Lessons From My First 8 Months at Glossier, a PMs Perspective

I joined Glossier with three key objectives in mind:

1. to create a new type of eCommerce experience that delivers value to the user beyond selling products — an experience that starts to resemble a standalone technology product (like Dropbox, where I spent 4 years in various roles including product management)
2. to build the teams and processes needed to actually craft this new type of product at this young company
3. Learn more about how a brand can influence user engagement with products

My transition from developing collaboration products at Dropbox, a mature tech company with juggernaut Product, Design, and Engineering teams, to Glossier, an earlier stage physical AND digital products company, has been full of lessons.

I’d like to share some of them.

“Why are you working at a beauty company when you’re from Silicon Valley?”

First, some quick level-setting: on its face, Glossier is a skincare and beauty company. Dig one layer deeper, though, and you’ll find that Glossier is digital-first and operating in an industry rife with unsolved and important user problems that technology is designed to solve. Beyond that, I believe the company has the distinctive brand, community engagement, and skillset to build technology solutions that solve these problems better than anyone else out there.

[Blanket statement coming] Traditionally, Digital Products teams at eCommerce companies support the business by solving marketing needs and systematically lowering friction in the buying experience. On the other end of the spectrum, at a place like Dropbox, the technology being built is what the company sells and the process for developing these products is less linear (iteratively discovering and validating unsolved user problems and exploring potential solutions until the product solves the problem for the user — finding product market fit).

For Glossier, success means doing both: being a successful eCommerce company and developing new, valuable technology products that deliver value beyond buying physical products.

With that out of the way, here are some nuggets I’ve learned over the last year at Glossier. Enjoy!

Lesson # 1: Focus, as Always, Is Important

No, the concept of focus isn’t new. But why & how to focus, for me at least, is. Working at a digital-first, marketing and creative-driven physical products company means balancing:

• innovating the brand by supporting the timeline-driven projects like product launches and campaigns (traditional eCommerce workflow)
• innovating technology to deliver value to the user beyond buying physical products. This is the long, iterative process of defining user problems, validating assumptions, and iterating until hitting product market fit (traditional product-driven technology workflow)

How on earth does one balance linear workflows with clear value (and deadlines) against non-linear, less-defined workflows with less validated outcomes that could change the trajectory of the company? No silver bullets, but some places to start:

• Create a North Star that democratizes decision-making: The team should have a shared vision for the outcome they are driving for users so that each person can make decisions, without PMs being the bottleneck. Democratized decision making requires that everyone consistently understands the outcome we’re trying to drive, which is difficult in a quickly growing team accustomed to tribal knowledge. At Glossier, we’ve started more formal project kick-offs to create a shared understanding of global requirements and to share knowledge, empowering engineers and designers to think creatively together and to drive towards the right outcome.
• Allow for honest reassessment of priorities: Quarterly goals are great for providing teams with measurable progress towards North Stars, but the needs of the business can change quickly. Having regular, honest reassessments about what’s really important has helped us focus on the right things. As all teams know, frequently changing priorities are not ideal, and the we’re reorganizing around more outcome-based objectives that are stable over time yet leave the flexibility for pivoting to the right solution.
• Go down the code quality rabbit hole, thoughtfully: Ah yes, the age old feature-work-vs.-tech-debt tradeoff. Moving projects forward — but not creating a mountain of tech debt — is always a hard balance to strike in a fast growing tech stack. By starting to develop a philosophy shared by both product & engineering, we’ve created a forum for discussing these tradeoffs and are able to be more thoughtful about where we’re actually spending our time.

Lesson # 2: Wear The Right Number of Hats

A mantra of startups is to “wear many hats” — in other words, do whatever needs to be done to make an impact. In technology, this can mean being a UX researcher, designer, PM, analyst, and marketer on the same day if need be. This setup works when teams are small, super agile, and sit next to each other, but as teams grow and bring on more specialized talent, things can quickly break down. Work might be duplicated and decision making made unclear (eek!).

Suddenly wearing more than one hat might become wearing too many hats.

How we’ve started to combat this

• Within the team, empower others to voice opinions and hold regular retrospectives that identify issues in our workstreams across engineering, product, design, and research. Together, craft solutions for these problems, and measure progress in future retrospectives.
• Outside the team, because stakeholders roles change as well, recurring round table discussions with partner teams has been helpful in surfacing opportunities for improving workflows and clarifying roles. Decision making authority should continually be crystal clear, and RACI framework is a reasonable framework to start if erring on the side of more structure.
• If there are unresolved questions around role responsibility, try to find areas of intersection between personal interest and team so people can develop the skills they’re interested in. Work with broader leadership to make sure this balance is sustainable in the long term, and expectations are set in hiring.

Clarifying ownership and responsibility within the team (across Engineering, Product, and Design) at every level and across functions, has the potential to empower teams to do their best work — from defining product strategy, working with cross functional stakeholders, writing productive code reviews, and ultimately delivering experiences to users. These responsibilities change will along with the company, so it’s helpful to deliberately reconsider whether roles make sense every few months to make sure the team is meshing.

Lesson # 3: Maintain Clear & Consistent Leadership

Setting the team up for success means clear and consistent Product & Design leadership that organizes the team around a consistent vision in the iterative march to product market fit — all the way from problem definition to a functional product in the market.

If leadership on a project changes, the following could be at risk of breaking, leading to a myriad of negative downstream effects which can make executing and hitting product-market fit elusive:

• The Team’s North Star: clear ownership can make the team’s North Star solid as a rock, helping the team execute with a clear alignment around product vision, user problem definition, requirements, prioritization, and scope of work.
• Disciplined Prototyping: clear ownership makes it more likely that the team will iterate design in a structured way. With clear ownership to define hypotheses the team is trying to validate and artistic ownership/freedom to explore solutions, the team is more likely to more quickly understand the value drivers, articulate the “a ha” moment, and get users there most quickly.
• Organizational Alignment: Consistent leadership can also reaffirm expectations with stakeholders, making it more likely that the organization has shared expectations for the project’s value and expected outcome. Not only does this make it more likely that stakeholders are happy, but the team will also be able to focus on driving towards a single outcome vs. constantly prioritizing against urgent business needs that can sneak their way in without a clear sense of shared priorities in the organization.

Like every fast growing teams know, things can change every day. Half the battle is knowing that what we do to address today’s learnings will break at some point, but that’s part of the fun of working at a fast growing startup like Glossier.