Ro knows: How to career switch from management consulting to startup business development

Ro Gupta landed his startup business development job by networking like crazy, catching a few lucky breaks, and crushing his interview with legendary venture capitalist Fred Wilson. Keep reading to learn how Ro successfully transitioned from the corporate world to leading business development at Disqus, one of the top discussion platforms on the web.

You were the 1st business hire at Disqus. How did you hear about the role and what was your interview process like? Are there one or two things you felt were critical to finding the job or doing well in the interview process? 

It was 2008 and I networked my way to Andrew Parker, who was an associate at the VC firm Union Square Ventures (USV). I specifically targeted Union Square Ventures because they were investing in really interesting startups and they were based where I live (in NYC).

Fred Wilson

Fred Wilson (Photo credit: Wikipedia)

Andrew was friendly and accessible. When we met I bounced a couple startup ideas off of him and also identified a few portfolio companies where I thought my background could add some value.

After we met, Andrew sent a message out to the USV portfolio CEO email group asking if anyone would be interested in speaking with me about potential opportunities. A couple of the companies that I mentioned to Andrew in our meeting responded with interest.

This led to some email exchanges and phone interviews with Daniel Ha, Disqus’ CEO and Co-Founder. The last part of the process was a combined in-person ‘interview’ (more of a group discussion) with Fred Wilson, Disqus’ first VC investor and board member. After the final interview we all seemed to agree it was a good fit and made it happen.

Looking back on the process there were several things that I did that I feel worked strongly in my favor:

  1. I played the intrinsic probabilities of networking.
  2. I helped others along the way without necessarily expecting anything in return.
  3. I came to interviews prepared with well defined points of view in certain areas – and willingness to admit that there were other areas where I had less certainty.
  4. Demonstrating a combination of strategic and operational / roll-up-your-sleeves capability. The latter is often what founders are most concerned with at early stage startups.

You spent your early career working in management consulting. What should people coming from a management consulting background be doing before they start their startup job search in earnest?

First, figure out what you’re really passionate about.

Working in consulting was a great experience. I learned a ton, made great friends, and travelled the world. But it was a job I took because I didn’t really know what I was truly passionate about in college and it seemed like a good way to figure that out.

And I eventually did, finding a consulting project in media that was relevant. I parlayed that project into a digital media role at Disney. In that role I had the chance to work a lot with startups who were pitching Disney for business. Earlier in my career I had also picked up a little startup experience as well, having worked at an internet radio station during the first internet boom.

All of these things helped set me up as a credible candidate to actually join a startup like Disqus. Others in a similar situation should think about how to string together relevant experiences like this – even if they are side projects or if the ultimate goal is still a couple steps down the road.

What are some of your favorite interview questions for business development hires at Disqus (and why) ?

When Disqus was still an early stage company, I’d press candidates on their understanding of the product and the underlying technology that powers it. I found those questions tended to be a good test of scrappiness and detail-orientation – two things that are highly valued at that stage.

I also like to have all BD candidates take me through a sample prospecting-to-pitch-to-close case study. This gives me more data that I can use to evaluate the candidate’s preparation, organization, and storytelling skills.

Finally, I want to know what apps or services the candidate is really excited about and why. Their answers help me get a sense of their product sensibilities. Plus, knowing what they’re excited about is a casual way to gauge their fit with our company culture.


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