I’ve recently joined the rocketship that is Teachable as a product manager for their burgeoning Discover platform.
How I got to this new role was anything but a linear process. In this post, I hope to share some of the experiences, resources, templates, and articles that helped me throughout.
First, some backstory.
My robotic handwritten notes startup, Wami, has been bootstrapped from the start, and the shock Covid-19 provided to the global landscape (and the corresponding reduction in all marketing spend) put us in the uncomfortable position of having to figure out how to keep our company alive in addition to paying our personal bills.
While we’re able to chart a course forward for the business to survive near-term and continue forward, it was clear that I needed to reassess what I wanted professionally in light of a vastly different world and quite uncertain future ahead.
I first tried freelancing as a product manager through the TopTal network. I met some great and interesting people through those projects but found myself wanting something different.
With the pandemic throwing the state of the world into general uncertainty for the indefinite future, I decided to take a full reset about what I wanted to do with the majority of my time for the next few years.
At one point in mid-May, I saw a tweet from Nassim Taleb that summarized my mindset at the time.
The output of this reset for me was understanding that I wanted to work full-time in a vertical where I had genuine curiosity and interest, where I could apply what I’ve learned so far while also being pushed to continue to grow.
Quality not quantity
Taking the time to think about what interests you and why you want to work on those types of problems will carry you well throughout the entire interview process. Spray and pray is not the best way to end up where you want.
The first thing I did was put together a list of verticals and companies that fit my parameters.
Once I was ready to start actively searching for a role, I invested some time cleaning up my portfolio and resume.
With interviews being conducted over Zoom, I knew that not all facets of my personality or past work would come out during the interview process. I used the problem, approach, outcome framework to unpack the strategy behind some of the products I’ve been a part of building as my portfolio case studies. I then solicited feedback from some of my friends and peers in the product space to make sure I wasn’t sharing gibberish.
Getting conversations started
With my targets, resume, and portfolio ready to go, the next step was getting in front of the right people at the places I wanted to be.
I was heavily influenced by Gibson Biddle’s article about cultivating your network and the process of getting to two conversations a day. I was not looking for a VP job at Netflix (as he was), but the mindset and “activity” focus made a lot of sense to me.
I tried a variety of different ways to generate these conversations to varying results.
As a starting point, I made this template to serve as a lightweight tracker to help me manage my outreach process to roles, recruiters, and in-network friends.
As every “how to get a job” post recommends, I went on some interviews with companies outside my targets to get some practice in. I got those interviews via recruiters. I was able to find quite a few product-focused recruiters simply via a google search and browsing LinkedIn. I used this template to reach out and followed up weekly if I didn’t hear back.
In terms of getting interviews through my own efforts, I had the most success starting conversations by cold LinkedIn messaging prospective hiring managers and internal recruiters with this template customized for each role and organization. One of the companies I interviewed with I found via the Masters of Scale podcast. I heard the founder give an incredibly passionate talk about their vision and outlook for the future that moved me to reach out.
The exercise of understanding what you want also makes it easier for your in-network friends and connections to make an introduction or point you in the right direction. I had shared with a former manager that I was interested in what Teachable was working on, and they were able to open the door for me to someone within the Teachable organization that would’ve been much harder to make happen on my own.
Going from interview to offer
Using this tracker template, I logged all my outreach, conversations, and in-progress interviews with all the next steps. Even if I could not get ahold of a recruiter or someone within a specific company, I still logged the outreach. This a) made me feel like I accomplished something (and the little victories come in handy in the midst of a job search) and b) kept me honest in terms of following up with each target.
As with anything that requires some form of selling, it’s often not the first touch that leads to success. Follow up at a regular cadence has to be a part of your process. This doesn’t mean you should harass companies you are engaged with for an update, but it does mean you should always be on top of understanding where you are in the hiring process and what next steps remain to put the company in a position to make you an offer.
I’m not going to go into great detail in this post about how to ace product interviews. Still, it’s definitely important to understand who you are interviewing within each company and what types of hard and soft skills they are trying to gather from you during each conversation. It should also go without saying, but you should spend quite a bit of time researching the product strategy and competitive landscape for any org you are interviewing with.
With most interviews happening remotely right now, I would also recommend learning how to properly use Miro or Mural as many of the organizations I interviewed with leveraged these for strategy presentations and brainstorming sessions.
Once I made it into the later rounds of interviewing with a few organizations I could see being a good fit for me, I then switched my focus to closing and receiving a written offer. I was transparent with each organization’s hiring manager about my comp expectations should they also see me as a good fit and that I wanted to make a decision within a specific time frame. I also leveraged friends’ input within the product recruiting industry to get insight into what fair comp looked like in our specific market.
Using this overall process, I was very fortunate to receive multiple offers to choose from.
Other notes from the interview process
If I had to pick one area that I think paid off the most in helping me open doors for conversations, it would have to be the portfolio. It took some effort upfront to put the content together, but it paid off massively to communicate strategy and outcomes in a way a resume falls short.
From when I started the search process, to when I accepted a job took about ~4 months in total. Some advice I got early in my process was to prepare for ~6 months and be pleasantly surprised if it happens sooner.
In addition to the templates I’ve shared above, I’ve also compiled some of the other resources that I found helpful during my search.
The job-hunting process is inherently stressful. The more you can relax and stay positive throughout the process, the easier the entire process becomes. For me, this meant riding my bike, reading books, and dedicated no screen time with my partner and dog to give my mind a rest. Take care of yourself, and good things will happen eventually. You got this!
If you have a specific question or want another set of eyes on your product resume, feel free email me, aaron (at) aaronroy.com, or reach out to me on Twitter.