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16 Lessons Learned by Software Startup CEOs

By June 24, 2014Article

“Don’t plan on overnight success, be prepared to work hard for a long time and, most importantly, open up yourself for learning. Take the experience of other people and don’t be scared to ask; even if you think it is the dumbest question in the world, it is relevant to you and your business.” That’s the advice of startup Drishti-Soft Solutions’ CEO, Bishal Lachhiramka. In keeping with the spirit of his advice, we present here a collection of insights and lessons learned shared by many startup CEOs we’ve interviewed at   

One of the questions we asked in our study is “If you could go back and do it all over again, what would you do differently the second time around?” 

Hiring strategies 

Mistakes in recruiting/hiring strategies were at the forefront of challenges and lessons learned for many startups we spoke with. 

Bikash Barai, co-founder and CEO of iViZ Security, says his mistake around timing was hiring the sales team early on. “I made the mistake of spending more money before going through the sales learning curve. As a result, by the time I completely figured out the game, I also ended up losing a lot of valuable money. I learned that you shouldn’t hire expensive sales guys until you have figured out the sales learning curve and can sell your solution in autopilot mode. Sometimes VCs push startup founders to spend more and grow fast. But it is better not to press the fast-forward button at the wrong time. 

Not realizing the need to invest in building a resources pipeline for hiring at a very early stage caused challenges for Qualitia, says Rahul Chaudhari, managing director. “Unless you have options for the right roles that are picked up over the period of time through conscious efforts of connecting people socially, it is really difficult to attract talent that mutually fits for each other. And if this is not driven well, then you have too much time pressure at the last moment to select someone, which could mean negotiating at least one of the key aspects of mutual growth.”  

Ryan Koop, director, products and marketing at CohesiveFT, explains that having to deal with long lead times in enterprise sales became a challenge for hiring and training new talent based on customer demand. “When a few projects start at the same time, we have to scramble to increase our headcount and get the new hires off the bench quickly.” 

Bad timing 

The majority of the interviewed CEOs experienced the same pitfall — timing was off for various efforts, especially around marketing. The comments below pinpoint the areas where they made a mistake. 

  • “We channeled our initial investments into building a robust platform. We didn’t invest in an online presence and visibility in the market space until later,” explains Seymour Duncker, founder and CEO, iCharts. “Of course, one has only so much capacity and has to determine where to focus energies. But looking back, I think we should have focused on our visibility earlier.”
  • “I would have started on our international expansion efforts much earlier. We ventured into overseas markets two years after launch. Had we started earlier, we would have made a significant presence in all these markets,” says Aneesh Reddy, co-founder and CEO, Capillary Technologies. “The other thing I would have done differently is to build a lead-generation engine faster.”
  • “If I had it all to do over again, we would execute much faster and hit the market early,” says S. New Melchizedec, partner, Cloud Infra.
  • “I would build marketing much earlier and much bigger. I think being a South-Asian entrepreneur I undervalued the value of good marketing and branding,” comments Jaspreet Singh, founder and CEO, Druva.
  • “I would raise venture capital early, which would have enabled the company to grow faster,” says Tushar Bhatia, founder and president, Saigun Technologies.
  • “I would invest into marketing right from day one. It’s all about marketing,” states Rahul Chaudhari, managing director, CEO, Qualitia.
  • Sunny Ghosh, CEO and co-founder, CollateBox Inc., says “We would have started actual customer iteration a lot earlier.” 

Product development 

Startup interviewees also cited lessons learned in developing software products. What happened at HireRabbit illustrates the mistake that founders most often mentioned around products. The company’s co-founder, Pipalayan Nayak, says “The time-to-market race is like a cat-and-mouse game where you constantly try to master it but fail to do it perfectly.” 

Nayak continues, “Getting the product in the hands of end customers really fast and then iterating it based on customer feedback is very important in the early days of a product life cycle. But we took six to seven months to come up with our minimum viable product and ended up realizing that we had built a lot of extra features. In hindsight, I would change this aspect if I were to do it all over again.” 

At InfrasoftTech, the co-founder and group managing director, Hanuman Tripathi, states if he had a second time around he would “adopt a lower capital utilization plan and smaller teams to have a single product approach for focus markets. That way the company may have stayed small but we would have managed customer expectations and need for profitability much better.” 

A second chance for Sanjay Mehta, CEO and founder of MAIA Intelligence, would involve “creating a better product development road map, not having separate client server and Web application as different applications.” 

Shirish Deodhar, co-founder and CEO, InnovizeTech Software, recalls his company’s core value proposition of increasing work output was ignored. “It was a novel idea and people could not quickly understand its value. Though we had invested significant time on the task-management component, we discarded it. Instead we opened up our solution for easy integration with existing applications. We ended up with a solution that is clearly differentiated and easier to position.” 

Apsona CEO, M.A. Sridhar, says several people advised him to define the target clearly. “But I did not really understand what that meant. If I were to start over, I would try to gain a better understanding — or perhaps a clearer definition — of the customer segment to go after and the specific real-world problem that the proposed product or service would solve.” 

What to do with advice 

In hindsight, lessons are clear. But at the time of execution, advice is sometimes lacking or not well understood. Frank-Robert Kline, co-founder and CEO, Adept Cloud, says his toughest lesson learned was about taking advice from others. 

“Given the breadth and depth of advice from a variety of accomplished, trusted sources, it’s a requirement to have the perspective, thoughtfulness and confidence to synthesize that advice into a cohesive world view,” says Kline. “In our initial inexperience, we were ready to take advice. But with a lack of cohesive, contiguous synthesis, our direction and progress suffered.” 



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