Why I Chose to Leave My Job at a Fortune 100 Company to Join a Startup

I recently left IBM in New York to join a startup in San Francisco. While this may be a fairly common story-line, I thought to share a bit about my experience to those who might find it helpful in thinking about or making a similar transition.

TL;DR: If you’re interested in my advice: At first recognition of an itch to peel off, begin working toward your next steps. Start talking to people. Don’t over-optimize for perfection. Pick a direction and go toward it at full speed. “Planning is useful, but returns tend to diminish. Start before you’re ready.”

Growing up at IBM

I joined IBM as an intern in semiconductor manufacturing operations as I finished up my engineering undergrad. I figured there was no better way to learn about large-scale enterprise business than starting on the ground floor. I focused on supply and demand planning, energy management, and environmental social governance. It was exciting. For the first time, I had the opportunity to work across time-zones with a global team. My work felt important.

After IBM “sold” the chip-making unit to GlobalFoundries, I moved to New York to focus on IBM Watson’s business development for the next two years. The AI and automation space was heating up — and I was enthusiastic to be at the forefront.

I joined a 12-person team. We were responsible for defining first-of-a-kind solutions with strategic IBM accounts around the globe. I had opportunities to drive a seven-figure commercial transaction with an automotive client, lead a project team of five in Milan to scale a financial services joint venture, and collaborate with a leading telco to monitor customer behavior via both audio and video meta-data cues.

As the team grew to more than 50, I shifted my focus to internal strategy. I worked with the Corporate Development team as the lead analyst to build the IBM Watson M&A Strategy. We analyzed the full IBM tech stack, assessed product suite maturity, contrasted competitive offerings, and identified unaddressed market opportunity. We then profiled companies that were operating in the white space. Shivon’s Current State of Machine Intelligence was obviously printed out and pinned to the wall.

Experiencing growing pains

Through my work at IBM, I developed a passion for investing. As I learned more about the founders of companies we profiled, I became more fascinated with the velocity at which they were able to define and scale new business models. In turn, I saw the way early-stage investors were able to identify industry trends long before corporates were. I had experience in advising the founders of a social enterprise in Vermont and of an international non-profit. Because I thoroughly enjoy helping small teams grow, I thought I could make the biggest impact by immersing myself in the world of venture capital.

While the first clip of my career had resulted in a tremendous personal growth curve, the Watson platform was evolving. The velocity at which we were able to move as an established corporation was limited — and we were operating in a rapidly growing market. I was standing on the sidelines of the real action.

The flattening of my learning curve coincided with feeling overly comfortable in my job stability and NYC lifestyle. I needed something to reinvigorate my enthusiasm for breakthrough technology. I needed to exercise a level of entrepreneurial energy I had not yet pursued. I recognized that I was quickly approaching an asymptotic glass ceiling. I would not get where I wanted to go by staying along a formulaic corporate professional development path. Perhaps this sounds familiar.

Deciding to take the next step

I took as many coffee meetings and introductory chats as I could fit into my schedule. I worked full days on weekends for several months. I met with colleagues who had recently joined startups to hear what they had learned. I reached out to recruitment firms and platforms specializing in technology, startups, and venture capital placements (CloserIQ, Cascade Advisors, Glocap, underdog.io, AngelList). I audited my network to find who was doing what. I referenced market maps (via Shivon, Venture Scanner, and CB Insights) to identify companies that could be a strong fit, and found other companies by digging through my favorite venture funds’ portfolios. I cold emailed if I didn’t have a direct connection. I became far more active on Twitter and meant to focus on a few Medium posts as well, yet here I am with my first.

Through these efforts, I managed to get on the phone with Anthony Pompliano, rob go, and Barry Schuler — thank you! — where the common advice was to “get in the room where it’s all happening” and “do something audacious”.

Re-evaluating my strategy

I quickly realized that I could not yet break into VC through a few fruitless referrals. The vast majority of associate candidates seemed to be from a top tier TMT investment banking background, a Top 10 undergraduate or MBA program, or were founders of VC-funded startups themselves.

So I decided to pivot. I shifted my focus to product management and business development roles within venture-funded startups to gain deeper experience operating and scaling a company. I knew immediately what I wanted to look for: companies operating in large addressable markets and focused on commercializing finite applications of machine intelligence.

I created a simple ranking mechanism for each opportunity — measuring what I consider vital attributes: team, role, investors, industry, technology, location, and business model — on a binary scale. I added these up to create a score that became a priority ranking. I then knew where to focus my energy. As my father has told me, finding a job is a full-time job in itself.

My efforts fortunately yielded several unique opportunities: one operations role for a startup in Bengaluru, one product management role in Prague, a tech deployment position in New York, an internal strategy role in the Pacific Northwest, and a handful of sales and business development opportunities in the Bay Area.

Interviews took varying forms: a half day worth of written testing, classic case interviews, brain teasers, an hour-long live demo, and a 30/60/90-day plan assignment and presentation. These “challenges” were typically paired with behavioral assessments, personality tests, and/or conversations with several executive team members.

Taking my spot in the room

I am now the Director of Business Development at a Series B stage company called Chute (YC W12). We provide visual content exploration, workflow automation, and customer engagement solutions to brands and agencies.

I focus on growth through strategic partnerships, channel sales, international expansion, and product strategy. I am now operating in the midst of a consolidating market. This role allows me to study funding and growth on the other side of the table from the established corporate players. I am now in the room where it’s all happening.

It is fascinating to learn how to operate with new constraint parameters — namely budget and resource availability. Chute, for instance, has roughly 1/10,000th the headcount of IBM. Prioritization matters tremendously. Every new development is an investment of precious time.

It is also critical to understand the company’s history. This team has been through 5+ years of successes and failures that has shaped the identity and trajectory of the company. It’s impossible to learn all that the team has during this time, but incredibly important to always listen for these nuggets of history. They are invaluable.

Now what?

Well, I am certainly enjoying the San Francisco lifestyle. What’s not to love about proximity to the ocean, hiking trails, and the Sierra Nevadas while consuming the output of the California food system? Since being here, I have seen Ron Johnson pitch his company Enjoy, Jyoti Bansal discuss the “last minute” Cisco acquisition, and met M.G. Siegler among dozens of incredible investors and entrepreneurs building incredible companies.

The mentality here is unique. There is a constant buzz of entrepreneurial energy with an intent to change the world. To tap into this energy myself, I am developing a new partnership with a former IBM Watson colleague. Each week, we pitch, critique, and defend new ideas. Stay tuned.

If you’re still reading this and contemplating about pursuing a next step in the Bay Area, I say go for it — and feel free to reach out when you get here — we can have a chat about the future.

A big thank you to Polina for the support and encouragement with my first Medium post.

Looking forward,