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10 Insights to Guide Product Managers, CEOs, and Founders

I had the honor of co-hosting a Menlo Ventures Product Assembly virtual event with Jen Kessler (Klaviyo’s new VP of Product). Jen was the CEO and co-founder at Bizzy before filling product leadership roles at SendGrid (acquired Bizzy), Twilio (acquired Sendgrid) and now Klaviyo. Here are the main takeaways, in her words. Jen is a powerhouse in building and scaling new product offerings.

Jennifer Kessler, VP of Product at Klaviyo

1. Anticipate where your customers will go next

It’s really important to think about who your customers are today and what they will do once they stop using your product. If your product is their step one, what will be their step two? What is their step three? That’s a great way to think through building up new offerings within existing companies. It’s all about finding that bridge between your product that already exists, the one that people know well, and the new one that you’re building. And if you can tell that story and find that bridge, then people can wrap their heads around your new product. This helps because your best clients are in your existing customer base. And it’s a better option than finding a brand new customer base, which is incredibly challenging.

2. To understand the customer, partner with sales

Product people focus obsessively on their customers, and rightly so. But it can be a challenge to balance that customer obsession with serving the needs of the sales team to accelerate customer adoption and velocity. Work with sales to identify challenges—how are they targeting customers and are they targeting the right customers? Do they understand which customer needs are “nice to have” and which are crucial? If the sales team is trying to sell to people who aren’t a good fit for the product, that’s going to be incredibly demotivating. The product team can’t be the only ones who know who the product is for and who it is not for. Everybody at the company needs to understand this to keep the whole team motivated and competitive. It sucks for salespeople to go into deals and lose them because they were targeting the wrong type of customer. That’s easily avoidable.

One of the things I like to do is have really clean processes for collecting information from customer-facing teams, as they have a wealth of information that can inform the product roadmap. They talk to customers all day, every day and if you’re not capturing that information, it’s a big loss to the product team. It’s also really important to listen for patterns from the salespeople in the same way that you are listening for patterns elsewhere. Once you identify a pattern, put a number on it. Say, “Okay, this is a market that we weren’t planning on serving but is it lucrative? Will it be revenue-generating? Will it be a distraction? Is it a direction that we can support as a company?” Because it’s not just about building the product, you have to deliver it to the customer.

3. The success of new products depends on the success of socializing internally within your organization. Can you get company-wide buy-in?

Historically, SendGrid had been selling to the developer and it was really a developer-first company given their initial product was the email API. With the launch of their second product, Marketing Campaigns, they were targeting a completely different persona—the marketer. There was an enormous amount of education that we had to do across the company, in terms of explaining to people that this was a different kind of customer. Marketers are less technical, have different needs and different concerns. One of the very first things we did was invest in creating marketing personas to get an understanding of who were the types of people that would be buying the product and spent a lot of time talking about the personas and explaining to different people internally how marketers would use the product. We relied on our partners and product marketing really, really heavily, to help us tell that story. And we also had to set goals, that the entire company could rally around. So we had this one goal. So our main persona was named Olivia. We set this goal called 10,000 happy Olivias, we wanted to have 10,000 happy Olivias using the product by the end of the year. And that was something that had a nice ring to it. It was nice and catchy and everyone could sort of rally around that concept. And that was really, really exciting. And then we hit 10,000. It was a success for everyone and it was really, really an exciting and fun way to get everyone rallied around this new customer type.

4. You don’t need to have answers right away.

Steve Sloan, CEO of Contentful, taught me that you don’t have to have all the answers right away. You can just ask questions, listen and gather information and help by creating clarity in the room. Then, eventually, you will have the answer. We are often taught just the opposite, that we have to have an answer for everything. Learning to not have answers right away has helped me gather the information I need to make sound decisions when the time is right.

5. Transparency is key

Before the Twilio acquisition of SendGrid, I thought that it was important to keep more things secret because they weren’t really for everybody’s ears. What I learned through the acquisition was to tell people as much as possible. “So this is what I know, this is what I don’t know. This is what I know that I can’t tell you. This is what I know that might change. This is what I don’t know, that will definitely change.” I focus a lot on transparency. And being entirely transparent creates an incredible amount of trust with the team because they know that you’re navigating it with as much authenticity as possible. Transparency is the only way that I’ve been able to navigate through tough times. Sometimes that meant telling people things that were tough to hear. But ultimately, saying the tough things and being trusted for being honest is the best course.

6. Don’t be afraid to ask for help

I went from being CEO at a small company (Bizzy) to guiding PMs at SendGrid. I was suddenly managing the product and my only experience had been at my own startup. Now, you could argue that I was technically a PM when I did my own company and I was also customer support and sales and customer success and all those things. But the reality of the situation was, I didn’t know the mechanics of how to be a PM. And I had to be really humble and learn from my team and say, “Hey guys, you’ve been PMs for longer than I have, and I need to learn from you. I’m here to help you define the roadmap, give you vision, help steer you in the right direction. But a lot of the mechanics you’re going to have to help me with.” That was a massive challenge and the learning curve was steep. Always ask for help.

7. The best tactical way to socialize your knowledge is the one-pager

I’m a huge fan of the one-pager. I know that there are different models—there are six pagers, five pagers, etc., but I love the one-pager. And I love it even more if that one page is a diagram. I think that naming things with very simple literal names is important and creates an easily consumable document. It’s not just about retelling the information, it’s about putting it in the clearest format. You’re creating a UI for the information that you want to transmit to the company. And you need to really think about that as you put it down on paper. One-pagers, diagrams, systems type diagrams with arrows, that kind of look like architecture diagrams but aren’t actually architecture diagrams, I find hugely effective at circulating information across the company.

8. Pull together with other companies to reach the same destination

Oftentimes, a company becomes stronger by working with others. The products we were building at Bizzy were multi-channel marketing tools for eCommerce businesses. So it was email and ads for companies that were built on Shopify and WooBlueCommerce. Given we were built on top of SendGrid (our email service provider), we approached them about a partnership. There were a couple of things we wanted to license—mainly dedicated IP addresses that we paid $20 a month for and then sold to our customers for $100 a month. But every time we wanted to buy an IP address, we had to pick up a phone and call SendGrid and that was too involved and annoying. We wanted to be able to automate that. So we had these partnership conversations that ultimately turned into SendGrid purchasing Bizzy. In the words of their chief product officer, “We’re all going to the same destination. Why don’t we go in the car together?” At that time, SendGrid had started a UI-based product for marketers called Marketing Campaign, which was different from their API-based product for developers. And we thought, “Yes, we’re going to the same place. Let’s do it together.” At that time, SendGrid was on an incredible trajectory. We could tell they were on their way to an IPO and it seemed like it would be a really fun opportunity to be a part of that.

9. Happy employees keep you competitive in the marketplace

First, your employees need to be happy. The people that serve customers need to be happy. Because if the people that are creating the product and the ones talking to and serving customers are happy, that will create a more positive customer experience. You can’t Gantt chart your way into a positive experience.

10. Product management is an amazing training ground for future founders & CEOs

The best founders share traits with product managers. Product managers listen to customers and understand what they want. They excel at breaking down customer problems to find and build solutions. They translate customer needs to engineers, but can also explain product offerings in a way that the sales team can sell. I like to say PMs are the ultimate clarity creators. They bring everyone along for the journey to deliver a product. It is very similar to what CEOs do: bring people along for the vision. Plus, product managers are people who just get shit done no matter what! It is also what makes a great founder.