A Co-Founder Aimed at Making you Thrive
Pennyworth’s Julia Hudson shares how Pennyworth’s philosophy - based on personal experience - helps Executives get the support they need by going way beyond a resume.
What is your role at Pennyworth?
I am the Co-Founder and CEO.
What’s the story behind Pennyworth?
Pennyworth was born out of an exuberant mixture of passion and experience. After years helping interview, onboard, and train candidates for support roles throughout various companies and alongside wonderful talent teams - I realized how much I enjoyed it. Not only did I find great pleasure in it, I was really good at it. Being an EA myself, it came quite naturally.
It wasn’t unusual for Lisa and me to be contacted on a regular basis by Executives and Principals within our network asking “Who do you know? I trust you - tell me where to look for my next great assistant.” Building Pennyworth has been incredibly natural, organic, and right for us. We were already there, we were doing it all along.
We often say we want to help people “thrive” and not just “survive” which is something that came to light for me once I became a parent and felt like I was just barely keeping boats afloat. Our time, attention, and energy are indispensable. We can’t buy more of it, we can’t save it for later. I realized the importance of support roles - not just from being in them - but needing them myself. We focus on all things support because it means something to us. We want our Executives and Principals to thrive in part because of what we can do for them.
What makes Pennyworth unique as an agency?
There are thousands of different agencies that consult on hiring, but Lisa and I focus strictly on what we know best because we have done the work ourselves. Pennyworth is unique because of Lisa and me, not our business model. We understand it intimately.
Not everyone can say that they have actually done the job they are helping to hire for, and that is unique to us. We know what works and what doesn’t from our own grind. We understand that this goes way beyond a job description, a bullet-pointed list of requirements, and lining it up to a resume.
We can read between the lines to hone in on the communication style and personality side of the match. We understand the particulars and nuances. We also can call on a broad and deep network we have built throughout our entire careers. Even new relationships with candidates come from a different perspective, from an organic and genuine place. These are our peers, our colleagues, and our friends - new and old. We understand them, and they understand us. It allows for a much more authentic and transparent dialog throughout the process which means we can make referrals and recommendations based on much more than you can glimmer from a job mill churning out hundreds of positions.
How did your own EA career begin?
The truth is, I really didn’t know what I wanted to do, or what I was even capable of doing. I went to graduate school early, but without a clear path ahead of me. So, I applied for a position and got the second job I interviewed for. I wasn’t quite sure what it would be like or where it would lead.
I was in Boston at a private equity firm before I moved into the operations and management side of the second-largest hotel in San Francisco. After that, I transitioned into a thriving tech company supporting the CEO and some other top leadership. We were acquired after a few years in that position, and I was promoted at our new ownership company, Yahoo!, into the Office of the CEO. That is where I had the lucky fate of meeting and working alongside my now Co-Founder and dear friend, Lisa Casson.
Looking back, the road always led here - my experience in various industries and beside such different, exceptional, and brilliant leaders, entrepreneurs, and operators gave me invaluable insight and an edge. I understand the support people need from the inside out, not only because I worked alongside it - saw it, heard it, felt it, learned from it - but because I did it.
For me, being an assistant was utilizing a collection of natural talents I didn’t know how to fully apply before then. When I was in Elementary School, I planned my birthday parties like Event Managers plan hundred-person offsites. If it were up to me, there would have been name tags and clipboards. My mom still reminds me of how I would list out all of the activities I wanted to do at the party and then work backward to plan the start and end points of each activity. There would be 30 minutes for Capture the Flag, 20 minutes for cake eating, 25 minutes for present opening, and a severe lack of bathroom breaks. To this day, my friends all think it is so hilarious that I send them calendar invites for our night out or holiday party.
What made you successful as an EA alongside such impactful leaders?
I've always been a planner. Sometimes I just calendar to alleviate stress. I call it, jokingly, “therapeutic calendaring.” Like a hobby or a pastime, I organize complex schedules and contingency plans, for fun. It’s a strength and a weakness.
I don’t idle well. I use time, I don’t pass time. Kobe Bryant once said, “I can't relate to lazy people. We don't speak the same language. I don't understand you. I don't want to understand you.” This one always sits with me.
I am innately ‘peppi’ - an acronym of my own invention I use to summarize candidates who are just wired for this kind of job. It stands for “proactive, energetic, problem-solving, prompt, and idealistic.” It boils down to someone who sees how things can be, and gets them done right. Someone recently told me that I struck them as the kind of person who would ask everyone at the bar to ‘scoot down one’ so we could squeeze in another person for our own party. We had a laugh about it because the truth can be very funny. More often than not, that’s the kind of person I look for.
I have never been one to sit back for the ride, though at times I am sure I should have. There are things I miss going my speed, I know that. But I am going, I am getting there, and that’s not going to change. I am warm by disposition but come with enough of an edge that holds me upright in challenges. I remember birthdays, special occasions, your kids' names, and things people said years ago. I could not, however, tell you what I wore yesterday or what I am making for dinner.
I think the most important part of being an Executive Assistant is not just experience as years will be earned, but those innate talents, passion, and natural strengths that we carry through our day-to-day. From our Elementary School parties to the Board Room. I always ask people to show me who they really are, it’s not an interview, it’s a conversation.
What makes a candidate successful?
As long as they have the right boxes checked with the baseline experience or skill set, it really all comes down to personality, chemistry, and style. I would add that matching to a season or chapter is actually quite important as well. What an executive wants next needs to meet what the executive assistant needs next - and those can ebb and flow on both sides.
When I look back on my own journey, I recognize how it helps shape the way I interact with people, and how to recommend a match between clients and candidates. Sometimes it’s not just what’s on paper, it’s explicitly what’s not on paper.
What is one thing you wish people knew about being an EA or PA?
One thing that I hear over and over from our senior candidates is feeling misunderstood by the broader audience. Their Executive knows how valuable they are, but others throughout the company presume the role is reduced to simply scheduling meetings or picking up lunch. We work with extraordinarily talented, smart, motivated, and experienced individuals. Many of them could, maybe will, be leaders themselves. There are times I wish people understood more deeply the power and position these individuals hold in shaping the success of an executive, a leadership team, or even an entire company! Executive Assistants play a critical role, though most often behind the curtain.
What types of clients do you typically work with?
We work with high-level executives from CEOs and C-Suite leaders to entrepreneurs and investors. Many of our high-profile clients come from tech, entertainment, and sports backgrounds.
We work with people who understand the importance of having exceptional support around them in order to thrive. The people we work best with truly understand the value of time and energy and want to optimize theirs!
Tell us about a time in your professional life that made you particularly proud.
There is not much recognition an assistant gets throughout their career. I don’t have plaques on the walls to point to or awards on my desk. For me, it’s all about relationships. They are proof that I have something to really be proud of. I have maintained relationships with almost all of the executives I have worked closely with from the beginning of my career. We email, text, and see each other when in various cities. It might not be every day, month, or even year, but it is certainly not lost on me that I have such genuine and material connections with these people to this day. Knowing that I was not only helpful, and good at my job, but always showed the human side of me along the way enough to build true connections - it’s very meaningful to me. Being an assistant involves so much - you are involved so deeply that this really does matter at the end of the day.
What do you wish you would have known at the beginning of your career that you know now?
At the beginning of my career, I didn’t fully understand the power of just being myself, of diving deep into what I was good at and welcoming the opportunities in front of me. It took a few incidents for me to realize this. After my first job, I never truly had to seek another position again. Each position led me, by chance, to the next one. Though, it wasn’t just random luck. I was working so hard to do well and succeed that doors were opening in front of me. I wish I had known earlier on that to get where you need to go, it’s a matter of embracing what you are good at, working your tail off, being genuine and kind, and developing strong relationships.
What is one thing that people may not know about you?
In my next life, I’d be an architect. I grew-up with a General Contractor father and spent much of my childhood following him around job sites of beautiful custom homes, at his carpentry shop, or in the showrooms for tile, flooring, and fixtures. I love what I do now - but I’ll always have a passion for construction projects and design. Growing up surrounded by my father’s remarkable work (and work ethic) really shaped me. He taught me, by example, about project management, the importance of communication and relationships, being a good and gracious person inside and outside of business, and that if I wasn’t early, I was late! My mother is an artist, and the influence falls smoothly into this realm for me - and has also had a great impact on how I see the world. Yes, if I was starting all over - I’d consider architecture and/or interior design as well. As a mother, I tell my kids they can be anything and many things in their life. This is something I think we all need to remember.
Is there any experience in particular that had the most meaningful impact on you thus far?
There is probably no one more well-aware on a moment-to-moment basis of the value and importance of time, than a working parent or working caregiver of any type. Being a working mother has shaped me to be the absolute best I can be for myself, my clients, and my family.
Beyond that, there are quite a few people who have impacted me tremendously. Some encounters occurred in a fleeting moment with something impactful that shaped me going forward, both good and bad. Others have been my long-term relationships with incredible leaders (Marissa Mayer and Tod Sacerdoti to be most specific). They both have truly changed the course of my career and who I am as a professional now. I could never truly articulate how grateful I am for them. I’d count my Co-Founder on that hand as well, every time.
Written by: Emma Chase
Posted by: Julia Hudson