Focus Wisely: How Calendly Grew from a Free Viral Tool into a Product-Led Business with a Sales Team

Pearl, who came to product from law school after joining a startup's founding team, says there are two broad routes into product management, one formal and one informal. The formal routes are associate product manager (APM) programs, which exist at Google and Meta but also at smaller companies (Box built one while she was there), and applying to junior PM roles on an internal job board. The internal route works best for people already near product, such as in customer support, implementation or sales engineering.

On the informal side she lists three options: shadowing or partnering with a PM and offering to take on work, becoming a subject matter expert paired with a product squad, or joining an early-stage startup where everyone does a bit of everything. Asked which path she sees most often, Pearl says the person who makes their interest known, is willing to do work on the side and demonstrates skills before getting the job has brought over the most people in her experience.

For those who want an APM role, she suggests that the famous programs are extremely competitive and that earlier-stage companies are a better bet. Searching Glassdoor for "associate product manager" will surface open roles. She adds that successful transfers tend to be curious, passionate about customer problems, and sometimes have tinkered with a side project.

APM programs are rare, she explains, because they take real effort. At Box the team had to define the interview process, the expectations for the role and a training element, and aim to graduate every associate into a full PM. Lenny adds that the same thing happened at Airbnb, where an enthusiastic PM's program never quite took off.

When Pearl joined about two years ago, Calendly had roughly 150 people and about 15 product managers and designers. Today the company is around 600 people, and the product organization (PMs, designers and researchers) is about 60, with roughly 20 PMs. She leads product, design and research but not engineering, a structure she carried over from Glassdoor because it lets one leader look at the end-to-end user experience.

Below her, teams are organized by persona. A core team serves salespeople, recruiters and customer success staff and also owns the product-led growth funnel from acquisition through retention. An enterprise team serves IT admins and departmental leaders, and a platform team handles integrations, partnerships and APIs so Calendly can sit inside other companies' business processes.

Calendly's use of OKRs has matured in three phases, Pearl says. At first there was no clear strategy or measurement. Then came a product strategy with product-only OKRs while each department kept siloed ones, and now there are about three company-level OKRs with tightly integrated plans and dependency mapping across the organization.

The biggest change, however, was narrowing the target. Calendly served freelancers, sales teams, recruiters, education and more, which made it hard for PMs to prioritize. Defining the market, its segments and the personas within them gave teams a rule for choosing, even though, as Pearl says, "the idea of saying no is scary" and building something great for the people who matter beats something average for everyone.

Narrowing the focus overlapped with a larger shift: when Pearl joined, all of Calendly's ARR came from product-led growth and the company had just hired its first chief revenue officer. Moving up market to teams, departments and larger organizations changed everything about people, process and product. Work that could be siloed in a self-service business now has to be highly integrated across the company.

The growth engine, she confirms, is a viral loop. Seventy percent of signups come from people who receive a Calendly link, and most start as solo users who invite teammates. The team lead then either contacts Calendly or shows up in product-qualified lead (PQL) data, which prompts sales to talk about expanding across the organization.

Two years ago product-led growth was about 99% of ARR. Sales-led growth is now around 20% and growing fastest. Pearl's advice for early sales hires is to match the motion and the buyer: with mostly inbound leads and PQLs, you need people who can work warm leads rather than heavy outbound hunters, and since buyers are department heads rather than CIOs, you should not hire a team of enterprise sellers from Oracle yet.

On hiring, she says background and the type of selling someone has done matter more than personality, and that PLG-style companies are a good place to look. A CIO-led purchase, she adds, is probably several years away.

Pearl argues that PMs should treat the go-to-market team as an asset rather than a distraction. At Box she spent a lot of time in the field, and salespeople were talking to ten times as many customers as she could reach in a week. She says she would not have known what to build without leaning on them as the voice of the customer.

To decide what to build next, she starts with a product strategy drawn from the book *Playing to Win*: an integrated set of choices about where to play (markets, segments, personas) and how to win. Calendly's winning aspiration is to become the best place to schedule, prepare for and follow up on external meetings, expressed as three horizons.

Resource allocation follows those horizons. In her first year it was 70/30 between horizons one and two with nothing on three. In year two it was 50/50, and in year three it is about 30% on horizon one, 60% on horizon two and 10% on horizon three.

A concrete example of a deprioritized request is a Venmo integration. Small businesses and solopreneurs want it, and Calendly already has PayPal, but it does not serve the core personas of sales, recruiting and customer success teams. Much of what is built for those teams will still help smaller users, but this specific feature is out.

Planning begins with a multi-year strategy, which is broken down into about three annual company OKRs with quarterly milestones. Product roadmaps are built to support those key results and sliced quarterly. Pearl notes that the three-year strategy is shared at company level, included in new-hire orientation, and tied to each year's objectives.

The newer practice is to commit only to dates within the team's control. Calendly can promise when a discovery effort will end, though not whether it will lead to investment, and then when a solution phase with user testing will end. Only once the solution is known does engineering produce an estimate and a delivery date, so the company avoids promising a project six months out before discovery and design have happened.

The phases are called discovery, solutioning, build, and launch, measure and iterate, and the product development lifecycle is designed around them. A discovery effort can be a roadmap item for a quarter, with the next step following if it goes well. Strategy documents are written in docs, turned into slides for presentation, stored centrally, and use templates by type of work, with Confluence as the main repository.

On tooling, Pearl lists docs and Mural boards for planning, Aha for roadmap tracking, Airtable, Slack and Loom for communication, Jira for bugs, and Pendo to educate users about new features in the product.

Pearl, after checking the story with CEO Tope that morning, says the founder came from sales and knew how painful scheduling external meetings was. He had evaluated the existing tools and found none good, especially for the person receiving the booking link. He then used his 401(k) and savings, raised no money, and hired an outside development firm in Ukraine to build the first version.

The first ten users were customer success agents at an education company that contracted with the same firm. They used Calendly to schedule calls with parents of K-12 students, the parents began using it for parent-teacher conferences, schools picked it up, and it spread from there. The product was also entirely free, partly because the team had not been able to build the billing infrastructure to charge.

Pearl says the biggest surprise today is that teams, meaning several users in an organization scheduling together, are growing much faster than solo users. She believes that is where future growth will come from, and that customers pulled Calendly there rather than the company choosing a new growth lever.

Lenny points out that viral growth eventually tapers. Pearl agrees: only so many solo users will take out a credit card, and at hundreds of millions in revenue the law of large numbers slows growth, so Calendly needs a next curve, which usage data suggests is teams and departments.

Pearl describes two product-team rituals. OPA, short for opportunity/problem assessment, is a PM-only meeting in which product managers spar over problems to investigate or decide whether to build a solution after research. She deliberately does not attend so that people can be open and not feel judged, and she says PMs value it rather than dreading it.

The other is competitive war gaming. Groups own a competitor for a quarter, immerse themselves in its product, run a SWOT analysis, and think about where it is heading and how that relates to Calendly's strategy. Teams then present on a competitive war-gaming day with prizes, which spreads market knowledge without everyone needing to be deep in every competitor.

Core to how Calendly builds product is its value of focus wisely, which Pearl credits for making it possible to define target personas in a way many organizations cannot. In a fully remote company the principle is embedded in templates, such as the OPA document, the PRD and product review templates, which keep asking who the target customer is and how the need is met better than any alternative.

Calendly began as a horizontal product, which gave it viral growth and its wedge into scheduling. Moving to horizon two, deepening support for teams, departments and verticals, is the inflection point at which it had to make real trade-offs and create focus.

Pearl says Box taught her to ask the right questions to understand the "why" behind what a customer requests and to build a scalable solution rather than a one-off for customer A, B and C. Glassdoor, a consumer marketplace with 60 million unique users a month, taught her funnel optimization, growth as a discipline, and data and A/B testing. At Calendly she combines the consumer-style PLG business with a direct-selling business that resembles Box's enterprise one.

She is part of the Skip community, started about two years ago by Nikhyl, the former CPO of Credit Karma, for product leaders at late-stage growth companies. It meets on Sundays, has grown to about 23 heads of product and CPOs, and now runs a podcast, an active Discord and experiments with helping companies make their first head-of-product hire. The group, she says, is a support group for a hard and sometimes lonely role.

In the lightning round she recommends *Playing to Win*, *Good to Great* and *Hooked*, and says her favorite interview question is to ask candidates about their biggest product flop. The rawer the answer about how bad it was and why, the better. Her five SaaS tools are Slack, Miro, Loom, Pendo and Confluence.

Her Calendly pro tip is a new feature called Customize Once and Share, which lets you change the title, duration or a date for a single recipient without creating a new event type. Lenny says he needs it for blocking dates and changing times.