How to grow from Sr. PM to Sr. Director of Product in 4 years

How to grow from Sr. PM to Sr. Director of Product in 4 years

4 years ago I joined Vimeo as a Senior Product Manager with a team of 8 people. Today I'm a Sr. Director of Product, leading a team of 60+* and a product suite that's attributing to $100m ARR.

Below I'll share how and why I was promoted, and how my goals, responsibility, and expectations towards me changed at every stage of the journey. This should be helpful for both PMs and most professionals who are interested in career growth.

Before we start, I have two caveats: 

  1. Everything I say here is my personal story & opinion, and you will likely find other practices in other companies and even at Vimeo. 
  2. This is an English version of my original article posted on dou.ua, and with both versions, I encourage readers to help raise funds for Ukraine's protection. You can find more details on that at the end of the article.

Senior PM

In January 2019, I started as Senior PM at Vimeo with a team of 8 engineers. For context, before Vimeo, I had 2 years of experience as co-founder and CPO of my startup, 3 years as a mix of product/marketing/sales at a developer agency, and 3 years as a software engineer. My goals in this role were pretty typical for a Sr. PM: grow MAU, engagement, and subscribers. Understand user needs, prioritize them, shape roadmap, write user stories, work with the team to launch initiatives, measure impact, start from scratch.

In April 2019, 3 months after I started, my PM colleague left Vimeo, and I'm was offered to inherit his role (lead a team of 6 engineers) while continuing my current job. This is a critical event in my journey, so let's double down on it. First, it served as a foundation to promote me at the year-end review. Second, it shows a very traditional career dynamic that you'll see a number of times in this article.

Generally, this is how career growth happens:

  1. you do your job very well
  2. management notices
  3. a new business task/opportunity pops up
  4. management decides to assign you to it
  5. you start from step 1 again.

I was lucky to be on both sides of this many many times. In case above, my manager had a choice: start hiring a backfill and drag business for 3-6 months, cover the role himself, reassign someone from another team, or extend my role. I helped him make this decision by doing my job well in the short time period we worked together. In those three months, I built rapport with the team, launched a few features, and presented a slick summary of user needs analysis and respective roadmap. So I was trusted with more scope, and if I proved myself well, it would mean I can be promoted and have the opportunity to grow even further.

I hesitantly accepted the offer. Doing a good PM job with a team of 15 engineers is difficult. I'd be stretched thin and will have to cut corners in user stories, analysis, or communication, or allow the team to work on non-validated work. But I was lucky to get 2 project managers for each team who were able to take on a lot of day-to-day operations.

Principal PM

It seems that I did a good job in my stretched role as in January 2020, at year-end review, I was promoted to Principal PM, and at the same time was offered to work on a larger product (some companies call this role Lead PM, sometimes Group PM, though definitions differ, see levels.fyi).

What was expected of me in the Principal PM role? A huge part was the ability to lead 2 products in parallel. I still feel mixed about whether it's the right approach, but here's the logic. As you grow, you can make decisions faster, persuade people more effectively, analyze data more efficiently, detect user insights with less effort, etc. So you can do the Senior PM's job more effectively; therefore you can lead two products in parallel. Also, this is a foundation for further development as for future growth, you'll need to lead much more than two products (by managing more PMs, though). The cost of such an approach, however, is that PMs might lose focus and make worse decisions.

There were other expectations from me in this role: ability to influence others, to find deeper signals in user feedback and in data, ability to work without manager oversight, ability to solve more complex product problems. We've described all of this in PM rubric, and each company is expected to have one. A good public inspiration is a suggestion by Reforge or a more detailed product competency toolkit by Ravi Mehta.


Going back to my story, in April 2020 as part of my new role I presented new roadmap to Vimeo's C-level in which I

  • reshaped one of my teams: reduce investment in existing product to launch a new one
  • sold the idea that if we want to succeed in this space we need to change the priorities of up to 10 other teams that don't report to me.

At the same time, all my products (pre-new role, post-new role, and not yet launched product) experienced a 10x demand with Covid, so I end up leading 4 products with a team of ~20 people as a single PM in IC role (individual contributor). This was the most intense and exhaustive time of my career, and it kicked off my transition to Director of Product.

Director of Product


In January 2021 I was promoted to Director of Product for the things I did in 2020. Let's break down how exactly this happened, and what was expected of me.


Path to promotion


In my view there was 3 key factors to my promo: launch of a complex product, contribution to company strategy, and management of 3 PMs.

Product was complex because:

  • I sold the idea of launching it nearly from scratch to everyone: from colleagues to C-level
  • We launched it with a team of 2.5 engineers
  • I persuaded 4 other teams to help us, and almost didn't piss them off (but yeah I did a bit)
  • I was still running 3 other hyper-growth products in parallel
  • It was successful very fast

On the strategy side, I participated in key strategy planning sessions and helped shape strategic multi-year plan for our target market and path to victory, providing data to back it up and outline of key large scale initiatives we have to tackle. (retrospectively, 2 years later I am proud to say that that strategy worked beautifully).

Hiring PMs was not less important, because Director, as opposed to Principal, is supposed to be a people manager (at least within the framework we had at the time). And I've shown the ability to effectively hire and onboard 3 PMs without prior experience in this. To give you a taste of timeline: in Spring 2020 I got the budget to hire a PM to my team, and in October 2020 I made my first PM hire. Then in December 2020 I hired second PM. And in Fall 2020 one of the project managers moved to Associate PM.

Behind the scenes of a promotion


It's so much more difficult to promote someone than it seems! Being in a manager role now I had to go through this a few times, and I call it 7 circles of promotion hell (btw there's similar hell with hiring). First, you as a manager make a case for promotion. Then your manager confirms this makes sense. Then your peers need to calibrate it to ensure everyone treats promotions with same criteria. Then HR needs to evaluate it to ensure there is no bias, and your promo along with others follows a typical distribution curve. Then finance needs to confirm there's a budget for promo. Then usually several members of C-suite need to balance promos across the company. So yeah it's not easy. Receiving 2 promotions in 2 years, as I did - is a rarity, and raises many questions from a lot of people.

For context, at Vimeo, like at most companies, promotion decisions happen primarily once a year, during the year-end performance reviews. And a key factor to promotion is whether the person has performed on the next level for the past 6 months. Think of it this way: from company's perspective it's important that everyone with a specific level/title meets a certain minimal level of performance, so that anyone who works with them could expect that level of professionalism. And usually, after you get a promo, the key expectation from you is that you can prove you're worthy of the new title and can keep performing at that level. So starting to perform on a yet next level right after promo is fairly unusual.

But in my case, I made the job for my manager a bit easier (and he told me as much). Throughout my work of pitching new product and strategic direction I personally interacted with majority of people who would approve my promo, and they were able to form their own view so my manager didn't need to do as much persuading. I got very lucky in this regard, and this shows that visibility of your performance among key leaders is very important to your career path, though it's not very fair as it’s not always part of your job to work with them.

This takes me to a very important point. Big part of career growth is managing up, ensuring your sponsors are happy with your progress, and key stakeholders are bought in. But it doesn’t have to include politicking and advertising your great impact all around. In great companies with great managers there’s enough trust to just do your job well, while your manager notices your strong performance and seeks for right opportunities for you (that's actually their job, more on that below). This is a healthy culture. In an unhealthy culture, you'll end up spending more time ensuring everyone thinks you're doing a good job than ensuring that the job is actually done well. Kinda like Director Krennic in Rogue One, or any Russian military officer (p.s. it's because of people like this the Empire fell!)



So if you're not getting recognition for a great job - I recommend raising it to your manager or their manager or whomever you trust in management. And if that doesn't help - I recommend you to find another company where you can spend your time more productively. I got lucky. I was just doing my job well, and my manager put me in a position where the right people noticed me. I thank Matthew Smith and wish everyone to have such a manager.

Another important point: I mentioned before that after your great job is noticed you wait for an opportunity to pop up. In this case, I created my own opportunity by pitching a new product and strategy. You can do the same if you're tired of waiting for the right opportunity.

Expectations from a Director of Product


While I had 3 PMs on my team, I still led plenty of initiatives myself. A big change from Principal PM role was that I was expected to spend at least 50% of my time on people management. i.e. Review their roadmaps, OKRs, user stories, underlying analysis, give feedback, push back when needed, help solve conflicts with their peers, detect strengths & weaknesses, build career path, find the right opportunities to stretch them, give them visibility among company leadership, and solve their personal requests (like someone wanting to relocate, get visa sponsorship, or publish a controversial article😊).

To me this was the most complex period of my growth. Because you not only need to learn to shift your mindset from managing products to managing people, you still need to keep managing some products. This polarity is very complicated for a seasoned PM, let alone someone who's learning to become a people manager. I'm sincerely happy this stage of my career is behind me as this was the time I made the most mistakes, which are felt until today.

I didn't give enough feedback to my team and was too hands-off, which led to a series of problems both for the company and for these PMs, as their reputation took a hit. Because of this, my responsibility was reduced, so I can fix my problems. It was the first time when I evaluated myself as "not meeting expectations" in a mid-year review. And I wasn't promoted at year end like in previous years (very justifiably).

A weird side-note on this is that I had my parental leave right when the problems started. And it both contributed to the problems (as I wasn't there to fix them and my manager carried things on while I was out), but also it helped me get back on track as I took 2nd part of my leave later and was able process my mistakes. The whole topic of parental leave amidst career growth is a very interesting, complicated, and under-discussed pool of controversy (I recommend watching this talk by beloved former colleague Tara Feener as a starting point)

Back to expectations for a Director - you're expected to drive strategy for your product area and influence company strategy, influence other teams when your product requires it, and to show real impact. To do all this you'll need strong skills in data and storytelling. Overall from my experience, you can usually tell a person's seniority from their communication skills.

Ability to show impact is a very interesting expectation. For more junior roles I believe it's not right to evaluate them primarily by the impact they make, because often there are things outside of their control (sales team not meeting their needs, marketing not driving quality traffic, or the opposite - another team releasing something that lifts all boats including your report's). So you have to take into account their actions and what they did right or wrong. But the more senior the person becomes, the more responsibility they hold over results, the more influence they're expected to show, and the more awareness over all pieces of the puzzle, to be able to predict and fix problems outside of their direct responsibility area (with CEO holding ultimate responsibility for impact).

When I ask my manager what I need to do to become a Senior Director of Product, he told me:

  • you shouldn't be doing IC work anymore
  • your team needs to be impactful
  • your team and peers need to be happy

Senior Director of Product


And that's how my shaky path to Senior Director was kicked off - in Summer 2021, when I got harsh mid-year reviews.

The first thing I had to fix was the peer and direct report feedback. I wasn't easy to work with. I got feedback that I'm like a bulldozer, I'm too direct, too critical, and don't play by the rules. On top of it, I wasn't present enough for my team. It's a lot to fix! While some of these traits helped me with my hypergrowth up to this point, and I still think they can be strengths, at this stage, they were too extreme and were blocking my further growth. So I needed to smooth them down a bit.

Another huge step up towards Sr. Director was building an extended team. In January 2022, after spending several months and 100+ interviews in hiring, I was able to finally close all the key hires. At the same time, we were lucky to get our team extended with an additional PM from another team, dedicated BI analysts, and PMMs. Along with designers and engineering leads we formed a dream team of 60+, and I feel great pride in setting up an environment where we were able to tackle the most complex issues together. Very organically with such a team, my focus shifted completely off of IC work and into leading the team and business area.

This additional time also allowed me to detect new opportunities for impact. I found that our collaboration between product and sales orgs needs love, and that improving it will have an outsized impact not only on my team but the overall company. I picked a contained problem with measurable outcome (improving feature requests process) and rallied key product and sales leaders around solving it, which had immediate positive results and made many people happy. Without realizing it I showed 2 traits of a senior leader: ability to influence people in other departments, and abilty to make impact outside your primary area of focus. But in reality it just started with me solving a process problem for my product area.

As a result of all these improvements, I was promoted to Sr. Director of Product in August 2022, via an off-cycle promotion. It's 1.5 years since my previous promo and makes for 3 promos in 3.5 years, which honestly I still can't fully grasp. I can only imagine the work my manager needed to do to persuade everyone that this needs to happen, for which I'm deeply thankful.

I want to highlight how lucky I was though:

  • Vimeo, similar to all video industry, was growing very fast. This allowed me to get approval for 3 new hires, which in turn allowed me to scale my impact and grow this fast. I wouldn't be able to do the same or have the same growth trajectory in today's environment when the majority of companies have either a hiring freeze or a series of layoffs.
  • Management had a high level of trust in me, which allowed accelerating a lot of decisions, reducing the amount of status reporting (and overhead that comes with it), and getting the right resources quickly. It's an extremely underrated advantage you get when you stick around with the same people (and btw that's why I'm skeptical of job hoppers).


Conclusion

  1. TL;DR for getting 3 promos in 3.5 years: join a fast growing company with great culture and great manager, and do an amazing job (I should get - get super lucky along the way :) )
  2. Remember key promotion dynamic: 1) you do your job very well, 2) management notices, 3) a new business task pops up 4) management decides to assign you to it, 5) you do a good job with it 6) you get promoted and 7) you start from step 1 again.
  3. Even though visibility of your work is very important for career growth, don’t overinvest in it. While there’s some managing up you need to do, it’s very easy to lose track and care more about visibility than real progress. I cannot recommend enough an environment where you can trust your manager enough to only care about doing a great job. 
  4. If you’re not getting new opportunities - create them yourself
  5. The more you work with same people, the faster trust keeps building up. Starting new job resets the trust growth curve
  6. Here’s my oversimplified view on PM leveling:
  • Sr. PM: seeks user needs, builds roadmap, prioritizes, writes user stories, launches features with their team, measures results, etc
  • Principal PM: solves more ambiguous problems, detects more nuanced user signals, leads more initiatives in parallel, is very autonomous, starts influencing others, might manage people
  • Director PM: spends 50% of time on people management/hiring, influences other teams, sets strategy & OKRs, tells stories with data, shows business impact
  • Sr. Director PM: zero IC work, works across departments, sets strategy and financial plan for a business unit, communicates with any seniority level, expected to make business impact

     7. Key areas that grow with seniority levels: 

  • Dealing with ambiguity
  • Communication & storytelling
  • Business Impact

With that said, every promotion story is unique, different companies have different criteria and paths, and your case might be far from what I described. Still, I believe you can reuse multiple parts of this story for your own growth.


Hope you liked this, and if so, I encourage you to help Ukraine protect its future products and their managers. You can donate via this link to my personal page on a fund built by Ukraine’s product leaders and my friends https://happy.koloua.com/en/campaigns/pms-supporting-ukraine-164120 . As a thank you, I will be happy to answer any of your follow-up questions in detail!

P.S. staying true to facts, I deliberately simplified the beginning of this article to say I'm leading an extended team of 60. That was the case when I wrote initial version of this article, 3 months ago, but since then this changed as Vimeo had a reorg, and I'm leading a slightly smaller team. This doesn't change a single point I'm making in the article but maybe reminds both me and you to not measure success with your team size - your impact stays with you forever, your team doesn't.

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