Annie Pearl
Annie Pearl is the Chief Product Officer at Calendly. Previously, she was Chief Product Officer at Glassdoor, as well as Director of Product Management at Box. She was named one of the most influential women in Bay Area business by the San Francisco Business Times.
Career Skills
Transitioning into PM can happen through formal APM programs or by leveraging internal roles in product-adjacent functions.
"I think there's really two paths. I think one is more formal in nature. There are associate product manager programs out there and many scaled companies... I think another "more formal" way to get int..."
Growth Skills
Calendly's growth is driven by a viral loop where recipients of booking links become users, eventually leading to team-based expansion.
"Seventy percent of our signups come through that viral loop that you referred to. And then, of those signups, then they're usually solo users and then they start to invite team members in and then the..."
Hiring & Teams Skills
Asking about product failures reveals a candidate's honesty, self-awareness, and ability to learn from mistakes.
"Talk me through your biggest product flop. What happened and what did you do about it?... I think the rawer the answer in terms of how bad it was and why, the better."
Leadership Skills
Sales teams are a primary asset for product managers to gain customer empathy and scale their understanding of user problems.
"I've certainly seen organizations or been in organizations where the product team doesn't necessarily want to be bothered by sales, but I sort of flip that on the head and say sales and sort of the go..."
Product Management Skills
Product strategy is an integrated set of choices defining the target market, segments, and personas to determine how the company will win.
"Strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose. And so, a good product strategy is going to answer questions like what's y..."
Prioritization is driven by a strategy that explicitly defines which markets and personas the company will NOT pursue.
"I like this framework that's taken from a book called Playing to Win and it talks about how strategy is really just an integrated set of choices that outline how you're going to win in whatever market..."
Effective OKRs require tight integration between company-level objectives and department-level key results to ensure alignment and dependency mapping.
"We have three main OKRs that we're focused on for this year, for example, across the whole company. And then we have department level OKRs, many of which are in support of the company level OKRs... th..."
Competitive 'War Gaming' distributes market research across the team, ensuring deep immersion into competitor products.
"We have assigned people into groups for the quarter to own a competitor. Their job is to essentially spend a lot of time immersing themselves into the product of the competitor, really trying to think..."
A dedicated 'Opportunity/Problem Assessment' (OPA) meeting allows PMs to peer-review and spar over problem spaces before committing to solutions.
"We have a meeting called OPA, which stands for opportunity/problem, assessment. And so, what this is, it's a meeting where basically PMs... debate and discuss with each other and spar around either ar..."
Commit to dates only for the immediate phase of work (discovery or solutioning) rather than long-term delivery dates for un-scoped projects.
"Something we've done over the last year is really kind of moved to a model of talking about dates and promising and committing to dates that are within our control. And so, if you think about the prod..."
Sales & GTM Skills
Early sales hires in a PLG company should match the current inbound motion and the specific target buyer (e.g., department heads vs. CIOs).
"In those early days, it's more inbound in nature, and so the type of sales reps you might need are not necessarily going to be outbound, heavy kind of hunting sales reps... making sure that the profil..."