Over the next few weeks, we will be discussing strategies for personal growth as well as ways in which to steer your career. As a precursor to these topics, I thought it would be great to interview a badass Chief of Staff as this role may be a path to consider as you start to envision what you want your career to look like. After all, how will you know how to steer your career if you have no idea of what to steer your career toward?

The role of Chief of Staff is relatively new in the private sector. As executives find themselves with more and more demands on their time and energy, they are finding the need to partner with a Chief of Staff in order to stay focused on items that are in their zone of genius. A Chief of Staff supports at the highest level, helping their executive not only execute their vision but also define, refine, and clarify it. They uphold the desired culture of the organization, effectively managing staff, and are able to keep a birds-eye view while still having their hand in the details.

I hope you enjoy this interview with Chief of Staff, Jennifer Connelly.

Check out the Interview:

A bit more about Jennifer:

Jennifer Connelly is Chief of Staff to Mr. Ryan Heckman and works across his portfolio of companies. At CiviCO, formerly Quarterly Forum, Jennifer serves as a liaison between staff, executives, senior leaders, and the Chairman regarding company culture, climate, employee well-being, project updates, and HR administration as well as, curating and administering the Mentorship Program at CiviCO. Jennifer joined Ryan Heckman in July 2017 as he was serving as CEO of EVP Eyecare. Prior to her employment with Ryan Heckman she was a private wealth manager at Continuum Partners.  She is currently attending the University of Denver and pursuing a master’s degree in Human Capital in Organizations. Jennifer and her husband Dan live in Denver with their two Pomeranians Mr. Stinky and Zora.

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Check out the Transcription:

Annie: Hey there. I'm Annie of, and welcome to another resource corner post. I'm really excited today because I've got my good friend Jennifer Connelly with me, and we're going to be talking about the chief of staff role. So over the coming weeks, we're going to be discussing ways in which you can grow personally and ways in which you can steer your career, and I think the chief of staff role is a good thing to aim for if you are interested in that role. And Jennifer is here to tell us a little bit more about her role and what she does for her badass executive Ryan Heckman. So welcome Jennifer.

Jennifer: Thank you for having me Annie. I'm excited to be here.

Annie: Yeah, so will you please just tell me a little bit about your role, a little bit of your background, a little bit about your history, let's just start there.

Jennifer: Perfect. Well, right out of high school, I did not go into college. I actually decided to get into the fashion industry. And so, I sent letters all over the country requesting an internship with fashion designers. I got two internships in Nashville, Tennessee. One was with a wedding dress designer Zavozina, and the other was with streetwear collection Prophetik, the designer's name is Jeff Garner.

Jennifer: So I worked for free for a year for both of them. And I ended up getting hired on with Jeff Garner at Prophetik and I literally worked my way up from intern, all the way up to brand director. So I did every job at the company besides design. I oversaw production, sales, PR, marketing. I also planned every single fashion show that he had in multiple countries, multiple cities.

Jennifer: One time we had three fashion shows in three days in three different cities. It was a crash course on what I do now. It really set me up for the skills that I still use today. So I started in fashion, and then after the downturn in 2018, my position was eliminated, and I went to work for an investment group and slowly worked my way more toward the private equity side of the world.

Jennifer: I think working at Prophetik gave me the inspiration that I was never going to be a fashion designer, I was not very good at it. Anything I designed never sold a single thing. But what I loved was the project management side, I loved the people side, I love logistics, I loved administration. I hated filing quarterly taxes, but I learned how to do it. I learned the 30,000-foot view of how an organization works and all the pieces and parts, and the strategy there is behind it. And so it really set me up for my career, and it also let me know that I was very skilled in this type of work, and not so much for creative design type work.

Annie: Yeah, but you still like working with creative people?

Jennifer: Yes.

Annie: And I think you and I have a similar background in that respect. I was an assistant to a lighting designer back in college. I studied lighting design in college, I was around a whole bunch of theater people. So I think that you do have a creative mind, even though your creativity is much more in the realm of how am I gonna make this work, how are all these logistics and all these pieces going to fit together in order to keep us moving forward, right.

Jennifer: Absolutely, yes. And there is a skill to working for a visionary type boss. They're a different breed, and so I cut my teeth working with a very eccentric boss. Jeff slept four hours every day, four hours only. He only ate a mono-diet of granola, Asai and yogurt.

Annie: Oh?

Jennifer: Only.

Annie: Oh wow.

Jennifer: That's it, every meal.

Annie: So can you explain just a little bit about who Ryan is? We were talking off-camera, and I was like, "I don't even actually know what Ryan does." We office out of the same office space. Jen actually coordinated this entire office space that we're officing out of. I know Ryan, and I was like, what does he actually do? What is his actual role? I know he's got his hands in so many things. Would you please explain a little bit about what Ryan does.

Jennifer: I think the important thing to understand about Ryan is that he's just on another level in every regard. He was the youngest member of the Olympic Ski Team at 16 years old, he's been into Olympics. So he started his career as an elite athlete. And then went to college up in Boulder, and then went into private equity early in his career where he spent 17 years in private equity before deciding that he wanted a different change, a different pace of life, and actually wanted to become CEO.

Jennifer: So no one would hire him as a CEO, so he bought a company and became CEO. He grew that company from 16 employees to 463 employees in four years. And went from one state to three states. Eventually, he became chairman of that company and move to chairman versus CEO, and I guess part of that change is what's really interesting to see, kind of how to transfer a new CEO into an organization was fascinating. But after being CEO, he has I think become more involved with his nonprofit leadership development organization, CiviCO, and he just can't stop, he just won't. He's just an incredible leader and every day I learn something new. But it's really hard to describe what it is that he does because it's not one single thing.

Annie: Right, he's got his hand in so many things. I think our bosses are similar in that way, that I know Pete's got his hand in so many different things too, so yeah, that makes total sense. So we're delving into the role of chief of staff, because I really want my viewers to consider this as a potential goal, like an end goal, and as a possibility for your guy's careers. Jen has a lot of wisdom and knowledge in this role. And it's a role that I think a lot of us know about, we've heard it before, but we don't exactly know the in's and out's and how that differs from a typical executive assistant role. So we don't even know how to steer our career in that direction.

Annie: So, would you please just explain what it is you do for Ryan, and I'm sure it's a lot of different things, but would you please just give us kind of an overview or some details on what you do for Ryan technically.

Jennifer: So struggle in describing what I do every day. It's hard even to tell my husband at night like what I did all day. So I took a few notes. So I'm gonna describe my role in the hats that I wear. So I wear a bunch of different hats, as we all do in our roles. One is a goalkeeper. So I manage the workflow. I have to prioritize across all of the teams, making sure activities are running smoothly and they are coordinating according to what their roles are. I'm also an operator, meaning I add structure to everything that we do, processes, procedures. I implement those processes and procedures in order to drive business and execute on strategy.

Jennifer: A lot of my time is spent on special projects, which is kind of a catch-all, but for example, building out this office space is one of my special projects and probably one of my favorite special projects.

Annie: She did a great job guys. I wish I could take you around and show you the space, because it's beautiful.

Jennifer: Yeah, it was really fun. I think ultimately though, integrator is my main role, meaning that it is my job to facilitate communications from every level of the organization up to Ryan, so he's not spending his time having those conversations, rather than just getting a download for me, highlighting what things are on fire and how things are going. So you're ultimately a facilitator of conversations, as well as you're doing a lot of project management.

Jennifer: You also serve as a proxy. So if Ryan is out of town or unavailable and someone on the team has a question, they'll probably start with me and ask kind of what my thoughts are, what do I think that he might say or some guidance. People will send their agendas for a review to me, so we're not wasting time on the wrong things. Or what things should we highlight on the budget, what does anyone see or not see. So it's all about saving your executive time, and also keeping your teams running very, very smoothly, so they're not just sitting in the water waiting for responses.

Jennifer: You're also an advisor. So your strategically advising your team, your organization, your executives on what you see, how you see things, giving advice is a huge part of what I do.

Annie: And Ryan too, right?

Jennifer: Yes.

Annie: You're an advisor not only to all those other pieces and [inaudible 00:08:42], you're also advising Ryan on what you see and what you've witnessed in these interactions with other people?

Jennifer: Yes, yes. And sometimes it's something super small as, don't forget it's so-and-so's birthday, and that's just a very important part of our co-brand, is celebrating people and being aware of their birthdays, and their anniversaries and their deaths in their families, and caring and showing care. So it could be as simple as reminding him of someone's birthday, or as much as saying, I think that someone's getting ready to quit, or maybe need some course correction on their behavior.

Jennifer: So it is a lot. In my role, you're dealing with the minutia, all the way up to the highest level of strategy. And you have to be able to live in both worlds and do an equally good job at both things.

Annie: That is really well put. I feel like a lot of us, even as executive assistants, do that to a certain extent already. But if you're considering a role as chief of staff, keep that in mind, that you'll be tasked with all facets, and there is nothing that is outside of the realm of your job description, because that's just what you do as chief of staff.

Annie: What we do largely as executive assistants as well, is just on a whole other level I feel. So, tell me about company culture. You were just talking about how you help Ryan maintain company culture throughout the organization. I know even just officing here, I just had a birthday, they were really great at celebrating my birthday, they're really great at acknowledging humans and those things and making everyone feel included and involved and special. Even though I'm not a member of any of Jen's or Ryan's organizations, I'm not a member of that, but I am a CiviCO, but it's not like I am an employee that you're looking after.

Jennifer: Absolutely.

Annie: Yet, you still desire to build this culture. Can you speak to a little bit about that and how the chief of staff is the holding of culture and the creating of culture?

Jennifer: Absolutely. So I think my role as far as culture goes, is setting the example. I have to live the culture, I have to believe the beliefs and exhibit the behaviors that we requiring everyone around us to do. I think I can sum up our culture in every organization that Ryan touches as, a desire to become a better version of yourself every single day. I think that's at the core of all of our beliefs in every organization that he has is, get better, doesn't matter, get better, the words of Ryan.

Annie: I love that.

Jennifer: It doesn't matter, get better. Ultimately that is what we're here to do, and we want to do that for everyone. And a part of that is celebrating everyone, and that's celebrating where they're at, and where they're going, and when they are getting better. So that is my role, is exhibiting living the culture, showing the behaviors, and that is just getting better every single day.

Annie: I love that. I know for myself, that's my personal goal too, is to always one-up myself.

Jennifer: It's hard.

Annie: It is, it is, but it's also a really awesome thing to strive for. I think we all should be striving for that, like let's one-up ourselves, let's go in, let's give it our all, let's see if we can be more innovative and come up with more creative solutions for our executives and organizations. So, thank you for sharing that, that's really awesome.

Annie: Let me see here, so when did you realize ... I know you just kind of fell into this role working for designers and stuff like that. Was there a defining moment for you, where you felt like, "Hey, I'm really good at this stuff, these are the things that I want to do personally." Was there a decision, what there a point in time that you could remember, where you decided hey, this is a legit career path and I'm totally going to pursue this?

Jennifer: I don't know if there was an exact moment. There were several moments early when I was working for a designer, that I realized that I was very, very good at what I do. And I can remember, I was 20 years old, I was at London Fashion Week, working backstage. And everyone's like six foot tall, like six-foot-tall amazon women, and I'm only 5'2", and so I'm very short, I was very young. And my role for that particular experience was working backstage, organizing the models, making sure that their outfits were perfect, and then calling the timing on the show.

Jennifer: So I would be holding their hands-

Annie: This is rough.

Jennifer: And being like, okay go. And then next, and check them, and okay go, okay go. And for me it was like that small role, even though I didn't design the clothes, that was such an important part of getting that right for that experience and that brand, that I realized that I really take pride in the backstage part of an organization. And I think a lot of people could relate, who are in an executive assistant or chief of staff roles, or even just general administration is, if you're really, really good at what you do, nobody knows that you're doing it. I will often wonder if my boss wonders what I'm doing all day, but he never asks, because he just sees things are getting done around him, and that is a sign of a really, really, elite, exceptional person. Is that you're just running your job so well, that no one even knows what it is that you're actually doing.

Annie: Yeah, that's a really great way of putting it. And sometimes I feel like I'll go to Pete, and I'll actually list out what I did for him because he wants to know. He's like, "So, what did you do this week?" And I'm like, "Here are the things, I did all of the things, that's what I did, I did everything."

Jennifer: How much time do you have?

Annie: Yeah. So, I know you and I in the past have had conversations around a personal brand, and I feel like personal brand is very important, and it's something that goes under-discussed in the EA role and in our world. And I just feel like you've got it nailed down and you know exactly what you want from your career, and you know exactly how you want to steer your career. Can you tell me how your personal branding has helped you kind of form the career that you want, that you love working with Ryan, how has it helped you? How has your own personal brand helped you?

Jennifer: Yeah, that's a great question. I think personal branding is very important, and another aspect about personal branding, before I talk about my own brand, is that when you work with an executive or an organization, you are co-branding your brand with their brand. So you want to be very aligned with your values and your beliefs about how you want to be perceived and how you present yourself. And for me, my brand isn't so much about the way that aesthetically I look, or how my work looks, but it's more about the experience of me, how you're experiencing me, whether that's on email, in person, or even just more peripheral, if you're attending an event that I planned. It's definitely a brand, and you definitely experience my personal brand.

Jennifer: And I think I can sum it up in three things. Number one is GSD. Which is get shit done.

Annie: I love that.

Jennifer: Yes. And I think ultimately that is our basic job, is just to get the shit done that needs to be done.

Annie: Yeah.

Jennifer: It doesn't matter what the task is. The second part is, I think big. And so I am thinking in a bigger way whether that's about the broader puzzle pieces of the team and how they're working together, or the event, or the project. I'm thinking bigger and for myself. And so, for my personal career, I've always thought in a bigger way. What do I want? Where do I want to go? How do I want to get there? And ultimately, who do I want to work with? Because life is short, and if you've ever worked, and I've been in a situation where I wasn't really aligned with the values or culture of the company that I was at, and the advice I would give people who are in that situation is, think big and take small steps every day to get there. Do something tiny every day to get better, to get where you want to go, and that will alleviate some of that negative vibes about being in the wrong situation or in the wrong role. Just take small steps.

Jennifer: So think big, take small steps to get where you want to go. So it's get shit done, think big.

Jennifer: But the very last piece is, you've gotta have fun. You have to have fun with what you're doing, it's not so serious, I'm not a brain surgeon, so I love having fun. I'm a little sarcastic, a little sassy, but ultimately I care about what I do and I want to have fun, and I want people around me to enjoy themselves as well.

Annie: I love that. And so guys, I really want you to take in what Jen just said about taking small steps every day toward the career that you actually want. Because I feel like we don't do that as much as we should. And I feel like I come in contact with some of you sometimes who are frustrated with their roles and frustrated with their jobs, and they aren't sure how to leverage where they're at to get where they want to go. And taking those baby steps every day will help you get to where you want to go. But first, you've got to get clear on where you want to go.

Annie: Which is why I'm interviewing Jen, because I feel like she is very clear on what she wants with her career, she wants to work with people she likes, she wants to have fun doing it. She wants to be a badass chief of staff, rocking it, and she's doing all those things. But she didn't get there overnight. So, it really is about taking small steps and leveraging where you are to get where you want to go.

Annie: If there's a piece of your job that you absolutely love, expand it, expand that piece. Work from that place, work from where you're at, so that when you change jobs, you have to have a vision for where you want to go, and you can look more toward your ideal role. And it may take you a few positions to get there, but just keep that in your mind all the time, and we're gonna be discussing that in the coming weeks, as well.

Annie: Okay, so my last question, which I like to ask everybody I interview, is what is one piece of advice that you'd give to your junior professional self?

Jennifer: I love this, I love this question. I think a lot of people can really [inaudible 00:18:31] answer is, in our roles, ultimately we just give, give, give. Like we are taking care of everything and everyone around us, and people who don't get a lot of care is ourselves.

Annie: That right there.

Jennifer: That's something I struggle with every single day, is how do I fit it all in, how do I take care of everyone around me, that's my work life, my home life, and it's usually ourselves that we miss. I would say to my younger self, just take time for you, make sure you're taking care of yourself, do the things that you would do for other people for yourself. I highly advise taking a mental health day every quarter, where you can step back and think about what you want, what your goals are, how things are going around you. Sometimes you just need a day of sleep.

Jennifer: But I would highly recommend that self-care should come to you as much as your job, as much as your family, take care of you.

Annie: Yes. You guys know that I harp on this all the time. So I'm glad I'm not the only one saying this. Thank you, Jen, for self-confirming.

Jennifer: You're so welcome.

Annie: And that I keep pushing on everybody. So, thank you so much for joining us today, it's been a pleasure to speak with you and to hear your thoughts on the role of chief of staff. And guys, stay tuned for the coming weeks, where I'm going to be going over how to steer your career in a direction you want it to go.

Annie: And that's all for now.

Jennifer: Bye guys. That's awesome Annie.

Annie: You were great, thank you so much.

Jennifer: Thanks.


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