Lessons from a journey of leadership and learning

Rick: Welcome to the show today! I have the honor of introducing you all to Jenny Dearborn. Jenny is both our Chief People Strategy Officer and our Head of Talent Insights, so she carries a double hat of both leading our organization internally, but more importantly, offering some real powerful advisory services to our clients. Jenny brings a wealth of experience across both sales and talent development and is an award winning author. We're so excited to have her as part of the BTS family!

Rick: Hey, Jenny, welcome to the show.

Jenny: Hi, Rick. Glad to be here.

Rick: So, I'm curious what's been going on in your world.

Jenny: Mostly these days I am getting my adult children off to grad school and starting their last year of college. So, a lot of moving kids into different apartments and things like that.‍

Rick: I totally get it. I've got four and one of them is in grad school. One's completely out. One's in his last year of university and one's in his last year of high school. So, I'm just about one step behind youJenny: yeah, I have four. 30, 26, 26 year old started the UCLA MBA program two weeks ago. 23 starts law school at UC Davis in like two days and then 21 year old who is a rising senior at Tufts in Boston. So, everybody's coming and going.

‍Rick: Oh, wow, that is a lot. Well, thanks so much for making the time today. I'm very excited for our audience to get to know you a little bit better and, to just hear a little about your story, where you are today, what some of the major milestones have been in your career, and how you ended up joining the crazy circus of BTS at the end of it is where we are now.

‍Jenny: Yeah, sure. So, I would say, education is the main theme. I started as a high school teacher for just a couple of years and then moved to Hewlett Packard where I was an instructor and taught all of the courses in the catalog in the HR space seven habits of highly effective people and all of that great stuff.And then moved into managing a learning team, pivoted to a startup, docent, which became Sum Total Systems and was in sales there. So, I sold education services to customers that bought enterprise software. And so, that flowed into the professional services LOB. And it was everything that a customer needed to be successful in their implementation of the enterprise software.So, from some total systems was then Sun Microsystems had the same scope at Sun Microsystems was there for six years carried a quota sold learning services, but it's really talent transformation services all of the assessment and readiness and the learning programs and all the change management programs that a technical team would need to move from their current state skills and abilities to a future state skills and abilities.So was that Sun Microsystems then back to Hewlett Packard for a pure HR role and then success factors back to sales in success factors. Same thing that I did sold learning services to global customers and then we were acquired by SAP and then I went back to human resources and was SAP's first global.Chief Learning Officer, then learning and leadership, then, and Chief Talent Officer. So, I had the full talent scope there. And I should say that the secret to my success throughout these operator roles was being a BTS customer, so I used BTS at HP and Sun and SuccessFactors and SAP to great success.And so, it was a huge BTS fan. When I left SAP in 2019, I then went to startups and I've been a Chief People Officer a couple times at different startups like Klaviyo that went public, and that was a great experience. And then most of what I do now is advisory work, so I'm particularly, adept at advising startups on how to sell into the enterprise and was doing advisory work full time and board work and investing and advising and a wonderful mentor friend, Jess, approached me and said you're a full time advisor.Don't you want to come advise BTS customers on the experiences you've had as a customer. And since you've been a Chief Learning Officer five times and achieved Talent Officer twice and achieve people officer three times, you have all this practical experience come and share some of that wisdom and advice with BTS customers.And I was like, that sounds absolutely perfect. I love that idea because I'm a huge, huge, huge BTS fan and really BTS has been the secret to my success and my relationship with Jess has sort of been like an MBA, in the trenches for everything that she's taught me about being data driven and being aligned to stakeholder needs and things like that.So, I was like the opportunity to work with the BTS team and to work with Jess is just something I couldn't pass up. So, I'm so excited to be here.

‍Rick: That's amazing. I actually didn't know until just now, that's really fantastic. And I was very aware of your roles in people development, and I wasn't so aware of your roles in sales.I too, spent most of my career in sales and marketing and then, once I had experienced the power of helping people do more than they thought they could. I did the same thing and pivoted into this world. So that's really cool.

‍Jenny: Yeah, most of my years are in sales and carrying a quota and certainly consider myself more of a salesperson DNA I've always been HR adjacent because I've sold professional services in the HR space and have been very close to the HR function.And every time I've reported to sales, I've had a dual reporting to HR at the same time because we have to make sure at each of these companies that what we are selling externally to customers is the same thing that we're implementing internally. So, we're not in a situation of cobbler's kids have no shoes.and we wanted the internal people to experience the same level of quality and service that we were giving our customers. So, it was always HR adjacent, but most of my time has been in sales.

‍Rick: Well, so let's go down that road just a little bit further because so many of our listeners aren't doing external selling, but they've got to do a lot of internal selling. And so, what is your best advice for someone who is trying to sell some big ideas internally.

‍Jenny: Yeah, I'd say, it's going to sound really simple. It’s understanding what is most important to the people you're talking to. So, if you're trying to sell to an internal stakeholder or a boss or something like that, you really start by saying, what is the most important thing to this boss’s success? Are there metrics that will make this boss wildly successful? And how do I make sure that what I'm doing aligns to their needs? You know, I had a wonderful relationship that I cherish when I was at SAP as Bill McDermott was my primary client and great conversations with him about what was the most important thing in leadership for him, and it was his legacy and creating a culture of leaders and having SAP have a leadership brand that really meant something in the marketplace and the same visibility and credibility that GE had in the nineties for their leadership academy, having that same credibility for SAP's leadership experience, and growing this diaspora of SAP alumni who are now CEOs at other companies that was his legacy.And so that's what we worked really hard to make sure that we achieve and with lots of years in hindsight, I track all the leaders that went through our programs. And yeah, disproportionately, they are CEOs of publicly traded companies out in the world. So, we absolutely achieved our objective.But I was 100 percent aligned to the goals and the mission and the strategy that my stakeholder wanted to achieve.

‍Rick: Yeah, it is one of those things that might sound obvious, but when you get very excited about what your initiative is, it's hard to remember to pause and say, but how important is this to the person that I'm talking to and am I using their language, their metrics, or am I using mine? so.Even though it may feel obvious on some level, it's actually, an important reminder. So, you mentioned your relationship with Bill McDermott and the amazing work that I actually even got to participate in a little bit as your facilitator from time to time and it was great to see, but who are some of the other leaders that made a big impact on your own personal growth and development?

‍Jenny: Yeah, for sure. Carrie Williard is a fantastic mentor and friend. And she was the first leader at Sun Microsystems that sort of picked me out of a crowd and said, I think you've got what it takes to do a whole lot bigger role than what you're doing now.And I was just chugging away, leading my team. I think when she came to Sun Microsystems, I was leading the learning function for worldwide operations and manufacturing. And she was Sun's first ever Chief Learning Officer and the first person to pull together the 10 different learning teams across all of Sun Microsystems.So, when we all came together in a big tent and I was opinionated and shared a lot and, after a couple of months, she said I'm building a new leadership team, and I want you to be on it. And I was like, Oh, okay. So, it was not a job I applied for. I didn't even know what it was going to be.And she just picked me out of a crowd. So, I will be forever indebted to her, and I've tried to model that. In my leadership to really look for diamonds in the rough people that are incredibly smart, but maybe overlooked or sort of stuck in the organization or buried multiple levels down in the organization.And throughout my career, I've made sure I have a skip level with everybody in my organization. So, I really get to know people's strengths and abilities regardless of where they sit in an org chart because I was so thankful for her doing that for me.

‍Rick: Yeah, I've only gotten to work with Carrie briefly through the years, but always found her incredibly impressive so that's a great story and also something that I think our audience can learn from perspective of really getting to know your broader team, not just your direct reports and looking for who are my future leaders that I need to be investing in.So, I'm also wondering a little bit about some of those critical decision points in your career that you could have gone left. You could have gone right and what were some of those big moments for you and what was your decision tree as you were trying to decide what's your best next step?

‍Jenny: So, some of the overarching themes are around following my curiosity and so, you know, about me, I'm super ADHD and I get bored easily and I now see it as a strength, but for a long time, it was a liability, and I would do a job for about two years and then I would be just like this.Itching and so angry like I got to do something new. I'm not learning anything new and I'm accomplishing and I'm successful, but I'm not learning and I've always have to be learning. So, I left HR and went into sales without any experience at all. I’m like, sure, that sounds fine. I can do that totally.No problem. No clue what I'm doing. And then just learn on the job. And then, Carrie said, you're going to manage this huge PNL, a hundred million dollar PNL. I'm like, okay, sure. Yeah. Let's just go. I mean, there's a lot of crying in the bathroom in between breaks in the meetings, but it was a fantastic experience.I ended up being successful even though it was outrageously painful to learn on the job, but it ended up being a good thing. When I was at SAP and was the Chief Leadership Officer, a conversation with Bill was we need to design something for the senior most leaders that will really help them after they leave SAP.And so, it was Bill's idea that we do board development programs, so I had the opportunity to start going around and testing a bunch of these board development programs to decide which one was best for SAP to bring on. So, it was the Stanford director's college and then the which is done through Stanford law school.And then, the Harvard business school has a bunch of board certifications that I went through those and so we created a curriculum path for SVPs and above to go through board development programs. And so just following my curiosity there was able to open up a whole bunch of more doors for me as a board director.So, the positive is following my curiosity and then there's negative regrets in my career where I was too cautious. I remember there's a startup right now that is now a unicorn and it’s a 5 billion, private company. And the CEO of that company, when it was 10 people came to me.A couple years ago and said, would you be on our board? And I said, no, I just don't think your product's gonna be a thing. I mean, I just don't see it.

‍Rick: Yeah.

‍Jenny: I was at a pitch meeting, cause I do a lot of listening to startup pitches and advising for investment for different VCs and yeah, it was in the HR tech space.And so, I'm supposed to be the HR tech expert and the founder came to me and said, you know, would you be on our board? I was like, nah you don't have what it takes. And I totally blew it. That was a huge mistake, but I go up to her all the time.I'm like, yeah, I blew it with you.Rick: Since you opened that door, I'm curious, are there any other things that you saw as big, missed opportunities?

‍Jenny: My two big ones which were two times that a board director role was offered to me and being a board director it is such a commitment to that company and it's a financial liability. You have to be so all in and ready to sell your first born and all of that and if there's any hesitation that it's not going to work, you're probably not the right board member for that startup.And there's been two times that I guessed wrong and yeah, one of the companies they already had a great exit that I missed, and the other one is still rising and I missed so I'd say that those were the regrets.

‍Rick: So, my last question is related to something we were talking about earlier and that is, what is your best advice for someone that is relatively new in their career or maybe been at mid-level longer than they think that they should have been?

‍Jenny: I would say, make sure you have a really good support system. I have so many girlfriends who are a thousand times smarter than me and more capable and more driven and all of that stuff. And their personal lives are a disaster, and they don't have the emotional bandwidth to focus on their careers because they are just barely holding it together outside the office.And I have been so blessed and fortunate to have a partner that is stable and normal and has a job. I just come home every day and I'm like, thank you for just being a normal, nice person. don't underestimate the importance of a whole life support system and balance because it is really hard to be awesome at work when you are struggling outside of work, and I don't know anybody that can separate that so for young people it's really about what are you passionate about? What can you make money at? Where what does the world need coming together there?For your work life and then for your life life. Make sure that you have balance. Also, you have a good support system, a good partner, friends and family that are healthy, healthy habits. Are you sleeping? Are you eating healthy food? Are you exercising? You cannot fire on all cylinders in the office if everything around you is not supporting that high octane effort.Rick: Yeah, and I have to go back to this whole follow your passions above all else position that so many have taken in recent years. It was very funny cause I was actually an ecology major.And when I first started looking for jobs out of college, I was offered a job as a freshwater chemist, making less money full time than I was working part time selling in a retail store. And almost unexpectedly, I went to one of my favorite professors and advisors and I was like, Dr. Galbeck, I don't know what to do.And he was like, well, Rick, at some point you have to decide, are you going to be a man that's asking for money for the rest of your life for the environment? Are you going to be the guy that can donate money to help the environment? And so, there are tradeoffs in both, and we need both. But also, that follow your passion above all else, I think is not great advice, even though I've not heard anyone voice that before.and then you got to manage yourself completely in the kind of spirit of you can't give if you're not full, I think is pretty great. So, with that, it was fun for me to get to know you better today, even though we knew each other before and I'm sure our audience not only enjoy getting to know you more, but took away some things that they can potentially go do tomorrow to help themselves grow.So, thank you so much

Jenny: Absolutely. My pleasure.

Rick: Thanks for joining me today. It’s always a pleasure to bring to you our Fearless Thinkers. If you’d like to stay up to date, please subscribe. Bios for our guest and links to relevant content are always listed in the show notes. If you’d like to get in touch, please visit us at BTS.com, and thanks so much for listening!