Welcome to GreatConversations, a podcast about leadership and life from GreatAmerica Financial Services. Mitch Leahy, VP and General Manager for our office Equipment Group, hosts our series of talks with thought leaders and innovators from across the business world.
On today’s episode of GreatConversations, Mitch hosts Jenna (Stramaglio) Miner, Channel Development Manager at ConnectWise, and daughter of industry icon, Mike Stramaglio. Jenna talks about growing up in the business and becoming entrenched in the industry for over two decades. She shares some of the lessons she’s learned when it comes to developing her confidence and overcoming anxiety around public speaking and offers her perspective on “the changing of the guard,” as legacy leaders begin passing the baton to the next wave of Gen X and Millennial leaders.
Listen to full podcast or read the abbreviated interview below!
GreatConversations with GreatAmerica- Episode 4: When NextWave Meets Legacy: Changing of the Guard and Developing Confidence | Jenna (Stramaglio) Miner, ConnectWise
Mitch: Hello and welcome back to another episode of GreatConversations. I’m Mitch Leahy of GreatAmerica, and today we have another special guest. You've likely heard of her with her consistent involvement in the channel for well over a decade. Odds are, if you haven't met her, you've at least met or heard from a very close member of her family tree. I'm excited to welcome Jenna (Stramaglio) Miner. Hi, Jenna.
Jenna: Hi, Mitch. Thanks for having me!
Public Speaking
Mitch: I'm always amazed and pleased to see how the dynamic is shifting and how you have been a part of that in the industry. I was just getting refreshed on your LinkedIn yesterday and my first question is, how do you keep it all straight? It seems like you're constantly everywhere. You're all over the place and that's not even including all the customer interactions you're having, how do you do it all?
Jenna: It just doesn't feel like work anymore, that's the most important thing. I say often that I love this industry. I know I’m partial to it because I grew up in it and started in 2005, but when I'm traveling, it doesn't really feel like work. Whether I’m at conferences or meeting with partners, solving problems, or just talking to partners/vendors, I look forward to all of it. So, I think that’s how I keep it going, by looking at the positive.
Mitch: Your enjoyment certainly shows through. We've interacted with each other in different forms over the years, all the way back to when you were with MWAI and now that you're at ConnectWise, we’ve circled each other at a lot of the different events. One thing that I've always been really impressed with is your confidence. Where does that come from? Is that familiarity or is that confidence in what you know you're speaking to? Or is that just Jenna as a whole?
Jenna: No, it's a complete lie. I literally just got off the phone with a partner and we were talking about public speaking. Behind the scenes you will see me sweating from my armpits and having to remind myself to take big deep breaths. Every single time before I step on stage, I die a little bit on the inside. So, it might come across as very confident, but it is still extremely nerve-wracking whether it's in front of one partner or hundreds of people. But my counterpart, my dad, told me when I was very young, “If you're not nervous, then you're not doing it right.” So, I think harnessing that nervous energy and translating that into confidence is key. Sometimes I hit it and sometimes I miss, but if I err on the side of hitting it more than missing it, then we're in good shape.
Mitch: I completely agree. I've heard someone say it's okay to be nervous. It means it's important to you, but if you feel panicked, it just means you're unprepared. Is there anything that you do to get ready? My wife speaks in front of big groups all the time and she tells me she has a specific routine. What do you do to get ready for a speaking engagement?
Jenna: I'm old school and don't know why I do this, but the night before I speak or present, I sit in the hotel room and write out my talking points, pen to paper. Then I record myself, listen to it back, and adjust. Usually, I do that only one time and then I can figure out what my talk track is going to be. But if fail to do that, I tend to miss what I want to say.
Mitch: That is good, and very disciplined. These days with the available technology, it’s probably easier than ever to do your routine and check yourself a little bit to get prepared.
Jenna: I do have to say, though I have an electronic notepad, I stick to the pen to paper method every single time.
Mitch: Stick with what works; if it's not broken, don't fix it, right?
Jenna: Exactly.
Exciting Industry While Changing the Guards
Mitch: In all the different roles and ventures that you've had in your career, what would you say is the thing that gets you most excited? What are the conversations you're having with customers or potential clients or peers? What are the things that you look forward to most?
Jenna: I think the most fun topics we're talking about right now involve things like cybersecurity, automation, A, and all those buzzwords that everyone is probably sick of hearing. However, for dealers and MSPs alike, it's another pivot for them. We're at an inflection point of growth and that growth is going to come from security, hyper automation, making sure you're utilizing the tools that you have today to increase efficiency for your people resources. It will be an interesting pivot to see how organizations are using AI and hyper automation to make money, but also to grow their companies. I think that's going to be the next rung in the ladder. Those are fun conversations because we're all in the same boat wondering how do we apply this to us and our organization? We're all on a level playing field and I think that's where you're going to see more growth and good conversations come from it. We all want to jump in and see what happens with it, so that's been fun.
Mitch: You really understand what you're talking about and it's very clear. I say that as a compliment because you are a consultative peer to so many people. You have customers who rave about working with you, regardless of the type of solution that you're providing or what you're helping them with. What do you feel like is the trigger point for some that makes it click and understand that diversification, new ideas, and being comfortable partnering with someone who might have a different model than you. What do you feel is the trigger point in your discussions?
Jenna: The most important thing is that you go in with an open mind and be ready to learn. Explain where you’re at and help understand the pain points. I really love listening to the older generation or the generation that's my age and applying new things like diversifying their business in some way, shape, or form. I know I'm on the MSP and IT services side, but these dealers are diversifying in many ways. Obviously, we want them to diversify with IT services and help them grow that side of the business, but whether it's production print or EV/AV. Finding out the trigger point is really when they start to open up and say, "This is where we see our organization going in three to five years, and these are the three different markets that we really want to get into.” Whether it's in IT services or in production print, that's where the light bulb moment is where I can say to them, “I can help with one of those five initiatives right now, so let's focus on that." As we continue to have those conversations, that's where we start to grow. We join forces, brainstorm and get to the point of either consuming services that we offer or even just being consultative where we can help and fill gaps. People like to talk about themselves and what they are doing, but I love listening to the next generation. There's been this discussion of balancing the old guard with the new guard. In my head I think there needs to be a marriage between the two. We got here because of the old guard, so we need to be respectful to that, but also focus on the new guard initiatives and what they want to bring to the table. There must be a healthy marriage between them. I hate the distinction between the two because you need both to have a successful business and eventually the old is going to go away, but for the time being, let's respect the marriage between the two different generations or guards.
Mitch: I 100 % agree. Here at GreatAmerica, we've seen a couple of those things that would give people the idea that there’s a change happening from old guard to new guard, and that’s secession planning for companies. The marriage between those two comes down to some humility and being willing to understand the other side's perspective as well as being open to say, “If I want to continue to have that next generation of leadership and team members, I've got to have a really clear vision for what this business looks like going forward."
Jenna: I couldn't agree with you more. In a way everyone has to put their egos aside and leave them at the door. There is such a great work ethic from the boomers that is now being pulled into gen-X and millennials with their thought process and work ethic. However, at the same time, the boomers have to understand that there's a younger generation coming into the workforce, and they have really great ideas. They're quick, able pivot easily and are going to go after what they want.
Generation Switch
Mitch: While being customer facing for the last 10 years, I’ve found it fun to see that there's such a difference in some businesses either regionally depending on what people are doing for their solution offerings, but also generationally with who you're talking to, shifting time and focus to identifying potential employees and cultivating culture. That's been exciting for me for the past few years because you're starting to see more folks in the next wave phase of leadership start to come to the peer groups. We were just at a meeting for an ECS peer group a few weeks ago. We both probably remember 5-6 years ago when it was a different crowd at those events than it is today. What are people telling you about that with industry involvement and how they are balancing different things through their life with work?
Jenna: You are absolutely right. I have loved seeing this shift. Seeing young people like Aubrey Ackervik from Marco or Carson Stone from Stone's Office Equipment coming into the industry and really affecting change is so cool. They're changing upwards to their executive team and then also through internal cultural within their organizations. The culture is going to shift within these organizations because of who you are hiring, which is currently 20-year-olds that speak a whole other language, have different demands, and different requests as they're looking jobs right out of college or out of high school. I think you're going to see an incredible shift in how people work. We've talked about whether it's work from home, flex time, or working in the office. How organizations are attracting to hire is different than how we’ve hired people in the last 10 to 15 years. In this channel, I believe it's shifting. I have this weird split brain, I've had dealers who have younger generation, male, female, all coming into the channel, and at ConnectWise, we have a ton of young people where I am not a part of that group anymore. With all new the tech, security, and AI, there are all these awesome new things coming out today that are attracting different people and a different generation that want to be a part of it. They understand the need for security and cybersecurity, and they want to start understanding hyper automation or other parts of the business. I think we are going to see a lot more people say, "I'm doing all this stuff in my personal life that's helping me. I want to start doing it in my professional life and find a role with things I really enjoy.” It’s slow but dealers are coming through and they're starting to attract a lot of young people which is going to build up the industry and workforce in general. It's interesting for sure.
Mitch: It’s a different dynamic. How do you see onboarding development continuing to evolve? I feel like those groups require very different things to stay engaged and feel like their work has meaning. Is that fair?
Jenna: Definitely. I can't say much for all dealers because everyone does some really fun and different things to attract and retain talent. But with ConnectWise, the way we onboard is very quick, online, and very aggressive, but also allows you access to our executives at different levels during training. That is something that is important for the young folks to not just sit in front of a computer screen, but also to have the ability to go to the C- level and say, “Hey I’m Jenna and I want to understand this aspect of our business more and I have some great ideas for the company.” I think that's where the shift is going to be. The younger generation wants to be recognized, but they want to affect change in some way, shape or form. At ConnectWise, that's part of our culture where we really give the younger generation an opportunity to have time with people that they normally wouldn't. At the dealer level, specifically with DOCUmation, they have a phenomenal culture where it is incredible marriage of legacy and next generation. You had Blue Scantlin all over the office and their grandmother's paintings on the wall to show who they are and where they came from. With the younger generation coming in, they are wanting to get into markets that are important to them like sports in the San Antonio marketplace. Also, with this new generation of hires, it stands out to them when you say, “We are working in an NBA team where we supply the printers and machines that they use.” Those are exciting things for them to hear when looking for someone to work for! You're not talking about printers and speeds and feeds, you're talking about how you're helping an organization be better, faster, quicker, and more efficient. You're allowing the next generation to come in and see how cool this could be for them and think they might get some seats to a game or some cool swag to go with the job. They want to be a part of that. We have this shift in thinking and what kind of clientele you're going after as well. It's going to be fun to see where this industry goes and who they're going to start to sell more to.
Mich: I completely agree. I think the runway is very long and they're going to figure it out if they can find the right partners to help them. I think it says a lot when organizations like DOCUmation have a focus in different areas that's very attractive for new hires. I've also been impressed with how much philanthropy goes on within the channel. Obviously, your father is one who's been at the epicenter of that for many years now. He does a phenomenal job telling a great story and getting individuals to buy into the story. I think the right initiatives and ensuring people understand how important it is, not only as a community of peers to help each other get better in business, but also give back and be very thankful and fortunate and contribute to their community and channel. And you've certainly been a part of that as well.
Jenna: That's awesome. This channel really does give back and you can see it with the Jilliann Fund and with Frank Cannada and the charitable donations that they raise. Even each dealer that you speak to, serves a higher purpose, whatever that might be in their philanthropic events that they host or that they sponsor. So, it's a fantastic industry and it's a big part of why I continue to stay. This is home for me.
Careers in the Industry
Mitch: Would you say there was ever a potential other path back in high school or in college? Did you ever consider anything else beside the industry you are in now?
Jenna: You know when I was playing beer pong at Arizona State University, I never thought that I'd be selling copiers and being here today. Everyone assumes the reason I’m in this industry because of my dad and I'm not. It's because of my older brother, and he's not even in this industry anymore. He was working for Rico right when he got out of college. He was hitting all his numbers, and involved in all the clubs and the trips. When I was about to graduate, he said to me, "Jenna, this is awesome, but it's way too hard. You can't do it. It's no industry for a girl." So, I thought, "Okay, game on." So, my brother and our sibling rivalry is the real reason I took a job with Global Imaging Systems with Frank Gaspari right out of college, and I haven't looked back since! Throughout my almost 20 years in this industry, have I thought about leaving? I mean, sure. I think everyone has thought about leaving for a different opportunity throughout their career, but what keeps me here is the incredible amount of people that I've learned from mentor-wise, along with the dealers and this channel. They are doing amazing things and continue to pivot and grow to expand their businesses. It's really incredible, and I'm happy to be a part of it in any way that I can.
Mitch: I think that’s interesting because I’m sure lots of people would assume that Mike had the biggest influence there, but let it be known that it was a sibling rivalry telling you couldn't do something. That gives a little insight of your personality, when you get a challenge, you’re going to lean into it. I think the other thing that probably keeps anybody around a channel, or an organization is feeling that you align culturally and from a values perspective. I think you strive for this and want to be helpful and help others navigate through this channel and all the changes that are going on to really be a partner as part of that. I can say, truthfully, that's what's kept me at GreatAmerica too. In addition to all the great people we work with, it’s understanding how we continue to help our customers evolve and achieve greater success. That just puts a different sense of meaning into what you're doing and helps motivate you for the next flight out for your Monday morning work trip and feeling okay about it.
Jenna: Exactly, it's a push and pull. Sometimes I learn and sometimes I lead, and I think that it's a good balance, and if you have that perspective, it's good for everybody.
Leadership
Mitch: I completely agree. I want to talk with you a little bit about leadership. You get to interact with so many different leaders and you've had leadership roles of your own. What do you feel has shaped your leadership style over the years? Have there been different influences or different ways of doing things that you've learned? How would you say collectively you've shaped your belief in leadership and how you would go about working with a team?
Jenna: I feel very privileged to have worked with so many different types of leaders. Obviously, my dad is one example. At a very young age, he would wake my brother and I up and say, "What's the word of the day?" And it never changed: it was always “initiative.” It was a response and almost a cadence that we said every single day. So, I think that shaped us from a very young age, that if you see something, do something so it can be changed or become better. So, my dad was a very big influence in my life and leadership. One of the other things that I've learned from all different types of leaders is that as long as you're in the service of others, make sure that you're listening and understanding what they're saying and not just talking to talk, but truly understanding and talking to speak and add value. I've also had leaders like Frank Gaspari, which I’ve loved and learned a lot from. He's aggressive in growth. He understands where there's opportunities and how to go after them. And right out of college, selling copiers, I learned that grit and going back to my roots with initiative to just go out there, cold call, pick up the phones, just do it and go after it. So Frank was a really big influence in my life as well.
However, I think the most important thing as I've aged is to just speak less, listen more, and overall, that'll get you to a good spot. So many people have put hours and hours into mentoring me and I'm at an age where I feel called if there's an opportunity to mentor or to shape a young leader. I'm cresting that hill a little bit, but I’ve had some phenomenal leaders, and I learned some really difficult lessons. I've made a lot of mistakes and I've been fortunate enough to have people pull me aside either publicly or privately and say, "Hey, Jenna, don't do that again. Just sometimes zip it. Don't send that email. Take the high road always. It's dry for a reason but you'll be better off in the long run to just take the high road.”
Mitch: Do you feel like most people are open to learning from those types of situations? Speaking from personal experience, I feel like there's so many things I look back and think, “I could have avoided that easily.”
Jenna: You know, hindsight is something to acknowledge. I'm going to answer it a little bit differently than how you asked it. When thinking about the younger generation that's coming up, I was afforded an opportunity. I take criticism very well. If I'm doing something that is incorrect or that I should be doing differently, tell me, and I do this with my kids too. If they put their hand on the stove and they burn their hand, I'm not going to wait a week to tell them, “Don't touch that. It's hot and can hurt you.” I tell them right in the moment in order to correct it and move on. So, that is the same mentality that I have as a leader too. If there's an issue, I'd like to correct it right away. But this next generation is a little different. How we were coached, spoken to, or parented is way different than the younger generation coming up. So, you must understand the nuances there. I would say if there's a coachable moment, don't let it pass you by, either for myself being coached or for someone else that needs to be coached. I think it's important not to pass those moments by because they hurt, but they make you better and that's okay.
Jenna Outside of ConnectWise
Mitch: Agreed. Growth doesn't come without some sort of discomfort or sometimes even pain. I think that's great perspective. I just wanted to touch on a few other things as we wrap up our time here, Jenna. Let’s dive more into who Jenna is: What are you listening to or reading when you're not on the road or in between stops? What are the things you do to sort of disconnect or help yourself improve in different areas? What’s your go to?
Jenna: There's a lot of different things that I do that are probably silly, but I am a huge sports person. I love all sports. I'm super into golf, NFL, NBA, and I think that you can learn a lot from the players and the coaches. There are a couple of podcasts that I listen to, but I think the most important thing is that I love stories. I love the Scotty Shuffler story. I love listening to Tiger Woods and his growing up with his dad. There’re so many lessons to be learned with sports and how team members interact with each other. Even Scotty Scheffler and his caddy! I don't know if you saw that moment as he won the Masters when he pulled his caddy up with him and they walked together and said, “we are better together.” The we is greater than the me. I think there's so many lessons to be learned in those types of situations. So, whenever I'm on the road and I want to unplug, it sounds silly, but I go to sports to get those feel-good stories and those coachable moments where you can really kind of apply normal stuff that you see in everyday life into your business life. I think that's the most important thing. A lot of times we overcomplicate business, and when it comes down to it, it's just people wanting to do the right thing to grow and to be better. If you take away all the BS around it and just listen to people as people, you'll learn a lot. And then personally, my boss knows this, I have to work out. That's the other way that I unplug. They say if people do CrossFit, they always plug it. So here is my plug for CrossFit. I find it helps me unplug, unwind, and just takes my mind off of work for a minute.
Mitch: Well, I don't know if I'll ever be joining you on the road for one of those workouts, but it's good to know. Thank you so much for joining us. It was great to get to know a little bit more about you and thank you for sharing your perspective with us. I appreciate it.
Jenna: Absolutely. Thanks for having me.
Mitch: You bet. Have a great rest of your day. Thank you.
This has been Great Conversations, a business podcast from GreatAmerica Financial Services. We hope you found some helpful takeaways from this episode as you're charting your own leadership journey. We'd love to hear your feedback for future episodes. Reach out to us on Facebook and LinkedIn or learn more at our website. Thanks for listening. We'll see you next time for more GreatConversations.
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