Annie Pearl
Chief Product Officer at Calendly, previously CPO at Glassdoor and Director of Product Management at Box
Where to hear and read about Annie Pearl1 episode or test
Annie Pearl is Chief Product Officer at Calendly, after serving as CPO at Glassdoor and director of product at Box. The most useful lesson from her is to choose a narrow target customer and a written strategy so teams can say no, then add a sales motion on top of product-led growth.
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
Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)
Annie Pearl: the story and the lessons
1Annie Pearl's path from startup to CPO
Pearl entered product by joining a startup's founding team after law school. She went on to become director of product at Box, then CPO at Glassdoor, and now leads product at Calendly.
She also sits on two company boards. Her advice to others is to show interest and do real product work, the route she has used to bring over the most people.
At Box she learned to ask why behind every customer request. She joined the Enterprise team as Box moved up market and spent her first year talking to customers.
Building what customers A, B and C each asked for would have tripled the effort and hurt the end user experience. The goal was one solution to the underlying problem that scales across customers.
At Glassdoor she learned consumer growth and owned both sides of a marketplace. Glassdoor served job seekers and employers, with 60 million unique users. She learned funnel optimization, how to build a growth team, and how to decide with data and A/B tests.
Calendly needs both: its self-serve side resembles Glassdoor and its direct sales side resembles Box Enterprise.
Pearl helps run Skip, a peer group for product leaders. Nikhil, a former CPO at Credit Karma, started it about two years ago for CPOs facing late-stage growth challenges. It has grown to about 23 heads of product and CPOs.
She says the CPO role is hard and can be lonely, so peer support makes leaders more effective.
2How Pearl narrowed Calendly's strategy and learned to say no
Pearl narrowed a broad user base to a few target personas. Calendly served freelancers, consultants, sales, recruiting, customer success and education users at once, so PMs had no basis for choosing between feature A and feature B. Early in her tenure she defined the market, its segments and the personas within them.
The core personas became sales, recruiting and customer success teams. Features built for them can still help others, but the personas now decide the trade-offs. She calls it one of the most impactful changes she made.
She defines strategy as an integrated set of choices. She borrows the Playing to Win framing: a winning aspiration, where to play, and how to win with that audience. Calendly's aspiration is to be the best place to schedule, prepare for and follow up on external meetings.
Writing down where the company will not play is what lets teams build for a clear set of people. A Venmo integration is declined for the core personas, even though a PayPal integration exists.
Resource splits across three horizons shift every year. Year one was about 70/30 between Horizon 1 and 2 with nothing on Horizon 3. Year two was 50/50, and year three about 30% Horizon 1, 60% Horizon 2 and 10% Horizon 3.
Horizon 3 got no investment at first because it was too far out. The split follows the strategy and progress against it.
Moving from Horizon 1 to Horizon 2 made focus unavoidable. A horizontal product helped virality and made Calendly the best horizontal scheduling platform. Horizon 2 means deeper support for teams, departments and verticals.
Pearl calls it the inflection point where clarity around focus became necessary. Most companies think they have this clarity, but PMs and designers often hesitate to say no.
She builds focus into templates instead of posters. The OPPA doc, the PRD and product review templates all ask who the target customer and user are, and how the product will beat every alternative.
Calendly is fully remote, so reminders live in documents. Pearl credits this culture for her success in creating clarity on target personas.
3How Calendly grows: the viral loop and the shift to teams
Calendly began as a free product built by a contractor firm. Founder Tope Awotona drew on his own sales experience, raised no money and used his 401k and savings. He hired an outside development firm in Ukraine and made the product free, partly because no billing system existed.
The first 10 users came through that firm, which also served an education company. Customer success agents used it to schedule calls with K-12 parents, parents then used it for parent-teacher conferences, and schools followed.
A viral loop that starts at the booking drives 70% of signups. An invitee sees a Calendly link, wonders what it is, likes it, signs up and spreads it further. Solo users invite teammates, and the team lead then inbounds or is flagged by product-qualified lead data.
Usage within a team signals when to reach out about expanding across the whole organization.
Pearl expects viral solo growth to taper and follows customer pull. Only so many solo users will pull out a credit card, and the law of large numbers slows growth at hundreds of millions in revenue. Usage data showed customers wanting to schedule with their teams.
The teams business is now growing much faster than the solo business, even though Calendly is still known as a solo tool. The new levers are externally facing teams, department sales and multi-department deployments.
4How Pearl layered sales onto product-led growth
Sales-led growth went from almost nothing to about 20% of ARR in two years. Product-led growth was 99% of ARR when Pearl joined. Sales-led is now the fastest growing segment, and a CRO had just been hired to build the team when she arrived.
She added sales because viral growth alone eventually tapers off.
Early reps are growers who work inbound leads, not outbound hunters. Leads come from people who reached out or from PQL usage data. Hiring is judged mostly on background and past type of selling, ideally at product-led-style companies.
A heavier outbound motion would need a different profile later. In her words, you wouldn't necessarily want "a bunch of sales folks who are you know at Oracle".
She sells to department heads, not CIOs. Early buyers are the head of sales, revenue operations or recruiting. The expected path runs from team lead to IT, then eventually to a CIO-led purchase.
She puts a CIO-led purchase several years away.
Moving up market changed people, process and product together. A self-service business can run in silos because the product runs itself. Selling to teams and larger organizations needs work that is highly integrated across functions.
She describes it as a cultural shift, not just a new sales team.
Pearl treats sales as the product team's best source of customer insight. As an Enterprise PM at Box she spent a lot of time in the field, because sales talks to about 10x more customers in a week than she could.
She says some product teams don't want to be bothered by sales, but she sees go-to-market as an asset that starts with customer empathy.
5How Pearl plans and commits at Calendly
She connected OKRs from the company level down to every department. OKRs went from none, to product-only OKRs tied to a new strategy with other departments siloed, to three company OKRs with integrated plans and dependency mapping.
They are annual, with quarterly milestones that shape roadmaps. Departments add their own that don't appear at the company level.
Teams commit only to dates for the phase they control. Discovery, solutioning, build, and launch-measure-iterate each can be a quarterly commitment. An engineering delivery date is set only once both problem and solution are known.
This avoids promising a project six months out before discovery and design are done. Calendly has gotten much better at commitments on work right in front of it.
Strategy is written in layers, from a three-year plan to feature docs. The top layer is a three-year company strategy, written as a doc and presented in slides many times. Product OKRs start as docs and become slides for company presentations.
The three-year strategy is being added to new hire orientation so everyone sees where the company is going.
6How Pearl structures and runs the product team
Product, design and research report to one leader. Pearl keeps product and design together so the team looks at the end-to-end experience as a whole. PMs prioritize problems and designers bring the solutions to life.
She led design at Glassdoor and kept the structure. A head of design was one of her first leadership hires, since Calendly had none and long-tenured designers had built a good experience without one.
The product org roughly quadrupled in two years. Product, design and research grew from about 15 people to about 60, with about 20 of them PMs, while the company grew from about 150 to about 600.
Teams are split by problem and persona: a core team for externally facing users, an enterprise group for IT admins and department heads, and a platform team for integrations and APIs.
She skips the PM debate meeting on purpose. OPPA (opportunity/problem assessment) lets PMs debate which problems to investigate and whether research justifies building a solution.
She stays out so nobody feels judged or acts differently. PMs bring problems they want feedback on, unlike a shark tank where plans get torn apart.
Each team owns a competitor for a quarter and presents at a wargaming day. Groups run a SWOT analysis and ask where the competitor is heading relative to Calendly's strategy. Teams present on the wargaming day, with prizes.
No PM or designer has to go deep on many competitors, yet market knowledge spreads across the team.
She interviews candidates on their biggest product flop. She looks for people who are brutally honest about how bad it was and why it failed.
The rest of an interview is usually a list of accomplishments, so the flop answer stands out.
7Pearl's practical advice on breaking into product and scheduling
Pearl says to break into product by doing real work first. Four routes exist: APM programs, junior PM roles posted internally, shadowing a PM while doing some of the work, or joining an early-stage startup. Internal transfers come from product-adjacent jobs like support, implementation or sales engineering.
Successful transfers are curious, care about customer problems and sometimes have a side project. She suggests looking beyond Google and Meta for APM programs, since earlier-stage companies are easier to get into.
She offers the recipient's choice of times before her Calendly link. Open the email with something like "feel free to share times you're available, or if easier, find time on my calendar." Paste open times straight into the email using the add-times-to-email option.
An invite feels like a power move unless the other person gets to choose first.
Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)
Annie Pearl explains how Calendly narrowed its target personas, structured product teams, planned against a clear strategy, and layered a sales motion on top of product-led growth. Calendly's viral loop drives 70% of signups, and sales-led growth went from nothing to about 20% of ARR in two years while becoming its fastest growing segment.
Pearl entered product by joining a startup's founding team after law school. She went on to become director of product at Box, then CPO at Glassdoor, and now leads product at Calendly.
She also sits on two company boards. Her advice to others is to show interest and do real product work, the route she has used to bring over the most people.
At Box she learned to ask why behind every customer request. She joined the Enterprise team as Box moved up market and spent her first year talking to customers.
Building what customers A, B and C each asked for would have tripled the effort and hurt the end user experience. The goal was one solution to the underlying problem that scales across customers.
At Glassdoor she learned consumer growth and owned both sides of a marketplace. Glassdoor served job seekers and employers, with 60 million unique users. She learned funnel optimization, how to build a growth team, and how to decide with data and A/B tests.
Calendly needs both: its self-serve side resembles Glassdoor and its direct sales side resembles Box Enterprise.
Pearl helps run Skip, a peer group for product leaders. Nikhil, a former CPO at Credit Karma, started it about two years ago for CPOs facing late-stage growth challenges. It has grown to about 23 heads of product and CPOs.
She says the CPO role is hard and can be lonely, so peer support makes leaders more effective.
Pearl narrowed a broad user base to a few target personas. Calendly served freelancers, consultants, sales, recruiting, customer success and education users at once, so PMs had no basis for choosing between feature A and feature B. Early in her tenure she defined the market, its segments and the personas within them.
The core personas became sales, recruiting and customer success teams. Features built for them can still help others, but the personas now decide the trade-offs. She calls it one of the most impactful changes she made.
She defines strategy as an integrated set of choices. She borrows the Playing to Win framing: a winning aspiration, where to play, and how to win with that audience. Calendly's aspiration is to be the best place to schedule, prepare for and follow up on external meetings.
Writing down where the company will not play is what lets teams build for a clear set of people. A Venmo integration is declined for the core personas, even though a PayPal integration exists.
Resource splits across three horizons shift every year. Year one was about 70/30 between Horizon 1 and 2 with nothing on Horizon 3. Year two was 50/50, and year three about 30% Horizon 1, 60% Horizon 2 and 10% Horizon 3.
Horizon 3 got no investment at first because it was too far out. The split follows the strategy and progress against it.
Moving from Horizon 1 to Horizon 2 made focus unavoidable. A horizontal product helped virality and made Calendly the best horizontal scheduling platform. Horizon 2 means deeper support for teams, departments and verticals.
Pearl calls it the inflection point where clarity around focus became necessary. Most companies think they have this clarity, but PMs and designers often hesitate to say no.
She builds focus into templates instead of posters. The OPPA doc, the PRD and product review templates all ask who the target customer and user are, and how the product will beat every alternative.
Calendly is fully remote, so reminders live in documents. Pearl credits this culture for her success in creating clarity on target personas.
Calendly began as a free product built by a contractor firm. Founder Tope Awotona drew on his own sales experience, raised no money and used his 401k and savings. He hired an outside development firm in Ukraine and made the product free, partly because no billing system existed.
The first 10 users came through that firm, which also served an education company. Customer success agents used it to schedule calls with K-12 parents, parents then used it for parent-teacher conferences, and schools followed.
A viral loop that starts at the booking drives 70% of signups. An invitee sees a Calendly link, wonders what it is, likes it, signs up and spreads it further. Solo users invite teammates, and the team lead then inbounds or is flagged by product-qualified lead data.
Usage within a team signals when to reach out about expanding across the whole organization.
Pearl expects viral solo growth to taper and follows customer pull. Only so many solo users will pull out a credit card, and the law of large numbers slows growth at hundreds of millions in revenue. Usage data showed customers wanting to schedule with their teams.
The teams business is now growing much faster than the solo business, even though Calendly is still known as a solo tool. The new levers are externally facing teams, department sales and multi-department deployments.
Sales-led growth went from almost nothing to about 20% of ARR in two years. Product-led growth was 99% of ARR when Pearl joined. Sales-led is now the fastest growing segment, and a CRO had just been hired to build the team when she arrived.
She added sales because viral growth alone eventually tapers off.
Early reps are growers who work inbound leads, not outbound hunters. Leads come from people who reached out or from PQL usage data. Hiring is judged mostly on background and past type of selling, ideally at product-led-style companies.
A heavier outbound motion would need a different profile later. In her words, you wouldn't necessarily want "a bunch of sales folks who are you know at Oracle".
She sells to department heads, not CIOs. Early buyers are the head of sales, revenue operations or recruiting. The expected path runs from team lead to IT, then eventually to a CIO-led purchase.
She puts a CIO-led purchase several years away.
Moving up market changed people, process and product together. A self-service business can run in silos because the product runs itself. Selling to teams and larger organizations needs work that is highly integrated across functions.
She describes it as a cultural shift, not just a new sales team.
Pearl treats sales as the product team's best source of customer insight. As an Enterprise PM at Box she spent a lot of time in the field, because sales talks to about 10x more customers in a week than she could.
She says some product teams don't want to be bothered by sales, but she sees go-to-market as an asset that starts with customer empathy.
She connected OKRs from the company level down to every department. OKRs went from none, to product-only OKRs tied to a new strategy with other departments siloed, to three company OKRs with integrated plans and dependency mapping.
They are annual, with quarterly milestones that shape roadmaps. Departments add their own that don't appear at the company level.
Teams commit only to dates for the phase they control. Discovery, solutioning, build, and launch-measure-iterate each can be a quarterly commitment. An engineering delivery date is set only once both problem and solution are known.
This avoids promising a project six months out before discovery and design are done. Calendly has gotten much better at commitments on work right in front of it.
Strategy is written in layers, from a three-year plan to feature docs. The top layer is a three-year company strategy, written as a doc and presented in slides many times. Product OKRs start as docs and become slides for company presentations.
The three-year strategy is being added to new hire orientation so everyone sees where the company is going.
Product, design and research report to one leader. Pearl keeps product and design together so the team looks at the end-to-end experience as a whole. PMs prioritize problems and designers bring the solutions to life.
She led design at Glassdoor and kept the structure. A head of design was one of her first leadership hires, since Calendly had none and long-tenured designers had built a good experience without one.
The product org roughly quadrupled in two years. Product, design and research grew from about 15 people to about 60, with about 20 of them PMs, while the company grew from about 150 to about 600.
Teams are split by problem and persona: a core team for externally facing users, an enterprise group for IT admins and department heads, and a platform team for integrations and APIs.
She skips the PM debate meeting on purpose. OPPA (opportunity/problem assessment) lets PMs debate which problems to investigate and whether research justifies building a solution.
She stays out so nobody feels judged or acts differently. PMs bring problems they want feedback on, unlike a shark tank where plans get torn apart.
Each team owns a competitor for a quarter and presents at a wargaming day. Groups run a SWOT analysis and ask where the competitor is heading relative to Calendly's strategy. Teams present on the wargaming day, with prizes.
No PM or designer has to go deep on many competitors, yet market knowledge spreads across the team.
She interviews candidates on their biggest product flop. She looks for people who are brutally honest about how bad it was and why it failed.
The rest of an interview is usually a list of accomplishments, so the flop answer stands out.
Pearl says to break into product by doing real work first. Four routes exist: APM programs, junior PM roles posted internally, shadowing a PM while doing some of the work, or joining an early-stage startup. Internal transfers come from product-adjacent jobs like support, implementation or sales engineering.
Successful transfers are curious, care about customer problems and sometimes have a side project. She suggests looking beyond Google and Meta for APM programs, since earlier-stage companies are easier to get into.
She offers the recipient's choice of times before her Calendly link. Open the email with something like "feel free to share times you're available, or if easier, find time on my calendar." Paste open times straight into the email using the add-times-to-email option.
An invite feels like a power move unless the other person gets to choose first.