Ep 86: Chloe Condon: Choreographing a Completely New Career

Diva Tech Talk interviewed actor-turned-technologist/evangelist, Chloe Condon , Cloud Advocate for Microsoft.   

Chloe is a passionate supporter of women in technology, with an extensive social media brand and robust following.  For an engineer, she has a “non-traditional background,” since she “grew up doing musical theater in all shapes and forms.”  Chloe’s father is a director/playwright. Her mother is a theatrical costume designer and graphics designer. “So, I grew up in a trunk!”  she said (quoting the Judy Garland lyric from the 1954 version of A STAR IS BORN).  “I didn’t know a lot about computers, although we did have a computer in our home. I played games on it.”  She had little exposure to tech. “I did not know what STEM stood for, until about 4 years ago! I had blinders on.  I just knew that I wanted to be an actress.”

After attending a performing arts high school, Chloe matriculated at San Francisco University receiving her bachelors’ degree in theater performance. “I booked my first starring role, playing Kira in Xanadu” a San Francisco stage production.  “My picture was on billboards. There was a cut-out of me in the lobby.  I thought ‘this is it’…”. But reality brought Chloe up short when “they handed me $500 for three to four months of rehearsal and performances.” She starkly acknowledged the negative economic ramifications of an early theatrical career. So she proceeded to address cashflow through “bizarre 9-to-5 jobs to support my nights/weekends in theater, although I am probably one of the only actresses, you’ll meet who never had a waitressing job.” Chloe took numerous retail jobs, then landed an Account Executive position at (pre-IPO) Yelp, selling online advertising to merchants in Kansas.  She became fascinated by the startup, tech environment, but “I was terrible at sales.”   Eventually, she “stumbled into other tech roles” including Zirtual, the first virtual personal assistant company.  There she met Ben Parr, (“he was then editor-at-large at Mashable”), who co-founded VC fund The Dominate Group. NOTE: Ben is now a columnist at Inc., a sought after speaker, and philanthropist.  (“Later in my career, I became his full-time assistant.”)  

During this discovery period, Chloe was unhappy. She had a deficit of free time, juggling acting and her “day jobs,” combined with minimal personal autonomy.  “It gave me a lot of insight” into others performing service work, who might not realize the world of self-actualization through tech opportunities. Then Chloe attended a Google-sponsored talk focused on getting girls interested in software.  It inspired her to take an online class and find a bootcamp for coders (“these can be life-changing”). Narrowing down her choices, “HackBright Academy, an intense 12 weeks, stood out.  It was all women. It felt very empowering.”  

Hackbright’s message, to the male-dominated programming world, is “change the ratio!”  Initially, surrounded by a select cohort of women, many of whom had math or science in their background, Chloe suffered from “Impostor Syndrome” which she thinks is more pervasive in technology than other fields (“tech is always changing;  it’s always growing. You’re never going to know everything”). A key to making progress, at the bootcamp, was to adjust learning style from simply reading about concepts to reading AND doing.  “I had to think of it like choreography.” Her tenure at the focused camp culminated in a project, based on skills she had learned (Python, Java and more). It was a social media application that rigorously timed postings to achieve optimal exposure, no matter your time zone --- a “set it and forget it” app using Twitter and Facebook API’s as the base.   As she prepared for graduation “Demo Night,” Chloe’s revelation was that “building the app was hard; talking about it was not. This was a huge light bulb for me. I had always viewed my theater degree as a setback. But I truly use my theater degree, every day, as an engineer, and doing public speaking.”

Initially interviewing for junior engineering roles, (“interviewing is brutal”), Chloe experienced “a significant change” when she “pivoted my brand to be more ‘developer relations’.”  She discovered a niche for her blend of speaking, performing, and communications merged with newly minted programming skills. She was hired by start-up CodeFresh, specializing in Docker innovation.  After a year, Chloe left CodeFresh  to join Sentry.io, a company focused on error-tracking for developers working in open source.  “I was their first developer/analyst.” This gave Chloe “a lot of creative control.”  She lauded the company’s culture. “You wanted to go to work, every day. The people were so fun and cool.”  There, she reveled in creative, fun projects. “I really had the freedom to throw things at the wall and see if they stuck.”  Most of them did. Through that work, she collaborated with Microsoft, (“it’s changed a lot in the last 5 years!”) and that behemoth extended “an offer I couldn’t refuse.” At Microsoft, Chloe currently works with the cloud-based Azure platform.  Most recently, she concentrated on cognitive services, infusing applications, websites and bots with intelligent algorithms to interpret in natural language. “I built an app that analyzes images of Cosplay Mario Kart characters to determine their mood and emotions” as one example.   “95% of my demos are either funny, quirky or solve a unique problem. I try to have fun elements in everything I do.”

Chloe shared classic advice. “Treat people like humans. As they say in The Book of Mormon, let’s just be really nice to everyone. It’s not that hard.”  When faced with a challenge that seems insurmountable (like code not working) Chloe advised: “Take a walk and come back with the solution.”  She also counseled people to take breaks for inspiration and to achieve higher productivity. And “ask for help!” When requesting help, Chloe enumerates steps she has already taken so that she is “not wasting anyone’s time.”   She also cited Twitter as a rich source of feedback and advice. “There are a lot of online communities, with many wonderful people.” Chloe is amazed by the generosity of experts in the tech industry. “People are willing to help.  This community is so welcoming and warm.”

Chloe has evolved to revel in her differences.  “I do not look like an engineer. And I fully embrace that,” she said, discussing the male, middle-aged technocrat stereotype. “I think it educates people” when she is the keynote speaker at a tech conference.  To build her brand influence “I began tweeting out my experience, getting a following” even as she was becoming a “junior” engineer. In 2017, she wrote an article matter-of-factly describing how it feels to be a sole woman at a tech conference.  (“You get kind of lonely.”)  It went viral, she thinks, because it allowed others to empathize without judgement. “Here’s the deal, and here’s what you can do to make it better.”  To protect herself, from Internet intrusion, she wryly said “I am very sharp, and witty, on Twitter. Anyone who comes at me, publicly, will get destroyed by my awesome jokes!” Pragmatically, she is building a bot to respond to inappropriate DM’s.

In terms of job-hunting, Chloe urged women to be selective.  “Work at a place you are comfortable.” She cited “red flags” that become obvious in interviewing. They include a company that is uncomfortable with negotiation; or who has a paucity of women leaders in the interview process.  Positively, she expressed appreciation for companies who cultivate sensitivity to issues experienced by women as the minority of engineers. She also cited Ru Paul’s advice to “silence your inner saboteur” and proceed with confidence.

Chloe noted the industry is missing the mark by not considering those with degrees that are not technical.  “There is a huge chunk of talent” being missed, by the automatic filtering out of those without computer science degrees.  “If you are going to claim you are a diverse company, be open to hiring people from bootcamps! Put your money where your mouth is.”

As an evangelist for Microsoft, and developers in general, Chloe measures success by “folks approaching me and telling me that the work I am doing changed something fundamental for them.  At the end of the day, If I have affected one person, or opened eyes to something new, that is success for me!” For other women in the field, she urged “be authentically you. Don’t feel like you must act like one of the guys. We need more ideas, and diverse thoughts.”

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