Inspirational Women in STEM and Tech: Charli Prangley of ConvertKit On The 5 Leadership Lessons She Learned From Her Experience
By: Penny Bauder
Tags: Tech

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I first became interested in design because of music. Specifically, album art. I used to love looking at the cover of a new CD and flipping through the lyric booklet as I listened to it for the first time. I thought it was so cool that someone had created this visual design that represented the audio contained on the disc. I wanted to learn how to bring ideas to life like that. So, I took design classes in high school, and then when I realized that design could actually be a career I went on to study visual communication design at university.

I worked as a print graphic designer for a couple of years while I looked on with envy as the other designer on our small team redesigned the company website. I realized that web design was the area I really wanted to be working in, so I revised my portfolio and applied to a tech company. I only had two website designs I could show (and one was the portfolio itself!) but I’m really grateful that the design managers saw potential in me and hired me. I’ve been working as a marketing designer at tech companies ever since.

Can you share the most interesting story that happened to you since you began at your company?

One of the most interesting things that happened to me at ConvertKit (a remote email marketing company with a mission to help creators earn a living online) is actually how I got hired here! I was speaking at a small conference in Austin, Texas. One of the other speakers at the event was Nathan Barry, Founder + CEO of ConvertKit and an all-round legend in the design and creator space online. After the conference we were chatting, and he asked if some mutual friends and I would like to get lunch with him. We ended up sitting in a little pizza shop for hours talking about design, life and creating. At one point he said to me, “Have you ever considered working remotely for an email marketing software company?” In response, our mutual friend, Levi, had to add “I think he’s offering you a job” because I didn’t quite understand where Nathan was going with that question 😂. I wasn’t looking for a new job at the time but figured it couldn’t hurt to explore my options, so Nathan and I met over breakfast the next day to discuss the role. Now I’ve been working at ConvertKit for almost 3 years. It’s fun to think that I made such an impression on Nathan at that conference that he wanted to hire me, but it means that I often don’t have much useful advice for people when they ask me how I found my remote job. I didn’t find it. It found me!

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?

Honestly, none of the mistakes I made when I was first starting felt very funny in the moment! There were several times I’d send something to print, only to find errors in the layout afterwards. The first time I found an error it felt like it was the end of the world and like I’d failed at being a designer! Now, of course, I know that mistakes happen and a spelling mistake in a brochure isn’t a fireable offense… But it definitely did teach me to proof things carefully, and to get someone else to check too.

What do you think makes your work and/or company stand out? Can you share a story?

One of my early projects at ConvertKit was to design the brand, website and a coffee table book for a project called I Am A Blogger. Keep in mind that we’re a software company! So it is not typical for us to work on a book, especially one where the purpose wasn’t to talk about our software but to tell the stories of creators (some of our customers), from how they started out to how they ended up earning a living online. Being a creator is a legitimate career path, but there are many people who still don’t see that. So the goal of this book was to help legitimize the industry.

I’d never designed a book before, so it was a really fun challenge to figure that out and work closely with the printer to bring it to life. It was a LOT of work and as we were a very small team there were definitely points in the project where I wondered if this was going to be worth all the time, energy and money we were putting into it. But ever since the book has been out and in people’s hands we’ve been getting the most amazing feedback. Creators have told us that the book gave them the confidence to quit their day jobs and go all in on working for themselves, or that they got their family to read some of the stories in the book and it helped their loved ones to finally understand why they were working so hard at posting blog articles or YouTube videos.

To hear that something I worked on has had a real positive impact on people’s lives in this way is just the best thing ever. And to work for a company that puts resources behind projects like this and sees the long-term vision of putting good into the world and helping people achieve their dreams is a great feeling too.

Are you working on any exciting new projects now? How do you think that will help people?

Something I’ve started working on this week is mapping out a plan for a Resources section on our website. Our content team is putting a lot of effort into educational content and resources and telling inspirational stories of creators and it’s my job to give all that great content a home on our website. We could just post everything as regular articles on a blog, but where’s the fun in that? I plan on creating templates for each content type to give the best reading experience for each piece, and organizing the content into tracks so that our readers can always easily find the next thing they need to learn to improve their online business.

Are you currently satisfied with the status quo regarding women in tech? What specific changes do you think are needed to change the status quo?

Absolutely not. We don’t have enough women in leadership or senior positions. I don’t know why, and there’s no excuse for it, but it’s an issue that needs to be solved. I hate how rare it is for me to attend a conference and see that the afternoon sessions are all talks from women, or that a panel about a general topic (not a “women in tech” panel) is all women. It’s always a nice surprise! But it shouldn’t be so rare. We’re very used to all-male speaker lineups and panels and while things are getting a lot better as conference organizers are being more intentional about sourcing diverse perspectives for their stages, it’s not changing fast enough for my liking.

I think we need more women in senior and leadership positions so that they can act as role models, and we need all leaders at companies to do the hard work to remove the deep-seated, generational bias that could be playing a part in who they promote.

What advice would you give to other women in tech to help their team to thrive?

Encourage each other! It’s not a competition where only one of us can win. So lift each other up and give feedback to help each other grow and improve.

What advice would you give to other female leaders about the best way to manage a large team?

I don’t manage a large team sorry!

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?

I’m really grateful to the design managers who took a chance on me for my first job in tech — Philip Fierlinger and Dan Newman at Xero. They saw potential in me that I didn’t even know I had. They gave me a lot of responsibility early on and I learned just as much in my 2.5 years at that job as I did in the 5 I spent at university — maybe even more! One of my main motivations for wanting to lead a design team one day is to be able to provide that level of mentorship and encouragement for someone else (ideally multiple someones!)

How have you used your success to bring goodness to the world?

My YouTube channel has been my way of teaching what I know about design with a goal of helping others, and sharing what life is like as a designer. As my audience for that channel has grown, I’ve been absolutely stunned at the number of people who have told me that my videos were the inspiration they needed to pursue their dream of being a designer. That means the world to me, and whenever I make content, I’m keeping those people in mind and providing the things that I believe will help them to be successful as designers. It’s my way of mentoring people on a larger, though perhaps more distant, scale. I’m really proud of it, and I think it was a huge factor in me being named one of Adobe’s UX Designers to Watch for 2019.

What are your “5 Leadership Lessons I Learned From My Experience as a Woman in Tech” and why. (Please share a story or example for each.)

There’s more than one way to be a leader — A design event series I really admire, Epicurrence, was hosting a retreat for design leaders. As I don’t manage a team of people I instantly thought it wasn’t an event that I’d be welcome at. The event organizers were shocked to hear this as they saw me as a leader in the design community, because of the knowledge I was sharing and the impact I’d had on others. Their belief in me made me realize what it really meant to be a leader, and that managing people may only be a small part of it. You don’t have to be at the top of the food chain to lead in an impactful way.

Sharing your knowledge isn’t “giving away your secrets”, it can help establish you as an expert — I don’t believe there should be such a thing as “trade secrets” in design. Keeping my methods to myself is of no benefit to me, especially when sharing what I know I could help others learn. In doing so I’m not widening the pool of people I’m competing with for a job, I’m actually establishing myself as an expert. I’ve landed both of my past two jobs in part because I had established myself as an expert in design on my YouTube channel. The people in charge of hiring could see that I knew what I was talking about, because I was teaching other people how to do it. So, don’t be afraid of teaching what you know.

Emotions don’t make you weak, in fact they can be your superpower — I’m an emotional person, which is something I used to view as a flaw until I was on my first ConvertKit company retreat and witnessed our CEO crying openly in front of us all as he shared a very personal story. I quickly learned that ConvertKit is a company that embraces emotions and encourages you to bring your full self to work, and I’ve never felt more at home in a role. I’ve realized that I have great emotional intelligence, which gives me a deep empathy for others. And that’s not weak at all.

A deeper understanding of yourself and your personality type will help you to understand how you work best, and how to optimise for it — I’ve learned that I need time to process things. I’m a deep thinker, and when someone proposes an alternate viewpoint I can find it difficult to take on board in the moment. I’ve learned that before reacting straight away, I need to just listen to them and then process on my own before reaching a decision. There’s no harm in saying “I’ll get back to you on that” and taking half an hour to figure out what you really think. Understanding fundamentally that we don’t all work or process in the same ways means you’ll find it easier to work with others and understand your differences too! On size doesn’t fit all when it comes to the way we work.

Learn how to network YOUR way. When I was getting started in my career, I thought networking was lame and tacky and just about handing your business card out to people. As an introvert I always thought I’d be terrible at networking because I wrongly assumed it was about boldly walking up to people at an event and pitching yourself. The more events I attended and the more people I met both in person and through Twitter online by having pleasant conversations — I realised what I was unintentionally doing was building my network! It’s a network I’ve been able to rely on for advice and support as those relationships grew. Networking is about connecting with people, and my approach at events now is to call it a “networking success” if I managed to have at least one good conversation with someone that went deeper than surface level.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Aside from solving climate change and bringing world peace? I think in general we need to be kinder to each other. I’m a firm believer in kindness and empathy and I think if the world as a whole had a lot more of that, we’d be in a much better place on many global issues. I don’t think I personally can inspire that movement, but I do think that we can all do our part and it will add up.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favourite quote growing up was “Shoot for the moon. Even if you miss, you’ll land among the stars”. And even now, it’s the attitude I try to have towards everything. I like to set big, huge goals and while it’s hard to accept sometimes when you don’t quite reach a goal, I know that even in the attempt I’m in a better place than I was before I started trying. It’s not just about reaching the goal, it’s about the person you become on your way to it.

Is there a person in the world with whom you would love to have a private breakfast or lunch with, and why?

I’ll keep it design based and say Jessica Hische. Though I’ve only met her once at a workshop, she’d been a role model for me (from afar!) throughout my career. Not only does she have fantastic taste and create beautiful work, but I really admire how she gives back to the design community by creating tools like her client email templates and her guides to pricing.