Career Pivot 2021

Life is funny. You make your decisions, but your predictions end up moving down a different path than you expected. I wish I had that magic crystal ball I’ve been asking for.


I’m stepping down as Head of Design at Warmly and will be a part time executive coach for them. Additionally, I will be joining Falkonry as Sr. Director of Product Design.

Executive Coaching

I don’t think I’m the right coach for everyone. In fact, I think I am only good for a small niche of professionals. I have had good outcomes coaching brand new entrepreneurs and designers. Especially if they are stretching themselves beyond what they have done in their past. This includes topics such as:

  • Managing under-performing employees (especially without causing drama)
  • Process improvements
  • Organizational structures
  • Storytelling (Explaining vision)
  • Culture (The pandemic makes this extremely difficult)
  • Design / UX (of course)

I really liked this part of the job, but it also gave me a double personality. On the one hand, I was supposed to be designing. On the other hand, I was supposed to look at the overall structure and give counsel on how to improve it.

Different People at Different Times

One thing I realized was that Warmly needed a different structure and a different designer at this stage in their development. They needed someone to report to product management with a strong sense of graphics.

In the early days of Marketo, it was mostly me and 10 engineers in a room figuring things out. I was the product manager and designer (among other things) all-in-one. Later, we hired Cheryl Chavez as PM and started to split the roles up. At that point, we developed the Eng/PM/Design collaborative dynamic that worked very well for us.

At Warmly’s stage, they have a person (Carina!) to be that single decision-maker. Having me in the mix would only slow things down. So I put on my coach hat and said that they should replace me with an engineer. Get more stuff done!

What’s next?

Well firstly, I am going to continue to coach Warmly. I love the people and what they are doing. Zoom is going through a fascinating moment where they may create a powerful marketplace of apps and Warmly is leading the charge. I think it’s a terrific partnership with loads of potential. Zoom meetings are often challenging and there needs to be some fresh ideas inserted into the experience.

Secondly, I am going to be doing some light UX/IA work for a cool company that I have been speaking with named Workstream. They make HR/Recruiting tools for QSRs (Quick Service Restaurants) who deal mainly with an hourly workforce. They have a terrific culture and are making some really smart moves.

These first two will be nights/weekends.


Finally, I am joining full-time at Falkonry. It’s harder to explain what they do because it’s complex software. Imagine a giant factory. It has thousands of parts with hundreds of components all talking to multiple computer systems. There are hundreds of people maintaining this stuff to keep the factory humming along. Downtime is bad. You want your factory going 24/7.

Falkonry makes software that uses AI/ML to know when things are about to go wrong. I think of it a little like the Precogs from Minority Report. They knew the details about a crime before it happened.

Like this, except not for crime

There is a ton of UX/IA/Design stuff that needs doing. I feel connected to the people and feel like they will be good mentors for me. Having a good relationship with your boss is one of the best indicators of staying and prospering in a position. I have had ups (Srini Venkatesan was awesome) and downs (He who shall not be named). I am looking forward to working with my new manager and learning this new industry.


How do you know it’s time? Time to change your location, your job, your vocation, your diet, your lifestyle? When do you keep going and when do you stop? These are challenging questions.

For most people change is awful and uncomfortable. One reason I blog is to let people know they are not alone. That at least one other person thinks the thing they secretly believe. You might be unhappy in your current role. Maybe it’s time to go? Or maybe you should rethink why you are unhappy and work on fixing it where you are?

Life is a constant stream of these choices. Some will be triumphs and some will be great learning experiences. Keep moving forward. If I can help you with a decision, please let me know.

2 responses to “Career Pivot 2021”

  1. Congrats on the bold move, which I think is also a very smart move, given the ever-increasing reliance upon AI and ML to create the factories of the future today. This is something I worked on a bit at Autodesk, and is definitely a huge growth area. Power on!

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