Paul Gubbay is the Chief Product Officer of Squarespace, recently valued at $10B. Paul oversees the product organization, which encompasses Product Management and Product Design. Paul joined the FirstMark Guilds to discuss the recent reimagination of Squarespace’s entire product organization.
Inspiring your workforce is a key task for any company executive, and often a very challenging one. While Paul had mastered the art of inspiring his product team while at Adobe for 15 years, scaling the same magic to the entire Product organization as Chief Product Officer at Squarespace was an entirely different challenge. It was Paul’s first time leading a team of that size, the Product organization was still young and largely uninvested in, and he found that the product strategy was very siloed––teams didn’t understand how their work laddered up to the broader company strategy. Paul’s mission was to create product leaders that felt like “they owned their destiny.” To reimagine the product organization at Squarespace, Paul leaned on the Empowered Product philosophy and outlined the specific strategies he used to create an empowered Product organization.
Align with Leadership on the Strategic Context
To Paul, an empowered Product team is one that feels that they have the agency to own their workflows. Creating this culture starts with a list of core pieces that the entire organization and company leadership had to align on:
- Mission Statement: The work of the Product organization starts at the company level. Empowered product leaders need to understand how the work they’re doing contributes to the larger mission of the company. Shortly after joining, Paul worked closely with the CEO and his fellow executives to refine the Squarespace mission statement so it was clear and easily repeatable by all members of the company.
- Corporate Objectives: Paul also spent a lot of time contributing to the corporate objectives. Aligning with company leadership on the corporate objectives would trickle down to how OKRs would be set for the Product org.
- Product Vision: Your organization’s product vision is its purpose––its “north star.” No matter what any specific team is working on, everyone can see and follow the “north star” and know that their work is meaningfully contributing to that greater purpose.
- Product Strategy: Product strategy refers to the plan for achieving the product vision. While this plan doesn’t have to contain detailed pieces like schedules, it should include major milestones which give your organization benchmarks and guidelines to follow so they feel empowered to discover the more tactical paths to success.
- Product Principles: Product principles reflect the values of your organization and company at-large. Setting product principles empowers product leaders to understand what tradeoffs should be made when faced with tough decisions.
The Product Org Structure at Squarespace
Paul spent the first 90 days of his time at Squarespace focusing on what his leadership team should look like––in his own words, ”finding the right seats on the bus.” Who should be on his staff long-term? What did his ideal product leaders look like? He ultimately decided that he worked best with a small leadership team of 6-8 direct reports who had strong leadership and responsibility over different parts of the product. Having a tight, intimate staff relationship was important to Paul in order to drive the organization forward in a united way.
In terms of other levels of org structure, each team has between 6-10 people and consists of a Product Manager, a Product Designer, an Engineering Lead, and then 5-6 Engineers. At Squarespace, Product Managers and Product Designers report up to Paul and Engineers report to the SVP Engineering who works extremely closely with Paul as well. Teams then report up to group departments associated with product group areas (ie: Commerce, Presence, etc.) that each have a designated leader.
The Empowerment Process: Setting OKRs
The Empowered Product Team philosophy comes to life in the OKR setting process. Leadership hands teams their objectives, and then the appropriate key results are mutually agreed upon. Teams are empowered to independently design and discover the solutions they think best achieve the objectives. What OKRs should not be are prescriptive of what to build or long laundry lists of things to do.
At Squarespace, OKRs are predominantly quarterly-driven. An evergreen challenge for product leaders is to decide how to set OKRs that are broadly tied to the company vision, but also drive tangible quarterly results so that they have something to show company leadership. Paul’s philosophy for tackling this is two-fold:
(1) Align with your CEO on the culture of your Product organization; for his org, Paul emphasizes a learning culture in which teams feel emboldened to experiment and potentially fail. In Paul’s words, “you shouldn’t always hit 100% of your OKRs. If you do, you’re not stretching yourself far enough.” If something doesn’t work, you at least learned something and can adjust for next quarter. To cultivate a learning culture, the Product org at Squarespace devotes a portion of their MBRs to sharing Wins & Misses. This time allows members of the team to know that it’s okay to have misses and to take time to reflect on them.
(2) While OKRs at Squarespace are set quarterly, Paul clarified that there’s no reason why an objective can’t span multiple quarters. What’s important is that you are creating milestones every quarter that can track the progress toward the overall objective. For example, if the OKR is related to a new, large feature area that may required a fair amount of discovery, it might be that in the first quarter, all you're really looking for is a signal. A small result like getting a few reference customers to sign up to say they would use the product to track that you’re on the right path is a key result within reason for the quarter.
Paul also always specifies whether an objective is a “roofshot” or a “moonshot.” A roofshot implies that results should really be achieved in the quarter, whereas a moonshot is a more aspirational goal that may be worked on over multiple quarters/experimented and innovated upon. Being specific around whether an objective is a “roofshot” or “moonshot” gives teams clarity around how much freedom they have to to try new, wild tactics vs. how tactile and performance-oriented they should be in tackling a specific objective.
Building a Product organization is a daunting task, but building one that is empowered and fundamentally driven by the company vision is monumental. Paul approached reimagined the Product organization at Squarespace by using a series of strategies inspired by the Empowered Product philosophy that allowed him to align with company leadership and create tactical ways for his team to own their product destinies.