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Steve Oliver

Executive Coach

Former CEO, Hollar

About

I’m a leadership coach who works with executives, founders, and senior leaders to navigate the chaos of big tech and startup life without losing their sanity—or their sense of humor. I’ve been in your shoes—I know what it’s like to manage competing priorities, scale teams, and still feel like there aren’t enough hours in the day. My coaching style is all about collaboration, curiosity, and cutting through the noise to get to what really matters. Together, we’ll focus on the kind of practical strategies and leadership skills that not only help you succeed but make the journey a little more enjoyable.


I’ve spent my career leading teams and growing businesses in both big tech and startups. I have significant experience leading large-scale changes that involved technology adoption, e-commerce strategy, and operational shifts. After earning my MBA from Stanford, I joined Amazon, where I managed P&Ls up to $1 billion and, in my last role as Country Manager for Canada, more than doubled the business in just two years. I worked closely with vendors—many of whom were adjusting to e-commerce as a new and disruptive channel—to help them define and execute their digital strategies.


Later, I jumped into the fast-paced world of VC-backed startups, taking on CEO, COO, and President roles—and seeing my companies acquired three times. I’ve worked on everything from scrappy early-stage ventures to scaling established businesses, which has given me a front-row seat to the challenges and opportunities leaders face at every stage of growth. Along the way, I’ve developed a deep understanding of what it takes to lead with clarity, confidence, and impact in ever-changing landscapes.


When I’m not coaching, I’m probably exploring the LA food scene with my wife, rewatching iconic films from my youth with my 10-year-old son, taking my dog on a long walk, or tinkering in the kitchen to perfect my next dish. I also enjoy meditating, journaling, and finding ways to connect with something bigger than ourselves—it helps me keep perspective and stay grounded. These are the things that make life more enjoyable and remind me why the hard work is worth it.

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