CTO to CTO

Abraham Rosenfeld, Jane Technologies

a Slack conversation on fostering creativity and the entrepreneurial spirit in your organization.

Abe serves as the CTO & Co-Founder of Jane Technologies, Inc. In this role Abe is responsible for the execution and delivery of the Engineering, Design, and Product teams at Jane.

Before founding Jane, Abe joined as the first employee of an energy startup (KGS Buildings) where he assumed the role of Director of Systems Integration for 8 years. Abe earned his Bachelors of Science and Masters of Engineering in Computer Science from MIT. Abe lives in Santa Cruz, CA and enjoys surfing, hiking, and spending time with his wife.

Substantial started working with Abe and the Jane team when they were a pre-launch, seed-funded startup back in 2017 and we've had a team with them ever since. Last year they closed their $100mm C round.

James Lee

James Lee

When Substantial first started talking about doing interviews with tech leaders, you were one of the first people I thought of. Jane has just seen so much success and growth over the years, and I wanted to get your perspective on things.

Abraham Rosenfeld

Let's do it - excited to be part of this first interview! 🙂

Abraham Rosenfeld
Creating a Successful Company
James Lee

Perfect. So, in your own words, what does Jane do, and why do you think you all have seen as much success as you have?

At the core - Jane has created an ecommerce and retail platform that provides a true technology partnership for brick-and-mortar retailers in this space. Our technology cleanses, structures, and digitizes the entire Cannabis market's product and inventory data - creating a local aggregated marketplace and enabling a number of exciting downstream effects.

I think we have seen success really due to timing and execution coupled with a mission that is truly win-win for all entities in this space. We solve problems that brick and mortar retailers in all markets face - but the solution we have is a real partnership where retailers can rely on Jane and our tech to empower them to compete efficiently in the digital world.

This solution - timed with almost all stores essentially having to go digital first through a pandemic - has led to our growth.

Abraham Rosenfeld
Optimism in the Face of Adversity
James Lee

Yeah, totally. Technology has played a huge part in how local businesses were able to maintain, and often grow their customer bases. What was the most challenging hurdle that you had to overcome?

Oh man there have been a lot - I'm not sure there is necessarily one that I could point to and say "this is the hardest one". For me personally - every stage of growth at Jane has had its share of intense challenges. I think if I were to look at it from a higher level - the real challenge for me is to do my best to stay true to myself during the hardest times. If I can be the same person, teammate, and leader no matter what the situation - that is something that I will be truly proud of. And I think that perspective that I have grown to understand has been both the biggest challenge for me personally but also the most rewarding.

Abraham Rosenfeld
I think if I were to look at it from a higher level - the real challenge for me is to do my best to stay true to myself during the hardest times. If I can be the same person, teammate, and leader no matter what the situation - that is something that I will be truly proud of.
James Lee

Oh interesting. Yeah, I've found it sometimes hard to bring the level of energy I want to different situations, it's tough for sure.

If you could go back in time, what would you tell yourself? Would you do anything differently?

I wouldn't do anything differently - I think the mistakes and challenges that we have faced were necessary to get to where we are today.

If I could go back and tell myself anything - it would just be a reminder that every failure/mistake is a real opportunity for growth. When those failures happen it's hard to keep perspective, but there is always a silver lining and there is always an opportunity to learn. Oftentimes those are the events that end up having the most positive impact in the long run.

Abraham Rosenfeld
Creating a Safe-to-Fail Environment
James Lee

Love the positivity. And I agree totally, failure is necessary for learning and growth. How do you create safe to fail environments at Jane?

I think an extremely important component is that all teammates check their ego at the door. Oftentimes it's not the team environment that makes it feel unsafe to fail - but really it's the individual. When working on something independently, if your desire to be right outweighs your ability to assess reality - you will end up not seeing mistakes/failures as early as you could have. Blinded by your own desire to be right in a sense.

So it starts with the individual. And I think we do a great job as a team of being very open and honest with each other (and vulnerable at times) to create the space for people to honestly assess how well or not well certain things are going. In turn that culture promotes that same mentality with ourselves and people feel like the team and company value that honesty and learning over anything else.

Failure is a necessary step in problem-solving. You just want to try to make them small and quick.

Abraham Rosenfeld
James Lee

Indeed. It reminds me of a quote I was told recently - "Seek to understand, not to be understood."

Amen - I love that.

Abraham Rosenfeld
Startup Mentality and Staying Competitive
James Lee

Do you still see Jane as a startup?

Man, that is a good question - I'm not sure I've really thought about that recently...

I think so - mostly because I just enjoy the classic "startup mentality". I love the grit, fearlessness, and determination associated with startups so I think I'm good with that label for a while.

Abraham Rosenfeld
James Lee

Yeah, I hear you, I think I strive to always keep that startup grit. When you think about that "startup mentality", how do you think small companies can compete with the giants out there? 👋

That's a tricky question - because I think timing always plays a factor. But let's not focus on the things that are not in our control. I think firstly, you and your team need to truly believe in the idea and genuinely love it. Starting a business is not easy (that is stating the obvious) but if you and your team love the idea, that will be an extremely necessary component in doing everything in your power to make something work. Then at the end of the day you need to focus on building a business that creates value - and hopefully differentiated value. If you and your team have identified a need and build a product that truly provides differentiated value - you are running your own race vs looking to the left and right at what the giants out there may be doing. Constantly comparing yourself to the giants will end up turning your company into a smaller version of one of the giants instead of something that is actually disruptive.

Abraham Rosenfeld
You and your team need to truly believe in the idea and genuinely love it...that will be an extremely necessary component in doing everything in your power to make something work.
James Lee

Do you find that harder as your team and business scales?

If you did your diligence and built a solid foundation off a truly differentiated solution it actually gets easier as you evolve the product off that critical first step. Then everything you build continues to differentiate and you start to build momentum. I don't think any step in the process gets necessarily easier or harder though - the stake just tend to get bigger. If this ever got easy I don't think it would be as fun. 🙂

Abraham Rosenfeld
Designing and Retaining Company Culture
James Lee

So what does keep you up at night?

Retaining our company culture (i.e. the reason people are at Jane) as we scale and grow. For me that is the #1 most important thing to ensure happens as the team grows. The culture will evolve - a team of 5 will need to evolve the culture as we grow to 40. But at the core, the values that we have all kept as extremely important to our collaborative culture must be maintained.

Abraham Rosenfeld
James Lee

Have you felt the effects of Conway's law yet?

Yes absolutely 🙂

Abraham Rosenfeld
James Lee

I've always found it really fascinating how organizational design impacts things. We need to be very deliberate about how teams are modeled and interact with each other.

It forces pace with hiring and onboarding as well.

Abraham Rosenfeld
James Lee

How is the Jane team structured now, and how has it changed as the company grew? Any lessons learned?

We have transitioned from a 10 person single team working on anything and everything with 1 PM - to more specification. We have teams of 4-5 that now work on different functional verticals directly with a dedicated PM. Some of the delineations are clear between teams and some are not quite as clear yet as we are still evolving as a team and as codebase becomes more modularized.

A lot of lessons learned and many more to come. A big one is you have to do your best as a team to evolve the structure and process of the team along with growth. You don't want to overdo process when it's 5 people sitting in a room - it's just not necessary and your flexibility at that point is an enormous strength. But as the team grows and distributes more - the evolution has to happen otherwise affects miscommunication become the norm due to lack of an evolved process and structure.

Abraham Rosenfeld
Prioritizing People and Culture
James Lee

What are things you all do to keep a consistent culture now that your team is more distributed? Has the way your company communicates changed since the pandemic started?

We prioritize people and culture above everything else - that is involved in the hiring + onboarding process. In our recurring meetings. In the way our people team prioritizes benefits that are really looking out for the team. I don't think it's really about creating additional meetings with the intent to grow the culture - when you do that it isn't really organic. You have to invest at the root of these issues and really make a commitment as a team as as an organization.

I think we benefitted as a product team of being an in-person team with extremely open and honest communication pre-covid. When covid started and we went full remote - there was already such a strong foundation in great communication practices, we were able to leverage that strong foundation as the team grew. And as we grew and hired more people (we have more than tripled the size of the product org since the start of covid) - communication, empathy, and low ego were extremely high value traits that we interviewed for and set expectations with new hires to retail what we were lucky enough to already have.

Abraham Rosenfeld
James Lee

Well, we're running out of time, so I'll end this with one last question: What are you optimistic or excited about in the world of technology?

One thing that has been amazing for us at Jane is how connected we have all been able to stay through the pandemic. I'm excited for more innovation in collaborative tools and communication platforms that allow us to not just stay connected but really connect with each other on a human level. I think that is (hopefully) an optimistic path towards learning more about each other and appreciating each other

Abraham Rosenfeld
James Lee

Building software is really all about the human interaction, isn't it?

100%. This was fun - thanks for including me in this James!

Abraham Rosenfeld
James Lee

It was an absolute pleasure having you Abe, thanks for joining!

Let’s build a better future, together.