Jeff Croft, CRO Kurvv.ai

1. What were you doing before you quit your job?

I was working at Microsoft in their One Commercial Partner organization. It was a Business Development and Strategy role looking at the next iteration of the partner network. AI, IOT, Teams centric partners that are driving differentiation and value into the ecosystem.

2. When did you know that you wanted to quit your job?

The day I started.

I had planned on learning as much as possible and finding the right time to leave and start something of my own. As I was exposed to other leaders within the company I heard time and time again the same story. “When I joined I figured I would only be here a year or so and then I would start a company…That was 20 years ago.” These were people with wonderful careers leading large organizations, but I took that as a warning that if building a company was really what I wanted, I needed to be careful not to get too comfortable. So I started preparing from the very start.

Microsoft is an amazing place. It is filled with some of the smartest people on the planet. For the most part, if you have an interest, there is someone or a team of people doing ground breaking work around it. It is a place where you can find what is compelling to you, and dive into it. My area of interest was AI. I became fascinated by it, and they allowed me to dive into and just explore, have access to world class technology, learning, and a community. The only thing Microsoft could not provide me was the ability to build something from the ground up, and own it. For that I needed to venture out.

3. What initial hesitations did you have about quitting your job & how did you overcome them?

When my discussion with Ryan (our CEO) became serious in January 2020 I started to think through what a transition might look like.

My main hesitations were:

• Is the timing right on this? (Is there ever a “right time?”)
• What’s the real cost of what I am giving up? (Risk vs Reward)
• Health Insurance for my wife and myself. (Negotiating needs)

Thought Process:

Is the timing right? Who knows? I knew that I believed enough in what we wanted to build that I would regret it if I didn’t give it a shot. And if the timing will never be right, why not now?

What is the real cost? Calculating the future cost of unvested stock and bonuses is a necessary exercise, and on paper you would never leave. Cascading vesting schedule is a ride that gets harder and harder to get off of the longer you are there and better the company does. (For reference Microsoft Stock had 3x’ed in the 3 years I was there). I countered that in my mind with What is the cost of not betting on myself? To me, that cost is far greater than the value of my unvested options. Time and experiences are fleeting, and as long as I could cover my expenses and save a little money, it was worth the risk of leaving.

Insurance for my family? I did a lot of research into private policies and how much that would cost us. Special policies for my wife (she has a pre-existing condition). And what if we have a child? How will that factor in. At the end of the day I made it a negotiation point that Kurvv would pay my insurance. It worked out. And we got a group policy for the 3 of us that were full time.

4. Can you remember the day you put in your notice? What was it like? What was going through your mind? How did your manager take it?

Leaving Microsoft was a mix of excitement, nostalgia, and fear. The day I put in my notice was a Friday at the end of February. For 3 years I had a standing 1v1 with my boss at the end of each month, so the meeting was not unusual. I had conflicted feelings of excitement for finally being able to go all in, nostalgia for closing a wonderful 3 year chapter where I learned and grew as a person with a great team of wonderful people, and of course, fear that there was no going back. I was about to burn the boat on the shore.

My boss was very excited for me. We frequently had discussions around career development and what I wanted next, so he knew this was a big step in my life and was supportive. It was his genuine excitement and happiness for me that I will always appreciate.

5. What are you doing now?

I am the CRO of Kurvv.AI, and we are building tools that make Machine Learning easier to adopt and use for non-technical teams and organizations. We are finding great traction in Predictive Maintenance, Healthcare, eCommerce, and Hospitality. Any given day I am wearing the hat of sales, marketing, partnerships, strategy, or the contrarian. I do really anything that we need to establish PMF. All hands on deck. The first 4 months have been fantastic, fun, scary, intellectually stimulating, and freeing.

6. Looking back at your experience of Venturing Out, what do you know now that you wish that you knew before?

Being scared is fine. But don’t let it stop you. Create a plan and take action on it. Don’t let the fear of the unknown stop you from testing yourself and finding out who you really are. Taking the leap is a great experience.

I am a better, stronger version of myself, and it’s only been 4 months. I absolutely made the right decision.

7. Any other advice you would like to share?

You may have done the math already to calculate when I left. March 16th  2020 was my last day at Microsoft. By my calculations the world fell off a cliff about the same time.

In the 4 months I have been at Kurvv we started with a global pandemic, economic recession, my wife got laid off, and massive societal unrest spread across the world. You can not play life backwards, but if I could, would I go back to February and make a different decision? Knowing what all was about to happen?

No. Absolutely not. I am better for it. Kurvv is better for it.

If we only get one shot at life, I’m playing all out. Win or Lose. That is the advice I would give my kids, why wouldn’t I take it myself?

Take the leap. Build the company. Venture Out.