According to Business Insider, Robert E. Williams spent 13 years at AT&T working his way up from account executive to assistant VP by 2018. In 2021, he left the telecom giant to join AWS as a sales leader, then moved to Palo Alto Networks before going all-in on startups in 2023. He joined an AI and quantum startup as head of global channels, working 12-hour days and traveling constantly before transitioning to VC board director and startup advisor roles this year. Williams says startup life is “invigorating” compared to Big Tech’s predictability, describing the difference as luxury yacht versus speedboat.
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The calculated leap
Here’s the thing about career transitions – they rarely happen overnight. Williams didn’t just wake up one day and quit his VP role. He asked himself a crucial question: “If all the money and safety were to blow up in Big Tech, what would I really want to do?” That’s the kind of thinking that separates impulsive moves from strategic ones.
His path shows the value of stepping stones. He didn’t jump straight from AT&T to a tiny startup. AWS gave him exposure to cloud innovation while maintaining some corporate structure. Then Palo Alto Networks offered a startup-style division. Basically, he tested the waters before diving in completely. Smart move when you’re leaving behind 13 years of corporate ladder-climbing.
Startup reality check
Now let’s talk about that startup life. Williams describes working 7 a.m. to 7 p.m. and being on a plane every other week. That’s the speedboat analogy in action – you’re moving fast, covering multiple roles, and seeing immediate impact. But is that sustainable long-term?
The compensation trade-off is real too. He mentions forgoing Big Tech cash for equity upside. That’s fine if you genuinely believe in the company and market, but let’s be honest – most startups fail. You’re basically betting three to five years of your life on that exit event happening. Still, as Williams points out, with AI disruption and Big Tech layoffs, maybe the corporate safety net isn’t as secure as it used to be.
Finding your anchor
What struck me most was his emphasis on knowing what you’re functionally good at. Williams identified go-to-market business development and strategic partnerships as his core strengths. That became his anchor through every transition.
And that’s the real lesson here. Whether you’re in Big Tech or startups, if you can pinpoint your unique value proposition, you’ll always have options. The title might change – from VP to head of revenue to advisor – but the fundamental skills transfer. So maybe the question isn’t “startup or corporate?” but “what am I actually good at, and where can that create the most impact?”
Williams eventually scaled back from the intense travel schedule to advise multiple startups while reclaiming personal time. That seems like the sweet spot – startup energy without the burnout. After all, what’s the point of chasing impact if you lose yourself in the process?
