This as-told-to essay is based on a conversation with Robert E. Williams, a 40-year-old VC board director and startup advisor based in Maryland. It’s been edited for length and clarity.
I spent the first 13 years of my career at AT&T, working my way up to an assistant VP-level position. Then, I remember asking myself a question that unlocked a complete shift in what I wanted: If all the money and safety were to blow up in Big Tech, what would I really want to do?
In 2021, I left AT&T and stepped down from my title to take a bet on myself. After a series of calculated career risks, I joined an AI startup, and now I work in venture capital as an advisor for startups I believe in.
The startup world has been invigorating and completely unlike the past predictability of Big Tech. If Big Tech is a luxury yacht, then startups are a speedboat.
I loved a lot of things about my time in Big Tech
In 2007, I came straight out of undergrad into an account executive role at AT&T, where I had a really supportive development system around me and was able to take on a lot of responsibility quickly. I met some great people and had mentors who really showed me the ropes. Plus, the money was safe, which meant a lot as a young twenty-something.
I worked my way up from sales manager to director and was eventually promoted to an assistant VP role in 2018. I had a lot of responsibility, but everything felt very structured.
From weekly meeting cadences to quarterly business reviews, I always knew the playbook we’d run for that day, week, and month.
During the pandemic, I had a lot more time to think about what was important to me
While I valued the stability of a big company, the relationships I built, and my time leading large teams, I wanted to expand my experiences into the growth areas of tech. In 2020, that was the cloud and the earlier days of AI and machine learning.
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I wasn’t ready to make the startup leap yet, but I knew I needed to join an established company with a culture of innovation and disruption in emerging tech. When I left AT&T, I joined AWS as a sales leader. It was a calculated risk, but I was willing to bet on myself to prove that I could thrive in this new environment.
A year later, I took another calculated step down to a startup-style division of Palo Alto Networks, and then I felt ready to go all in on startups.
I found startup life invigorating
In 2023, I joined an AI and quantum startup as its head of global channels, and later its head of revenue and partnerships. We were building partnerships around the world, so I was probably on a plane at least every other week, getting in front of customers.
I worked most days from 7 a.m. to 7 p.m., building the team, responding to customers, and negotiating contracts. My scope of work was much broader than it ever was in Big Tech, and it was invigorating. I’d quickly see the fruits of my labor as new customers, partnerships, and media came through.
The startup world is inherently unpredictable, and I had to wear a lot of hats
In one moment, you could be helping the team respond to a critical RFP response deadline, and then in another, you’d be briefing investors from a $100M VC fund.
The pay is high risk, high reward. It’s very common to forgo some of the typical Big Tech cash “on target earnings” for additional equity upside. I found it important to have a genuine conviction in both the market and the startup before making that tradeoff. It needs to fit into your lifestyle goals for three to five years until an exit event.
Now, as a VC, I have more time to focus on what matters to me
There wasn’t anything I disliked about startup life, but after a few years, I wanted to scale that impact across multiple companies.
In May, I stepped down to an advisor role at the startup, which allowed me to become a board of director for a VC, and an advisor for two other startups: one fintech company and one medical device startup in Africa.
Even though I’m covering more ground in terms of companies, I’ve gotten so much time back, not having to be on a plane every week. I’ve been spending more quality time with family and reconnecting with old friends that I haven’t seen in some time.
I’ve also had time to double down on mentorship and advisory work with startup founders and students from historically underrepresented groups.
The most important thing to do in your career is find out what you’re functionally good at
At a startup, you can have a lot of individual impact. You can take the risk of getting equity and stock options, but you have to remember that most startups fail. That being said, when you consider reduced job security and the AI boom, Big Tech isn’t the safe option it used to be.
Beyond anything else, it’s important to find out what you’re functionally good at. I’m great at go-to-market business development and strategic partnerships, and that’s been my anchor throughout my career.
If you can narrow in on what you’re good at, you’ll be incredibly valuable in Big Tech or startups.
Do you have a story to share about quitting Big Tech? If so, please contact the reporter at [email protected].
