How to Grow Great Product Driven Companies in NYC — A conversation with Brent Tworetzky, EVP of Product at XO Group Inc.

Brent Tworetzky has vast experience working at and advising early stage companies such as WebMD,, Chegg, Udacity, and ClassPass to name a few. Currently, he is EVP of Product at XO Group, a multi-faceted company that helps couples navigate the biggest events in their lives, such as weddings (through leading site/app The Knot) and pregnancy (through leading site/app The Bump) and leads their 50 person product group, including product management, design, and user research.

Brent Tworetzky wants more product driven companies in New York.

Recently, he joined us at the Expa offices for a conversation to share his views on building and leading a high performing, sophisticated product strategy and team. Below is a summary and key takeaways from our discussion:

  • “At a high level, Product Managers need these six skills: strategic thinking, good communications, good collaboration, sufficient technicals, delivering quality, and user science/empathy.”
  • “Strategy means you need to be smart enough to figure out the right problems to solve, the directions to go in, and then how to implement them,” he explained.
  • “For the product manager to steer their team, they have to be a great collaborator because, if they’re a jerk, no one wants to work with them.”
  • Tworetzky divulged the way XO Group works is to have a dedicated team called a squad; every squad has a PM and a product designer, plus several engineers and possibly a marketing person.
  • “As part of the system, the PM is the facilitator of the team. They’re not the CEO, and they’re not the note taker. They’re accountable for the team figuring out what to work on.” To Tworetzky, this means getting ideas from everywhere, including talking to CX as well as the Sales team.
  • Tworetzky likes to give squads as much latitude to work as possible. The way he does that without micromanagement from above is making sure they have really good communications. Every week, the squads send out a missive explaining what they are up to as well as what’s coming up next. “Transparency enables a lot of autonomy for the team,” said Tworetzky.
  • Understanding tech is also important to being a PM. “If you recommend dumb things, it just happens that your engineering partners won’t want to work with you and it makes it harder for you to be successful.” Knowing the basics of SQL and how databases work as well as the in’s and outs of Internet, apps, and design systems are also critical, Tworetzky remarked.
  • Delivering quality is more challenging in today’s world. When Tworetzky worked at Microsoft in the early 2000s, the company had as many software engineers as software testers, which was common across tech companies at the time. Cloud based software, automated testing, and modern development practices have reduced the need for QA and test engineers. “That’s generally a really good thing, but no one catches your bugs anymore.”

Coming to New York from San Francisco and eventually joining XO Group, Tworetzky noticed a big difference between the coasts.

“New York is an ecosystem that leans towards solving the business model first and user needs second. There are more MBAs here. There’s just more business focus in the air. In the Bay area, you have dreamers and capital to support teams to build for user needs first, and then business models second,” he said. “That’s why having a culture in New York that is more user-centered, as opposed to business-model-centered, will help us build more ambitious high impact companies.”

For the past two years, Tworetzky says he’s been building a “product school” at XO Group where he hopes to train a new generation of product managers. “We have enough scale where we’ll bring in 10 new PMs every year. Some of them inevitably will leave and either found companies or run product in other places,” he stated.

To do this, Tworetzky developed a product management style where product can still drive the process and also highly involve engineering and other cross-functional partners. He was happy to reveal his “secret sauce” to Expa and has a number of excellent resources on building, running, and efficiently handling a product organization that we are excited to share with you here:

(From Brent’s post below)

What is a Product Manager? (Overview)
What skills does a Product Manager have? — further details below
Why user science + research is the superpower of a Product Manager
Interviewing Product Managers

Finally, he talked with us about user science, which is something that has not been taught in classrooms. “The best way to understand your users is by understanding their intent combined with understanding their behavior — and these are two different things.”

Tworetzky asked the group for examples of behavior versus intent and got a lot of health-oriented responses (intending to go to the gym vs. actually going, dieting, etc.). But, it’s really larger than that, according to him.

“The truth is, in most things your intent and your behavior tend to be a little different from one another. The whole theory behind the book Predictably Irrational is the fact that there’s a delta between these two. If you want to really get your users, you need to be able to understand what they want and need, and also how they act.”

The Power of the Diary Study

Tworetzky found a powerful example highlighting the different between intent vs. action when he worked at Udacity. The company’s online courses were free, but if you paid they would give you a certificate. Many users starting strong with high intent to complete the course but abandoned their courses after only a few weeks. To find out more about their behavior, Tworetzky implemented a diary study, an intensive research process that interviews a select group of users once a week over a period of months.

What they found was that when people started a course where they had strong intent, no matter the number of hours it would take per week, the students would do the work and enjoy it a lot in that first week. In the second week, they would spend a little less time and start to realize that learning is harder than they expected. By the end of the third week, many would drop out. The reason they cited: the courses were too expensive.

“While a natural solution to consider would be changing price, that’s not the full story. Users stopped putting in time because learning is hard. We wondered if the product might need work to be easier to use, but that wasn’t it either. The endpoint was actually that students didn’t think it was worth it enough to put in the hard time week after week after week, so they didn’t stick with it.”

That’s when a lightbulb went off. Tworetzky felt Udacity needed not to lower their price or reduce product friction, but to make the reward bigger. They worked out a partnership with Google and other companies who agreed to recognize Udacity certificates and consider those certificates in job applications.

“Every metric grew meaningfully when we made that announcement. It wasn’t actually by solving the user experience. It was by solving the carrot at the end of the experience. We wouldn’t have figured that out unless we had done the diary study.”

“To me, diary studies turned Udacity from a company ‘still figuring it out’ into a unicorn. As soon as we made that change, the cumulative effect was marvelous.” Having energized the room, Tworetzky said he hoped to see more unicorns in New York.

“I would love for New York to have a $100 billion homegrown tech company.”

Obviously we are working on that last goal for Tworetzky here at Expa, and generally speaking. I hope you found this overview and mini interview helpful. If you have someone that could benefit from this product driven thinking, please share this with them.