Women Of The C-Suite: Jessica Vann of Maven Recruiting Group On The Five Things You Need To Succeed As A Senior Executive
An Interview With Candice Georgiadis
Pace yourself. It’s a long haul for CEOs, especially if you’re a founder, as well. Give yourself the courtesy of kindness, breaks, proper vacations, and unplugging. After all, if you sacrifice yourself until all your energy is depleted, the jig is up.
As a part of our interview series called “Women Of The C-Suite”, we had the pleasure of interviewing Jessica Vann.
Jessica Vann has founded and grown Maven Recruiting Group to a renowned, nationally recognized recruiting firm and brand. Specializing in connecting high-leverage executive and personal assistants to the nation’s most prominent companies and individuals, Vann and her team assert that strong support staff are the bedrock of Silicon Valley and have spent the last decade evangelizing the value of executive assistants and teaching executives how to work with them effectively. An active thought leader in the administrative support community, Vann hosts REACH — A Podcast for Executive Assistants, with over 180,000 active listeners and has created an e-course and executive assistant coaching program as well. Once a brick-and-mortar company, Vann’s COVID pivot was to transition her team to a remote organization that also spends time together at a horse ranch in the Sonoran Desert of Arizona. Maven has since been recognized by California Best Startup as one of the most innovative corporate training companies, which may have something to do with its balance of remote and ranch work. Since its inception in 2010, Vann and Maven Recruiting have been recognized in Business Insider, Inc Best Workplaces, Inc 5000 Fastest Growing Companies and San Francisco Business Times Top 100 Woman Owned-Businesses.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
For as long as I can remember, I’ve had an entrepreneurial spirit. I’ve always aspired to have some level of agency and influence in my life.
When I was 15 or 16, I noticed that all of the open houses advertised by real estate agents were always on the weekend. I remember thinking the agents must hate sitting in empty houses for hours and hours during time they could be spending with family. So, I dressed up, walked into a real estate brokerage, and asked if they would hire me. I told them I would put up and take down signage and welcome visitors. It was a perfect arrangement. At the time, I was taking summer classes, and was able to study when no one was there. When a home buyer stopped in, I showed them around and answered questions. The realtors thought it was a clever idea and agreed to pay me. They even told me if any of the houses happened to sell, they would give me a small commission. When one of my homes did sell before the end of the summer, they mysteriously forgot all about that little arrangement. On the bright side, that taught me the very valuable lesson to get everything in writing.
Looking back on my childhood, I’m not surprised to find myself in this position. I’ve always wanted to define my own path. In most traditional jobs, your promotions, salary, and progress all hinge on how others perceive you. I’ve never been comfortable with letting others make those decisions. I was inspired to create a company that would be best in class. I had a clear vision for approaching things with candor, authenticity, and integrity, and was excited to build the company I wanted to work at. That challenge has been a part of my entrepreneurial journey for years.
Can you share the most interesting story that happened to you since you began leading your company?
I’ve always believed if you do something from your heart, and do it with integrity and authenticity, the purity of that message resonates with people in a way that it doesn’t when it’s contrived or forced. Recently, my team and I were creating a media page on our website, and I Googled Maven Recruiting. The first hit was a Business Insider piece featuring us along with Sara Blakely, the founder and former CEO of Spanx. I didn’t know anything about this piece, so I dug further. I discovered the article was based on a podcast I’d done with Sara Blakely’s former executive assistant and personal assistant. Somehow, our podcast, REACH, fell into the lap of Business Insider, and they decided to write an article about it for their 118 million monthly viewers. When things happen organically and synergistically in that way, it’s pretty cool. We happened to do that Google search on the exact day the story broke.
That foray into the podcasting world was catalyzed by a desire to build support resources and community for Executive Assistants and because we saw that there was a dearth of resources for Executive Assistants’ professional development. It was a delightful episode. I had the chance to talk with two incredible women. They were at the top of their craft and had an incredible synergy together that spanned over 10 years. Our connection was evident in the episode. We had fun with it. When you do things from that place, you never know where they will take you.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Most of my mistakes feel more tragic than humorous, but one does come to mind. At Maven Recruiting, we match executives with executive assistants. Once in my career, we crossed wires and scheduled the wrong candidate to meet with our client.
The client looked at our options and said, “Great, I want to meet Janine.” But instead of scheduling Janine to meet with her, we scheduled Mary. So, that day, our client met Mary all the time thinking she was Janine. When Mary called to report that the meeting went extremely well, you can imagine my surprise. I never intended to send Mary because she had zero relevant experience.
Ultimately, the fact that our client loved Mary as much as Mary loved our client goes to show the power of the intangibles and authentic connection. We’ve always said the kind of hiring we do is less about a finite skill set and more about interpersonal connection, resonance, and chemistry between people. Mary didn’t have any of the experience the client said she wanted. We sent plenty of people with that experience, but our client chose Mary. It’s a powerful experiment in psychology. If you think about it, the client met her without preconceived notions or judgments because she didn’t know what her experience was. She took her at face value. They had a fantastic conversation and clicked. All the people with perfect qualifications on paper fell flat.
It turned out well, but I apologized profusely. The client laughed about it and thanked me for introducing her to Mary. As a leader, I’m okay with being wrong. People who admit to mistakes get to grow. It takes a level of vulnerability to be wrong, so I’m very happy to stand corrected.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
So many people have had a part in helping me become who I am today. My team here at Maven was the driving force behind positioning me as a thought leader. During the first years of running the business, I was internally focused. I wasn’t in a place to think about putting my voice out there. They encouraged me to step into a public-facing role and come out from behind the curtain.
Another time, our team went to a spiritual retreat. The facilitator asked us to circle up for a drumming session. The point was to express ourselves by tapping out the beat of our own voices. After the session, he took me aside and said, “You have a voice and a message that wants to be heard. I don’t know if you’re a writer or a public speaker, but something inside you needs to come out and be shared with the world.” I heard that right before we launched our podcast series. The timing affirmed we were on the right path.
On another occasion, Lyle Fong, the founder and CEO of Lithium Technologies, shared something very impactful with me. He told me, “If you’re going to be known for Executive Assistant recruiting, then be the absolute best Executive Assistant recruiting firm in the universe. Don’t do a little of this and a little of that. Be the recruiting authority. Aspire to be the recruiting expert in the Bay Area, then California, then the United States, then the universe.” I took his advice to heart. It came at a pivotal moment when we were making strategic decisions about shifting to a narrower focus.
I’ve had the privilege of knowing so many supportive, encouraging people over the years. It’s difficult to single out any one person because they’ve all influenced who I am today.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
Emerging from the pandemic was the single hardest thing I’ve had to do as a business owner. To endure that time, we encountered the agonizing necessity of paring back and cutting jobs. Sacrificing several roles to preserve the larger company is any leader’s worst nightmare.
Even after that moment, Maven wasn’t out of the woods. By the time San Francisco allowed us to come back to the office, most of my employees had moved. It necessitated a period of reflection and change. I spent weeks wondering whether to pull people back or to move forward as a remote organization. There were a million changes to navigate, but it all started when we took the plunge to pull up our roots as an in-person company and go remote. After that, decisions all cascaded in line like dominos.
Okay, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
When you’re a CEO, you’re in the hot seat 24/7. Every decision, deliberation, and consideration rests on your shoulders. You take all the input you can get, but at the end of the day, you are the one who has to make the decisions.
The decisions you make span an extremely broad purview. As CEO, you’re expected to be a generalist and have a general understanding of all of the elements that comprise a healthy business. You need to know enough to weigh input from every expert on your team. You’re not the CFO, but you need to understand enough about corporate finance, governance, best practices, forecasting, and projections to be involved with decisions. You’re not a CMO, but you need to have enough of an understanding of how marketing impacts your company to contribute to its strategic direction. Your team provides input, recommendations, and suggestions, but the buck stops with you. Ultimately, the decision is yours, and the consequences are yours to bear.
When you’re the Founder who’s started the company, you don’t see your role as temporary. The stakes are higher because you have skin in the game. You weigh every decision pertaining to financial and strategic direction, market specialization, brand, culture, team synergy, team incentive, and team rewards, and you’re there to stomach the consequences. There’s no bail out for a small business owner. The choices you make impact you, your business, your family, everyone who works for you, and their families. You have nowhere to run or hide.
What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?
Many people have the idea that being a CEO is glamorous, but the role actually comes with an incredible amount of sacrifice. People overlook the intensity, emotional drain, and fatigue that comes with 24/7 responsibility. The level of pressure and risk is ever present. To me, that’s not glamorous or sexy — it’s just hard.
People think that being a CEO means you are your own boss. Yes, you have discretion in terms of how you spend your time, but that doesn’t mean you have full autonomy. In reality, you’re fettered by responsibility. A CEO is not completely free. Even though we may not have a person overseeing our role, we are still responsible for everything we and our teams do, and we have to be accountable for the results our businesses do or don’t produce.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
If women decide to have a family, there is a very clear distinction. Of course, men are also parents, but female executives who choose to become mothers encounter a level of complexity and responsibility we would be remiss not to discuss. Pregnancy entails the physical burden of carrying a child and the logistical burden of dozens of doctor’s appointments. After delivery, there is healing and sometimes postpartum depression that women balance in addition to work. Every woman’s experience is different; some rebound quickly, and some navigate postpartum depression for years. Negotiating those realities in combination with your responsibilities and duties as an executive is challenging, to say the least.
The other piece of the equation I experience is subtle sexism. I imagine, male leaders obtain a level of assumed respect that women don’t. I’ve had people approach me in an entitled or demanding way, or expect me to succumb or be less formidable in negotiations. For example, a former employee once referred to me as his “colleague.” That was staggering because it showed me how much harder I had to work to achieve the same level of acknowledgment and respect for my accomplishments. I doubt that men have to correct employees by saying, “I’m not your colleague. I’m actually the CEO and founder of this company.” That subtle disrespect is something that female CEOs may have to confront.
What is the most striking difference between your actual job and how you thought the job would be?
To be honest, I started with no preconceptions about what this job would be like. Before this role, I had only been responsible for myself. Suddenly, I found myself responsible for building, growing, and sustaining an entire company. I had absolutely no idea what was involved. It’s been a non-stop education.
Just when I think I’ve come to grips with the role, legislation shifts, the market changes, economic trends create new factors to negotiate, or team morale dips. I never stop learning because the challenges never stop coming. For example, to deal with Covid’s curve ball, I facilitated a full transition to remote work. Now, we have employees who want to work internationally, and five million regulations are associated with that. You never reach a static state, but that makes being a business owner, an executive, and a leader interesting.
Is everyone cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
It seems to me that this world functions most harmoniously and we achieve the most interesting outcomes and results when we allow people to play to their strengths. If you had a kitchen full of head chefs but nobody willing to be sous chefs, purchasing managers, line cooks, or runners, meals would never get cooked.
Being a CEO requires a few specific traits, and the first is comfort with risk. If you’re not comfortable putting it all out there, you shouldn’t aspire to leadership. However, if constant risk motivates you to show up with a better version of yourself, you may have what it takes.
Comfort with risk goes hand-in-hand with another vital trait. You have to assess whether or not you are prone to overthink things. Successful entrepreneurs have a level of conviction behind their ideas that compels them to action. Overthinking, over-critiquing, and overanalyzing your idea or your vision can lead you to sabotage your own dreams. It’s the folly that prevents so many ideas from getting airborne. At the end of the day, it’s a choice. You’ve made good calculations. You feel reasonably good about your direction. You can’t stay on the precipice. There comes a moment when you have to jump. That crucial willingness to jump is what sets CEOs apart.
Finally, you have to be your own locomotive train. Every CEO has an inner hustle or drive that propels them forward like a steam engine.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
1. Pace yourself. It’s a long haul for CEOs, especially if you’re a founder, as well. Give yourself the courtesy of kindness, breaks, proper vacations, and unplugging. After all, if you sacrifice yourself until all your energy is depleted, the jig is up.
2. You won’t ever be able to expect the unexpected, but you can anticipate it. Nobody expected a worldwide pandemic. However, part of running a company well means anticipating downturns and planning for hard times. You hope for the good times, but you have to prepare for the worst.
3. Be wary of cancerous people. Culture killers and culture assassins are an unfortunate element of every business. It never pays to keep someone like that around because they are a good performer, produce great results, or are the best at what they do. As leaders, we often rationalize keeping them on because of their talent or brilliance, but leadership is also about the broader picture. You have to see the whole thing, including the destruction those people leave in their path. I’ve learned that lesson the hard way.
4. Don’t accept or tolerate people who minimize you. You need to be around people who respect, encourage, appreciate, and believe in you. I’m not saying to surround yourself with people who never challenge you, but they should be people who at the end of the day make you feel encouraged and capable.
5. Never attempt something if you’re only going to do it halfway — give it your all. Think about athletes like Serena Williams, Michael Jordan, and all of the greats. They don’t go into their profession lightly. Running a company is similar. If you’re going to make something happen, you’ve got to give it your all. If you don’t, you’re wasting everybody’s time.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
As an employer, I think a lot about demonstrating decency, respect, and kindness toward employees. If people worked for companies that treated them with transparency and humanity, the world would be a very different place. If we based decisions on the best interest of employees rather than on profit, we would see better outcomes as leaders.
When you read the recent headlines about Meta and Twitter, you have to wonder what’s governing these decisions. Apply a simple rubric to your decisions by asking, “Would I want this done to me?” “Is this the honorable thing to do?”
How we treat people at work has massive repercussions in all parts of life. The way our employees feel about their work influences how they show up in their lives and for others.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
I would jump at the chance to have lunch with Marianne Williamson. Her platform centers on understanding yourself and seeing the goodness in the people around you. It’s influenced the way I lead, and I’d love to share that with her. Her book, “A Return to Love,” is about meeting people in a place of positive regard. I think that we lead better if we tap into our self-awareness and seek that out in other people, too.
At the end of the day, leadership is fundamentally about people. It’s not about how useful a person is but how you activate the people around you. The more you know about yourself, the more empathetic, kind, and ready to lead you will be.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
It was a pleasure!
Women Of The C-Suite: Jessica Vann of Maven Recruiting Group On The Five Things You Need To Succeed… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.