Team is everything: Anil Jwalanna, CEO and founder of WittyParrot

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Anil Jwalanna

Anil Jwalanna is a technology entrepreneur and product visionary based in Silicon Valley. He is the founder and CEO of WittyParrot. Anil has built and managed SaaS and technology product platforms at start-ups and large enterprises for over 15 years. Anil previously served as CEO of PushPoint Mobile and CTO of iCharts, both mobile commerce and data visualization SaaS companies.

As VP at Allianz Insurance, ACC Capital Holdings, he led Enterprise Architecture teams in IT strategy big data analytics. Anil holds MBA from Haas School of Business, UC Berkeley and Columbia Business School with an undergraduate in Engineering from Mysore University, India. 

anil jwalanna

What’s your job title?

Founder and CEO of WittyParrot

What do you actually do every day?

I do literally everything :-). As an entrepreneur in the early days of a start-up, typically founders become the biggest bottleneck, depending on the style of management. In my case, though, I do not micro-manage and we have a fairly mature and seasoned team. Still, though, many people want to discuss each and every thing before acting, be it product development, sales, marketing, etc.

This gives me an opportunity to be hands-on and provides me with a greater degree of visibility into everything happening in the company. On the fill side, I am not an expert in all the things and my availability for each & every thing becomes very challenging, and as a result, I am often the cause for delays.

Also, I feel responsible to be involved and take care of everything, which can be both overwhelming and unrealistic. I am trying to balance my time and focus on only getting involved in critical discussions that impact the company’s strategy, measuring progress, and resources allocation.

In ten words or less, what is your leadership philosophy?

Be transparent, delegate with accountability, have regular oversight, and closely watch & measure progress (spend, revenue, adoption, conversion funnel, etc.).

Team is everything in start ups and companies of any size. It is very critical to have the right leadership to make employees and stakeholders happy and build the sense of ownership to succeed. I always break down the team into 3 circles: management (makers or breakers), leaders (super critical) and worker-bees (replaceable). I personally hand-pick the team for inner-most circle, significantly influence hiring of leaders, and delegate hiring of worker-bees to leader and management.

Once I have the right team in place, I would be 90%+ transparent with management team and 70%+ transparent with leaders. I have a flat structure  in the company and any one can talk to me or any of the management team openly without any fear.

I believe that it is super important for management and leaders team to be fully aware of the company progress as a whole and what is at stake. I hold these two teams’ members accountable for their deliverables and encourage them to experiment with crazy ideas to drive innovation.

I strongly believe in open communication among the team and critiquing ideas to get the best foot forward to succeed. Empower the team without micro-management, but hold them accountable for results with oversight. Encourage the team to take risks and experiment with new ideas, even if it fails. Accountability, disciplined follow-up, measurement & monitoring of progress (KPIs), continuous evaluation and feedback to improve, etc. are critical success factors that are tried and proven.

What company besides your own has an amazing culture? What do you like about it?

I like GE because of their focus on accountability, continuous churn at the bottom, delegation with authority & ownership, and transparency.

I like Apple for their ability to continuously innovate to stay ahead of the market and willingness to experiment at heavy cost. In addition, they strive to to achieve perfection and break the limits to accomplish the same.

What are the key qualities (in order of importance) that you look for in a great hire?

1. Self-drive & Initiative: One should be self-driven with passion to work towards achieving goals with continuous course correction. Willing to roll-up their sleeves and learn new things with the focus of reaching goals and delivering results with accountability. Entrepreneurial drive with the sense of ownership and determination to succeed.

2. Street Smartness: This is something that I think is very critical. My hires should have common sense, be willing to take risks, and be quick to grasp the situation and think on their feet to respond /react instantly with relevance and context. They need to keep their eyes & ears open with ability to connect dots and think both tactically and strategically.

3. Expertise: The hire should be a real expert in his/ her area of specialization, with deep knowledge coupled with broader knowledge in the related areas.

4. Team Player: This is an important quality for certain hires depending on the role or responsibility, but it is not a critical requirement for all hires. Qualities I look for in hire as a team player are: collaborative attitude with strong opinions, persuasiveness, and ability to constructively influence others.

5. Flexibility: Hires should have an open-minded attitude and take feedback constructively & positively. Multi-tasking with multi-skills are important to accommodate the needs of the company at different points in time. 

If you had to give career advice to yourself 10 years ago, what would you say?

I had a great job for almost 15 years in a large corporation. I had a great career and success in climbing up the corporate ladder coupled with great pay. But the job satisfaction started diminishing as I grew up in the ladder.

I ended up spending more than half of my time managing my superior’s expectations and personal agenda, political manipulation, and doing things that are against my principles, which was highly frustrating. I had less and less time and opportunity to work on things that drove value and satisfied my intellectual curiosity.

That’s when I realized that I have to focus and work on things that I am passionate about. That gives me great satisfaction.

That’s when I started thinking about building my own business. The hard part of the transition was taking the extremely high risk of switching gears from a great corporate job & hefty pay (golden handcuffs), family commitments, etc. to a start-up life with almost no pay for couple of years, and a change in lifestyle. I had to think in many directions before taking up such a huge risk and be willing to sacrifice many things in life.

If I had to give myself advice earlier in my career, it would be to focus on my dream and work on things that I am passionate about. I would have built multiple successful businesses and made enough money to take bigger risks. Once you are past 5 years in your career, the chances of switching career becomes extremely difficult, especially with life commitments over time.

It is very important for a person to realize their strengths and weaknesses, and it is crucial that a person recognize their dream and passion. In addition, having a great mentor and an advisor is equally important to help influence you as you work towards the dream.

What was the last thing that inspired you?

As I mentioned above, I was getting frustrated with my corporate job that gave me good money and security but poor job satisfaction (very stressful). I had great knowledge of business, creative ideas, and an awesome network of contacts. I started to re-thinking my career and started evaluating the pros and cons of doing something else, which meant taking a massive risk.

It took couple of years of constant struggle and being torn between the choice of continuing with my corporate job versus doing something on my own. Eventually the internal burning desire won against all odds, and I decided to jump into working on something that I always wanted to do. However, this was not a fun ride, and led to many scarifies with family, lifestyle, etc.

End of the day, though, it is almost 4+ years since I made the switch and I strongly feel that the risk was worth taking. The caution here is that the success won’t come overnight. It is very important to continue the struggle for many years, even with the monumental difficulties that we face at each step that can pull you back. It is like making a step forward pulls you back by two steps, and the challenge is to focus on flipping the equation.

What were you like growing up?

I grew up with my grand-parents in a tiny village in rural part of India with a population of a couple of thousand. I studied at schools where we are on our own with no faculty, etc. This, in a way, helped me to become a self-minded, independent person with shrewdness.

I learned to be honest and direct in my communication, though it hurts sometimes and cultivated to be an opinionated person. As a result of this attitude, I started taking risks, being persuasive and aggressive in getting what I want. It wasn’t an easy ride, and I made costly mistakes along the way, but eventually things worked out and I am very proud of my accomplishments to date from where I came from. 

In your mind, what does it take for someone to be crazy successful?

One has to have a dream of doing something! I think a lot that this has to do with the environment where we grew up. Circumstances of life influence us significantly during childhood and shapes up our attitude, interests, lifestyle and career.

Apart from having a dream, the next big required quality is to have the passion and determination to follow the dream no matter what. I think most people fail in pursuing the dream. This involves many sacrifices in life but we have to keep on inching towards the dream little by little with life pivots and continuous course correction. It is also important to have the ability to connect dots and visualize the future that leads to reaching the dream. In a nut shell: Have a Dream; Be shrewd & take extreme risk; Unparalleled pursuance; and disheartening /devastating sacrifices.

What’s the best career advice you’ve ever received?

Be yourself (good or bad) and do what you believe in. I had several great qualities that I didn’t initially see as valuable assets for my success until I heard it from others. E.g. My directness without any fear and my intellectual curiosity stood out as prominent qualities.

In addition, I am shrewd and results-driven with serious commitment. Constant appreciation and comments about my good and bad qualities along my life /career helped me to realize my strengths and weaknesses. In my case, it is not one career advice that changed my life; instead it is an ongoing realization of life experiences with success and failures that shaped my personality over time, coupled with feedback from well-wishers along the way.



Lightning round:

What’s one of your favorite techniques for getting things done?

Open, straightforward communication of expectations or feedback (on good things and not good things) and being one among them with sympathy & empathy. 

Favorite books about career or business?

-Steve Job’s biography

-Innovator’s Dilemma

-Blue Ocean Strategy

What does the most valuable person on your team do differently from anyone else?

Calls me out that I am wrong without any fear or hesitation

What’s the coolest part of your job?

Visibility into everything, endless learning, and the ability to influence the future to some extent. To see the future by connecting dots. And most important, I enjoy my work and feel proud of making a difference in the society.



More Anil Jwalanna:

Where do you live/work?

Cupertino, CA (live & work, both)

Where is the best place for people to learn more about you?

Anil Jwalanna


Where can people connect with you?



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One Response to “Team is everything: Anil Jwalanna, CEO and founder of WittyParrot”

  1. Sumukha Rao says:

    A very nice article.

    Every entrepreneur goes through the grind but it is more difficult when you do it at your terms.

    After having known Anil for just about a year, he is a person who walks the talk. First thing first, he gives a very patient-full hearing while he maps the ideas coming out of the conversation to his vision and provides a viable workable solutions. Kudos to your points on employees and transparency which today is very important to nurture the culture of trust and honesty (important especially in a start-up and also when you grow the company which is lacking otherwise)

    Pleasure to hear your views and lot of inputs for budding entrepreneurs.

    Thanks for the writeup

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