16 lessons from a chaotic year of transformation at a B2B company

What we learned re-inventing ThoughtSpot as a cloud company

"I don't believe that you can reinvent ThoughtSpot as a SaaS company as fast as you think we can." 

Last year, a departing leader in our company told me that during their exit interview. 

Two weeks ago, we announced an exciting partnership with Microsoft Azure. This week, Snowflake, the creator of Data Cloud, announced that they made a strategic investment in ThoughtSpot. Snowflake is not just another data company; they are doing what Oracle did in the 1990s, and Salesforce did in the early 2000s, building the modern ecosystem for all things cloud data. 

Their investment validates our decision to build ThoughtSpot Cloud. We can now deliver cutting-edge capabilities to our mutual customers faster than ever. It also gives credence to our new vision for a Modern Analytics Cloud. The innovation is happening across this new data ecosystem accessible to anyone, regardless of their technical sophistication. 

Getting here, however, wasn't easy. 

As we faced an economic-slowdown at the start of 2020, we had to change and re-tool the entire company while employees adjusted to working from home. 

It was, as Dickens said, the winter of despair and the spring of hope. 

It was also a crash course in company building, leadership, and rebirth. Everyone, myself included, learned some important lessons as we carefully transformed the company to face the crises presented by 2020. 

Here, I am going to list a few of them. 

1. To feel the thrill of a sky-dive, jump fully out of the airplane. Silent dissent kills. Commit entirely to the plans and directions. Find different paths for the unconverted, the fence-sitters, the skeptics, albeit respectfully. 
2. Decision-making is a team sport, but know who the team captain is. Decisions are better when your teams are bought in and help execute them. Keep the last call for yourself, but delegate authority deliberately and liberally. Doing so isn't decision-making by committees, but a process designed to eliminate blind spots.
3. Ego is antithetical to leadership. We romanticize leadership with decisions made by a strong leader in solitude. But that only happens if the leader has a bigger ego than their head. Identify egotistical leaders who make decisions by themselves by looking for the ones kissing up to you. Big ego leaders often kiss-up and expect their teams to do the same to them. 
4. Startups aren't noble journeys everyone should take. Just like sprinters differ from marathoners, finding the right fit for the right people in your business is key to winning the race. People who thrive under constant change will enjoy working for startups. 
5. Never undervalue internal talent or overvalue external talent. When looking for leaders, I would pick a teammate who's 80% fit in experience but 100% fit in attitude over an outside candidate who checks all the boxes. 
6. Seek the ones who are calm in the middle of chaos. In times of crisis, which of your people have steady hands and can think rationally. This is an invaluable skill to have as a leader and a good indicator of who your company's future leaders are.  
7. Set the communications standard. Lead by example and lean into challenging issues in public forums. Encourage discussions that focus on problems, not personalities. Be as transparent as you can and make communication bi-directional. 
8. Humility and confidence don't cancel each other out: Be yourself and embrace your blemishes with humility and vulnerability, but remember that no one gives you anything you don't deserve in the meritocratic world of startups. Be confident and trust your capabilities objectively and dispassionately. 
9. Let your actions speak loudly. Words alone won't convey the full extent of your grit, tenacity, integrity, courage, and ambitions. Walk the talk. 
10. Trust your allies. Cultivate real partnerships to build and sell your products outside of your company, and prioritize those that deliver added value to your customers. 
11. Build the right board. If you are a young company, only have operators and entrepreneurs on your Board of Directors. Number-crunchers can wait. Don't be in a hurry to grow up and be average. 
12. Vulnerability and forgiveness are strengths. While providing help is one of the most rewarding things you can do, asking for help is one of the most courageous. Forgiving someone multiple times lightens your soul; grudges are an unshareable burden that serves no one. 
13. Learn to control your initial impulses. This was hard for me, as my initial instincts often got me in trouble. Even a second of mindfulness may save you from saying or sending something you'll want to take back later. 
14. Only people inside your company know your problems. Read and listen to others, but don't let any single person or piece of advice shape your actions conclusively. That goes for Tweetstorms from investors and entrepreneurs, including this one. 
15. Value your friendship and personal loyalties. You will not make a lot of new authentic friends as you grow older. Hold on to the ones you've cultivated over the years. 
16. Sleep. You are no good without it. 

When I said goodbye to my former colleague, I didn't think of it as a judgment on the company or a measure of their will to fight. It's how things go in a startup in the middle of a transformation. I wished that person the best and moved on.

We just closed our first full-quarter after releasing our cloud product, and 61% of our new business came from the cloud, far exceeding our expectations. With these public validations from Microsoft and Snowflake, our journey to building the Modern Analytics Cloud just sped up. 

This is still day one at ThoughtSpot. We know we have a long way to go, but we also know that this is the way. 

Onwards!