By Rohit Gupta of Palerra

I have always been an entrepreneur at heart. The thought of dreaming up a product idea, establishing a team to develop it and creating a business to support it has long lived in the back of my mind. Now a year into this dream, I have learned a great deal — most importantly that running a business is really, really hard work. That said, it is also a lot of fun and, with the new year upon us, I have found myself reflecting often on the past year of running a start-up. To other “new” entrepreneurs, I’d like to pass along a handful of my most important lessons learned (or in some cases re-learned).

business lessons, entrepreneur advice, young business owners, hr advice, building a strong business team

Rohit Gupta
(Photo courtesy of Rohit Gupta)


 1. Talk To Customers All The Time

When you enter a market segment with domain experience (like we did), you always run the risk of having background knowledge influencing your approach but does not necessarily translate to what customers want. The only way to challenge your assumptions and stay on track is to talk to customers all the time. We are getting better at this, and we’re going to keep improving.


2. A/B Test Everything

Well, almost everything. Something that young companies don’t always have the luxury of is testing multiple approaches and verifying what works better. A/B testing is the de facto standard in marketing, but the approach works just as well in almost every other function. Whether it’s the best place for a button on a product console, the right language for a call to action on a website, or the right incentive that draws clicks on email, you can A/B test almost everything. I don’t think we did this enough initially, and I still think there’s room for improvement. But we now take this very seriously.


3. What Works For Netflix And Google May Not Work For You

I recognize this may be controversial. Many great tools and technologies have originated from some of the greatest tech companies of our time. But what works for them may not always work for us. The lesson: you have to find (or build) the best tools for your own situation and strengths. Don’t get caught up in, “If it works for Netflix, it must work for us.”


4. Investing In Customer Success Is Critical

One of my early decisions was to bring in a customer success leader, and it was one of my best. Customer success is much more than customer support. It encompasses the overall experience that a customer has when they interact with our company. We put this in place before launching our earliest beta programs, and it has paid off beyond reckoning. Our customer success function maintains the trust of every client we service.


5. Provide Structured Enablement For Your Field Teams

Another lesson that we learned the hard way is that we need to enable our field. As a SaaS company, we release new functionality in almost every weekly sprint. But assuming that a founder or an engineer knows what’s in a sprint isn’t good enough. You have to invest in the field and create tools and collateral to continually help them communicate with our customers. Founders are almost always the best communicators of the core vision, but they have an equal responsibility to make sure that messaging can scale without being in the conversation.



This was a new acronym for many of us. Our early sales leader brought in a sales qualification methodology called MEDDPIC. It stands for:

  • Metrics: Quantify the impact of our solution, ideally in hard dollars.
  • Economic Buyer: Identify who has the purse strings or signs the check.
  • Decision Process: Have a step-by-step process to help the customer evaluate and perform a purchase.
  • Decision Criteria: Help identify specific criteria that can enable a decision, including functionality, proof of concept, and benchmarks.
  • Partners: Identify partners in the account and dependencies or leverage points.
  • Identify Pain: Knowing what keeps customers up at night and why does a particular issue bother them, as it often defines a compelling event.
  • Champions: Find key people who will sell for you in your absence (different from a coach).
  • Competition: External and internal.

screen shot 2015 08 31 at 3 41 10 pm1 9 Lessons Learned: An Entrepreneur’s First Year Journey

Every step is relevant for us and challenges our assumptions. Doing a MEDDPIC review for all major opportunities is critical. And I’d say that skipping a MEDDPIC review can mean coming up short.


7. Get A Mentor

A founder CEO role is lonely. I faced multiple challenges and critical decisions daily. I have to live up to the trust of both the families of our employees who are hoping for a better future and the investors that have placed their bets on us. I found it important to take the time to recruit and be coached by a mentor. This is someone I can talk with openly, bounce ideas off, and get a fresh perspective or approach from. I found it can do wonders, especially during the tough times.


 8. Team Chemistry

I know this has been said many times…Great teams achieve. Teams of superstars that lack chemistry can be a catastrophe. This is one of the first things I’ve learned to try to identify early in the interview process. Chemistry is hard to build, and it’s even harder to spot during interviews when everyone presents their best side. Reference checks can help, but they’re imperfect. This was one of my major lessons this last year.


9. Have Fun And Make The Most Of Your Time Together

Startups are hard, and to make the experience work for everyone, I had to figure out how to enjoy simply spending time with the group. DevOps and Sales are team sports, and the best teams usually have fun while fighting the fight. We had many, many good times, and I have great memories from the past year.


This is only my list—there are many important lessons I have missed. Please comment on this article and let me know of your own “lessons learned” during your entrepreneur careers!


Rohit founded Palerra in 2013 with the vision of ushering in a new paradigm in security and devops; one that would enable enterprises to confidently embrace and accelerate the move to the cloud. As CEO at Palerra, Rohit is responsible for creating, communicating and delivering on the overall vision and strategy for the company. Connect with Rohit on Twitter and LinkedIn.

The views, opinions and positions expressed within this guest post are those of the authors alone and do not represent those of CBS Small Business Pulse or the CBS Corporation. The accuracy, completeness and validity of any statements made within this article are verified solely by the authors.



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