Get to Know: Andy Whelan, Creative Lead
Joined Job Portraits: October 2018 | Based in: San Francisco
What do you do at Job Portraits?
My role is split between a couple different functions. I handle some business development — when a potential client reaches out, I’ll talk with them about their goals and how Job Portraits can help. I’ll also make sure they’re interested in the kind of work we do, because it’s about more than content. We take a strategy-based look at where they are now, and what it’s going to take to grow their team. Once we’ve gotten to know each other, I’ll write up a proposal.
The other side of my job is the traditional “creative lead” role, which means I’m the main point of contact for a client as we work through each piece of a project. I like that I get to maintain those ongoing relationships, because employer branding is so much more powerful when you build it over time. If we can get clients regularly putting out content that’s aligned with their mission and who they are, we’re helping them attract the right people.
What were you doing before Job Portraits, and why did you want to join?
Starting out after college, I was an actor. My first real job was at Second City, the improv comedy theater in Chicago. Then I moved to New York and did primarily commercials and plays. I also worked for Late Night with Conan O’Brien, doing characters between guests. And to support my acting career, I built a green cleaning and maintenance company that served luxury high rises. I also managed a restaurant and led training for a Fortune 500 retail company. I’ve done a little bit of everything.
Eventually I moved into career coaching — first at a couple of art schools, then at General Assembly in San Francisco, where I spent the three years before joining Job Portraits. When I saw the post about the creative lead position, I’d actually just stepped down from my role at GA so I could do some fun things and spend more time with my family. I’d decided I wasn’t going to look for work until next year. But the job posting immediately caught my eye. I thought, “This is what every candidate I’ve ever worked with wishes companies would do when they’re hiring.” So I reached out.
I loved the tone of the posting and the way it was presented, but I was also drawn to the actual work. Because of my background in career coaching, I know how to help companies find candidates, and I understand what those candidates are looking for. There’s so much hiring going on right now. But people still struggle to make a change, because starting a new job is hard. It’s uncomfortable. You can dangle the carrot of salary and benefits, but what the people I’ve coached want to know is what it’s really going to be like to work there. That’s what we do at Job Portraits.
And on a personal level, I liked that there were so many elements to the creative lead role. Wearing new hats appeals to me because it’s a chance to make new mistakes, learn from them, and build new skills. Writing is a good example. I’ve written plays and scripts for corporate clients, but I want to be a stronger writer. When I saw the quality of work this team was doing, I knew there was a ton I’d be able to learn.
What was the interview process like?
At the bottom of the job posting, there was a note from Miki that said to reach out with questions. I thought, “Okay, founder, let’s see if you really want me to reach out,” so I sent an email — and she wrote back in less than 30 minutes. We hopped on a call the next day, talked for about 45 minutes, and I said, “I don’t know where you guys are, but I’m interested.”
From there, I moved through a couple of different challenges, one doing some editing and another creating and presenting a proposal deck. I also had one-on-ones with the rest of the full-time team, and the thing that struck me was everyone was exactly as advertised. Every company says they’re transparent, but at Job Portraits it’s actually true. I remember one in-person meeting I had with Miki and Jackson where they just laid out a specific situation they were dealing with and asked me what I thought.
When Miki and Jackson called with an offer, it was again a fully transparent experience. They were up front about the fact that I’d need to start right away, because Miki was about to go on maternity leave. I said I’d take the night to think about it and talk with my family, but I told them, “I really want this job and I’m pretty much going to take it.” Miki just started to cry, and I’ll never forget that moment. I knew I’d found a place where what I was doing would truly matter, where I could help. That’s what I’m always looking for.
Tell us more about the team culture.
There’s a real focus on growth, not just professionally but personally. You even see it in the way we start our meetings — it’s like, “Let’s check in about you. How are you doing?” Even though I haven’t been on the team long, I feel safe to be who I am.
There’s also a level of trust that was a little intimidating at first. I sent out four proposals in my first two weeks, and it felt a bit like being handed the keys to someone’s fancy car, rather than the old station wagon. I was like, “I don’t want to break your business!” But that’s all pressure I’m putting on myself, and I’ve felt totally supported. I always have a safety net. Everyone on this team is sort of “generally specialized,” in that they’re all pretty familiar with the clients and the workflow, but at the same time, I know who the go-to person is on a given topic. Whenever I have a question — and I sometimes have about 100 of them — they are always happy to help. I learn best by doing, so I’m just putting one foot in front of the other and going with the flow.
Lightning Round!
What’s your morning routine?
I wake up around 5 or 5:30 a.m. to my dog, Bowie, jumping on me and licking my face. I take her out and feed her; then my wife, Lara, and I sit and have a cup of coffee, work out together, and meditate. After that, I take Bowie for her morning walk, and I’m usually at the desk by 7:30 or 8.
What’s your superpower?
When I was a career coach, I found I could kind of get to the bottom of most people in our first conversation. I’d sit with a student and talk about their past, and we’d be able to break down why they made certain choices and what had brought them to where they were. I think it’s because I’ve been there — I know what it’s like to struggle to do what you love. As a coach, I’ve found that much of the work is just understanding how the stories we tell ourselves prevent us from taking action. When you help someone take an honest look at their situation, they often know what needs to be done.
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What’s the worst advice you ever followed?
Most of my family and friends told me I would suffer as an actor, and for a long time, I did. I set myself up to pay my dues and struggle and have no money because I thought that’s what I was supposed to do. Then I realized I could just hustle and build up my own source of revenue. I decided, “I’ll just find my own way.”
What’s your spirit animal?
Probably a shark, but whatever the least harmful kind is. Definitely not a Great White. I’m not a shark because I think I’m scary or tough or anything; it’s just because I can’t sit still.
Tell us about a book that had a big impact on you.
When I was in college, I was studying pre-med and my roommates were all theater majors. I ended up taking a theater class and reading some Shakespeare — Othello, King Lear, a couple of others. At the end of that semester, I auditioned for a play on a bet, was cast, and changed my major to acting.
If you could interview one person, living or dead, who would it be?
My wife’s father. He died when she was seven, and he was an intriguing guy. He was a super-smart math and English double major, and then he became an artist. He ran a tree-trimming business, back when that was not particularly safe work. He was a photographer — his work is hanging in our house. I can still see the impact he had on her family in the way they talk about him, and I’d love to meet him myself.
What unpopular opinion do you hold?
That everything needs to be clean and organized. That’s why my cleaning business grew so quickly — I came by it honestly! For me, external chaos breeds internal chaos. I can’t go to sleep at night unless everything’s put away, and I clean before I go on vacation so I can come back to a tidy house.
What’s your next adventure?
Professionally, challenging myself in this new role at Job Portraits. Personally, my wife and I try to travel somewhere new every year — this year was Cuba, and next year will be Spain. But I think the bigger adventure for me is how I connect with my family. I left my last job in part to do more with them, and I’m glad to be in a position now where I have that time to spend.
