Thoughts on building products, entrepreneurship, bicycling and whatever else strikes my fancy.

How I got a product job during the pandemic

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.

My product targets
Some of the companies I was interested in

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 to reach out to me on Twitter.

Covidsupplies.NYC – Helping source PPE in NYC

These past few months have been incredibly strange. In early January / February, we started to hear murmurs from our luxury industry customers at Wami about a global slowdown in consumer spending. 

As the pandemic picked up speed in the U.S., it was evident that there was a shortage of personal protective equipment (PPE) for hospitals in the NYC area.  

With the majority of Wami’s customers significantly impacted by the global slowdown in consumer spending, we teamed up with 3D Brooklyn to build Covidsupplies.NYC to link healthcare organizations in need of personal protective equipment (“PPE”) with on-demand 3D printing in the NYC area. 

I’m very proud to share that as of May 27, this project has produced and shipped 15,000+ face shields to 200+ hospitals and raised $60,000+

Version 1.0 of the Face Shield

My role was to lead user tests with doctors and health care organizations and then build the website and requisite functionality to securely link organizations in need with local manufacturers able to produce face shields. 

While user-testing with doctors and nurses, it was clear that this needed to be a mobile-first experience, and it needed to be secure and straightforward to submit a request for supplies. 

I used Sketch for the initial designs, and WordPress + Elementor Pro to build the website. I went with Typeform (Typeform even covered the project!) for the form inputs and Zapier for email automation.

The entire MVP was scoped and launched in under one week. With this lightweight tech stack, we were able to implement changes based on rolling feedback from the healthcare organizations on the fly. 

Video: Loyalty 360 thought leadership series

I recently had the chance to chat with Loyalty360 on how brands are adapting their outreach initiatives, and how marketers are recalibrating playbooks to be successful in Q3 and Q4.

It’s quite strange to make predictions right now about how businesses will reopen back up for business. Still, I think it’s a fair assumption to assume customer loyalty will be a critical component of success for the brands that do succeed in the new normal. 

Case study: Unlocking revenue through app redesign


As a member of the cross-functional leadership team at Bond, I realized that the sales team was spending a disproportionate amount of time and cost onboarding SMB customers. These customers represented one of the highest lifetime value segments for Bond and often made repeat purchases. They shared their frustrated feedback with the slow and manual existing process and would often drop off before completing their order through an account executive. 

I hypothesized we could better serve these customers by redesigning our product suite to include features for this valuable and underserved audience. 


I prepared multiple presentations (example above), leveraging current data and customer feedback to persuade marketing, sales, and C-suite leadership in the new direction for the product portfolio and initially encountered resistance at making such a substantial change.

I led the product team to conduct user interviews, where we quickly confirmed the hypothesis and demand for this redesign. We used this knowledge to build clickable prototypes with InVision, which we then tested with potential first customers to understand and inform what features were necessary at launch.

Armed with a substantiated hypothesis, and the learnings from multiple customer interviews and user tests, I was able to get stakeholder buy-in to move forward with the redesign. I put together the product requirements documentation (available below) and go-to-market plan. These assets were our guiding light and were shared broadly across the company to make sure all teams moved in the same direction.


We shipped the minimum viable redesign of the web and iOS mobile applications in >3 months. The new feature set added $1+ million in top-line revenue, a 433 percent jump YoY (Report from Stripe below).

Additionally, the sales team was also able to shift focus to Enterprise deals, increasing their average deal size from $4,000 to $10,000+ over the same period.

Tools and tech used:

Case study: Lowering the barriers of entry to 3D printing


In 2014, 3D printing was one of the hottest markets for venture capital dollars and media coverage. I joined up with the brilliant team at 3DPrinterOS to initially build encryption for the secure cloud transfer of 3D printing files (known as “gcodes”) from computers to machines. 

We realized pretty quickly that while the encryption problem was real, the much bigger opportunity to solve was lowering the barriers of entry into 3D printing so new users could embrace this disruptive technology. 

We hypothesized we could lower the barriers of entry into 3D printing and increase utilization of machines if we built a cloud-powered operating system that worked across multiple types of 3D printers, analogous to how Microsoft Windows worked across PCs from Hewlett Packard and Dell. 


I set out to understand the current state of 3D printing by researching the market and testing out software from 20+ printer manufacturers. We filmed unboxing videos for many of the printer tests, to establish ourselves as thought leaders and improve our SEO. 

I also conducted user interviews with Fortune 500 companies, such as Ford and John Deere, to understand how they were currently using 3D printing, and what pain points existed within their current workflow. 

This work validated our hypothesis and built relationships that led to our first customers. The research gained shaped the MVP requirements, feature backlog, and user stories. With the MVP scoped out, I then spent two months in Estonia with my team driving towards a beta release. 

During this process, I built wireframes and prototypes to test the onboarding process with prospective users and used the knowledge gained to create in-app messaging, tutorials, and walkthroughs to improve the onboarding process.

Aaron Roy - Wireframes
Wireframe example

We launched a free beta version of the product in March 2015, and all focus shifted to feedback gathering, evangelizing the platform, and improving the feature set. I served as the primary tester of the platform with our beta users and established a robust forum for sharing walkthroughs and soliciting community bug reporting. 

I put together feedback surveys and created incentives (free t-shirts, early access to future new features, 3d printer filament giveaways) for users to test the beta release. I went on-site to multiple companies and educational institutions to observe how they would interact and add internal users to the new platform. I also used Intercom to communicate in-app with users and deliver A/B tests of different walkthroughs to understand the impact on improving metrics.  

Aaron Roy - Using Intercom for walkthroughs
Intercom is terrific for in-app messaging


Launching a new product is just part of the challenge. It’s what you do once it’s out in the wild that defines whether or not it will survive.

In analyzing our metrics post-launch, I was able to identify and guide the team to build low development, high-yield features that led to the first $500,000 in ARR.

3DPrinterOS has 100,000+ users in 100+ countries. Users have printed 1.3+ million parts and have logged 4.5+ million print hours. Clients include Google, NASA, John Deere, Duke, MIT, and Yale.

Aaron Roy - 3DPrinterOS Dashboard
Screenshot from 3DPrinterOS dashboard

Tools and tech used:

In appreciation of the internet

What a time to be alive!

We’re in the early stages of a global pandemic with covid-19.

The stock markets are searching for a bottom amidst skyrocketing infection and death rates.

And at least here in NYC, we’re doing our best to practice social distancing, which means staying away from physical human contact.

It’s in these moments I am so grateful for the internet and the infinite world of wonder it provides.

There will be a new normal after this pandemic subsides and we have a better feel for merely how to exist in a world with covid-19 as an additional threat.

The stock market will recover once again one day.

The rebuilding process has started already and will continue gaining strength from the footholds of the digital world.

Stay safe friends!

Wami is the featured product for TPG!

Aaron Roy - Product Manager

It was an absolute blast serving as the featured product of the month for the Product Group here in New York. 

We had the chance to talk through our lessons learned while bootstrapping Wami, and how vital failure (and learning) is as part of the product cycle. 

This 20,000 members strong group is an incredible resource of knowledge, expertise, and support for current and aspiring product managers in the NYC area. I highly recommend attending one of their meetups

Why startups should focus on staying alive

For the first few years of any company’s existence, people are naturally skeptical of its ability to endure. Especially in the B2B space, Enterprise and SMBs have no desire to purchase from a young company that may fold up shop as soon as the ink dries on the contract. The stakes of this skepticism are even higher for bootstrapped companies that lack the helpful TechCrunch or VentureBeat articles which highlight their latest funding round to aid in credibility.

It’s been my experience that, provided you create something of value for customers, after a certain threshold of time and energy, your endeavor starts to gain legitimacy on its own to the outside world by the sheer force of its continued existence.

After a certain amount of time investing energy and passion into a startup, something wonderful happens. The skepticism begins to fade. The exact amount of time and energy varies between products and founding teams (as some “products” shouldn’t exist in the first place) but the company starts to make leaps organically.

Potential customers begin to trust you can deliver what you promise slightly sooner. You notice sales cycles begin to speed up. No one moment is the precise cause, instead, it’s a sum of the total input from the organization. These moments inspire the team to keep going, and often open additional doors for the growing company. For new products, the sum of these moments often manifests as “finding product-market fit.”

In the early days of 3DPrinterOS, these leaps of credibility made all the difference. While our competitors would throw spaghetti against the wall hoping something would stick, we focused on delivering an awesome product for schools and gained momentum one school at a time. This focus and passion to survive led to 3DPrinterOS making it through the 3D printing crash of 2012, and to this day they are still adding schools and establishing further credibility.

At Wami, we’ve seen these moments manifest in a variety of ways. It’s the customer who lets us know they felt comfortable purchasing our handwritten notes after researching us online. It’s also the initial case studies from our first customers showing that our handwritten notes did indeed make a significant impact on customer retention.

None of these moments happen if you fold up shop during the early difficult times. The longer your company can exist and compete in your respective market, the better chance at finding a positive outcome. It seems like common sense, yet we see other companies burn cash way ahead of their revenue pursuing growth in unhealthy and unsustainable ways. Don’t be those companies. Stay alive.

Researching student loan products

We all know student loans suck but are you familiar with how much they actually impact our society?

Student loan debt is now the second-highest consumer debt category – behind only mortgage debt – and higher than both credit cards and auto loans.

I’m working with some friends who are set out to help solve this crisis.

Check out this super quick survey to be part of the student debt solution:

Insights from the first month as a founder

As I wrap up my first full month of being back full-time in the start-up game at Wami, here are 3 insights/reminders that I think may help my fellow founders and early employees:

1. Always remember to ruthlessly prioritize.

I have a million things I could be doing right now, the most difficult (and most important) thing is figuring out the exact action that will keep me and my team around in 30 days, in 90 days, and in a year. When I was younger, I would often default to attacking the easiest tasks, and count that as being productive even though the larger, more important tasks remained wide open. The big difference today is my team now refocuses our efforts on accomplishing the single most important task, even if that takes multiple days or weeks to complete because ultimately that’s the only way we will survive.

As a team, we ask ourselves, “if we don’t do this one action, will the other open tasks even matter in 30 days?” For example, although we know we need to spin up our website, it’s more important at this stage for us to focus on generating revenue from potential customers from within our own network. With revenue comes the flexibility to hire incredible freelancers who would do a kickass job on the design with what we’ve budgeted at this early stage.

2. Understand your COGS or they will crush you.

Being that we’re bootstrapping our company, we are hyper-aware of the unit economics of our business model. As producers of an end physical product, we are simply not in a position to lose money on every customer. One of the most important parts of our business is managing and optimizing our cost of goods sold (COGS). Slight changes in materials cost, such as the recent rise in Forever stamp prices from 50 cents to 55 cents in early 2019, can have a monster impact on gross profit for a business sending 50,000+ handwritten notes in a single campaign. It’s our job as a company to understand where potential changes may come from an appropriately anticipate them in our pricing model.

In my former role at Bond, we threw in stamps as part of the single price customers would pay, sometimes a year in advance,  to reserve our services. While this was great for focusing on pure bookings growth, we were essentially subsidizing the costs of new customer acquisition. This created strain for Bond as rising COGS put strain on gross profit and, without transparency in pricing, all price increases were met with strong resistance by our customers. Ultimately, this was not a sustainable business model and, I believe, was one of the contributing factors to the closure of the company. At Wami, we’ve broken stamps out as it’s own line item, and charge our customers only for what they actually consume. Thus, we are much more protected from potential shifts in our underlying COGS, and able to provide much more pricing transparency to our customers.

3. Embrace the roller coaster.
“We landed our first few clients and they paid us! Things are awesome!”
“The base of our stamp machine broke down and cost us thousands of dollars we had not planned for. Things are not awesome at all.”

The highs and lows happen daily, weekly (and often feel hourly), but we know, if we are going to build anything that lasts, we must stay focused on our long-term vision, celebrate the wins as they come, and buckle down during the hardships.

About Aaron Roy - Product Manager

My name is Aaron Roy. I’m the Senior Product Manager for Discover at Teachable, and the co-founder of Wami.

Previously, I was part of the founding team at 3DPrinterOS.

Here is a bit more info about me and feel free to explore my work or contact me if you have any questions.