It’s October and that means it’s planning season for Product Managers. There aren't many great resources out there on how to structure planning from an organizational standpoint - so I thought I would share the construct that we’ve set up at Wonolo.
But first a slight pre-amble. At Wonolo we’ve structured the organization so that Product + Engineering = “Tech”. Product is where Product Managers, Product Analysts, Product Designers and User Research live so that the “Tech” organization has a holistic view on the needs of the end user. This structure ensures that Tech has the ability to identify problems for the user and implement solutions.
Thus, Product + Engineering = a “Tech team”. This “Tech team” is made up of engineers plus the Product support that is needed for that team to function autonomously and achieve their goals. Almost all teams have Product Managers, albeit a few are solely engineers. Product Analysts and Product Designers are members of teams based on the scope of that Tech team. All tech teams have Northstar metrics. And it is the goal of each Tech team to move their metric in the way that is advantageous for the business.
The way that we have structured planning at Wonolo is that each team is given a strategic objective. Much like the “O” in an OKR, this objective is a simple statement that leadership believes is the primary output that the tech team should achieve. An example objective might be “Reduce churn due to admin burden” which implies both a metric to be moved (reduce churn/increase retention) as well as a thesis as to what moves it (admin burden). Tech teams have the ability to “make their case” to change a strategic objectives. This type of change is on the Product Manager to synthesize what is happening with the business, where the business is headed, and put together an argument why a new strategic objective is warranted over the current one. Teams can only have so many objectives at once, thus this process requires Leadership to agree to tradeoffs. At Wonolo we endeavor for only one strategic objective per team but most have two. One team actually has three but we are working to change that.
The Flying W
For the actual planning process, Wonolo follows the “Flying W” format. I learned of this format from Eventbrite CFO Lenny Baker when I was and Entrepreneur-In-Residence there. The Flying W follows a 4-step process to ensure a feedback loop for each planning cycle using the following structure:
Leadership sets or re-confirms the strategic objectives for each tech team
The Product Manager uses various inputs and data to create a series of initiatives that align with the strategic objective. Each initiative also has a strong thesis behind why it will move the Northstar metric for that team. These initiatives are put into the Roadmap format with each initiative having a key result (the “KR” in OKR) tied to it
Leadership and stakeholders have an opportunity to give feedback on the initial roadmap
The Product Manager evaluates the feedback and then finalizes the roadmap
There are some nuances here so I’ll dive a little deeper into the structural setup of Product @ Wonolo.
For #1, we endeavor to not change a strategic objective for at least six months so that tech teams have enough time to deliver impact against that objective.
For #2, Product @ Wonolo does not have “quarterly OKRs” but rather each initiative has a Key Result (KR) tied to it. This is because some of the most impactful initiatives can span multiple quarters.
For #3, we use Value / Cost to assess the impact of each initiative. During the feedback cycle the thing most likely to change is the assessment of Value. This typically leads to the re-prioritization of smaller initiatives but not larger ones
For #4, we have added an additional section for initiatives that don’t make it to the roadmap but will begin “Product Discovery”. This addition has become a critical component for business and stakeholder communication. The Product Discovery section indicates which initiatives are likely to be worked on the following quarter, as it is generally unlikely that a new initiative will make it to the roadmap the same quarter it is proposed.
Conclusion
We have found this process to be incredibly helpful in scaling the planning process at Wonolo. As we become a larger organization this process will likely change. But we are steadfast in our belief that each team is the best to answer the challenge posed by the strategic objective - so that won’t change. Hopefully this format can help your product organization plan and execute more effectively.