Annie Pearl

One of the most impactful things we did pretty early on in my tenure here was to hone in on our overall product strategy, but a core piece of that being what's the actual market we're going after? What are the segments of that market? Who are the personas within the segments of that market?

The ability to say no is going to allow you to make sure you're building something that's going to be amazing for the people that matter most and not something that's going to be average or okay for a lot of different people.

Strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose. A good product strategy is going to answer questions like what's your winning aspiration? But maybe more importantly, where are you going to play? What are the markets you're going to go after? What are the segments of those markets? What are the personas in the segments of those markets? And then, how are you going to win with a target audience?

When you transition from PLG to adding this direct sales motion, the buyer is usually just the department head. It's the head of sales, it's the head of rev ops, it's the head of recruiting and it's not a senior person in IT or the CIO. And so, selling into this audience is different than selling into IT.

Seventy percent of our signups come through that viral loop. And then, of those signups, then they're usually solo users and then they start to invite team members in and then the team starts using Calendly and then usually the head of that team either inbounds to us or we have some sort of PQL data to know we should go after that team lead.

Seeing the sales team and the go-to-market team as this really great asset that can help you as a product manager get closer to the customer. Sales and the go-to-market teams in general could be your biggest asset to helping you get your job done well.

The folks who have successfully transferred over, they tend to have a couple of characteristics. They're usually very curious, they tend to be really passionate about the product and solving customer problems. And sometimes, they've even tinkered with a side project as a way to hone their PM skills.