How I got a Technical Director Position

Working from an Airbnb during a team retreat, Los Angeles, CA

The goal of writing this blog post is to help others, and especially women in tech, get their dream job position. I have mentored a few people at my current job using my own experience and I decided that writing it down might help another handful of people.

This is how it went:

I had my annual review in March 2020. My manager asked me how I wanted to grow within the company and this made me think of where I really wanted to be and what I wanted to do day in and day out. At that point I was a lead experimenter and managed other experimenters, and my job consisted mostly of running lean experiments in the chatbot space, analyzing data from those experiments, reporting results, iterating, and scaling successful models.

After my annual review and evaluation meeting I opened a new Google Doc and wrote my dream title “Technical and Data Director”. I set myself a timeframe of one year to get there.

Here is what I did next:

1. I went on Glassdoor.com and I read through fifty or sixty job descriptions for CTO, Data Directors, Data Managers, Technical Managers, Technical Directors, etc in the same space.
2. I copied and pasted all the qualifications that I found often in those job descriptions in a Google Sheet and that could be applicable to the company I worked at. I ended up with quite a long list of skills and experiences.
3. From our HR department I obtained my most recent job description. I made a list of skills and experiences I had based on the job description and based on what I actually did for the past two years at my job.
4. I compared both lists. The list of the CTO type skills and the list of my current skills as the Manager and Lead Experimenter. Majority of skills and experiences overlapped. I created a third list, a list of the skills and experiences I needed to gain. I looked at this list and took away those that I deemed non-crucial. I ended up with three “must-have” skills that I knew I lacked: Data Science, Strategic Management, and Data Systems Architecture.
5. I asked for a meeting with my manager and showed her my spreadsheets and my findings. This way I got her to buy-in. I explained to her that I would be more helpful to the company in a Tech Director role and that here was the list of skills I needed to gain to get there. I asked for her opinion and insights. She told me she needed some time to think about it.
6. We met again after two weeks and she told me that she considered my path and plan reasonable, however after she ran it by the company’s HR and HQ she was told that to aspire to the director’s role I would also need to be able to prove a financial model for a business (or a new branch of a business). I told her that I needed some time to think about it and that I would get back to her.
7. I went forward and looked at every director at our company. While majority of the directors had proven a financial model for a business and run their startups (in the company I work a director role is a C-level role), there were two directors who were not running a startup and have never proven a financial model (they were the Director of Finance and Operations and the Director of Venture Strategy). I asked for another meeting with my manager and showed her these examples. Long story short, after two more meetings HR agreed that proving a financial model shouldn’t be a “must-have” for a director role. I would like to add that I like working on financial modeling and I think it is vital to understand how financial sustainability works and to build (or be part of a team that builds) the financial model. However I didn’t want it to be a requirement for the role I was aiming at because finding a proven financial model for a business can take years.
8. By the time we finished our “negotiations” it was already June and I had about eight months to gain the three skills I needed: Data Science, Strategic Management, and Data Systems Architecture. I reached out to other CTOs and CEOs and asked for recommendations of a coach to learn strategy and strategic management. In a few weeks I got introduced through a friend to an amazing coach, Jeff Malone, and we started our work together in September. Jeff helped me create a strategic method for experiments, develop a management style, and set the team I was managing for growth while setting boundaries and expectations. Since then “The Strategic Method” he taught me (and that I wrote down diligently) spread out into other divisions of the company and people started reaching out to me to teach them and let them use it (which I did gladly).
9. In July I signed up for a Data Science course in a community college. Since the beginning of COVID all education has moved online and I was able to find a great and affordable course with a real teacher. Spending my nights in class and weekends doing homework, I quickly gained some skills (not of a data scientist, I didn’t aim at that) to do data explorations and orient myself in predictive models.
10. Learning data systems architecture turned out to be a bit more challenging. There was no concise course to take, there was a variety of platforms and solutions, and our work with outside partners, chatbots, and Facebook had its own requirements. I ended up digging information through Twitter, reading tons of articles, and looking at many different platforms and tools. I took a few classes on Datacamp about databases and systems. I reached out to our internal IT department to read the documentation on our current data structures, asked them what other similar companies are using, and engaged in a series of learning sessions with our IT team. I reached out a lot and many times I felt terrible taking up people’s time, but this was the only way to learn.
11. I made sure I kept my manager posted on my progress. Each check-in I included a short update on my professional development and where I was with each of the skills.

What happened next was a bit more exciting than I expected. In February 2020 (before my annual review and before I started this whole process) I was asked to jump on a side project as a tech support. I built a chatbot architecture for a small project within the company. We made it possible for organizers to go digital and use chatbots and automation to gain constituents, virality, and generate actions. I was first expected to spend five hours per week on this project, then ten hours per week, then twenty hours per week. By mid July I was working over sixty hours per week. Twenty of them on my “full-time project” squeezing all my work in twenty hours and rigorously skipping meetings and fourty hours on this side gig. The side gig gained traction and grew. In August we hired our first two employees to help build our tech. In October the side gig got funding for a two year runway. In November the CEO of the project asked me to step up in a CTO-type role as a Technical and Data Director. I was excited about the offer and after a brief back and forth accepted the position transitioning into the new role on December 15th 2020.

Since then I have been approached by my previous team with questions about the growth and how they could get the positions they wanted. I shared my process with them. I am currently coaching a part of my old team on professional growth. I am also coaching my new team how to get to their goals and dream jobs within or outside of our comapny. The process is very simple and can be summarized as follows:

1. Write down the job you want to do in two, three or five years.
2. Find twenty plus job descriptions that fit your dream job.
3. Make a list of your dream skills and your current skills.
4. Create a list of skills you need to gain for the dream job. Prioritize.
5. Keep you manager involved and helping you.
6. Make sure HR and company management think your plan is reasonable.
7. Set your plan in motion: sign up for classes, read, get coaching, volunteer, do side gigs, basically do whatever it takes to gain these dream skills.
8. Keep your manager updated on your progress and adjust where needed.

I think that opportunity shows up when you put the work, not before that. I was extremely lucky that I got asked to help on the side gig. However, it was my decision to accept it, knowing that it might take more time and I will have to work long hours. It was luck that our side gig grew that fast, however it was us that did the job and built all the tech. Without the builds luck wouldn’t show up. I was lucky to get offered the job I wanted before expected and in a different scenario than I envisioned it. However, it was not a gift. I remember that I wasn’t even happy when I got asked to be the CTO. I worked so hard to get there and was so tired when it happened that I just felt that it was a natural thing to occur.

A month later, around the New Year holidays, I told my kids and my family and friends about the promotion. And that was the first time it dawned on me that I’ve reached my goal. And I was happy that the process worked and started sharing it with those who asked. I even shared it with our HR department in hopes that it will become a “standard” process and help others. For the same reason I am writing it here. I think it works if put in action.

I have to add that the only thing that wasn’t hard work and was pure luck was having a good manager who was supportive of my growth. I don’t think this process would have worked that well otherwise.