What I Learned When I Left Microsoft for a 100-Person Startup

Devang Thakkar
May 18, 2016 9:05PM

Throughout the course of our careers, there are times when we make moves in pursuit of new skills, more responsibility, or better compensation. These changes occur somewhat frequently as our careers mature, our industries evolve, or the job market shifts. For all of these stages of professional development, however, very rarely—maybe once or twice in our lives—do we make a meaningful change purely in pursuit of passion, in belief of a mission. I recently made such a change when I decided to transition from Microsoft in Seattle—where I had been for 10 years, amongst a team of 100,000 colleagues—to Artsy in New York City—a 100-person startup whose mission is to make art accessible to anyone with an internet connection.

Devang Thakkar, Head of Auctions, joined Artsy in 2015 after 10 years at Microsoft.


The Decision

Leaving a reliable gig after a decade at Microsoft was not an easy decision. I had established myself as a leader and built a personal brand along with a strong support system, all of which was hard to leave behind to start from scratch elsewhere. During my tenure at Microsoft, I had made several moves internally, from switching teams to changing practices (engineering to product to business development). Every quarter, I’d ask myself three simple questions to decide whether the time was right for a change:

  1. Am I learning new things?
  2. Am I having fun?
  3. Am I being paid enough to do this?

If too many of my answers came back as “no” then it was time to move. After having wrapped up a multi-year product release, I decided to take a trip to Hawaii in early 2015 to step back and think through what I would like to do next. During this trip a new guiding question emerged: What matters to me the most? I asked myself that question for the first time on this trip with a clear head and a belly full of poke, and gradually the answer became clear—impact.

So I set out to find where I can have the most impact and discovered that it was at the intersection of technology and art. My passion for technology and product building had only grown stronger after working and learning from some of the brightest technologists at Microsoft. I grew up surrounded by art (my mom is an artist) and have painted all my life. Technology and problem-solving challenges me and being surrounded by art soothes me. It is this yin and yang mix of art and technology that has been the balancing force in my life thus far. So I knew it was this blend of tech and art that provided the greatest opportunity for me to have the most impact at this stage in my career.

So for those who are looking to make a switch, I urge you to ask yourself: What matters to you the most?


The Transition

Once the domain was set, the next step was finding the right company. Artsy’s mission was bold and it was clear that the company’s impact on the art world would be immense. Upon returning from my Hawaiian adventure, I reached out to Carter, Artsy’s Founder & CEO, and was thrilled to learn the growing team was looking for someone to lead the auction product team. One month later I had an offer and was faced with the next daunting phase of my transition to a startup: equity.  Unlike many companies, Artsy presents its prospective hires with a range of choices for base salary and equity options. Resources like Glassdoor and AngelList were very handy to understand comparable compensation packages at companies in a similar stage as Artsy and how to think about the role of equity vs base-pay. On top of that, a very open dialog with the Artsy Leadership team made understanding and accepting the offer much easier. 

For those looking to make such a transition to a VC-funded startup, I urge you to study the comparables and anticipate some tough decisions between immediate compensation and potentially larger, long-term impact and payout. Also, have a candid conversation with your new boss about your expectations to make your transition a more positive and transparent experience for all involved. 

Once all of this was set it was time to say goodbyes to my friends and family at Microsoft, but I won’t go too much into that as everyone has their own ways of saying their goodbyes—so you are on your own for that one!  

Members of the Artsy Auctions, Communications, and Engineering Teams rally together following a live auction event.


The Learnings


At a large company, along with a lot of processes come a lot of bottlenecks. We often get into a “mother may I” culture and wait around for someone to come approve an idea or project. Folks at every level become used to asking for permission before they go do things. In order to be nimble and efficient, startups don’t have time or the manpower to do this. When you move to a small firm, be ready to get outside your comfort zone and wear many hats, chipping in wherever you can.

I think the biggest lesson I have learned in my time at Artsy, albeit sometimes the hard way, is to leave my ego at home and just roll up my sleeves to get things done. For example, at Microsoft, there was a team for each area (communication, event planning, marketing, etc.) and folks were more often than not discouraged from stepping into each other's realms. Stepping into Artsy I noticed that given our small size, teams and individuals often need to get used to getting out of their comfort zones and do what it takes to make the overall team/project successful (be it packing and lifting heavy boxes after our Sotheby’s auction in San Francisco or jumping in and learning how to orchestrate digital marketing campaigns to help support our online sales). This mindshift has enabled me to understand areas of the business quicker and start forming trust bonds with new colleagues. 

Introduce processes to enable (not hinder) business

Processes are great as long as they help to create value and drive progress. In a big company, there is a large number of processes, sometimes duplicating each other. When scaling your experience to a startup, bring with you the lightweight processes that can help you and your team move fast and forward. There are certainly some valuable processes that I learned at Microsoft, about which I’ll write more in upcoming posts. I recently used two of them to quickly align teams and ship our product with high quality control:

Shiproom: Shiproom is a tool that I picked up at Microsoft that allows cross-functional teams to align priorities and deliverables and make combined progress against shared timelines. At one point, Microsoft maybe had too many of these even for my own team. But here at Artsy we agreed to have one weekly meeting across our Auctions product lines that allow different teams across engineering, design, business, ops, and communications to get in sync and work towards shared goals. The notes and outcome of these weekly meetings also helped us with clear communication to the leadership and team at large.  

Quality Checks: ZBB stands for Zero Bug Bounce and is a health metric that I learned and used at Microsoft in my teams as we got close to our shipping milestone. ZBB indicated that a team had bounced off of zero known bugs as we continued to QA and fix issues to improve the quality of what we were trying to fix. As we were making progress towards our Sotheby’s partnership last fall we used this tool to efficiently track and close down “show-stopper”  issues and plan our engineering timelines efficiently.

reestablish your coaching and support systems

After working for a long time at any place you develop a support system. You also get used to having this network to help you when you need advice or tools to make progress on a project or a just a good sounding board for bouncing off ideas. This is also the system you tap in for mentors to guide you through your career. When you move from that to a startup, two things to keep in mind—you have to quickly work on reestablishing your new network and you will more often than not switch to being a mentor/coach to a lot of team members who are early in their careers. The best thing I have felt I could do for the former is to establish a network with senior folks in the domain that I meet (e.g. folks at auction houses) so I can learn from their experiences. For the latter I have found it useful to share my anecdotal experiences in shipping software in both formal and informal settings with the members of the team.

In summary, know what you want to do and be ready to leave your ego behind. Roll up your sleeves and get ready to run at the speed of light!


Devang leads the Auctions business at Artsy. He and his team are responsible for providing Artsy users with access to the world's best art auctions being conducted across the globe via top auction houses. Devang joined Artsy in 2015 after spending 10+ years at Microsoft, where he worked in various engineering and leadership roles at the company. Devang holds an MA in Economics and Computer Science from Columbia University and an MBA in Finance from the University of Washington.

Devang Thakkar