figure that out with EI, he took time off. And it's been, that's been like the basis of all of the success because dad knows how to do naptime. Dad knows how to, like manage the baby schedule, Dad's doing bottles. Well, my partner and I are travelling to the clients to deliver the results of this, and I'm pumping in the backseat, and we like don't look in the rearview mirror, you know?
Leah 15:22
I love this. Don't look in the rearview mirror, buddy. Wow, that's amazing. Okay, but you know, this is a funny story. We're having a giggle now. Okay, but I have had a couple of kids myself when you're in it. And you're in a moment, tell me what's going through your mind? Like, are you thinking to yourself, is this even possible? Like, can we pull this off?
Jenn 15:0
So, not with the first one, the first one was like, that was a pretty good breeze. And by the time we got super busy, like full daytime work, and that customer that we were working with was like implementing little one could go off to daycare. So, it was great. And then because we had to try for a little while, we weren't thinking it would be super easy to get pregnant again. But it was. And with the second, we had a customer in the pipeline who was moving really fast. And I'm like I am expecting and I don't know when this is going to close. So, it was like, I can't stop a biological clock here. I remember it was like around the eight-month mark and it was clear, they were going to close, and I was going to have this baby. And so I just had to get creative. And I went to my mom and I said, can you help us out? And so she retired early, she took a lower pension, and she moved in with us and took care of the baby. Now that was all like fine and dandy. I was back at the desk, 10 hours plus a day, within two weeks. And so it was a really big strain. But we needed to do it. I was the only person on the team at that point who was customer-facing implementation and delivery. And so we hired some help. And they joined all the trainings that I was doing. It was really great timing, they could listen to me, you know, do the training for eight hours a day, in and out. And then they took that part over and I was doing more of the like customer success and like working with the stakeholders and managing the project. We implemented that customer in four weeks, like a large cohort of their contractors, and they had over 50 million in spend through our platform in the first three months. It was an incredibly busy time. But it was also the time when I was like, What am I going to change here at home to make this sustainable because I was starting to get some postpartum anxiety. I didn't really realize that at the time, it was during COVID. So, it was bit normal for me to have a baby on like, you know, baby noises like on the camera while I’m training users and stuff. So, I was super thankful for that. But I noticed every day around like 11, I was starting to become like short of breath. And I would just like choke it back thinking that I might have a dry throat from talking all day, having water. And then it took me a couple months to realize this wasn't happening to me on the weekends. And I was like, is this a stress thing? I've never gone through anything like that before stress or anxiety. And then I had a panic attack in the middle of the night, while I'm feeding the baby. And I'm like shaking. And I'm like, I know that these hormones are going to be passed to my baby through the breast milk because it's actively happening and he's attached to me. How was this baby going to go to sleep and then I'm not gonna be able to go to sleep. And it's just like compounding, it was spiralling for sure. Luckily, I got the baby to sleep. And I was freezing. Like I had the chills. I was like super, in a weird state. And I like went in the hot tub at like four in the morning and just like calmed myself down long enough that I could wake my husband up, have a conversation and like decide to change a few things. It was a really interesting place to be. I think I also had like some health complications and you know, was dealing with fevers and like infection, basically. And so once I manage that, all of the issues went away. Like they tested me for like congestive heart failure because of some of the things they were seeing in my blood test results and a whole bunch of different things. And I realized that yeah, it was like a weird combination of postpartum anxiety, stress and like it's an infection and internal infection.
Leah 19:14
Wow. Yeah. And this is all happening and you're building your company, and you've got this little tiny baby?
Jenn 19:21
Early days, super small team, need to be at work every day. I remember was feeling so weird, like taking half a day off and like driving, you know, down to see a specialist like in Calgary and going to these like appointments and like being like away from my desk like it's a bit weird. Even now, it's a bit weird to be like I'm on a vacation day. And like I'm just not looking like it's you really have to retrain yourself at these different stages.
Leah 19:48
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Leah 20:12
Okay, so you know, the part of me that's not an entrepreneur is sitting here going, Okay, why would you do this to yourself?
Jenn 20:18
It's very interesting. Just seeing like, I've had a conversation recently of like, okay, well, that's personal. And like, this is professional. And I was like, oh, that's an interesting perspective. I was like, I don't have that. It's all personal to me. It's all my, you know, my baby, like, I've sacrificed so much personally for this. And this has afforded me so much personally, as well. And so the blend to me is just, it's just my time. And you know, whatever is the highest priority in the moment gets my time. So, there's not a clear distinction between like that professional hat and the personal hat. And I'm okay with that. I think I've always operated on that plane. And I look at work-life balance as like a lifetime. Not like a day or a week or a year, right? Like, what will my work-life balance be like in a lifetime? And so I'm hopeful that, you know, this business will afford me time back with my family or, you know, special memories with my family because of sacrificing a lot of the time with them as a small babies.
Leah 21:14
Thank you for sharing that. That's an incredible story. So, that's on the personal side, we could say even though you just said it's all personal. But is there also a moment for you when it comes to actually building the company itself, where you're thinking, this is the do-or-die moment? Like this is a pivotal moment in the building of this company, where this is a no goes or go situation? Like it may or may not work? And we just gotta go for it. Is there one of those when it comes to actually building PayShepherd itself that comes to mind?
Jenn 21:43
Wow, that's a great question. I think about like all the go, or no-go moments. It's so funny. It's always been around people.
Leah 21:53
Around people?
Jenn 21:54
It is around. Like, I think about everything in the perspective of the human. I mean, the product is designed to help the human experience and to help the relationships. And so, it's end users that use our product. And it's people who develop our product, and it's people who scope out the activities that the product is going to need to solve. And so, I always think about it, is it the right people for the time? Is it the right clients? How do we motivate those users or motivate these teams? And so that's the perspective that I always think about, do we have the right combination of people?
Leah 22:30
And how do you feel about making those decisions? Like do you know, okay, actually, this person needs to go or this person needs to change how they're working or engaging with clients, or whatever the case may be? How do you feel about approaching that situation?
Jenn 22:45
It's so embedded in PayShepherd culture, the product is about accountability, a transparency, like honesty, doing what's right, acting with integrity with, you know, going where the data shows you to go. Everything we talk about with our customers is feedback. Our anomalies, our contract compliance is all feedback. So, feedback with our team is super critical. It's very important, and it's fast. And so if team members are not activating on that feedback, or they don't want to hear the feedback, just like a contractor, we need to be accountable to the feedback for their contracts. That's how we, like really manage people within our team. And I would say that, as a founding group, we've attracted really incredible people to join the journey, super long standing relationships, the relationship always comes first. That's another like, you know, critical thing for the product and for our industry. And that's how we operate in the team. And we also, you know, just trust our gut. And so, we have a lot of those conversations around like, this just didn't feel right. And, you know, maybe we're not going to, you know, bring that person in the team, like, love them, got them all the way across, almost to the finish line, and like something changed the game. Like we really trust that intuition.
Leah 23:58
I mean, I've heard from people that it takes a while to learn to trust that intuition. Did you find that?
Jenn 24:04
Muscle? I mean, I see that in every facet of my life, if you're not open to something, or if your pathways aren't used to operating that way, it will just be kind of ignored. It'll be overlooked, right? People's attention is like a few moments, and if you don't capture it, you know, you don't get it. So, I think that it's a muscle that you definitely practice.
Leah 24:25
Yeah, there's a lot of practice when it comes to venture building isn't there? You got to practice ways to be and practice all kinds of ways of thinking and so on. Yeah, yeah, for sure.
Jenn 24:33
It's a big transformation. You're constantly transforming, like the business as like a team of three founders is different than a team of 10 people. And the team of 10 people with, you know, a handful of customers is different than a team of, you know, 30 people with dozens of customers. And, you know, a team of no financial backing to a team of multiple different stages and different investors is a different beast as well. So, it's kind of like parenting, I always relate it to like, I'm constantly learning about this new phase. It's kind of like that. It's an ever-transformational journey, which can be hard, which changes your heart.
Leah 25:11
Of course, it can be hard. Yeah, absolutely. How do you deal with that change? How do you deal with that constant evolution?
Jenn 25:16
I would say that on the business side, that comes a lot more naturally to me because I'm doing it way more. The parenting transformations, they're harder because like didn't come with a manual. I haven't been practicing it for 10 years. And they're faster, they're a bit faster. But yeah, it's just about time. It's about reflecting on those. And like, kind of knowing where you want to get to.
Leah 25:36
Right, keeping that outcome that you're going after in mind. Yeah, how do you take time for yourself now, to stay sort of sane, and well, as you negotiate all these transformations, and change and venture building?
Jenn 25:48
I've recently stumbled upon like, generating some better habits for myself. I mean, my habit used to be, well, the work needed to happen, and I'm like a night owl. So, it'd be like, do I have my refreshments, which is like half a bowl of chocolate chips and like a tea, like a caffeinated tea at 11pm. And I'm going back to work when I finally get the kids down, and I know I have like a four hour solid stretch before they wake up the next time. That used to be my like habit. And even then, the like, one hour that I've got to myself is after that. So, I would still like watch a show before going to bed, I had to like transition to be able to sleep. I don't do that anymore. Like for sure. Like focusing on nutrition kind of focusing on like getting outside and doing that like bilateral movement. So, like riding a bike or walking or doing anything I have to think about strategically while moving, because you can activate both your analytical side of your brain and your creative side of your brain. So, I get a lot more success. Learning, so, listening to something, having our walking meetings. So, I'm not distracted by like pings and slack and things like that. Walking anytime I want to think about critically by myself. I want to be walking. So, walking. Yeah.
Leah 26:58
Good for you.
Jenn 27:00
It’s like a recent change.
Leah 27:02
Is that right?
Jenn 27:03
It's pretty recent. Yeah.
Leah 27:05
Was there something that made you go I need to make some changes, like right now.
Jenn 26:07
So, three kids back to back under two years, apart from all of them, and never taking a mat leave really. I was in a state where I was like, I kind of just realized that I wasn't handling stress well. I was like, Okay, I'm not. I have a bit of like a workload paralysis, like I'm not navigating through and being effective. So, then it took me a couple of months to navigate, well, what do I do from here, and then I was just like this, I need to change. I need to have a bigger change, like a lifestyle change. And so I instituted that like maybe just over six months ago. And it has been really a game changer like prioritizing sleep, eating better. And getting like that getting walking and moving and a little bit of identity back to, I mean, that's pretty isolating as a parent as well, and an entrepreneur. So, just like the double whammy of those two things, just trying to like hark back a little bit of like what old Jenn would have been like.
Leah 28:01
What does Jen need? Yeah, not just everybody else in the business. Yeah, I get it. I get it. Good for you. That's amazing. The other thing I want to talk to you about is impact. Impact is really important for us at Thin Air Labs. And I know it's very important for you at PayShepherd. When you think about impact, what do you think about?
Jenn 28:23
I think about it kind of threefold. I think about our team, the team that we're building, the culture that we have, and like how our team shows up and celebrates that. I think about our clients and I think about community and I have a couple of examples. For our team, we work really hard. We work peak at like, you know, long hours when our customers are in peak periods, the industry is, you know, very leanly resourced, and during those peak periods, like adding one more new thing to someone's plate, like a technology can be really challenging, and we lean all the way into those people to make sure that it's as seamless as possible. And so that affords our team to have more flexibility and manage their own day, you know, they don't have to be at the desk between, you know, eight to five, you know, if they need to go and, you know, attend their child award ceremony that they've never been able to do at any of their past careers, they can now do that and like see their kids face light up like I've my mom's never been here for one of these. Those are the moments that are just like, incredible, we built that. That's never going away. And like people show up differently when, like, their life is valued like that, and their big life moments are valued like that. For our customers, there's a lot of leakage, you know, there's a lot of savings that our customers can have, and when we can report big numbers for the return on the client's investment, and then they can come back to us and tell us it was even more than that, because of the litigation we saved them. Different industries are going through different, you know, macro economy effects where there's a lot of pressure on certain industries. And when there's high amount of pressure on industry and projects get shut down or, you know, facilities have to close or, you know, they cut half the staff that can really greatly impact the community, the small towns where these people live, their livelihoods, the dynamic of the team that remains after that. And so if we can, you know, make a facility a little bit better margin, like operational margin. You know, performing a little bit better, be able to delay those, or completely put them off, that can change the community and like really impact the client.
Leah 30:36
Like that's bigger than the company, it's bigger, it's it affects the whole community, to your point. That's incredible. That's amazing. When we talk about impact, it's often what drives a lot of people. For you, when you think of staying motivated, how do you stay motivated to keep doing what you do? What's your driver?
Jenn 30:54
Like, I wake up every day, and like, get to work with a great group of people who want to solve problems. You know, it's not fun to show up when, you know, someone doesn't want to be part of what they're solving. And they don't, you know, want to, like lean in and support their team. Like the way our team shows up is, you know, anyone needs help, it's there, it might not be my deliverable might not be my client, but like, oh, you need some support, like, boom, let's get it done. We move fast, we, you know, collaborate, and we attract some of the brightest minds coming from the industry that are looking to be able to be part of the solution and have, you know, experienced the problem for so long. And the enterprise organization is a dinosaur, and it takes a really long time to change, and here at PayShepherd, they can just be like, boom, making changes every day, seeing impact and seeing value. Like that's super attractive to them. So, they're very energized, and I just feed off of that energy, and I just love working with them.
Leah 31:50
That's incredible. And then they get to participate in this incredible culture that you built, you know.
Jenn 31:56
Participate, form, you know, every individual that comes onto the team, like they, you know, add their own spark to the team, and, you know, motivate and inspire us all. And so, we really look for that when we make each hire.
Leah 32:08
How many people are, you know, I forgot?
Jenn 32:10
We're north of 40.
Leah 32:13
Wow, congratulations.
Jenn 32:15
Thank you.
Leah 32:16
You just broke into a really huge grin, when I asked you that question. What does that mean to you to have, you’ve got 40 People now, on your team?
Jenn 32:26
It's a lot of responsibility.
Leah 32:29
Sure, it is.
Jenn 32:30
It's been a lot of fun. Like, it's been great to see the momentum change with different individuals come on the team, learn from people who have done it before, see the different perspectives like I have a really strong vendor perspective. But you know, a lot of people that our team now come from the client side, and I love the collaboration that comes from those two sides coming together. We hire really diversity for skills. And so each new person that comes to the team is offering something that we didn't already have, and we're all learning from that. So, it's just, like, have been super incredible. We're coast to coast. You know, we can hire from like, you know, remote, small towns, and like, you know, we're bringing talent to the industry that might not have been able to come to that before. That adds its own like layers of conflict, complexity. But yeah, we’re really intentional about forming relationships, getting pop-up offices, getting the team together, we're actually all going to be together in Calgary in September. So, we'll all come and you know, be buzzing around here probably.
Leah 33:34
That sounds great. We look forward to it. That's amazing. Well, as we start to wrap this up, I always like to end on a couple of questions. You're the founder of PayShepherd, you're one of the co-founders, and you're writing the story for your company. How do you want the story for PayShepherd to go?
Jenn 33:52
I can't wait to see PayShepherd as like a standard name. The brand is recognized across multiple different industries, I want to be working with the most mature sophisticated clients and industries, you know, right up to those really heavily regulated industries that are very problem aware, they're trying to solve this. And they're like looking at performance management. PayShepherd can play in that field, and I want us to be like a known brand, a household name in all of industry, and really benefiting both sides of the relationship vendors and clients. And from there, you know, globally recognized is the goal. So, transcending industries, and transcending continents is kind of like my star.
Leah 34:33
Whoa, that's so exciting. I love it. And as a founder, you know, you are a founder, you founded this incredible company. How do you hope your story goes?
Jenn 34:45
I mean, I really hope that my three young boys are seeing, like, what hard work and dedication can do for themselves, for their families, you know, for their livelihoods. I want to be able to, you know, give them all the opportunities and like build little feminists like I want them to walk into any room and you know, be totally aware and be an ally and, you know, like, Let all perspective shine. And so, if I can do that by how I show up at work, at home, you know, they will understand what the mental load is like to run a business, to manage a household, to, you know, take care of other people, and that doesn't all need to fall on any certain person or any certain gender, then I'll have been winning.
Leah 35:32
You sure are? Jenn, thank you so much for this.
Jenn 32:36
Of course. Thank you for having me. It was really fun.
Leah 35:42
As the lead investor in Thin Air Labs - Fund One, Sandstone Asset Management believes in building the commons through innovative founders who are creating meaningful, positive impact, both locally and globally. Sandstone is doing just that by backing the next generation of emerging entrepreneurs. Picture this, a founder start-up goes from idea to international impact supported by strategic investors who believed in their vision. That's the power of Sandstone's approach. Sandstone doesn't just manage wealth, they cultivate it, supporting founders at all stages. Visit sandstoneam.com to learn how sandstone builds legacies that last.
Leah 36:36
Innovation is what drives our economy forward. The Opportunity Calgary Investment Fund is investing in opportunities that will accelerate innovation and build a diversified and resilient economy. Explore how OCIF is funding Calgary's future at opportunitycalgary.com



In this episode of The Founder Mindset
Leah Sarich interviews Jenn Hunter, Co-Founder of PayShepherd, a contractor management platform for heavy industry. They discuss Jenn's journey into entrepreneurship, the challenges of digitizing workflows in heavy industry, and how PayShepherd has transformed contractor-client interactions. They also touch on the experiences of working in a male-dominated field and the changing landscape for women in heavy industry.
Jenn shares her journey of balancing entrepreneurship and motherhood while prioritizing personal wellness. She discusses transformative changes she implemented, including better nutrition, sleep, and physical movement, which enhanced her productivity and well-being. Jenn also emphasizes fostering a healthy work culture at PayShepherd, highlighting flexibility, team support, and the value of life’s big moments. She explains how the company’s approach positively affects clients and their communities, offering valuable lessons for entrepreneurs and business leaders.
About Jenn Hunter
Jenn Hunter is a Co-Founder of PayShepherd, a contractor management solution that automates contract compliance, resulting in real-time cost reporting, shared accountability, and effective risk management, providing clients with improved operating margins. PayShepherd is ranked #13 in “Forbes 2024 Best 200 Canadian Startup Employers” and “2024 Products That Count” winner in the category of AI & Data.
Jenn's focus is on customer outcomes. She brings deep domain expertise from her background in heavy industry and has navigated every phase of the customer journey, from solutions and delivery to end-user support. Jenn is an EY Entrepreneur Of The Year 2024 finalist, an associate member of the A100, as well as mother to 3 boys under the age of 5.
Contact Information
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Contact Jenn Hunter:
Leah Sarich interviews Jenn Hunter, Co-Founder of PayShepherd, a contractor management platform for heavy industry. They discuss Jenn's journey into entrepreneurship, the challenges of digitizing workflows in heavy industry, and how PayShepherd has transformed contractor-client interactions. They also touch on the experiences of working in a male-dominated field and the changing landscape for women in heavy industry. Jenn shares her journey of balancing entrepreneurship and motherhood while prioritizing personal wellness. She discusses transformative changes she implemented, including better nutrition, sleep, and physical movement, which enhanced her productivity and well-being. Jenn also emphasizes fostering a healthy work culture at PayShepherd, highlighting flexibility, team support, and the value of life’s big moments. She explains how the company’s approach positively affects clients and their communities, offering valuable lessons for entrepreneurs and business leaders.