5 Practical Tips on Unlocking the Secrets of Startup Growth with Casey Winters

Welcome to the latest issue of the Product Management Learning Series - a series of live streaming events and newsletter articles to help you level up your product career! ??

In our 34th installment, our speaker was Casey Winters . Casey is an advisor and operator for scaling startups. Until recently, Casey was the Chief Product Officer at Eventbrite, having joined with impeccable timing a short time before the pandemic started. Casey led the PM, design, research and growth marketing functions. Before Eventbrite, Casey led the growth product team at Pinterest, helping them grow from 40 million to 150 million active users. Casey was also the first marketing hire at Grubhub, leading demand side growth from series A to IPO. Casey has advised companies such as Airbnb, Faire, Canva, Thumbtack, and reddit on scaling, product, and growth. He blogs at caseyaccidental.com and built the Product Strategy, Retention & Engagement, and Advanced Growth Strategy programs for Reforge.

If you missed the event, you can watch the full event recording here.

Below are the main takeaways from the conversation I had with Casey:

The key factor for building successful cross-side network products is to be laser-focused on what drives more demand and selection.?

At Grubhub, while Casey initially had a lot of ideas for new products and growth opportunities, he quickly realized that none of these ideas mattered unless they were directly tied to increasing demand or selection. For Grubhub, the product for supply was the people ordering food, and the product for demand was the selection of restaurants.

To achieve success, Casey and the VP of Sales had to measure supply and demand at an extremely local level by poring over zip code level data. This information helped them come up with ideas on how to get more restaurants in supply-constrained areas or get more people ordering food in demand-constrained areas.

Casey also highlighted that startups go through different phases in building their company, and focusing on the right area of the business is crucial for success. At Grubhub, the founders were excellent at focusing on the key area of the business, and saying no to other ideas. This laser focus helped the company scale from early stage to IPO.

Identifying the most critical constraints in your business model is the key to driving growth.

Casey stressed the importance of identifying constraints in your business model (i.e., understanding the part of the business that is holding back growth) to prioritize projects and aspects of your company that create real leverage and move the company forward. In the example of Grubhub, the focus was on getting more restaurants and users to improve acquisition, activation, conversion, and purchase frequency. For a SaaS company, the constraint might require adding more features, building a new product from scratch, or addressing technical scaling issues. Casey emphasized the importance of having a dialogue with others in the organization to ensure that everyone is pointed in the right direction. The goal is to work on the most important projects that will move the business to a new level, rather than focusing solely on experiments and optimization.?

How to gain 20 years of experience in just 5 as a product manager: Casey's advice on choosing the right company to accelerate your product career.?

Casey suggested that the best way to gain valuable experience as a product manager is to join an early-stage company with a high degree of confidence that it will work. However, he cautions against joining a company that is too early, as the chances of success are low. Instead, he recommends looking for a pre-IPO company that can provide a solid learning experience. By working in such a company, you can gain an understanding of business models, build essential skills, and learn what a good company looks like.

Casey shared his experience working for Apartments.com to build his understanding of business models, learn about specific growth levers and develop his skills in areas like SEO and email marketing. This knowledge helped him evaluate the opportunities and risks associated with joining Grubhub, a company that ultimately grew to a $7 billion enterprise. Casey's general advice is to optimize your opportunities to learn about business model tactics and develop essential skills in your early stage of career. Once you have built your knowledge base, you can pick the right company and get valuable, action-packed years of experience that will set you apart. Some signals that Casey used to evaluate a startup company include revenue growth, unit economics, user retention, user satisfaction, profitability, and payback period.?

How Casey doubled Pinterest's activation rate and grew active users from 40M to 150M by building a powerful SEO growth loop and driving international growth through iteration and experimentation.

When Casey arrived at Pinterest, the social media platform was struggling to acquire new users after Facebook Open Graph was turned off. Casey shifted the focus to SEO, which helped to drive a lot of traffic. However, initially, people internally thought this was low-quality traffic. Casey optimized the onboarding flow for users who came from Google, which doubled activation rates. The growth loop that is still the primary loop at Pinterest today is to distribute boards to search engines, hook people on boards, show them a free preview of the content, and then activate them by showing them a feed of great content in multiple topics and incentivize users to save content which in return share back to Google.

During his time at Pinterest, the company became very popular in the US, but to become a sustainable business and grow beyond 300 million users, Casey and his team had to focus on international growth. This led to them traveling to other countries and fixing various product market fit issues. Casey emphasized the importance of iteration and experimentation, both in terms of the product and the team itself. The team's success was due to their willingness to adapt and experiment: they experimented with optimizing processes, goals, tracking, and training, which helped the team operate better every quarter. Casey also learned to go off-device at every step of the loop, to push in the right direction and to throw everything you have at the problem to make sure you win.

How Eventbrite survived the pandemic by adopting a wartime culture and shipping bundled features to deliver customer value fast.

Casey's experience leading Eventbrite during the pandemic forced the company to shift to a wartime culture, where they had to quickly come up with ideas to help their customers. Instead of prioritizing ideas based on effort, impact, or chance of success, they focused on shipping anything that had a chance of helping their customers. As the Chief Product Officer, Casey had to navigate an unprecedented crisis: Eventbrite’s revenue went below zero, the company had to lay off 45% of its staff and raise $100 million in debt. Casey rewrote the strategy of the product on a Saturday to share with the executive team on a Sunday and started pitching private equity investors on Monday.

To evaluate the success of their efforts, Casey encouraged the team to think about the bundle of features they shipped during the crisis and how they impacted their customers' ability to manage the crisis and save their businesses. They didn't have time to evaluate individual features, but they were able to save the business by shipping a variety of features quickly. Casey acknowledges that normally, they wouldn't want to be building a feature factory, but in this case, they had to do everything they could to save the business. In the end, the business is now cash flow positive and growing healthy.

?? Spotify is Casey’s favorite product ?

?? Scott Belsky , the Chief Product Officer at Adobe, is Casey’s product role model.

?? Casey advises everyone to focus on where you can leverage opportunities in your company to learn new skills quickly. Instead of focusing on the title or the promotions, spend your energy on making an impact on the business.

?? Special kudos to Anoushka Ramesh for writing this article.

Next up, don’t miss out on an important live conversation with Adam Greco , one of the leaders of the digital marketing analytics industry and a product evangelist at Amplitude , on the future of Product & Marketing Teams!

?? RSVP here (Replay available upon registration)

Next up,

• May 12: Gamification for Product Builders: Lessons from Building Duolingo
• May 19: Building Impactful Products People Love with Jiaona Zhang

More sessions coming… subscribe to stay tuned!?

Learn more about the Product Management Learning Series and view past recordings here.