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What Type of Job is This: My First Year as Chief Product Officer

Casey Winters

I have written about the Chief Product Officer role in the past, and why the job is so hard. I also wrote about being a product leader during a crisis. But not much is written about starting as a new product leader. So, I thought I’d write a post about my first year as CPO, and share some general lessons. First, a reminder of the situation I started in. I had been an advisor for Eventbrite for about two years, so I had a lot of comfort with the CEO and many of the executives before ever starting the role. I believe this is an underrated way to start new roles for senior people because you can de-risk the culture fit and alignment issues that plague many new executives. When I started advising Eventbrite, the company had a business unit structure, so it didn’t even have a CPO role, but product leaders embedded into different business units. The company reorganized functionally, and created this role and asked me to consider it.

What Type of Job is This?
I believe the most important question a product leader needs to ask when they get started is what type of job it is they have to do. I wrote in the past that there is frequently a misalignment on vision vs. execution roles. There may also be a misconception of what type of product work is needed to help the company i.e what the product strategy should actually be. In the Reforge Product Strategy course, we teach that there are four different types of product work:

Old school product leaders would just do their preferred type of product work even if it wasn’t what the company needed, or adopt a primitive portfolio approach to the four types of work even if part of the portfolio was wasted work e.g. building a ton of features for a network effects business, or doing a lot of growth work for a pre-product/market fit product. As a modern product leader, it’s important to understand based on the company and its lifecycle, what type of product work has leverage, and these crude approaches are usually not the best approach.

Usually, the best place to start is looking at what the company is actually working on right now. In Eventbrite’s case, the company was:

Julia, our CEO, had told me she wanted me to focus on growing the self-service business faster. So, first off, what you should notice is that there are too many things going on for a company of Eventbrite’s size (sub one thousand people). In other words, the product strategy lacked focus. So, I had to spend my first few months understanding these different strategies to understand which ones to focus on. So I gathered as much information as I could about these different strategic initiatives, as well as digging into the core self-service business.

What Was Going On With the Core Business?
The core self-service business was growing steadily at significant scale and was profitable. Most of the sales clients we brought in stressed our product/market fit, which we compensated for with manual services at no charge, straining margins. We didn’t have a good sense of who our self-serve customers were, how we acquired them, or what retention looked like. As we dug into these questions, we found that while Eventbrite’s product/market fit was strongest with making it really easy to host a single event, but the bulk of our growth and profit was coming from frequent creators hosting small events very often. So, while the product roadmap was scaling for size of event, the market was scaling with frequency of event. The product did not handle this frequency very well, causing these event creators to hack the product to get what they needed, and a higher churn rate over time as those hacks proved problematic to execute. The gaps in our product to strengthen product/market fit for these creators didn’t seem insurmountable, but none of them were actually on the roadmap.

We also were able to get a clear picture of the core competencies and competitive advantages of the Eventbrite product. The fact that Eventbrite supported events of all types and wasn’t focused on one vertical e.g. conferences meant the company had a scale of data no other company had. Secondly, the self-service acquisition model meant the product had very low acquisition costs overall. That model was also a good fit for many different types of creators. Lastly, the company had leveraged its scale of events to drive consumer demand through channels like SEO, emails to previous ticket buyers, and distribution partnerships with companies like Facebook and Spotify.

What Did the Team Say?
As I talked with the team about the state of the product and what they were actually working on, let’s just say the team had a lot to say. Breaking it down by project:

Upmarket Music Vertical Expansion
We tried to integrate music customers too quickly into the Eventbrite platform, and we were much further away from product/market fit with the more traditional enterprise approach those customers were used to than we thought. The space is low growth and low margin, and relies on enterprise sales, relationships, and high touch human service, which doesn’t match our self-service capabilities well.

Consumer Marketplace
Frequent creators drive most of the inventory consumers are interested in, and if frequent creators’ efficiency tools on Eventbrite don’t work for them, they will leave the platform even if they sell extra tickets because of the platform. This is an interesting strategy, but needs to be sequenced after we have a great product experience for frequent creators.

Technical Scaling
Internal developer productivity was incredibly low due to low level of investment in developer tools. Our infrastructure was rickety and frequently had stability problems during big “on sales”. Multiple versions of every feature made it hard to build new things quickly and at high quality. We never deleted features because some sales clients use them and would complain. Everything we build is an MVP, and we rarely iterate.

Developer Platform
While the strategy of leveraging external developers to build specific features for a large array of customers with different needs makes sense at Eventbrite’s scale, we internally lacked the capability to service our own engineers well, much less external developers.

New SaaS Products
Many of these products are very far away from product/market fit and do not have a path to scalability. There is one partnership related to creator marketing tools being run out of this program which is doing well though, and it has been easier to talk with creators about that than our marketplace demand.

Developing A New Product Strategy
Strategy is about making choices among many options that optimize across a few key dimensions like:

Eventbrite failed to make a lot of hard choices with its product strategy when I arrived, so it was time to make some tough calls on what to focus on. There are no simple answers here, but in evaluating the initial strategy, it became clear we should do the following:

The new product strategy is remarkably simpler and more sequenced over time:

2021

 2022

2023

Frequent Creators

 Marketing Tools

Consumer Marketplace
Technical Scaling Technical Scaling

Technical Scaling

Frequent creator investment will be measured by improved frequent creator retention. Technical scaling will be measured by internal developer velocity and our say/do ratio. Marketing tools and consumer marketplace will both be measured by revenue from those sources. So, going back to what type of job this is, my initial directive would have made this product leadership role to be primarily about growth. Instead, the focus is on scaling with some product/market fit expansion. 

Your Product Strategy Probably Isn’t That innovative
One dirty secret behind the work of many executives and product leaders is that our strategies aren’t that innovative. There are a few playbooks we generally run to improve performance in companies depending on the business situation after we’ve gathered the right insight. You can run through them and rule most of them out like the con men strategies in Ocean’s 12:

Yes, product leaders also rule out strategies because we don’t have enough people or can’t train a cat that quickly.

The new Eventbrite strategy was a combo of two common strategic playbooks. The first part of the strategy is what Chris Zook calls “profiting from the core”:

“The greatest strategic error stems from an inaccurate understanding of the core and its full potential.”
-Chris Zook, Author of Profit from the Core

However, if you’re an Arrested Development fan, you might call it the “there’s always money in the banana stand” strategy. The idea behind this strategy is that many companies as they scale pursue too many expansion strategies and leave behind growth that is closer to their initial core business, plays more to their core competencies, and requires less work and less risk to execute. Eventbrite was pursuing expansions in verticals (music), business model expansion (SaaS), and value props (driving demand) while ignoring improvements that could help the growth of the core product (features for small, frequent creators). At Pinterest, VP Product Jack Chou ran a version of this he called “make the basics great”.

The other component of the strategy is probably most known from a blog post (and soon to be book) by current Snowflake and former ServiceNow CEO Frank Slootman. In Amp It Up, Frank Slootman basically divides up his strategy into three elements:

Personally, I would flip the order and revise the language to be more software specific:

By the way, if you’re a public market private equity investor, and you aren’t running this strategy on every sub-rule of 40 tech company, I have a question for you.

So, in Ocean’s 12 language, Eventbrite is running a banana stand combined with a Slootman Special. We… may need to work on these code names. Recently, Etsy has run this same strategy combo to grow its market cap from $2 billion to $25 billion in four years after many years of no market cap growth at all.

There is one other element to Eventbrite’s strategy, and that is presented by the table above: sequencing vs. parallelizing. There is a reason Eventbrite started to pursue a lot of these adjacent opportunities in the first place: fear the core business could not grow itself fast enough. But in trying to pursue multiple adjacencies at the same time, it not only failed to make the progress it wanted on any of them, but many were not set up for success because they would gain from other strategic elements of the plan already having been completed.

The goal of this post is not to geek out on all the generic strategies, though I could do that all day, but to give a sense of the work new product leaders need to do to understand strategy and make it explicit to the organization. Frequently, there is a mismatch between what the customer or business needs and what the team is working on today. Usually, by talking to the team, your customers, and looking at the data, you can identify the mismatch and position the team toward a more likely to be successful product strategy. Then, product leaders can move to the meat of the role, which is building and optimizing the structure and processes of the team to execute against that strategy more effectively over time, or adjusting to changing market dynamics *cough* pandemic *cough*.

Currently listening to the Housewerk EPs by Tusken Raiders.

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