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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  • Wally West

    These are great tips and they have helped me make a decision with what I should do with my issues. I have been needing consultation for a while now because I have a few questions that can’t be answered very easily. We have been considering joining with another company and we need some advice before we commit.

  • Sam Winters

    Is it really difficult to find jobs via trditional job board sites (, etc.)? Maybe this is kinda specific of startups or something like that…

    • My husband and I were reading about that on last night. Many sites like that are a hit or miss. Many find success and others don’t. I prefer to reach out to businesses in my line of work rather than browsing the job boards online.

  • Great initiative and startup. I appreciate the thought process. Practically as per my understanding on the management and entrepreneur world, there are a lot of ambiguities. The best part is to how you take it forward.

    Being in the IT world for more than a decade, I have come across a lot many people who have a strong fire in them to go with start ups. And among them I am also one. And as usual I too have a fire on me to start up mine in some time. Great sort of inspiration here with I have gained and grasped from this posting. Waiting for some more discussions like this.