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Annie Pearl (CPO)26 February 2023

Behind the scenes of Calendly’s rapid growth

8Frameworks
15Insights

Frameworks in this episode

Productivity4 steps

Commit Only to Dates Within Your Control

Roadmap the phase, not the feature: Discovery, then Solutioning, then Build, then a ship date.

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Strategy4 steps

Competitive Wargaming

Assign each squad one competitor for a quarter, then pool the intel on a presentation day.

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Entrepreneurship5 steps

Four Paths Into Product Management

Two formal and two informal routes into PM — the informal ones convert most often.

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Sales4 steps

Match the Sales Hire to the Motion and the Buyer (PLG to SLG)

Layering sales onto PLG: hire growers for inbound and department-head buyers, not CIO hunters.

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Leadership4 steps

The OPPA — Leaderless Peer Review of Problems and Opportunities

A recurring PM-only forum to spar on problems and opportunities — with the CPO deliberately absent.

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Leadership5 steps

The Three-Phase OKR Maturity Ladder

No OKRs, then siloed team OKRs, then company OKRs with cross-org dependency mapping.

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Strategy4 steps

Three-Horizon Resource Allocation Shift

Express multi-year strategy as a yearly percentage split of resources across three horizons.

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Strategy5 steps

Where-to-Play Product Strategy as the Prioritization Engine

Turn an integrated set of strategic choices into the filter that decides every roadmap trade-off.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 1

Hot Take29:30

Treat Sales as Product's Biggest Asset, Not a Nuisance

Annie pushes back on the common product-org attitude that sales is a bother. She flips it: sales and go-to-market teams are your biggest asset for getting close to the customer. As a Box PM she spent huge time in the field and couldn't have known what to build without leaning on reps who talked to 10x more customers than she could reach in a week.

  • Many product orgs don't want to be 'bothered' by sales; Annie flips that on its head.
  • Sales and GTM teams get you closer to the customer and are a huge product asset.
  • As a Box Enterprise PM, she spent a ton of time in the field with the sales team.
  • Reps talk to 10x more customers per week and can act as the voice of the customer.

“I don't know how I would possibly know how to have what to have built or how to build it to solve the needs of…”

Annie Pearl · 30:00
#sales#product#customer-empathy#collaboration

Explainer· 4

Explainer06:00

Four Paths Into Product Management From Another Function

Annie, a former lawyer, lays out the routes people can take to break into product without a technical background. On the formal side: APM programs and applying to junior PM roles via internal job boards. On the informal side: shadowing a PM (often via a subject-matter-expert program) or joining an early-stage startup where everyone gets their hands dirty. She's moved the most people over through the informal shadow-and-volunteer path.

  • Formal path 1: apply to APM programs, which exist even at smaller companies, not just Google/Meta.
  • Formal path 2: apply to a junior PM role via an internal job board, easiest from a product-adjacent role.
  • Informal path 1: shadow or partner closely with a PM and volunteer to take on product work.
  • Informal path 2: join an early-stage startup where you can try PM among many roles.
  • The most successful transfers tend to be curious, passionate about the product, and have tinkered with side projects.

“they're usually very curious they tend to be really passionate about the product and kind of solving customer problems and sometimes they've even like tinkered…”

Annie Pearl · 11:00
#career#product-management#hiring#advice
Explainer25:00

How Calendly's Viral Loop Drives 70% of Signups

Annie confirms Lenny's mental model of Calendly's growth: someone signs up, sends a link, the recipient discovers the product and adopts it. 70% of signups come through this viral loop. Solo users then invite teammates, and once a team is using it the team lead either inbounds or gets flagged as a product-qualified lead (PQL) for an expansion conversation.

  • 70% of Calendly signups come through the viral link-sharing loop.
  • New signups are usually solo users who then invite team members in.
  • Once a team adopts it, the team lead often inbounds to Calendly.
  • PQL (product-qualified lead) data tells sales which team leads to pursue for org-wide expansion.

“yeah 70 of our signups come through that Viral Loop that you referred to and then of those sign ups then you know they're usually…”

Annie Pearl · 25:30
#growth#plg#viral-loop#calendly
Explainer26:00

Adding Sales to a PLG Business: Hunters vs. Growers

As Calendly layered a sales motion on top of product-led growth, Annie explains that early sales in a PLG business is inbound in nature, working leads and PQLs who already show intent. That calls for a 'grower' profile, not the outbound 'hunter' you'd hire later. The target buyer is also the department head (head of sales, RevOps, recruiting), not IT or the CIO, so hire for that background rather than someone who sold into CIOs at Oracle.

  • Calendly's SLG (sales-led growth) now makes up ~20% of ARR and is the fastest-growing segment.
  • Early sales off a PLG base is inbound-heavy, working leads and PQLs with existing usage.
  • That requires a 'grower' profile, not an outbound 'hunter'.
  • The early target buyer is the department head, not IT or the CIO.
  • Hire on background and prior selling motion; don't bring on reps who sold CIOs at Oracle too early.

“that's a very different profile of a sales team member than you might need after you know you you need to pursue more of a…”

Annie Pearl · 27:00
#sales#plg#go-to-market#hiring
Explainer43:30

What Surprises People: Teams Now Outgrow Solo Users

Annie says people are surprised that Calendly's teams business, multiple users collaboratively scheduling, is growing much faster than its solo-user business. That's where they see the future of growth: teams in externally facing roles, selling into departments, and multi-departmental deployments. Notably, customers pulled Calendly there through how they used the product rather than Calendly chasing a new growth lever.

  • The teams business is growing much faster than the solo-user business.
  • Future growth is expected from teams in externally facing roles and departmental deployments.
  • Customers pulled Calendly toward teams through their usage, not a top-down growth push.
  • Viral solo-user growth inevitably tapers as you hit hundreds of millions in revenue scale.

“that's really where the future of where we think growth will come from is you know supporting these teams of users who are in externally…”

Annie Pearl · 44:00
#growth#teams#strategy#calendly

Story· 4

Story34:30

The Feature Calendly Deliberately Won't Build

Asked for a concrete example of strategy in action, Annie points to a Venmo integration that solopreneurs and small businesses keep requesting. Calendly has a PayPal integration but won't pursue Venmo, because its core ICPs are sales, recruiting, and customer success teams inside organizations. It's a clear case of deprioritizing something popular because it doesn't serve the target personas.

  • Small businesses and solopreneurs want a Venmo integration; Calendly already has PayPal.
  • Calendly's primary personas are sales, recruiting, and customer success teams in organizations.
  • Venmo doesn't serve those core ICPs, so it's clearly deprioritized.
  • Concrete example of the strategy forcing a 'no' on a requested feature.

“it doesn't make sense within those personas to pursue something like a venmo integration”

Annie Pearl · 35:00
#strategy#prioritization#product#focus
Story40:30

How Calendly Got Its First 1,000 Users (via Its Own Dev Firm)

Annie tells the origin story she fact-checked with CEO Tope that morning. Tope, an ex-salesperson who knew the scheduling pain firsthand, raided his 401k and hired an outside dev firm in Ukraine, taking no funding. The first 10 users were customer success agents at an education company that used the same firm. Those CSMs scheduled with K-12 parents, who then used Calendly for parent-teacher conferences, and it spread organically from there.

  • CEO Tope had a sales background and knew the external-meeting scheduling pain deeply.
  • He raided his 401k and savings, took no outside funding, and hired a Ukraine dev firm.
  • The first 10 users were customer success agents at an education company that used the same firm.
  • Those CSMs scheduled with K-12 parents, who then adopted Calendly themselves.
  • Rare case of the team building your product also being the source of initial growth.

“the first 10 users were actually customer success agents at a company in an educate in the education space that contracted with the same firm…”

Annie Pearl · 41:30

“so he rated his 401k he took out all his savings he didn't hire it he didn't make he didn't raise any money”

Annie Pearl · 41:00
#origin-story#growth#founding#calendly
Story42:00

Calendly Was Free Partly Because They Couldn't Build Billing

Annie reveals that Calendly's entirely free early product came partly out of necessity: they couldn't build the billing infrastructure needed to charge. The combination of a better product than the alternatives plus being free helped drive the first thousand, then ten thousand, then millions of users. Lenny recalls being an early free user wondering how they'd ever make money.

  • The entire early product was free.
  • Part of the reason was they couldn't yet build the billing infrastructure to charge.
  • Being both better than alternatives and free accelerated the viral loop.
  • That combination fueled the jump from a thousand to millions of users.

“the entire product was free some of this came from honestly not being able to actually build the billing infrastructure that would be required to…”

Annie Pearl · 42:00
#growth#pricing#origin-story#plg
Story46:00

Calendly's Team Rituals: OPPA and Competitive Wargaming

Annie shares two culture rituals on the product team. OPPA (Opportunity/Problem Assessment) is a recurring meeting where PMs debate and spar over which problems to investigate and whether to move forward, deliberately without Annie present so people stay open and unjudged. Competitive wargaming assigns groups to own a competitor for a quarter, doing deep SWOT immersion, then presenting on a wargaming day with prizes.

  • OPPA stands for Opportunity/Problem Assessment, a frequent PM-only debate meeting.
  • Annie intentionally doesn't attend OPPA so PMs feel free from judgment.
  • PMs find OPPA valuable and seek it out, unlike shark-tank-style critique meetings elsewhere.
  • Competitive wargaming assigns groups to own a competitor for a quarter and do a SWOT deep-dive.
  • It culminates in a wargaming day with team presentations and prizes.

“we have a meeting called oppa which stands for opportunity problem opportunity slash problem uh assessment”

Annie Pearl · 46:00

“another fun one we do is something we call competitive work aiming”

Annie Pearl · 47:30
#culture#team-rituals#product-management#competitive-analysis

Q&A· 2

Q&A04:00

How to Send a Calendly Link Without It Feeling Like a Power Move

Annie answers Lenny's opening question about the social awkwardness of sending a scheduling link. Her fix: open the door by first inviting the other person to share their availability, and only then offer your link. As a second step, paste your available times directly into the email to cut another point of friction.

  • Start the email by inviting the recipient to share their own availability first, before offering your link.
  • This subtle framing lets the other person take the lead if they want to.
  • Use Calendly's 'add times to email' option to paste your availability directly into the message.
  • Reducing the click-through friction keeps the burden off the recipient.

“so opening the door to let them choose before you offer up your channel link I think is you know a little bit of a…”

Annie Pearl · 05:00
#calendly#etiquette#scheduling#product-tips
Q&A11:30

Why So Few Companies Run APM Programs

Lenny asks why APM programs are rare when they seem like such a win. Annie, drawing on building one at Box, says it's a huge amount of work: you need clarity on the interview process, role expectations, and training, and enough scale and excess capacity to invest in graduating everyone successfully. She adds that PM roles are simply hard to break into because there are far fewer of them than engineering roles.

  • Running an APM program well requires deep intentionality and a lot of setup work.
  • You need clarity on the interview process, role expectations, and a training element.
  • Companies must be at a scale with excess capacity to invest properly.
  • The goal is to graduate every APM into a full PM role, which raises the bar further.
  • PM roles are inherently hard to break into because there are far fewer than engineering roles.

“yeah I think when we built this hitbox so kind of drawing on that experience is a lot of work right you want to if…”

Annie Pearl · 11:30
#product-management#hiring#org-design#career

Tool· 2

Tool10:00

Tactical Tip: Search Glassdoor for 'Associate Product Manager' Roles

For people who want APM programs but don't know where to look, Annie suggests going to Glassdoor and searching the 'associate product manager' title to surface a host of open roles across companies. Lenny flags it as a tip he hadn't heard before.

  • Search 'associate product manager' as a job title on Glassdoor to find open APM roles.
  • Prestige APM programs (Google, Meta) are extremely competitive; earlier-stage companies can be easier entry points.
  • The search surfaces companies that run APM-style programs you can apply to directly.

“you could just associate product manager and you'll see all the open jobs out there and then go apply to them”

Annie Pearl · 10:30
#career#job-search#product-management#tools
Tool59:30

Annie's Calendly Pro Tip: Customize Once and Share

For the closing pro tip, Annie recommends a newly launched feature called 'customize once and share.' It lets you tweak an event type on the fly, changing the title, duration, or overriding a date, based on who you're sending it to, without creating a whole new event type for a one-off change.

  • 'Customize once and share' lets you edit an event type on the fly per recipient.
  • You can change title, duration, or override a date for a specific person.
  • It avoids creating a brand-new event type just for a one-off tweak.

“we just launched a new feature that I'm loving personally called customize once and share so this really allows you to make changes on the…”

Annie Pearl · 59:30
#calendly#product-tips#tools#features

Takeaway· 2

Takeaway21:00

The Biggest Unlock: Narrowing Who You Build For

Annie says the single most impactful change at Calendly was honing in on a clear product strategy and target market so PMs could actually prioritize. Previously a broad horizontal user base made every feature call a hard trade-off. The hard part is cultural: saying no feels scary, but it's what lets you build something amazing for the people who matter most instead of something merely okay for everyone.

  • A broad horizontal user base made it nearly impossible for PMs to prioritize feature A over feature B.
  • Clarity on target market, segments, and personas gave teams rigor to prioritize.
  • Core ICPs became sales, recruiting, and customer success teams.
  • Saying no is scary but is what enables building something amazing for the people who matter most.
  • Most companies believe they have this clarity but lose it once you get down into the weeds.

“the idea is saying no is scary when in reality the ability to say no is going to allow you to make sure you're building…”

Annie Pearl · 23:00
#strategy#prioritization#focus#product
Takeaway36:30

Only Commit to Dates That Are Within Your Control

Annie describes a shift over the past year to only promise dates the team can actually control. You can commit to when a discovery effort will conclude, and to a solutioning/user-testing phase, but you only give a real delivery date once the problem and solution are known and engineering can estimate. This avoids committing to a project six months out before enough discovery and design have happened.

  • Commit to dates that are within your control, tied to the product development life cycle.
  • You can commit to when discovery concludes, without committing to shipping.
  • A solutioning and user-testing phase can be committed to next.
  • Only after problem and solution are known can engineering give a real delivery date.
  • Avoid committing to a project six months out before enough discovery and ideation exist.

“something we've done over the last year is is really kind of moved to a model of talking about dates and promising and committing to…”

Annie Pearl · 36:30
#planning#roadmap#estimation#product