Crossing the PM Career Chasm

Tom Walsham
APM Toronto
Published in
9 min readFeb 22, 2018

“The objective of the APM Program is to collectively create the next generation of top product leaders in our ecosystem. This will be done through vocational entry level roles, a practical curriculum and the creation of a network of support for a group of hand-selected candidates.” — Toronto Distributed APM Program Proposal, 2017

Graphic: Stella Konopski, for Toronto APM

It’s May 2016, and I’m standing in a bar at the afterparty for the Mind The Product Conference chatting with Ken Norton when two aspiring Product Managers come up to Ken and ask him the well-worn question — “How do I get my first job as a Product Manager.” His answer is succinct: Apply for an Associate Product Manager (APM) position at one of the companies that offers a rotational program : Google, Facebook, Yahoo, LinkedIn, Twitter. Do your tour of duty and 2 years from now you’re a Product Manager!

My response was less satisfying, but probably more applicable to aspiring PMs outside of the Valley. Use your skills (Designer, Engineer, QA Analyst, Project Manager) to land a role in a small company or startup without an established Product practice. Research the role and seek out a vacuum in your company that you can begin to fill. Eventually you can position yourself as the de facto PM, ask your manager for a role change and 2 years from now you’re a Product Manager!

Only one of these looks like solid career advice, but the latter is how most folks I meet got their start as Product Managers. It’s a well known experience Catch-22 that’s relatively unique to Product in the modern tech economy. Designers come with hard-earned portfolios, developers can take a relevant degree and work through a well-worn career track, but it seems PMs need to spontaneously appear at the intermediate level.

That conversation stuck with me. There had to be a better way.

As we moved past the summer of 2016, I began thinking more about the inequity between the two paths. Large organizations can deliver meaningful value to a cohort of prospective PMs, and this model has a decade of track record for delivering results. Many smaller companies and startups have a desire to grow our teams without jumping straight to senior roles, but lack the resources to execute an impactful training program.

That said, I strongly believe in investing in training, the need to create opportunity for the next generation, and that there is an impending talent crunch in our local tech community.

TORONTO

The past 4 to 5 years have seen a well documented explosion in the Toronto tech scene. Traditionally, success was mostly in enterprise B2B products, but we’ve seen great diversification towards everything from high growth consumer plays (Wattpad), leading consumer fintech (League), IoT (ecobee) and of course Toronto is the second home for Canadian tech’s runaway success story (Shopify). These and other factors have contributed to the emerging confidence of founders and investors pursuing ambitious software startups in the 6ix. With modern software products comes a need for modern Product Management.

The core Product community in Toronto is of high calibre, tight-knit, but suffers from a lack of scale and accessible entry-level roles. Years of capacity building through organizing and participating in meetups such as ProductTO and ProductTank have demonstrated the hunger for opportunity and training. Interviews with hundreds of candidates as we’ve grown TWG’s current team to 15 PMs has given me perspective on the chaotic nature of PM career development. I believe a shortage of experienced Product Managers will soon become a limiting factor in the Toronto ecosystem, and in similar municipalities globally.

In early 2017, conversations with other Product leaders in Toronto validated and expanded on the problem. On the organizational side companies were taking on junior PMs but often felt they weren’t doing justice to the need for training and mentorship. For candidates, aspiring PMs were taking short bootcamps but having trouble finding roles on the other side — the academic theory component of the role is a minimal success factor compared to practical experience. The solution needed to be vocational, appropriate for small organizations, but with the structure and training needed to accelerate fundamentals.

IT TAKES A VILLAGE

In the Summer of 2017, we drafted (with the help of some invaluable feedback) the fundamentals of a model that could achieve the scale needed to deliver value while allowing smaller organizations to both contribute and receive the benefits of a graded approach to the PM career path. We started by shortlisting Product-focused companies with the internal capacity to mentor APMs, the senior experience to bring value to the cohort, in addition to an ethos that leans towards Agile, Human Centred Design and Lean principles. An initial shortlist of 8 outstanding Product leaders at these companies were approached with a pitch for a distributed APM program.

Shopify, Wattpad, League, Freshbooks, ecobee, Tulip, ChefHero, Roadmunk and TWG

The proposal, in short, was that we form a collective training model with 6–8 companies, and a cohort of 10–12 APMs, operating over 6–9 months. Each organization would hire or cross-promote 1 or 2 APMs — those candidates would be part of that company, selected for the nuances of their specific business.

The candidates would spend the majority of the week working in their respective companies — shipping product as an entry level Product Manager. We would then, on a weekly basis, bring the group together for an intensive session focused on a blend of semi-formal training, shared learning and peer interaction. Outside of this we would provide community management in the form of Slack groups, periodic socials and a budget to allow the APMs to operate independent outings as a team. This was designed to create lasting value through a highly connected alumni group.

To ensure the program would run smoothly, TWG committed to providing a program manager to organize the practical aspects of the program. Participating organizations need only put forward a small financial stipend into a pool to fund food, social programming and ad hoc costs, and commit to running 3 sessions over the course of 6 months. In exchange their APMs would get the full benefit of 24 dedicated sessions, 6 months of network building with their cohort, and direct access to some of the best Product leaders in Toronto.

It was not a hard sell.

MAKE IT SO

We convened a dinner as the first meeting of the (prospective) steering committee to discuss what could make for a successful program. I run a lot of workshops with clients in my role at TWG, but there’s little more intimidating than seeking consensus amongst a group of your peers.

What’s the collective noun for a group of naive optimists?

We had tabled a number of potentially blocking issues to discuss, and fundamentals we needed to agree on. We largely resolved these before dessert.

Program Duration

The Valley model is usually 18 months to 2 years. That seemed longer than ideal for an MVP of an alternate model. Conversely 3 months would not provide enough time for any meaningful value delivery, or ensure the depth of commitment needed from participating organizations. We settled on 6 months as a viable test period. There’s a chance it’s too short to fully bridge the gap, but we’re confident we’ll be providing significant learning and meaningful connections in that timescale.

Pedagogy

How do you ‘teach’ Product to candidates from 9 different companies? Across any single aspect of process these organizations have many varied approaches so there could not be an opinionated curriculum. We realized that this could be turned into a benefit when the model of Self-Directed Learning was proposed by Jeremy Bailey. Provide the spectrum of (reasonable) methodologies with weekly talks, materials to stimulate personal research, and mentorship to aid the evaluative process. Through this we can ensure the APMs are both informed and flexible but intentional about their execution of the PM craft.

This led to a planned curriculum that balances vocational, tactical and soft skills while giving room to tackle contentious topics through panel formats, and ensuring we steer clear of dogmatic preaching of ‘the one way’.

Diversity

Organizations can (and should) implement principles that encourage applications from diverse candidates and remove bias from the hiring process, but this is harder to coordinate with a distributed group. As an entry-level program we are in a position to do even more to accelerate the careers of traditionally marginalized parties. The foundations of a strong Product community should effectively represent the diversity in our users to ensure we build products that serve all audiences.

While I’m pleased with the balance in our initial cohort we know we can always be better. In future cohorts we will need both to improve the opportunity to participate, cast a wider net for hiring initiatives and implement checks and balances to ensure diversity in the cohort in spite of the distributed nature of the group.

Blockers

There’s plenty of ways to kill a concept like this early on. We’re a group comprised of early stage startups through publicly traded companies. NDAs, non-solicitation agreements, and many other formal processes could have rendered this a non-starter. I’m thankful to the leadership of these organizations for pursuing this endeavour with an open mind, allowing us to commence this initial cohort. As we develop we need to improve our sophistication in this respect to create a playbook that’s usable globally. We will though always be referring back to the core mission of developing long-term Product talent in our communities to ensure that we all benefit from the outcomes of a successful model.

“OK, now a silly one”

GETTING STARTED

Once aligned on the approach, we were mainly dependent on hiring, and coordinating the timing between organizations. We had a fun social mid-December, and formally kicked off the program in the first week of January 2018.

Running a collaborative effort between Product leaders is both entertaining and challenging. We’re dogfooding the Product process with a plan that’s clear 1 month out and hazy 4–6 months out as it should be. We’ve instigated regular feedback (Breanna ran a great meta-retro in week 3!) and fully expect to adapt the format over the coming few months. We are now 5 weeks in, going through the hardest part: delivering value, realizing our own blindspots, and learning. While it’s early days, I now believe it’s possible to create a meaningful, intentional track to PM without needing the weight of huge corporations.

EPILOGUE

Aspirationally I hope we can further the growth of the Product discipline globally and in smaller communities. If we find the success we expect with this program in Toronto, the principles should be broadly applicable in other cities, from New York to Mumbai to Berlin. As we’ve been getting more visibility we’re hearing an immediate demand from many companies for more cohorts locally, significant interest in starting the program in other cities and a constant stream of interested candidates.

There’s a lot more detail in the thinking behind our structure that we’ll outline in subsequent posts if you’re interested in running something similar in your city, and we’re looking to create a chapter-based model that can bring the benefits of scale to all participants.

We started down this path with a goal : If we can create value, and understand the mechanisms for doing so, we will create an open playbook so cities globally can implement this model to solve a universal issue facing our profession

Please reach out if you’re interested, have questions or comments, or just want to say hi! Watch this space for future updates— next up : Principles, Getting Started, and Early Learnings.

I’m on Twitter as @tomwalsham and updates will be provided through @apmtoronto, and our contact address at APMtoronto.com

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With thanks to the following folks for invaluable inspiration, collaboration & support in the creation of this program :

Oksana Salamaszek, Seema Lakhani, Breanna Hughes, Brandon Chu, Jeremy Bailey, Kim Phelan, Lindsay Rothman, Latif Nanji, Warren Faleiro, Oz Nazili, Casey McKinnon, Jan Kotowski, Satish Kanwar, Johnathan Nightingale, Holly Knowlman, Stella Konopski, ZJ Hadley, Amanda Connon-Unda, Sarah Prevette, Richard Banfield, Ken Norton, and all the APMs in cohort#1 who are super willing guinea pigs!

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Tom Walsham
APM Toronto

VP of Product, @twg | Amateur taxidermist | @apmtoronto