Epochal Growth | Empowering Leaders to Create Transformative Change

Stepping Back and Stepping Up with Jenn Southan

July 11, 2024 Sarah Caminiti / Jenn Southan Season 1 Episode 11

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When you think of your career journey, does it look anything like you thought it would 5, 10, even 20 years ago? 

Get ready to be inspired by the remarkable journey of Jenn Southan, Senior Director of Customer Support at Olo, in her podcast debut. Jenn takes us through her transformative five-year tenure at Olo, marked by navigating the tumultuous waters of a global pandemic, the excitement of a company going public, and the complexities of multiple acquisitions. Discover how she transitioned from outsourced support to leading an internal team, all while offering invaluable advice on setting non-negotiables, establishing boundaries, overcoming imposter syndrome, and embracing career pivots.

Jenn's story is a testament to resilience and reinvention, as she shares her experiences of taking significant time off to raise her children and then re-entering the workforce with TeamSnap. From growing the support team at TeamSnap to facing unexpected layoffs and rebounding with a role at Olo, Jenn's journey is filled with lessons on respecting new roles, drawing motivation from colleagues, and rebuilding passion in the face of adversity. Her narrative emphasizes the importance of a balanced approach to career growth and the power of glowing recommendations from peers to reignite one's professional drive.

But the inspiration doesn't stop there. We explore how Olo's intentional hiring practices and support for internal mobility foster a thriving and adaptable workplace culture. Learn how encouraging shadowing, cross-departmental projects, and career coaching can reduce imposter syndrome and boost employee satisfaction. Jenn's story highlights the significance of confident female leadership and the societal challenges women face, all while embracing the "Ownership Era" of her career. As we wrap up, we leave you with a call to action to take bold steps in your own career journey, ensuring you're always moving toward personal and professional greatness. 

Don't miss this transformative conversation with Jenn Southan—it's bound to leave you motivated and ready to make great things happen.

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“Change will not come if we wait for some other person, or if we wait for some other time. We are the ones we’ve been waiting for. We are the change that we seek.”
- Barack Obama

Jenn Southan:

And I still remember and I think this is where just a lot of my philosophy came from you sign, they call it a corporate creed, which sounds very like fancy, but it is this thing, and you signed it and you framed it and they put it on your office wall. But the very first thing was always deliver more than the customer expects. And I still remember that and that is heavily influenced. You know kind of how I look at things.

Sarah Caminiti:

How many times have you thought there has to be a better way?

Sarah Caminiti:

Welcome to Epochal Growth, a podcast where we invite industry leaders and change makers who thought that very thing and realized that, yeah, a better way to lead or to grow or to build does exist. And once they trusted themselves enough to discover what's possible, they created the foundation for a new era that's revolutionizing the landscape of success, for a new era that's revolutionizing the landscape of success.

Sarah Caminiti:

The word Epochal refers to these very moments in time, because when you commit to being better, the impact will last for generations to come. I'm your host Sarah Caminiti . Join me to uncover practical insights and strategies that will empower you to be the change that you seek.

Sarah Caminiti:

This is Epochal Growth. I'm so happy that you're here

Sarah Caminiti:

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Sarah Caminiti:

Hello listeners, welcome to Epochal Growth.

Sarah Caminiti:

This is an episode with a lot of firsts. This is not only our guest, Jenn Southen's first time appearing on a podcast. This is also the first time that I am publishing the podcast all by myself. Up until Su pport Driven, has been kind enough to be publishing the podcast for me, and I have been feeling brave and have decided to take over that piece myself, and it was perfect timing, because sometimes the universe brings you the right people at the right time in more ways than one, and that's exactly what happened with Priscilla at Buzzsprout. She's the head of customer support there and I am so thankful for her. I am so thankful for everyone over at the Buzzsprout team for helping me get set up. Priscilla also has a fantastic podcast. It's called Happy to Help. It's a customer support podcast with incredible content and I definitely recommend. You won't be disappointed. This isn't even an ad. I just love celebrating great people doing great things, and that is Priscilla and her team over at Buzzsprout. So I'm so grateful for you guys. Thank you for everything. We have an exciting road ahead.

Sarah Caminiti:

Speaking of Buzzsprout, you can now find Epochal Growth pretty much anywhere you could possibly imagine. I'm talking Podcast Index, I'm talking iHeartRadio, amazon Music TuneIn, podcast Addict. The list goes on and on. So stream Epochal Growth wherever it is that you like to stream podcasts. Make sure you're following the podcast. Sometimes I may even sneak in a bonus episode, and the best way to be notified is if you're following the podcast. And if you haven't subscribed to YouTube, please do. I'm putting some great clips in there, so when you don't have the time to listen to a full episode and you just need a reminder of what's Jenn possible. Go to the Epochal Growth YouTube page and find those snippets from the incredible leaders that have shared their stories with Epochal Growth.

Sarah Caminiti:

For today's episode, I want you listeners to think about what you thought your career was going to look like. I'm talking. Think about what you thought your career was going to look like when you were 20 years old and how, when you were 25, what you thought success was going to look like changed, and when you were 30 and 35, and so on and so on. And when you were 30 and 35, and so on and so on. Some key takeaways from this episode will be identifying what your non-negotiables are, how to set those boundaries, navigating imposter syndrome and embracing a career pivot. I've gotten to know Jen through the Voices Carry women's group. I've always admired how she articulates her experience with so much respect and honesty. It tells you a lot about who she is as a leader and why it's no surprise she's as successful as she is. Let's jump into episode 11 of Epochal Growth Stepping Back and Stepping Up.

Jenn Southan:

I'm Jenn Southan. I'm the Senior Director of Customer Support at Olo. Olo is a restaurant tech company that is a platform for many of the major brands that you know and love to utilize for online ordering. I actually today is my five-year, as we call it, oliversary, so I have been with the company for five years, thank you, and I just recently took over the support team from my previous manager, who had been at the company for 17 years Wow and she is on a sabbatical, living her best life For her well-deserved after 17 years.

Sarah Caminiti:

Yeah, absolutely Well. Congratulations to you. What an awesome period of career transition and just excitement for you.

Jenn Southan:

Yeah, it's been a great ride. In the time that I've been here, we've experienced COVID, which, in the restaurant industry, was a bit of a roller coaster. Wow, the company went public. We have acquired a couple of other companies, so it's been nothing if not exciting, yeah.

Sarah Caminiti:

What a ride you've been on within that five-year period.

Jenn Southan:

Yeah, absolutely, not to mention that support had been outsourced and I was, I believe, the second class of people that they hired in to help with standing it up internally, with standing it up internally, so that has also been super fun.

Sarah Caminiti:

Yeah, that's. That is a very interesting like intro into this space, especially after what you've shared with me about your career journey. What an interesting space to enter. From that regard too, I don't know if you want to give a little bit of an overview of what brought you to Olo and how things were in the past, but you've had a really cool career trajectory.

Jenn Southan:

Yeah, absolutely. It's been nothing short of a ride, for sure. It's been nothing short of a ride for sure. I had decided to stay home with my kids for a while, so I took a step out of the workforce for about eight or nine years and so when I went back into the workforce, I started working for this company called Team Snap. They are a youth sports team management and I was the first person they hired outside of their founding team to do support. It was a great setup for me. I was working remote. They were based out of Boulder, colorado, and worked with them to grow the team to about 25.

Jenn Southan:

Unfortunately, at that point I got laid off, went to work for another like super small startup and that one did not work out so well. We just had kind of differing visions, if you will. But upon leaving there I just realized how burnt out I was between you working for a startup and growing that team and then kind of moving right into this other startup. And you know, everyone knows kind of startup life is a little crazy. There aren't traditional work hours, typically, and things like that. So I was. It was quite a ride.

Jenn Southan:

When I decided to leave the second startup, I took a couple months off before even considering looking for another job Good and then decided I just wanted to go back to being an individual contributor. As I told my soon-to-be boss during our interview, I said I just want to come to work, do a good job and, at the end of the day, close my laptop right, not be on call, not have all the pressure and responsibility. And thankfully she took me at my word and hired me into this IC role, and I think she did it with an eye towards the future, knowing that the team was going to grow, and so it was a really great experience working for her and getting my passion for the job back. I really enjoyed kind of getting my hands dirty again. I really enjoyed kind of getting my hands dirty again and really just kind of getting to know the product.

Jenn Southan:

Olo itself is a pretty complicated product, so it was a great kind of trajectory for me within the company and through kind of her demonstration of work-life balance and what that could really look like, I was able to just get excited about leading a team again, and so within Olo I moved into like a tier two more technical role. Prior to staying home I had worked in more technical roles software development, things like that. Oh, wow, okay. And then I moved into a leadership role, helped build out all of our tier two teams the way they are now which are focused on products.

Sarah Caminiti:

And yeah, here I am now, because your work history before you joined OLO was so perfectly connected to what was needed in OLO. But the cool thing that you gave them was I want to build this as an IC instead of as a leader, which is a totally different approach, and I can only imagine what opportunities presented themselves by looking at things from that lens and structuring things from that lens rather than from like an overarching space. Did you know when you were entering into this role that you were going to have the opportunity to shape things and influence things as much as you have?

Jenn Southan:

No, I had no idea. Like I literally was, like I just want to be in IC, I want to do a good job. I knew that I would bring some experience to the table. So my boss that hired me on shout out to Maureen. She had not worked in customer support before. She had hired a manager that had, and so she had to lean on. But I knew that I would bring some you know experiences that maybe neither of them had.

Jenn Southan:

At the same time, I was also very cognizant of the fact, and probably overly so, that I like not to step on toes or, um, the one habit to break was I was so used to making the decisions, yeah, that it was hard not to just like make decisions in the moment. But, um, again, it just goes back to kind of being cognizant of what my role was and and being respectful of those that were in those roles and, and I think it it worked out well, I have to say, over the years. You know, I think Maureen would say she learned as much from me as I did from her.

Sarah Caminiti:

So it was. It was really a great partnership and worked out really well over to building something and still being laid off, which I'm sure that must have been an incredible shift in perspective of what it actually means to work for a company.

Jenn Southan:

Yeah, that was the first time I had experienced that and kind of the way it all went down was a bit of a shock too. They had announced some company-wide layoffs, like the Friday before, and I was not part of that. I was supposed to go to an event. There was some miscommunication. I ended up not going. Apparently they didn't include me in that because the CEO wanted to tell me himself. I had reported to him for a number of years and so whereas I thought shoo, you know I made it through that wasn't the case, and so in the end I'm glad I didn't see him face to face when he told me, because it was upsetting and unexpected. But you know, ultimately, ultimately it turned out for the best. So you know, no hard feelings.

Sarah Caminiti:

No hard feelings, no, I know, but I'm sure it was a journey to get to that place, especially knowing what you did. Like you, you built it and that is a huge win for you and something that I hope that you allow yourself to be very proud of and acknowledge what it was that you accomplished, Because not very many people can say that they do that, especially to scale it the way that you did that's. That's not an easy task.

Jenn Southan:

Yeah, it was. It was a great team. And if I'm ever like feeling a little down on myself or having that, you know, imposter syndrome, when I left TeamSnap, a lot of my colleagues wrote some really glowing recommendations for me on LinkedIn and so I go back and I read those and I'm like on LinkedIn. And so I go back and I read those and I'm like, okay, yeah, I got this.

Jenn Southan:

Like I can do this. We had a really great group of people that work there. We still stay in touch. We have a Slack channel or Slack group that we're all still in, so it was a unique experience. It was a really great company to work for and, yeah, I'm very proud of the team that I've built, seeing some of the people that are still there and what they're doing, seeing people that have moved on to other companies and what they're doing there. Like you know, when Jenn you can see someone else succeed and realize that you had like a small part in that, it's pretty satisfying for sure.

Sarah Caminiti:

Definitely, definitely. I think that's one of the best pieces of being in our industry, of being a customer focused professional, where our goal is to help others be successful, and how that translates to leadership and connects, and you're able to see, not just a this is an email that happened, someone was really happy and it was great. No, you get to see, like, the true personal impact that your approach to connect with them gives them, and that's not surprising from what I know of you, jen, that you had that kind of an impact on your team there and they continue to, just, you know, support you and praise you for that.

Jenn Southan:

Yeah, thank you, I appreciate it. I've always kind of lived by the mantra, you know, do unto others as like, give people the support that you would want to receive. Um, and ultimately, you know, yes, we have a job to do, but we're all human and you don't leave that humanity at the door when you come to work, um, so if you're having a hard day and it's just not working out or things aren't going well, I want to know that Right Cause, um it, it affects you as as a person and a human being, and not everybody is a hundred percent every day.

Sarah Caminiti:

No, no they're not supposed to be, because that wouldn't be uh, wouldn't be any fun. My North Star is the golden rule. It is how I handle support, exactly the way you described it. It's how I lead my teams. It's how I mentor others. It is how are you feeling in this? How can I put myself in your position? How can I put myself in your position and in difficult conversations? That has proven to be one of the greatest gifts of having that be so foundational. Have you found that to be true as well?

Jenn Southan:

Yeah, absolutely. I think, particularly as you get a title, that means something more in an organization or is higher, people tend to be afraid of you, and whenever anyone new joins the team, I always tell them like look, everybody makes mistakes. There's not going to be anyone who doesn't. There's not going to be any month, year, whatever where you don't make one and it's okay. All I ask is that you one take ownership of it. Like accept the fact that you did it, um, and learn from it. That I mean that that's really it. Like make it right if you can. If If not, we'll figure it out, but just learn from it. Like just don't keep making the same mistake and that's it. And that really has kind of served me pretty well, in that people are not afraid to say like oh, hey, I think I might have screwed up here. And then you sit down and you have that conversation of like okay, what happened? What do we need to do to fix it and what do we do so it doesn't happen again?

Sarah Caminiti:

Yes, yes, that is the biggest opportunity for a shift in the relationship of someone that is in a leadership position and anyone, even if they're not on their team directly. If you can create a space something that I always ask anyone that I'm working with, whether in my company. I mean, I even asked my husband it's, why did you choose to do it this way? And it takes a little while for people to understand the sincerity behind it, regardless of how explicitly I tell them I really am coming at this right. But it takes the ownership out of it, like that guilt piece out of it, and it puts it into the processes and improvement, and I love that. That is exactly what you do for your teams, because you reduce the chance of so much just issue and fires to put out, because people aren't afraid to say this is what I did, this is how I went about doing it, because of X, y, z, and now let's take this as a chance to reevaluate.

Jenn Southan:

Yeah, absolutely. Is it just a training opportunity? Is it an opportunity to update documentation because something wasn't you know, something had changed, or whatever the case may be, it's. I mean, I don't think I've ever run into a case where someone has done something maliciously. So you know, I don't know why people often get treated as if it was the case. It's, yeah, again, just about like kind of owning up to it, accepting the responsibility. I am a big believer in accepting responsibility, but beyond that, like okay, what do we need to do now? Let's learn from it, let's move on.

Sarah Caminiti:

Yes, yes, it is so much faster, so much less painful. And I'm an overthinker myself and if I let things sit, I stew and it becomes a way bigger deal than it ever needed to be. And if you create that kind of a foundation, then you can have those conversations immediately without some ominous. We need to have a talk in three days about something, maybe, kind of. I won't tell you what it is.

Jenn Southan:

I'm also a big believer in immediate feedback, right, Like why wait three days Because that's just going to give someone anxiety and putting my neuroses on full display. I have anxiety, I am an overthinker. If there's a worst case scenario, I've got five of them in my head and so it's like if something happened, it's like, hey, can we check real quick, you know, and just be like, hey, this is what I noticed, you know, and kind of take the conversation from there and not make it a big deal. I think when it becomes this like scheduled, you know, formal conversation and there are times for that, for sure, Sure, but just kind of everyday feedback is not one of them.

Sarah Caminiti:

No, no, it's. I mean, you are definitely a kindred spirit and I'm so happy that the folks that listen to this podcast will be able to hear your approach to communication and the reason why it can be this way and why it's so helpful to talk about these things and say that it's okay to do it this way and it does work, and you are definitely proof to that. So I'm so glad that you brought that up.

Jenn Southan:

Yeah, thanks, thank you, it has served me well.

Sarah Caminiti:

And I do wonder. So, when you joined OLO and you came into a space where you weren't the leader, you weren't the one that was finding these mistakes and having these conversations how was the dynamic with you and your boss and the rest of the folks in the department?

Jenn Southan:

You know I've been very fortunate that it was always really good. Um, we you know not to brag, but I am we hire some amazing people here at Olo and they're all very like conscientious people, always wanting to improve. That's what I look for when hiring people, more so than like technical skills necessarily, unless something specific is needed, necessarily unless something specific is needed. And I think we all just came into it knowing we were building a team and that we had the opportunity to do something special. There were some people on the team that came in with like certain skills, like with a POS system, because we work with restaurants and that's needed. There was someone else who had been a leader and had a lot of Zendesk experience. She now leads our support and CX ops stuff, and so it was just really really collaborative and thankfully, you know, maureen and the other gal who was a manager on the team, like they didn't have egos, they knew they didn't know it all and so they were willing to listen and you know kind of factor that into decisions they were making.

Sarah Caminiti:

It sounds like you created a space that was true to your values, true to your experience, but you had support in such a great way from your, who understood the power of everything and being intentional in how you hire is one of the most important things that you can do. Especially, I feel in support because there is such a higher rate for turnover and it is a special type of person that enjoys this work for a long period of time.

Sarah Caminiti:

What was it in the hiring at Olo that was different than the hiring at the other places that you worked?

Jenn Southan:

Honestly, I don't know that it was terribly different from when I worked at TeamSTOP. I used a lot of the same philosophies there and was very fortunate we've been very fortunate at Olo as well to not have I don't want to say we haven't had a lot of turnover at Olo. We have. However, it's been almost entirely internal moves.

Sarah Caminiti:

Oh, that's a turnover then.

Jenn Southan:

Yeah, it's turnover on our team, but they moved on to other positions and that's kind of another way that we lead is by understanding what people's career goals are and helping them get there get there. But honestly, I think in both places the companies had such a good reputation of being a great place to work that it made it easy to hire good people. And I think reputation only takes you so far. But being able to speak to them about, like, how we we deal with feedback or how we help people move in their career, or how we help people get you know training opportunities or whatever the case may be, that, I think, demonstrates that we are invested in them as a person and not just as a number or a you know seat to fill, if you will.

Sarah Caminiti:

Yeah, it's a different mindset and it translates into how each individual contributor, each member of your team, starts their day. It's a foundational piece starts their day. It's a foundational piece and I love hearing that this is happening where you are and that you've been able to continue to foster that as you've grown into the leadership role that you've recently moved into.

Jenn Southan:

Yeah, thanks, it has been great. I mean, I'm just thinking back in my head of all the people that have kind of moved through our support team. I had, of all the people that have kind of moved through our support team and it's exciting Like we had people move not just into like more technical roles, like our developer engineering team, but also into CSM roles and deployment managers. We had one person no, I'm sorry, two people move into like our people ops team and so just lots of different opportunities that came because we listened to what they wanted to do and didn't get territorial about them. Right, because you can either support someone in what they want to do and help them grow within your company, or you cannot and they will leave your company, correct?

Sarah Caminiti:

Yeah, that is a perfect way to articulate it, and it is something that you don't see actually happening happening, and sometimes it's because it's not possible, maybe because it's a small startup and they don't have the resources for movement or those sort of training situations. But what do you have at Olo that allows these sorts of paths to be explored? Is that what it's always been for everyone on the team?

Jenn Southan:

I think so. Most of the opportunities are things that come up internally and working with other team members. You know, if you want to become a deployment manager at Ola, which means you're working directly with these brands, helping them get up and running, there's not really a training class you can go to for that. What I encourage people to do is go talk to people on those teams, spend a few hours half a day, maybe a couple of different times shadowing them.

Jenn Southan:

Look and understand what the job really is. Don't just make the leap thinking that's what you want if you don't know what it is yet. And then if you do that and you enjoy it, then let's talk about it. And maybe it's taking on a project or two or working with them or sitting in on kickoff calls. Whatever the case may be, it's just helping them, like, get their feet wet, show that they do really have an interest there and that they're capable of doing the job. Then when a job opportunity comes up, it's almost a no brainer, right. They know the company, they know the product, the other team knows what they're getting in an employee and it it really just is an easy, easy sell, if you will. It's not even a sell, no, it's true, and it also I'm.

Sarah Caminiti:

I feel like that would eliminate a lot of the imposter syndrome that would prevent someone from moving forward with pursuing it, because you've given them space to explore.

Jenn Southan:

Yeah, I would hope so, as someone who still regularly experiences imposter syndrome. I don't think it ever goes away, but I mean I would hope so. And even I remember having a conversation a few months ago with one of the managers of one of my tier two teams and he was considering applying for this product role or product manager role, and I was like OK, great. I was like are you really sure? Like that's what you want to do? Do you know what the day? And he was like no, and I said, well, why don't you like look into it a little bit? Like I'm happy to support you, but like if you take this other job opening, you can't just say oh I'm sorry, it's not what I thought it was, and come back. And he did, it ended up not working out and and he, I think, is happier where he is now.

Jenn Southan:

But you know, same thing applied is what I've told other people, though. Like, if you still want to look into it, like let's find a way to get you involved. There are ways to do that. That, you know, yes, is some time away from your day to day, but you know we'll make allowances, we'll, you know, make it happen, and but he seems to be happy where he is now, so that's all good, yeah, no, that is good.

Sarah Caminiti:

And the grass is always greener is something that everybody experiences from time to time, and in the support industry at least. For when I began in this space, it was sold as this is your introduction to the company and you're not supposed to stay here. And then, with the startup world happening and support becoming an actual career with a place in the greater ecosystem of impact within the company, things shifted a little and it wasn't as easy to admit that you were curious about something else and you wanted to learn about something else. Because you committed to being in support and finding that even like ebb and flow of. I want to support you, but I also want to support you to stay here If this is what makes sense for you. That's new. That's not something that really exists very, very often, and I love hearing that not only is it something that's working, obviously, but it's something that you're committed to as a company and growing it and learning from it as you go.

Jenn Southan:

A lot of it came from just my own career path. Right, I kind of alluded to it earlier, but I have a degree in information systems. So when I came out of college I was doing IT support and then moved. I worked for a government contracting firm, because I live in the DC area and everybody worked for a government contractor at some point. And so I moved on to a project at one point where we did everything. We did the requirements gathering, the software development, the maintenance, the testing, the deployment, support, like soup to nuts. We did it all and it was probably the best experience I could have had because I saw so many different aspects of it and I moved roles even within that team.

Jenn Southan:

I started out doing like just deployment and training and then I picked up some of the software skills. Then we did like a whole rewrite and I was on that software development team and then I ran the support team and it was just a lot that I was able to try in a very short period of time. It was after that project that I decided to stay home with my kids for a bit and take a step back out of the workforce. And then I found the role with TeamSnap, which was for a customer support specialist, and was able to step into that. But you know, having gone through kind of so many iterations myself, I understand like, just because you make a decision today, two years from today, you're not the same person. Decision today, two years from today, you're not the same person and so expecting you to have the exact same wants and needs is unreasonable. We do ask people to stay in the role for a year, which seems very reasonable, yeah, and then beyond that you know it.

Jenn Southan:

That's when we started having the conversations about what else they might want to do, if anything, some of our folks have chosen to move into leadership and have taken on like manager or associate director roles. Some want no part of leadership, and that's okay too. We've created roles for them that are, you know, allow them to kind of keep growing in their technical skills and seniority. It just it's ever evolving, and that's one of the things that I really love about OLO. They've been around for a very long time. I think it's 19 years now. Oh and yeah, we just went public in 2021.

Jenn Southan:

Is that right? Yes, 2021. And so we've had to make this change to a public company. But we still have a lot of these like startup mentalities where you know, try, things fail fast, right, and and it's okay if things don't work out. So it's been a really unique position to have that. You know, we certainly have some other, some things that are more structured now because they have to be, but, um, you know, generally it's still very much the same kind of um, core values and and philosophy, since I've been here five years now no, that says a lot.

Sarah Caminiti:

It's I. It's interesting that you were saying how you're allowed to feel and try things and that startup mentality hasn't really changed, because this is something that I've noticed has come up a few times in conversations I had in places where people feel like they are able to lead the way that they want to lead because of the environment around them and the culture around them of experimentation, because there's only so much that you can do when you are the leader of of a company I mean out of a company, of of a department to create the space that you want to create for your team.

Sarah Caminiti:

If the company lives a very different world, that bubble it's, it's not it's not going to stay intact for too long and the longevity that happens when they create that kind of a space as part of the culture and don't lose it as they grow and make that not only something that like actually happens, but they make it known that this is, this is something that's important for a reason and they're going to do what they need to do to to continue it as best they can. Um is not talked about enough how important it is to create that kind of a space. Coming from the consulting world, where you have a very set path of what is needed and you have that feeling of you don't actually work for the company you know they brought you on as a consultant. How has that translated with the failure and the experimentation that that you see in these startup environments?

Jenn Southan:

Again, I think I was like really lucky with the companies that I've worked for. So I was employee number 77 when I joined this company out of college, so it was also still very startup-y, right. It was um. We got a lot of contracts under like small business association and things like that Um, and so I feel like it was not as much of a bureaucracy as it as it could have been Um, and even though we had contracts with um, these government agencies, we still always felt like we were part of the company.

Jenn Southan:

And I still remember and I think this is where just a lot of my philosophy came from you signed, they called it a corporate creed would sound very like fancy, but it is this thing and you signed it and you framed it and they put it on your office wall. But the very first thing was always deliver more than the customer expects and I still remember that and that is heavily influenced. You know kind of how I look at things I, so my husband works as a government contractor still, okay, and we have conversations a lot and I'm just like, wow, I am so glad Jen Like I don't still get in that environment because I think, as lucky as I was, things have changed and you know everywhere you go, money is tighter. Getting money for funding whether it be like private equity, from the government, whatever the case may be is getting harder and harder, and I think having to work within those constraints is I would not fare well these days constraints, I would not fare well these days.

Sarah Caminiti:

No, I hear you, I definitely hear you, and looking at your career and the choices that you've made in your career, it's obvious that you have made it so. Part of just every decision that you make is rooted in your values, your companies that you choose. You're not only drawn to them because of their values, even if you don't know that they're those values, but then they're also drawn to you because of your values and the match that that has. And you've been lucky, yes, in finding places that has allowed you to operate the way that you should be operating. But you, jen, have also obviously been such a bright light in these places that they knew that they had to continue to let you be who you and find ways to enhance that and spread that.

Sarah Caminiti:

Um, because it's very easy, especially when companies are growing, to say they are doing one thing and do the exact opposite, even if they were wonderful in the very beginning. And you are evidence that the relationships that you build, the just like empowerment of this is right and it works, and staying true to that but then also allowing yourself to leave and giving yourself permission to say this is not the right fit is testament to who you are as a person and the kind of impact I'm sure you are having on the other people that that you work with, especially women, because you are an important person to have in this world and I'm glad you're in leadership because what you're doing trickles around and people thank you.

Jenn Southan:

Thank you so much. That was very sweet. I really appreciate that. I think you know, particularly in like the support driven group there are so many strong leaders in support. When I was working at TeamSTEPP I kind of waxed and waned with my participation there, but it was so wonderful to find a community that has a lot of the same values and beliefs. Personally, coming to work as who I am, it's easy, Like it's just easier. Like if I had to put on this like persona to come to work, like who wants to do that? Unless you're an actor and I'm not. No, um, so it just yeah, like, oh, who am I supposed to be today?

Jenn Southan:

no, this is not me, um and and this, like I talk to my team members and lead team meetings like this too, sometimes I have this like ditzy blonde moment and I'm just like, oh sorry, like brain fart it happened. I don't think we can sit there. And you know, when people put on this like uber professional, professional front, like they're perfect and things like that's not real and that's not me and yeah, that's too much work.

Sarah Caminiti:

It is a lot of work. It's a lot of work. It's exhausting, I'm sure, and you've been able to solidify yourself as just owning who you are and seeing. I mean, this is just it and I'm going to do my work well and I'm going to treat people kindly and we'll talk about it if there's a problem, but you allow yourself to be the adult. I think is what it really comes down to. If you approach things in a way that is even keeled and direct and there's no personal malice or any sort of vendetta behind it, intentional or not, you show other people, whether they're on your team or not, that this is how you should approach these situations.

Sarah Caminiti:

This is how we're able to grow together in these situations.

Jenn Southan:

Yeah, yeah, absolutely. And I think one thing that I participated in with OLO last year that helped me grow tremendously was a program they had it's actually called Grow and we had like this online learning platform that we could utilize. They got us a career coach for like six months and we also had like a group meetup and exercises and stuff. And I think for me, the really great thing about that program was not like this is how you should be a manager, and it wasn't like black and white, this is how we do management at Olo. It was like here's some of the principles we live by and you know, um, let's talk about how that works for you and how like you do that. And then even the career coach was so helpful because it's someone that is truly like, impartial and you're able to talk through and bounce ideas off of like.

Jenn Southan:

I had not utilized one before that and did not realize how invaluable they are, and so I was really appreciative that they kind of put the investment into a program like that. We're actually trying to get them to do it for leaders earlier in their career, so before they become like, because originally it was like for associate director level and above, and then they opened it to managers. We would like to see it even like people that want to become managers, or very early in their manager career. So we'll see TBD on how they're doing it this year. That's very cool. That's very cool.

Sarah Caminiti:

Is that what shifted your like? Because you didn't want to do this, you didn't want to lead, you didn't want to be in this position. And now look at you you're a senior director. What was? I know that your manager, your boss, really gave you the space to to explore this, coming back into a leadership role, but what was it in the journey that kind of let you do this?

Jenn Southan:

Honestly. So that was really what kind of gave me the confidence to say yes, like I want to take over the team when you leave and kind of take on this new role. I got back into leadership. It was probably like seriously back into leadership. About two and a half years ago so about halfway into my journey, I had started up one of the tier two support teams. So I was kind of leaning more into my technical skills and enjoying that and, honestly, I myself had considered taking on or applying for a product role.

Jenn Southan:

I have always had a keen interest in like, where the customer and the product meet.

Jenn Southan:

Um, that's one of the things I'm super passionate about is like voice the customer from support and getting information back to the product team.

Jenn Southan:

But, um, so I I had applied for this product position. I ended up not getting it, but it was really a blessing in disguise because as that position evolved I realized like I did not take my own advice, like I hadn't really looked at like the day to day of it and all of that. But what it did make me realize is that I really still enjoyed support and I still really enjoyed kind of building teams in. However that looked, whether it be like just the team I was on that kind of expanded to tier two as a whole and building out new teams there and building out new teams there, and now we're kind of at this inflection point with the full support team in that, you know, we're introducing some like AI tooling and automations and some other product enhancements to make things more self-service, and so the team is also kind of at this inflection point. So I'm excited to kind of help them build and grow and change through this process.

Sarah Caminiti:

so what an exciting time for you. And, uh, your career has brought you to this point. I mean, you were supposed to get back into this space and pull. You're pulling everything from every job that you've had, and I'm sure even that time that you were with your kids. I mean, you learn a lot about leadership when you're working with small child. But, yeah, like it all has brought you to this new space, which brings me to the final question of what era are you in now, or what era are you moving into?

Jenn Southan:

I think, if I had to label it anything, I think I am moving into what I would call like my ownership era and it's where, like, I'm comfortable with myself, I am comfortable with my skills and I'm comfortable with where the team needs to go next and I'm excited about it Great news I love this era for you. Yeah, me too, like it should be a whole Taylor Swift album all on its own.

Sarah Caminiti:

It really should, I will listen to it if it is, but I'm glad that you were able to start this era talk on your very first podcast, which is another. I mean this is a transition to. I mean you're kind of in yourself and you know what you're capable of, and I think that other women especially who have found themselves in a similar career path between burnout and leave and starting in something totally different and being able to experiment and move forward with staying true to yourself the whole time that's inspiring and I'm so happy that you were able to share that.

Jenn Southan:

Thanks, yeah, I think you know, as women we Jenn are often led to believe that we shouldn't act confident and we shouldn't I don't, I don't want to like say the word because I don't think it's that, I don't think that is what it is right. But I think when you have a confident woman, they often come across, as you know, sometimes brash or something like that. So women oftentimes try to make themselves smaller. I was very fortunate. My dad never raised me that way. You know. He always believed in and told me I could do anything. I put my mind to confidently step up and be like, no, like, I know this. It's a good place to be for sure, and hopefully someone will hear it and it'll resonate with them. They ever want to chat. I'm always happy to chat and be someone's cheerleader and happy.

Sarah Caminiti:

Yeah, well, good, I'm so happy for you, jen, and I think that this is a journey that will resonate with a lot of people and people will want to talk about it, and I'm so happy that you allowed yourself this space to connect with me and you gave me your time and your candor and honesty, and I'm just very grateful for you. So thank you.

Jenn Southan:

Yeah, thank you, I am grateful for you as well. I always enjoy any conversation. I'm a Jenn of where you're there. Oh, thank you, I appreciate the invitation and, yeah, always here. If you want to chat more, awesome, I will definitely take you up on that. Definitely take you up on that Jenn

Sarah Caminiti:

I told you you never would have realized this was her first time on a podcast. Thank you, jen, so much for trusting me with this special, special episode. Thank you, listeners, for spending time with us and being so open to change. Hopefully you feel inspired or empowered after listening to the incredible leaders like Jen that have gifted me with their time on this show. Thank you again to Buzzsprout. Also, thank you to Elevate CX for letting me bounce ideas off of all of the folks in that community.

Sarah Caminiti:

If you haven't picked up your tickets to the event in Denver, don't wait. September is coming soon. Also, if you're looking for an option closer to you, if you're not in the United States and you're in Europe or you're in the UK, I will be heading to London on November 8th for the Elevate CX event there and I would love to see you. Feel free to reach out to me or to Sarah Hatter if you have questions about that event. We can't wait around to see change happen when you feel it in yourself that a better way exists. You owe it to yourself and to those around you to try, because great things happen when you do. Thank you again for spending time with me. Thank you to Jen for trusting me. Have a great day and I'll see you soon.

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