If It Doesn’t Open, It’s Not Your Door: What Corporate Taught a Career Officer

In this episode, we meet Stephanie Hahn, an Air Force Reserve Colonel with 21 years of service, who transitioned from intelligence and cyberspace operations into enterprise software sales. Through a prestigious Secretary of Defense Executive Fellowship at Cisco, she gained a front-row seat to corporate leadership and discovered a completely different way of working and living. Stephanie shares how a mentor became a sponsor, how she found the courage to take on a quota-carrying sales role, and why being fully present as a mom was just as meaningful as any promotion. Her story highlights the difference between mentorship and sponsorship, the power of betting on yourself, and her mother’s wisdom: if a door doesn’t open, it simply wasn’t your door.

Chapters

• 01:10 – From Military Household to Air Force ROTC & Intelligence
• 04:10 – The SecDef Fellowship: Cisco, Corporate Life & New Lexicons
• 10:15 – Meeting a Mentor Who Became a Sponsor
• 14:10 – From Fellowship to UKG & Discovering Life‑Work Balance
• 18:05 – Facing the Fear of Quota and Commission‑Based Pay
• 21:00 – Negotiating Your First Offer & Understanding the Upside
• 24:15 – Mentor vs. Sponsor & How to Ask for 15 Minutes
• 26:00 – “If It Doesn’t Open, It’s Not Your Door”

Key Takeaways

• Your Path Doesn’t Have to Be Linear: From “I’ll do four years and get out” to 21 years in uniform to software sales, Stephanie’s journey proves you don’t need everything figured out on day one.
• Military Skills Translate More Than You Think: Leadership, accountability, decision‑making under pressure, and grooming successors are deeply valuable in corporate roles, from fellowships to customer‑facing and sales positions.
• Know the Difference Between a Mentor and a Sponsor: Mentors coach you and help you think through things. Sponsors know your strengths and ambitions and say your name in rooms where decisions get made—sometimes even creating opportunities on your behalf.
• You’re Allowed to “Just Try It” and Pivot: Leaving a culture of guaranteed pay and 20‑year plans makes sales and commission scary, but in corporate, you can try something, learn from it, and move on if it isn’t right. It’s business, not a lifetime contract.
• Be Intentional and Direct About Relationships: Asking for 15 minutes instead of an hour, coming prepared with questions, and clearly stating your intent builds genuine, long‑term relationships instead of transactional “help me get a job” conversations.

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Transcript

Stephanie Hahn 00:00
She said, “Well, just try it, and if you don’t like it, then you’ll do something else.” And that, for me, was so eye-opening. And I think most of the people who have served a long time in the military can understand this and empathize with it. We are so used to the concept of “I’m going to do this thing for 20 years,” and not “I can try something, and if I don’t like it, I can leave. I can quit. I can get fired.” There are so many different opportunities. It’s not necessarily forever.

Kathleen Smith 00:31
Welcome to Exit Buddy: Veteran Stories to Guide You. This podcast shines a light on the real struggles and triumphs of veterans navigating life after the military.

Rachel Bozeman 00:41
In each episode, we dive into heartfelt stories of resilience, setbacks, a little humor, and growth as veterans transition and find new purpose in civilian life. And here for the journey, we’re your hosts. I’m Rachel,

Kathleen Smith 00:54
and I’m Kathleen. If you’re looking for inspiration, practical advice, or just a reminder that you’re not alone in your transition, Exit Buddy is here to help you thrive beyond the uniform. Enjoy today’s story from our next honorary Exit Buddy.

I just wanted to share that I absolutely love doing the show. It’s a passion project. It’s something that I know my fabulous co-host Rachel and I just love doing. So thank you, Rachel, for being in the studio with me today. It is always a pleasure and always so much fun to get to hear some new stories and meet some new friends,

Rachel Bozeman 01:30
and gosh darn it, just spend a little time together. So without further ado, I know we have somebody incredible in the studio today. Kathleen, don’t make them wonder who we have.

Kathleen Smith 01:40
We’re excited to welcome Stephanie Hahn today, a colonel in the Air Force Reserve with 21 years of service, who has made a very interesting and remarkable transition into enterprise software sales. Welcome to the studio, Stephanie.

Stephanie Hahn 01:55
Thank you, Kathleen. Thank you, Rachel. I really appreciate that warm introduction.

Rachel Bozeman 02:00
Absolutely. Well, speaking of introductions, I think this is the perfect place for the first question, which is: we would love to hear your introduction into the military. How did you decide to join? Tell us a little bit about that.

Stephanie Hahn 02:15
Yes, well, I can tell you my path into the military was almost inevitable. I grew up in an Army household. Both of my parents are retired Army O-6s. They both served 30 years to their country, and so it was just something that I think was natural. They didn’t even have to discuss it with me. It was a path that naturally was something that I wanted to do. I always wanted to be a pilot. I always loved aircraft and aviation and appreciated flying.

Unbeknownst to me, there are other paths to become a pilot. I thought, both my parents are from small rural towns, and my dad said, “Hey, if you want to be a pilot for Delta or United one day, you go into the military and they train you, and then when you’re done there, you can go off and fly in the civilian sector.”

I went ahead and did Air Force ROTC, and my ultimate plan was to become a pilot. Unfortunately for me, I was a little bit too short at that time when I was commissioning. A lot of people wanted to be pilots, and the Air Force could afford to be very, very picky. The height waiver that I required I was not able to attain, so I said, okay, I will do my four years since the Air Force paid for college, and then I will get out.

But fast forward 21 years later — once I got in, I loved it and enjoyed all things intelligence and then cyberspace operations, which are two of the things that I’ve been blessed to be able to do. I am still here serving.

Kathleen Smith 03:41
Absolutely wonderful. And I think this is what’s great about our show: we get an opportunity to talk about people’s various different paths, because too many times we think that it’s one and done — it’s 1-2-3-4-5 and that’s the way you go.

I think you had a very wonderful opportunity to be part of the Secretary of Defense Fellowship, and it sounds like that was something that not many people knew about. So can you share a little bit about what it is and what it opened for you?

Stephanie Hahn 04:15
Absolutely. So in the Air Force, there are a couple of different points throughout your career where you can request to go to school. For my SDE, my senior developmental education, I competed and I applied for the Secretary of Defense Executive Fellowship.

As an Air Force reservist, there are only two non-traditional, non-schooling type of SDE opportunities: one is a Harvard fellowship, the other is the Sec Def Fellowship. I competed, put my name in for both of those, and got selected for the Sec Def Fellowship, and that was an awesome opportunity.

The intent of that program is to determine what best practices the Department of Defense should adopt from industry. There were 17 of us across all of the services — Air Force, Army, Navy, Marine Corps, Coast Guard, Air National Guard — and I was the one Air Force reservist selected for this program.

It was so eye-opening. We were all plugged into various Fortune 500 companies, and the one that I got assigned to was Cisco. Cisco is a company with incredible scale, but it’s not necessarily a defense-first mindset. You don’t think of Cisco necessarily and think DOD like some of the other options. There were fellows who were at Raytheon and Khaki and Booz Allen Hamilton — those really military-adjacent companies where you have a lot of retired military and senior leadership. Cisco was not that.

So it was so fascinating as I had to learn a new lexicon and learn to navigate business outcomes and customers and margins and things that were very different from mission and operations. The metrics were just vastly different. But even with that, it ultimately shaped how I looked at leadership, how I looked at accountability, how I looked at speed.

And just one pivotal moment for me during that fellowship, as I was a fly on the wall looking at how corporate operated, was I also leaned on my leadership lens coming from the military. As I connected with very senior leaders at Cisco, I shared, “Hey, these are just some insights that I have, and perhaps you’d like to know what I’m seeing as a neutral fly on the wall.”

I met with so many senior leaders within that company, but one was Rachel Barger — not to confuse anyone on this podcast. At that time she was the head of sales for the Americas. I met her and I just shared with her as I got her insights and tried to understand how she was leading sales for Cisco. I offered, “Hey, do you mind if I share just some things that I’m noticing about leadership and about developing teams?” At a very tactical level that I was at, to someone very senior, because that’s just not necessarily a vantage point that someone extremely senior always gets to see.

She really appreciated that, and from that we just had this great connection. I told her probably in one of our very first calls, “You’re going to be my mentor. You’re going to be my friend. You’re just awesome.” There were just so many great things, and she’s such an amazing talent that she was someone who I just really, really connected with.

Fast forward, you know, the very nonlinear path that I took while I was in that fellowship — I always planned to go back to the Air Force Reserve full time. A lot of people don’t necessarily know that you can be full time as a reservist. That is an option for your status, and that is what I had done up until that point.

It was another mentor in the Air Force Reserve, Jay McManus, who, when I was just chatting with him about halfway through the fellowship, which lasts for about a year, asked me, “Chappie” — which is my call sign — “why aren’t you leveraging this fellowship to see what else is out there?” And up until that point I hadn’t even thought about it. I was just used to “this is what I do, this is what I’m going to do. I’ll stay until I get about 20 years, and then I’ll figure out what life looks like after.”

As I started doing more research and really looking at what I was currently doing and what I would like to do, it just weighed on me more and more that maybe this is a viable option. And then on the personal side, I can tell you one of the biggest things for me: I had been swimming very hard in my career up until that point. Naturally, to be the one person chosen from the Air Force Reserve, you can imagine I was working pretty hard, burning the candle at both ends.

While I was at that fellowship, it honestly was the first time that I fully felt present as a mom. I have two young daughters, and not the rush of “okay, I’ve got to hurry up, I’ve got to pick the kids up late, drop them off early.” Back in the days when my kids were daycare age — they’re now almost 12 and 13 — I would get charged at least twice a month. Anyone who has daycare-age children knows that late pickup fee. At least twice a month I would budget for me showing up late just because a meeting ran long or something happened.

During that fellowship, on the professional side I was seeing a different vantage point from the military — not better, not worse, just vastly different — and then also on the personal side, seeing how life could look with two teenage daughters now and knowing how I want to really be present for all of the things, chaperone the field trips, and not have to leave them early. It just made sense to me.

So again, my very long answer to your short question: when I started looking at what the options were going to be, Rachel was one of those people who, as I stated, I was connected to at Cisco while I was at the fellowship. She left Cisco to go to UKG, and so I just reached out to her as a mentor, a friend, and then a sponsor. She then became a sponsor — someone who was speaking my name in rooms that I wasn’t in — and ultimately created this Chief of Customer Operations position that I ultimately ended up going to.

I had the wonderful opportunity for a solid year to be her right hand for anything external customer-facing. So all of her meetings, whether on site or virtual, to connect with UKG customers and ensure that from a sales standpoint and a go-to-market standpoint that they had what they needed.

Kathleen Smith 11:07
And I’m really glad that you sort of mentioned the difference between mentor and sponsor, because a lot of people don’t understand that. And I’m just going to do a brief little ad lib here: a mentor is someone who coaches you, someone who you run questions by. A sponsor can be a completely different person, and usually is, who knows your capabilities, knows your strengths, knows your desires, and as you said, can be in that room where decisions are being made to advance you that you’re not going to have access to. So thank you for sharing that.

Back to Rachel in the studio.

Rachel Bozeman 11:46
You know, I’ve never met a bad Rachel, so I definitely understand why you became quick friends there, Stephanie. And I also want to say I love the story you shared about kind of stepping out. I think I heard two things in that journey there in your career jungle gym, if you will, that I don’t hear very often. One: kind of challenging upwards, providing feedback and things that you don’t see oftentimes in the corporate space. And then secondary to that, I love that you discovered life-work balance — again, something you don’t always hear in the corporate space.

So thank you for pointing out both of those, and I’m sure we’ll dig into that a little bit more. But I do want to talk a little bit more about that transition. So I know you had a wonderfully named mentor who provided some guidance and you took that new career opportunity over there. But going into sales is a pretty big leap, if I do say so myself. It’s one where there’s a lot of uncertainty. It can be a little nerve-wracking. It puts you kind of out there having to have all of the conversations, and dare I say, quota can kind of be a little scary. So what really caused that leap of faith?

Stephanie Hahn 12:51
Yes, so sales was never the original part of the plan for me. It scared me tremendously. For anyone who was in the military, we know down to the cent what our paycheck is on the first and the 15th. It is very consistent, with the exception of government shutdowns. You know that you’re getting paid. So sales and commission and quota-carrying just really was something that I didn’t understand. It terrified me.

As I was working for Rachel, I got the opportunity — she’s the president of Go-To-Market at UKG, so essentially everything from marketing to sales to software sales to customer success after someone has implemented our software — all of those things fell in her purview. And so I got the opportunity to see various sides of go-to-market to see, okay, well, maybe there’s something else that I can do. Maybe it’s partners, maybe it’s services, maybe it’s something else, because I was just so terrified of quota-carrying and commission-based.

But it just kept pulling me back. And again, leaning on that great mentor Rachel Barger, when I chatted with her I said, “You know, I love customer-facing. I love engaging with customers. I love being on site with customers. But man, that commission just really worries me.” And she had some great advice. She said, “Well, just try it, and if you don’t like it, then you’ll do something else.” And that, for me, was so eye-opening.

Kathleen Smith 17:02
Okay, so I have to ask, did you go to the Taylor Swift concert?

Stephanie Hahn 17:07
My daughter really, really wanted to go, and so I was looking at all of the concerts and thinking maybe we can fly somewhere. However, when I saw those prices, we had to say no to Tay Tay, and we went to Sabrina Carpenter. And I can tell you that Sabrina Carpenter did a phenomenal job. It was her Short ‘n Sweet tour. She did a phenomenal job.

Kathleen Smith 17:26
Wonderful. So we’ll pull back from the Taylor Swift shake, we’ll shake that off, and we’ll move on to back to that ad lib that I did a little bit earlier about building relationships in the corporate world. And you know, I think that this is not something that I hear a lot of people in the military are trained to do. So how do you do that building of relationships, because they’re very important and very valuable.

Stephanie Hahn 17:55
Absolutely. So it’s interesting — in the military, you’re ultimately assigned a mentor. Your rater, your supervisor is in essence your given mentor. However, I have always found that true mentorship — someone who truly understands what it is that you’re trying to do, understands you — and I also look at mentorship as a long-term relationship, not something that’s just for one assignment. I truly believe that doesn’t just happen, and I have always chosen to be intentional about it.

The mentors who I seek, and the people who I mentor myself as a senior leader in the Air Force, I’m very intentional about it. And as I mentioned earlier, I always seek and I always recommend you seek someone who has walked the path that you are intending to walk. People mean well, especially those of us who are at the twilight of our military career and we are getting ready to go off and do something different. I love the jailhouse lawyers, if you will, who give advice about what people should do. However, if you haven’t actually negotiated a salary, if you haven’t done those things, it is very difficult to give advice on them.

So I just always seek out people who’ve done the thing that I’m intending to do. And I’ve always taken a very direct approach in that. Like I said, with my mentor Rachel, I said, “You’re going to be my mentor, and oh by the way, you’re also going to be my friend, because I think that you’re awesome.” And I’m happy to say that she is both now. And that is something that I’ve always done throughout my career. Naturally when I was a young captain I didn’t put it in that manner. However, I would go up to someone, I would email, I would just say, “Hey ma’am, sir, do you mind if I get 15 minutes?”

And I always share this with people: everyone has 15 minutes. I don’t care how busy you are — if you are the president of a company or of the United States, everyone has 15 minutes. So asking someone for an hour, that is a lot. Sometimes 30 minutes can be a bit much, but 15 minutes, most people will not say no to. And I have yet to have someone turn me away for 15 minutes, and I have yet to turn anyone away who only asks for 15 minutes.

I’m very deliberate and intentional with that time, with the questions that I have. You should always have some ask, because people who are giving mentorship tend to expect that. And just being very deliberate, and the directness that my approach has been has always been rooted in both respect and then clarity of my intent. And I think that if you lead with that, people are more receptive.

Rachel Bozeman 20:40
To it. Absolutely. So to kind of go back to earlier in our conversation, where I was giving you some kudos there for just the career jungle gym and just being willing to kind of share that, I want to kind of apply that now as we talk about folks that might be transitioning out. So do you have any advice? Because I know we started the story — it was “I’m going to be a pilot, I’m going to fly planes, I’m going to do these things” — and then it transitioned into this and this, and just really kind of bobbed and weaved and did all of the things. So is there any advice that you would give to some of those transitioning service folks that might be stepping out?

Stephanie Hahn 21:14
I think the first thing is you don’t have to have everything figured out on day one. I think I am a walking billboard of that. My path has not been linear. I truly believe if it doesn’t open, it’s not your door. That’s something that my mom has always said, and that’s something that I live by. And I choose to take the lesson from it and not get too wrapped up around why it didn’t work out. So you do the best that you can. Perhaps that’s not your door, and there’s another door waiting.

So that has always been my approach. As you are transitioning, as you’re thinking about what is next, I say don’t underestimate how valuable the skills are that you presently have — leadership, accountability, decision-making under pressure — all of those things are just so inherent to the Department of Defense in our business model. And the way in which we operate, our whole business model is about grooming and developing someone to one day take our job. That’s not how corporate is necessarily. So lean on those skills and the fact that you know that you are very capable.

I will also say be open to a path that you never considered. Again, a walking billboard for that. Be open to talking to people who are in software sales or in perhaps a frontline workforce. You never know. Just be open to it.

I’d also say build relationships early and intentionally. You never want your first meeting with someone to be where you’re asking them to get you a job. That comes off very transactional. And again, in those first meetings that I had with Rachel, I was learning from her, and I was also giving her something, and then I was saying, “Oh my god, you’re awesome. Can I please stay connected with you?” And so it was a very personal relationship that was not transactional. It truly was a relationship.

And then lastly, I would say just bet on yourself, even when it feels uncomfortable. If you’re comfortable, you’re not growing. You’re not learning. Try something new. And then when in doubt, like my mentor Rachel told me, if it doesn’t work out, you can do something else.

Kathleen Smith 23:28
So much goodness in there. So much goodness in there. Thank you so much, Stephanie, for joining us. And we didn’t even get to talk about your love — you all, but it looks great. Love everything that’s behind you. And just thank you for sharing so many really great stories. We really appreciate it.

Stephanie Hahn 23:45
Thank you both for having me. This has been such a pleasure. Oh my god, can I come back again?

Kathleen Smith 23:50
Yes. It was so great hearing Stephanie’s journey, and she touched on something that I just love talking about, which is the difference between a mentor and a sponsor, and being really direct when you want someone to be your mentor — that you’re not just immediately asking them for something, that you’re giving them something in return. She was giving sort of her point of view or her points, but also making sure that it’s mutually beneficial when you’re asking for a mentor versus a sponsor, who is somebody who knows your capabilities, knows the value that you bring to an organization,

Rachel Bozeman 24:30
but also knows what you’re trying to strive for, and then they are the executive that’s in a room that can speak for you, because you’re obviously not going to be in that room.

What goodness did you gather from Stephanie, Rachel? So much to gather. But I think what I really walked away with, I just loved her “why not” approach to everything — not “why” or “you know, what I was told,” or “this is my plans.” She didn’t let height bring her down (no pun intended) when she wasn’t able to be a pilot. And when things just continued to shift and change, I just appreciate that she said okay. And I love her mom’s advice. I think it’s such great advice: that door that didn’t open wasn’t your door.

So thanks for listening. Make sure you go out there and follow for more episodes and subscribe to our LinkedIn newsletter. You’ll find the link in today’s show notes. Till next time, see you later, Exit Buddies.