Jack Randall on How to Break into Tech Comms
Mixing Board Studio Session
Jack Randall is the Head of Communications at the e-commerce startup, OpenStore. He’s an angel investor in 15+ startups such as Wander, Parafin, and Hang, and advises startups on comms and launch strategies. Previously, he was Robinhood’s Head of Communications for 6+ years, helping them scale from seed stage to an $11 billion company.
In this Studio Session, Jack and Mixing Board Founder Sean Garrett talk about how to break into the industry (it might not be the way you’d think), why you should always say yes to that coffee, what to do when you’re just starting out and what veteran execs can learn from those in their early days.
SG: I was looking in my email, and one Jack Randall reached out to me in 2013 asking for an internship at Pramana Collective. Do you remember that?
JR: Yes! Wow, I completely forgot I emailed you! I wonder where I first learned about Pramana. Maybe from TechCrunch? I saw the people involved — you, Brandee (Barker), and Brian (O’Shaughnessy) — and I was like, holy shit, these are the greats. I want to work with them. This would have been in college, after my internship at Apple wrapped up and before Robinhood. I wanted to get into the startup space.
SG: One consistent thread of Mixing Board members is longtime experience in comms and marketing. You bring a unique perspective because you don’t have decades of experience but you broke in fast and accelerated your career quickly. So let’s take a step back. You’re in college at Santa Clara University in 2013. What were you trying to do?
JR: I grew up on the Peninsula in the Bay Area so I was always surrounded by tech. I was lucky to attend a private high school in Atherton, where all these major VCs and CEOs sent their kids. I remember being obsessed with learning how my classmates’ parents made their wealth, which was mostly through tech.
So I started reading as much as I could about the tech industry. I’d go to TechCrunch first thing in the morning. I remember watching Apple events at lunch in high school. In college, I interned at Apple where I first cut my teeth in PR. It was Katie Cotton’s PR era, who was one of Steve Jobs’ long-time lieutenants. I learned a lot through osmosis there and became fascinated with positioning, public perception, and the dynamic between people building companies and press.
SG: For the people who didn’t go to a Valley private high school with the children of venture capitalists, what could they learn from you?
JR: I was very fortunate to grow up there. But a lot of the things I did to learn and get my foot in the door, other people can do too. I developed this curiosity with startups, the tech press, and watching these startups launch products or handle different situations. I read as much as I could…in lieu of having that desirable internship or that well-known logo on your LinkedIn, become an expert in the space as much as you can — lean into your curiosity and the wealth of information that’s available online for free. There’s never been so much free content from people actually building things in tech. Everyone seems to have a Substack, podcast, First Round Review article, or Tweetstorm on how they did X or a breakdown of how they made it as Y discipline. This is true for people looking to break into comms, marketing, product, VC, or looking to become a founder.
SG: How and when did you first get in touch with Robinhood? And what was it like then?
JR: I joined Robinhood in June of 2014. They had 11 employees and raised $3M from Index and a16z.
In high school, I started investing in stocks like Netflix and Apple. I’d check Yahoo! Finance during office hours, email my grandfather who was a broker at Stifel Nicolaus, and ask him to place trades in my custodial account for me. He’d respond an hour later, the stock had of course moved, and I’d be left with a fat commission fee. It was so archaic.
I remember convincing my Dad to let me move away from my grandfather’s brokerage and get an ETrade account so I could make trades myself. They had an app! And only $10 commissions! Looking back now, it’s funny that I was begging to set up an ETrade account.
In college, I read that the social, stock prediction app I was using, called Robinhood, was building a zero commission stock brokerage, now that they got their FINRA license. I didn’t realize they were a few miles away from me, and I needed a summer internship after my Apple one ended.
I DM’ed Vlad on Twitter asking for a job. I joined that summer truly thinking it’d be a three-month internship… Two months in, we were at a team retreat in Tahoe. I was sitting outside answering support tickets with the founders. And Baiju randomly asks me, “Why don’t you drop out of college this fall and join us full-time?” I was so confused by the question. I looked at him and I was like, “What do you mean?” Dropping out of college never crossed my mind. I remember telling them, “I need to talk to my parents.” We decided that we would take it quarter by quarter. We did that for a quarter or two, and then we never discussed going back again.
SG: You were at Robinhood for six years, which is a long time in startup. You’re obviously well-read, but you had no actual hands-on experience doing communications for a startup, much less one that is eventually going to be a public company. How did things evolve and how did you learn on the job?
JR: Thankfully, we had enough funding to hire a PR agency. And we had a great agency partner in OutCast. I learned a lot through working with them. I quickly got to see how the sausage was made, this time at an early-stage startup vs. Apple.
I supplemented what I was learning at Robinhood by meeting with the top comms people. I was really proactive about this. I remember meeting Andreessen Horowitz’s Margit Wennmachers at her office and grabbing breakfast with Katie Cotton after she left Apple.
SG: You even had coffee with me.
JR: Yep! At Blue Bottle in Mint Plaza. I wanted to learn from others who’d been around the block. It all helped me think bigger and see around corners — what if Robinhood becomes a significantly bigger company, what issues will we have down the road, etcetera. If you’re early in your career, even if you have a great boss, supplement what you’re learning and grab lunch with the most senior person on your team or account. DM people on Twitter. People in tech, and specifically in tech comms, are happy to help others. That was true for me a decade ago and it’s true now.
SG: Robinhood was, and still is, on an interesting ride. While you were there, you saw different times of the tech era, you were there when everything was great and then when things were less great, in terms of how media covered tech. As the vibe shifted, how did you manage for that? And as this thing was growing bigger, I assume now you’re in the hundreds of employees and beyond. But as someone who was there among the first dozen, how are you evolving communications for Robinhood as this thing’s getting much bigger and about to go public?
JR: The vibe definitely shifted! For everyone. We were super proactive on the comms side for many years and had created this huge appetite to cover us.
Things shifted when our valuation hit the billion-dollar mark, which was rare-ish at the time. Within a week of announcing that, very established reporters from top-tier outlets that didn’t give us the time of day before, suddenly wanted to dig into the good, the bad, and the ugly. We would have the smallest little hiccup, like 12 minutes of downtime, and Bloomberg and Reuters would write about it. The vibe shifted again 1–2 years later as we had even more growth and some self-inflicted issues.
I hired people from Square, Facebook, and Palantir who had experienced some of the positive and negative moments we were about to face. We also shifted our media strategy. Instead of saying yes all the time, we became more selective with media and event opportunities. We gave exclusives and held background meetings with various newsrooms. We elevated our bench of executives and highlighted less sexy things like financial literacy initiatives and product controls to signal maturity in the business.
Now, I tell startups I advise and invest in that they should be surgical in their approach to mainstream media. Supplement your GTM or comms strategy with additional media like VC or operator-run podcasts and newsletters. Invest in community and owned channels like your blog and social, even if you think no one is listening.
SG: What were the considerations in leaving Robinhood?
JR: Leaving was a really hard decision. I loved my time there. There was never a boring day. But I was tired and I felt like I’d done everything I wanted to do there. We had just come off a crazy year with wild growth and funding, a gnarly outage, and a few other big moments. We were finally on solid footing externally, and our team was strong. I was burnt out. You have to listen to your body.
SG: For people who are currently Heads of Comms, there’s very few of them who are not considering a moment, if not a moment soon, where maybe they do consulting. What was your experience with consulting?
JR: I sort of fell into consulting. I got introduced to Alt, initially for their head of marketing role. I wasn’t ready for another full-time role but I liked the team so I made a small investment and consulted with them. That took me down a path where I dabbled with consulting and worked with startups across consumer fintech, autonomous vehicles, b2b, and crypto. I loved working with early-stage founders, but I missed the magic and camaraderie of operating in-house. I still do some occasional advising.
SG: Now you’re running communications for OpenStore. What does that job entail, and why did you choose that? I know you had multiple opportunities.
JR: Yes! I joined OpenStore in January. We’re making it easier than ever to run or sell your e-commerce store, and on the consumer side, we’re launching a consumer marketplace for you to discover unique products you can’t find elsewhere. My responsibilities span b2b and b2c communications, content, social, and employee communications.
I’ve spent most of my time operating and investing in consumer fintech but I wasn’t married to fintech as I searched for a new operating role. I was conscious of finding the right mix of ingredients that would be compelling. OpenStore checked a lot of boxes. It’s in e-commerce, a space I haven’t played in before. It’s b2b and b2c. And at the Series B stage, we’re in this sweet spot where we aren’t too early-stage but also aren’t riddled with process.
SG: What other advice would you give people who are in college or who are entering into comms? What should they do and what should they not do? Beyond doing the reading and the research that you mentioned earlier, what are some basic steps people can take?
JR: One common piece of advice I hear given to college students is to join an agency. If you want to break into PR, join an agency because you can work on different accounts and get a taste for which stage or sector you like best.
I disagree. You should go in-house. The ideas are formed, the decisions are made, and the strategy is mostly set in-house. You’ll get paid more. You’ll get equity. And you’ll learn a little about many other functions like marketing, sales, product, and design.
If you follow traditional advice and join a big agency, you’ll find yourself with a small project on the account, that your boss will then email to the client
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