strategy is really just an integrated set of choices that outline how you're going to win in whatever Marketplace you choose right and so a good product strategy is going to answer questions like what's your sort of winning aspiration but maybe more importantly where are you going to play you know
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 welcome to Lenny's podcast where I interview world-class product leaders
and growth experts to learn from their hard-won experiences building and growing today's most successful products today my guest is Annie Pearl Annie is currently Chief product officer at calendly before that she was Chief product officer at Glassdoor and before
that she was director of product management at box she's also a member of skip a community or chief product officers and she's on the board of two different companies in our conversation we cover a lot of ground including how calendly builds product how calendly has grown including
the wild story of how they got their first thousand users and also how they built a sales team on top of what historically has been a very product-led Growth Company Annie also shares a ton of great advice on how to get into product management I learned a ton from
Annie and I know you old too and he also shares a few killer tips for using calendly which I loved and so with all that I bring you any Pearl through a short word from our wonderful sponsors today's episode is brought to you by Nero an online collaborative whiteboard
that's designed specifically for teams like yours I have a quick request head on over to mymeraldboard at miro.com Lenny and let me know which guests you'd want me to have on this year I've already gotten a bunch of great suggestions which you'll see when you go there so just keep it coming and while
you're on the mirror board I encourage you to play around with the tool it's a great shared space to capture ideas get feedback and collaborate with your colleagues on anything that you're working on for example with Miro you can plan out next quarter's entire product
strategy you can start by brainstorming using sticky notes Library actions a voting tool even an estimation app to scope out your team's Sprints then your whole distributed team can come together around wireframes draw ideas with a pen tool and then put full mocks right into
the mirror board and with one of miro's ready-made templates you can go from Discovery and research to product roadmaps to customer Journey flows to final mocks all the in Miro head on over to miro.com to leave your suggestions that's miro.com Lenny this episode is brought to you by Coda
you've heard me talk about how Coda is the doc that brings it all together and how it can help your team run smoother and be more efficient I know this firsthand because Coda does that for me I use Coda every day to Wrangle my newsletter content calendar my interview
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startup credit on your first statement at coda.io Lenny to sign up and get a startup credit of one thousand dollars coda.io Lenny Annie welcome to the podcast thanks for having me Lenny super excited to be here I've been a big fan of yours from afar we've crossed paths a little bit on
reforge on Twitter probably been at events that maybe we didn't know each other at yet so I'm really excited to finally be chatting sort of real life in real time at least me as well I've got a calendly question to kick things off it feels like with Callum Lee one of the
most awkward elements of it is I have to like put the burden on someone else to book account list so I'm sending a link and I haven't figured out a good way to send it to someone without it coming across like a power move so my question to you is how do I set a calendly to
someone without it feeling bad all right well I love this question to kind of kick us off we actually have a whole blog post about this if you're curious to learn more but I think at a high level I think I recommend first really just kind of opening the door for the person you're trying to schedule
time with to share their availability first right so instead of just sending the link I usually start the email with something like you know looking forward to connecting feel free to share sometimes you're available or if easier you can choose you know to find time on
my calendar using the calendar link here 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 subtle way to let them take the lead if they want the second piece I would recommend too is once you kind of open
that door you can kind of further reduce the effort on the recipient by adding times you're available directly in the email so when you go to share a Cali link there's an option to add times to email and you can then just paste those directly into the email you're creating
so that reduces yet another sort of point of friction to ask the user to click the link and you know get taken to account only so opening the door and then you know adding times to email are two things that I do to really make sure that it's not awkward and it doesn't put
the burden on the other person that is awesome advice that first one is kind of what I ended up doing actually that's really interesting where you don't send the link immediately you first just ask okay send me your account only and actually always say send me your
calendly like I don't even I assume that's what they're using it's kind of funny I'm not even like anyone else is out there that's good that's what we like to hear yeah absolutely it's like its own word now okay that was awesome oh look at this already actionable advice for anyone listening a sweet
transitioning a little bit to product the main focus of our chat you transitioned into product from being a lawyer you told me at one point that a lot of people ask you for advice about how to transition into product from other functions especially non-technical functions someone without a technical
background so what advice do you give people for when they ask you how to transition into a product role I got you know what I'll call Lucky which is I kind of stumbled into product management after law school joined the founding team of a startup and you know ended up
doing product management there but when I think about folks who are looking to get their product management I think there's really two paths I think one is kind of more formal in nature right there's associate product manager programs out there and many you know
scaled companies Google meta all have APM programs that you can formally apply to and actually when we were at box much earlier Stage Company than either of those companies I just mentioned we actually created a an API program to help grow our bench of more two year PM
so I think you can actually find APM programs even at smaller earlier stage companies than even on a big Tech so that's one it's just formal APM programs I think another kind of more quote-unquote formal way to get into PM is really by I just you know directly applying to a junior PM role where
there's no expectation of any sort of experience I've usually seen this work best when you're kind of already working somewhere in some sort of product adjacency you know maybe you're in Customer Support implementation or maybe you're a sales engineer but you can kind
of look at the internal you know job board and find Junior PM roles that are posted and that's a one way to make the move so that's kind of on the formal side like APM programs and just applying via internal job boards I think on the informal side really two suggestions
here the first one is to kind of seek out opportunities to kind of Shadow or partner closely with with a product manager and maybe even offer to take on some work so some of the kind of best PMS that I've brought over to product from kind of other functions they really
start by expressing interest in product and then like start partnering closely with the product manager and maybe even doing a little bit of product work before they make that transition and one kind of tactical suggestion is there's oftentimes companies will have subject
matter expert programs where they want to pair someone from a go to market function with a certain product squad or a certain product area and so that's you know becoming a Smee it will allows you to really get more involved and embedded into the product team so that's that's
one suggestion and then maybe last one is just you know going the path I did which is joining an early stage startup there's really use really an expectation that everyone's going to get their hands dirty doing a lot of different things and so I think that's one way where you
might have an opportunity to you know try product management if you end up kind of joining an early stage company so the four maybe it was four maybe it was more paths that you described join an APN program what was the second one again internal job board apply to it
when you're in the company as just like a junior PM twos find someone that kind of like mentors you and helps you start doing the role and is that internal kind of is that the internal Transfer app yeah exactly and then another sort of flavor of that is you know sometimes
companies will have these sort of Snee programs what is a Smee program a subject matter expert so you know you'll say hey I want to make sure we have subject matter expert in our CS team on this area of the product and they'll partner really closely with you know the
product manager and designer within that area got it and then the fourth bucket is join a startup start doing PM work and then you end up being a PM which are those four do you find most common and would you push people in One Direction or another yeah you know I I've brought
a lot of folks over internally through the through the path of someone's really interested in product they express they're interested they want to help they want to learn they're eager they're curious and so they make that really well known and they're even willing to you know do some work on the side to
help out and really show and demonstrate the skills before they have the job so I've seen that one to actually probably bring bring the most folks over in my role in terms of being on the product leadership side on the APM program route are there any APN programs you recommend
because you know I'm sure people hear this and they're like yeah but I don't know where to apply I don't know which ones are good I don't know if you have a list but just like what comes to mind is like APM programs to go pursue you know the the sort of the folks who started it
all was was Google right with the Google APM program and you know meta obviously has a pretty strong robust APM program but as I mentioned around box I think you know those are obviously very very competitive and most people want to get into them it you know it may be better
to try and find a company like a box or a company that's a bit earlier stage not as scaled to think about looking at those APN programs and I'm sure if you want to go to glassdoor.com where I used to work at Glassdoor so I had to you know throw that in there uh you could
search for associate product manager and I think you'll find a whole host of open roles that you might be able to apply to that is a cool tip I haven't heard of that go to Glassdoor and search for APM so you search for companies that have an APM like title yep you could just
associate product manager and you'll see all the open jobs out there and then go apply to them that's cool okay good tip what I find and you mentioned this like the best if you have the option is to internal transfer you're right if you're just like another function you find
someone that can help you move into the role yep you have the relationships you you know you can show you can show your work really well the other thing I would say is you know when I think about folks who have successfully transferred over I think they tend to have a couple
characteristics right 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 with a side project as a way to cut a Holland RPM skills so I think as you're thinking
about making that transition those types of characteristics really showing eagerness and interest in in the product itself and solving customer problems are also great ways to get noticed and increase your chances why do you think it is that not more companies have an
APM program feels like such a win for so many people why is it just so rare 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 you're gonna do it you want to do it really well and you want to create an environment where you can help the
associate product managers be successful you know the goal is to ultimately graduate everyone from the APM program into being a product manager and so I think it takes a lot of attentionality and for us it took a lot of you know a lot of work right we had to make sure we
had Clarity around the interview process we had to make sure we had cleared around expectations in the role we wanted to have a training element we wanted to make sure that again we're setting people up for Success so I think companies have to be at a stage of scale
where they can really invest and have the excess capacity to build the program in a way I think that's going to help make sure everyone who comes through it has a chance at really learning growing and ultimately being successful that's the same thing we found at Airbnb
there's a PM that was so excited to like make the APN program and just just never really happens just take so much work and to your point you have to set up for Success you want to make sure there's clear paths and what do you when do you upgrade to a regular piano and how do
you interview and you know and are we doing you know is this really an APM program for internal folks is this external you know are we going to be really trying to promote this so I think there's a lot of ancillary activities around the actual program itself that have to be taken into consideration to
make sure that it is actually very successful yeah maybe at last point we should probably imagine you agree with is generally just hard to get into product management that's like the default there's just like not that many roles at companies versus say Engineers or some
other functions so I think that's just like there are not that many roles it's like a difficult role to break into but these are the ways you can do it if you actually want to that's right okay so I want to transition a little bit to talking about calendly there's
kind of two areas I want to go one is just how do you build product accountantly what have you learned about product development and team building and then two talk about how Cal only grows and what you've learned about growing a product like calendly it's such an interesting product especially
from a growth perspective so to start on just how product is built at calendly just a little context like how many product managers are there and yeah how many PMS are there how many people total roughly just give us a little bit let's see when I joined about
two years ago I think the company was about 150 people and I think we're about 600 now and then the product team worked out there were about 15 product managers and designers when I joined again about two years ago and I think were around 60 uh this year wow so 60 product managers
product managers designers and research team yeah got it what about just like PMS pianos probably my guess is 20. cool 20ish yeah cool and then can you talk about how the product theme is structured roughly like if you think about a tree recharge tree so we have as
I mentioned we've got product managers we have designers we have a research team and then product operations and then on my product leadership team we have a head of design head of research head of product operations and then within the product management team I have leaders across core across
Enterprise and platform got it so you manage the design team and engineering team you said not engineering design product and research yeah got it something that I find is one of the big differences between product orgs is design reporting up to a product leader versus not what's the rationale
there and then has County tried a different approach yeah so when I was at Glassdoor in the CPO role I had the opportunity to lead design for the first time so coming into County I had led both product and design as well as research and so I think you know it kind
of made sense given I'd already done it once to sort of keep that structure coming into calendly I think at the end of the day the the real benefit of of the structure is really to say you know we want to be thinking about everything we're doing through the lens of the
end-to-end user experience and so if we have you know product managers who are really prioritizing the problems we're going to go after and we've got designers who are really trying to think about how do we you know bring solutions to life to solve those problems having
both of those functions roll into one person just really allows us to think more holistically around the end-to-end user experience so certainly can work where you have product and design reporting into you know sort of different leaders that ultimately report into the CEO but when you you know get
to this level of scale from just a pure people management but also just the scale of the business you know you often see this consolidation where product and design start to roll into one leader and you know at least if in my experience I think it can help ensure that all the
the different pieces of work are kind of integrated well together and ultimately deliver you know better experience for customers so it sounds like before you joined it wasn't like that and if that's true was there like something that improved with that shift so the
structure was there that way at the time we didn't have a head of design so we had a you know a lot of really great individual contributors and who had been many of whom had been with the company for for quite some time and really contributed to the great user experience
that existed in the product but we didn't have a design leader so one of the first leadership hires I made was to bring in a head of design to really build out that function and then that you know head of design is is sort of a peer partnering with the different heads
of products across the product management organization as well what about in terms of those structure whatever you can share like one level below like how do you structure teams is it around outcomes is it around features of the product is it around type of persona how do you think about that yeah
so we have you know core team who's really responsible for the core you know end-to-end user experience and you know in many ways they're both building you know doing feature development and then they're also doing Growth work right so they're they're thinking about how do we
build new features and functionalities to help our core personas which is typically folks who are in sales recruiting and customer success so anyone in an externally facing role we're really trying to help them do their jobs better so the core teams thinking about features and
functionalities to to really help our core end user Persona and then you know Growth work to think about the the plg funnel right everything from acquisition activation conversion and retention that's one group and then second group is our kind of quote-unquote Enterprise
Group and they're really thinking about two different personas one is the sort of it admin uh right the sort of person who needs to make sure that calendly is secure and that they have all the reporting mechanisms to be able to manage their account and all the tools
to you know manage users and groups at scale and the second piece of that is also kind of departmental leaders right so as calendly selling into or being used by a sales organization the head of sales is not the it admin but they are a kind of you know a teams admin who needs
to manage their organization within calendly so the Enterprise Group really thinks both about the admin but also sort of the Departments and how do we better serve departments and then lastly we have a platform team who's really thinking about you know how do we embed
calendly into the business processes of the organizations that we support and that we you know provide our product into and so that's everything from you know Partnerships and Integrations to our apis interesting so it's kind of like problem focused slash Persona Focus like who are
you trying to sell it to that's right that's right yeah trying to sell to and then sort of the Persona of who's going to be using the functionality and then you know really having those teams hone and own those personas as they're you know developing functionality within the
product what's your take on okrs do you all use okrs in some form yes we do we use akrs both at the company level so 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 uh level okrs but then you know there's additional things that we'll be doing at the department level for example that aren't going to show up at the company level so yeah we use them both at the company as well as on the product side is there anything you've learned about making
okrs work there's a very uh people love them people hate them is there something you do to make your cares work some you've changed some of you've learned over time and how to work with who cares yeah you know when I first joined I'd say we you know we didn't have this
muscle well built out right we we didn't really have a clear product strategy at the time or clear okrs guiding the work and so there was a lot of great work happening but it really it was unclear how it all kind of fit together or how we were going to measure success and
that works that was kind of a first phase I think the second phase for us was we developed a product strategy we then had product team okrs that corresponded to the to that product strategy but they were really contained to the product team and each department across the organization had their own
kind of siled okrs and then phase three where really I'd say we headed into this year we have a really clear set as I mentioned of company okay hours and then these really tightly integrated plans across the company around how we're gonna support the key results and
ultimately you know deliver on the objectives and this has been a really incredible transformation of dependency mapping uh you know being able to make sure that we're pulling all the levers across the organization to drive our most important objective so I think it's
just a kind of maturing of the business from almost you know no okrs to product team okrs to now company okrs in a really tight planning process to make sure there's a lot of integration across the company to support what we need to do as a business so what I'm hearing is
one of the biggest changes in learnings was to connect our carers across from the top to the bottom right absolutely absolutely is there anything else that has made a big impact on your ability to build and ship and execute as a company in terms of like changes you've made in
terms of how the company and how the teams build I think one of the biggest changes that you know we've made when I first joined again we we had a product that served a lot of horizontal users right we help solo users who are Freelancers Consultants we help you know
sales teams we help recruiting teams we help customers success we help folks in education so as a very broad user base and what that means is that product managers in particular I think had a really hard time prioritizing right at any point in time it was really difficult to say should I do you know
work on feature a or for future B without that Clarity and so I think the one of the most impactful things we did pretty early on in my tenure here was to hone in on overall our overall product strategy but a poor 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 and so we've made a pretty you know a pretty clear distinction now that while a lot of the feature work that we'll do to support our Target personas of sales teams customer success teams and recruiting
teams will impact folks who are not in those personas those are the core icps that we're going after and so you know historically that would have been always a sort of a trade-off decision and a question and now I think we have a lot of rigor around who the target do you
know who our target market and their and then Persona we're going after and so teams can use that to prioritize and also just deliver better value for those users so it sounds like the biggest unlock and one of the biggest unlocks for making the team more efficient move faster make
decisions quicker is narrowing in on exactly who you're going to be selling to I think it's one of the harder things for companies to do uh so it sounds relatively easy and I think most companies believe that they have Clarity around this but then when you go you
know down into the weeds of you know asking someone who's product manager or a designer you know I don't know that it's always as clear because there's there's always a bit of a hesitation to say no right and 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 something that's going to be amazing for the people that matter most and not something that's going to be you know average or okay for a lot of different people was there anything that was really hard about actually executing that like
convincing people we're gonna narrow and not worry about these people and any lessons from going through that process because I imagine a lot of Founders listening are like oh that sounds we should be doing this but oh man we're leaving all this money on table people
are gonna be pissed yeah I think it's a pretty big cultural shift so some of this intersects with the shift from product LED growth to adding in kind of a sales motion so you know when I joined calendly all of our error came from our plg Channel we didn't have a you know a
sales team we just hired a cro who's going to build out a sales team and so you know in that world the way you think about product the way you think about processes even the people you have on the team are tailored to that business model and then as we sort of moved up
market and have now you know explicitly started to one you know go after teams of users and Departments of users and and organizations of larger scale everything about people process and product all changes right I touched on culture because I think that's pervasive
across the entire organization the way that things get done you know has to be highly integrated versus can be a bit more siled when you're just you know sort of the self-service plg business that in many ways runs itself through the product being well optimized so you
know there's a lot of process change that needs to happen the type of people that you need to bring into the organization that changes as you layer in you know the new selling motion and then the product itself of course has to change so I guess let's just say the example of plg and SLG or the direct
selling motion is you know tying to your question around what are the things that need to change in order to get clear on on your sort of your target user and I think it's highly cultural in nature across people across process and even and then obviously across the actual
product itself I have a whole bunch of questions about how can only grows and maybe we just get into some of the stuff because I imagine a lot of people are interested first let me ask this imagine can only mostly grows through I sign up for countley I send it to everyone when
I book a meeting they're like oh what is this and they're like oh cool I'm gonna use this and then they start using it spreads and then sales eventually find people at a company that are using it a lot and tries to get the whole company is that roughly right 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 solo users and then they start to invite team members in and then you know the team starts using calendly and then usually the you know head of that team either inbounds to us or we you know
have some sort of pql data to know we should go after that that team lead to try and have a have a conversation around you know expanding calendly across their entire organization in pql product qualified lead right you got it yep wow what a what a loop what a magical way to grow
that everybody wishes they could it's pretty incredible I will say no man okay so going back to the question when did Colony hire their first salesperson like any learnings about just how to start down that road once you yeah once you start you know as I mentioned when I
joined two years ago we just hired our first cro and uh the plg business really represented you know 99 of our error and then over the last two years we've you know scaled the sales team and our SLG motion or sales LED growth motion now represents about 20 of our ARR and it's
actually the fastest growing segment of the business I think there's probably two things I would touch on in terms of early sales hires I think the first is you know when you're making that transition from plg to adding in the sales let motion um because you're starting from plg it
tends to be much more inbound in nature right you've got these sales reps who are working leads who have usually proactively reached out interested or as I mentioned pqls you know they have data to tell them that this is a you know someone who has usage within their team
and therefore we should reach out and so 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 heavy outbound motion more of like a hunter profile than a grower profile so I think that's the first
piece is just make sure you're you know you sort of you think about the the motion when you're moving towards a sales lab model 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 you know outbound heavy kind of hunting uh sales
reps just one quick question on that actually because that's really interesting I don't know how involved during hiring these folks but is it like look at their background and they've worked at a company like that or is it a personality type like is there anything to look for
specifically there yeah I think it's mostly background and the type of selling that they've done previously um more so than than personality type but in the second I think the second piece that's important too and I'll answer your question on that one too
which is the target buyer so when you transition from kind of plg to sales LED or you know adding this direct sales motion the buyer is usually just the department head right it's the head of sales it's the head of revovs it's the head of recruiting and it's not you know
a senior person in it or the CIO and so selling into this audience is different than selling into it and so I think you have to be sure again that you have the right fit of sales folks uh with the target buyer in those early days and so in the to your to your question around
what's that mean you know you wouldn't necessarily want to bring on a bunch of sales folks who are you know at Oracle right who are heavy in selling into cios in their early days because that's just not who you're the buyer is going to be and you think we'll you know graduate
there eventually but it's probably going to start from Team lead to someone in I.T to eventually you know a cio-led purchase but that's you know that's certainly several years away and so making sure that the the profile of the folks you're bringing on early match
that Target buyer in addition to match the motion around how you're going to be acquiring you know customers and to see that is it similar you look at the companies they worked at like it's like plg-ish definitely yeah exactly yep okay so along the same lines as a product leader working with a
strong and large sales team anything you've learned about just how to build that relationship and build a product drawing that works really closely and well with a sales org the first piece it really starts with is customer you know empathy and at the end of the day seeing the sales team and the
go to market seam as this really great asset that can help you as a product manager get closer to the customer so I've certainly seen organizations or been in organizations where you know the product team you know 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 to market teams in general could be your biggest asset to helping you get your job done well when I was at box I was a product manager on the Enterprise team and I spent a ton of time in the field and you
know 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 our customers if I didn't have that close relationship with the sales team and be able to like you know lean on them because they're talking to 10x
among more customers that I was able to ever talk to within any given week really lean on them to be the voice the customer to help you know me make the best product decisions that I could this episode is brought to you by vanta helping you streamline your security compliance to accelerate growth if your
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claim your discount get started today I'm curious how you prioritize work that you could be doing as a product team there's sales people coming at you there's issues you're probably having there's the founders wanting to ask you first do stuff just like you know classic product management question but
curious if you found any Frameworks or approaches for just deciding what to actually build of all the things you're hearing the core challenge of being a product manager right just so that that like I feel like the core job of PM is just tell people what's next what's the
next thing that's right and hope and hopefully you have a a good reasoning as to why that thing right uh you know next is going to have the biggest impact which is really where I start you know I think it really starts with a clear product strategy that will dictate a few
things and I like this framework that's taken from a book called playing to win it talks about how strategy is really just an integrated set of choices that outline how you're going to win in whatever Marketplace you choose right and so a good product strategy is going
to answer questions like what's your sort of winning aspiration but maybe more importantly where are you going to play you know 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 and so what I think this framework does kind of dovetails back to what I was saying before around prioritization is it forces you to create Clarity around where you're going to play and where you're not Gonna Fly right and so this really helps the product team kind of
hone in on delivering value for a very clear set of people versus trying to build something for everyone and so once you've established kind of what that strategy is or what the you know playing field you're going to go after then I think you can divide up your product
work and service of that strategy so I'll give you an example at Galilee we have the sort of vision Our Winning aspiration to become the best place to schedule prepare for and follow up on your external meetings and then we've articulated kind of three Horizons
around how we're going to get there now the year one that I was here the percentage of resources we spend on sort of that first horizon and the second Horizon was about a 70 30 split and we put zero percent of our resources on Horizon three that was too far out in the future and we weren't you know we
didn't want to make any Investments there quite yet but we knew where we were going in year two it shifted we went to like a 50 50 split between Horizon 1 and Horizon 2 but still no explicit investments in Horizon 3 and then you know as we entering to year three now we've significantly scaled
back the investment in Horizon one that's about 30 and then we've got 60 in Horizon 2 and you know call it 10 in Horizon 3. so I think just to close on the question of prioritization I think it starts with a really clear product strategy which defines where you're
going to play and how you're going to win and then the work and the percentage of allocation just should feed right into that product strategy and and how you're doing against uh where you need to be in order to achieve your ultimately your winning aspiration I
don't know how much you could share here but is there a feature that is like people keep asking for it and it hasn't been built because of the strategy the long-term Vision something that's like nope doesn't fit We're not gonna do this yeah I think the best example I I can
give is you know there's lots of small businesses and solopreneurs who would love us to have a venmo integration uh we have a PayPal integration but you know our target market that we're really trying to go after as our primary you know Persona are as I mentioned these
sort of core icps within organizations so sales teams recruiting teams customer success teams and so it doesn't make sense within those personas to pursue something like a venmo integration now there's a lot of things we'll build for those personas that are going to help
the small business the solopreneur the freelancer but that's a specific specific feature or something that would be clearly de-prioritized given the current strategy that's an awesome example I want to get back to the growth stuff but before I do that we're kind of on
this topic of planning and who cares and organization I'd love to know just how you do planning accountantly like how far out do you plan in detail how far I deal road maps how often do you plan anything you can share there this starts again uh I sound like a broken record
but with this like really clear strategy around where we're going over the next couple of years and then we take that and we break that down into what are the most important things we need to do as a company this year in order to be able to make the right progress against that
strategy so we have the company level uh okrs and I mentioned we have about three of those this year and then those KRS within the company um okrs are are measured annually but we have Milestones across a quarterly basis so we can measure progress you know more frequently than obviously on the annual
or a semi-annual basis so I think that's kind of at the high level and then you know obviously our product roadmaps are going to be in support of those key results that we need to deliver to the business over the course of the year but then kind of broken down on a quarterly
basis I think one thing I'll just touch on real fast on on kind of estimations and dates 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 dates that are within our control and so if you
think about kind of the product development life cycle you know we can commit to a discovery effort of you know doing research around a certain problem space and we can have a general sense of when we know that effort is going to conclude we don't know if we're going to
actually end up going and based on the results whether we're actually moving forward with investing in that area but that's a a body of work we can commit to from there we then move into okay if this is something a problem space we want to go after we're going to go you
know work on a couple different solutions and we're going to do some user testing and we're going to land on a solution and that's another sort of phase we can commit to then once we actually have that completed and we actually know not just the problem but the solution we can do estimation
planning and actually have a date for delivery from an engineering perspective and so we've gotten a lot better at making the commitments around the work that's right in front of us versus making a commitment around a project six months out when we haven't even done
enough Discovery enough design and ideation to have a real clear understanding of estimation that is really cool do you have terms for these phases kind of like these phases you have to get through these kind of gates yeah how do you describe that yeah so
the first phase you know we sort of just call generally Discovery um the second phase we call kind of solutioning the third phase build and then the fourth phase is sort of launch measure and iterate and then we've we've kind of designed the product development life cycle around that framework so
Discovery for example is that like a roadmap item for a quarter and that's like what you've committed to and if that goes well the next quarter has the next step yeah exactly you got it sweet okay in terms of the strategy artifacts how does that look or do you have like a
Google doc with a template that you all use what does that look like because what's interesting about people not working at a company or working in just one company is they only have access like strategy documents are really hard to see and see examples of so I'm always curious what these look
like so whatever you can share about what they look like and where you put them and how long they are and that kind of thing we have a couple different sort of layers of this I think the first is this high level three-year strategy and this is actually called at the company
level so it's a doc uh it also has slides that have presented been presented many times to the company and we're in the process of sort of making sure that that is part of new hire orientation uh so that you know everyone should understand where we go on over
the next three years and you know then therefore how does this year's objectives fit into that so I think that's at that level and then you know from there we've got our our product team okrs these generally start by docs and we write them in docs they usually get translated into slides at some point
for presentation purposes to the company and those are you know sort of stored centrally in a location and then you know you kind of get down to the feature level or or the project level and we have you know different kind of templates for the teams to use you know
based on the type of work that they're going to be doing and we're a pretty heavy Confluence culture so we tend to use confluences as one of the tools for sort of Housing and storing information around the work that's being done cool so maybe on that topic what are what
else is in the stack of calendly product Team Tools we talked about roadmap planning some combination of starts with docs there's mural boards involved uh usually it ends in slides then kind of actually roadmap tracking we use Aha and we use airtable collaboration you know
slash communication we use slack we use Loom bug management we use jira trying to think of confidence Confluence yep with confluences when we use quite a bit pendo uh we use we use quite a bit of pendo to help you know to help educate users within the product when we're launching new features yeah I
think that's the main stack and docs is Google Docs and slides as Google Slides you got it yep sweet that's right okay I'm gonna bounce around and go back to growth questions and then I have a couple more product team questions how did calendly get their first thousand
users sorry a great question I had to to fact check it with my CEO uh earlier this morning but there's actually a few really interesting things about this story uh and a few things that Tope did in the early days to get 2 000 users so for those who aren't familiar Tope our
CEO and founder uh you know started his career in sales and he spent lots of years in sales and so he was very used to the challenges of trying to organize external meetings with prospective customers so he knew the problem space really really well and he had evaluated
kind of all the scheduling solutions that were on the market and kind of come to the conclusion that there really any great products out there and especially there weren't any great products for the recipient of the actual booking service and so I think he saw this as an
opportunity for disruption um 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 it's a lot of penalties that's a very good point I've never asked him about that um and hired an outside development firm actually in out of the Ukraine to build
the first version of colony so that's the background accounting why it's important is that 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 that Tope was using to build calendly so
he really found his first set of users through the firm that he was using to build the product and then those csms or you know customer success managers were actually using Cali to schedule calls with parents in K-12 and you know K-12 education and so then those parents
started using calendly for their own parent-teacher conference scheduling and then from there you know school started using it and then all the parents within the school started using it for a lot of other use cases and it kind of grew organically from there so that was one
piece I think the other piece that's really important is that he started off by you know just having a free tier 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 actually charge so it came a little bit
out of necessity but it was also free So Not only was it a you know a better product than the Alternatives out there but it was also free so the combination of the viral Loop and kind of coming in through getting those first 10 10 users as part of that the firm he was using
and then sort of the free aspect or I think what what led to the first a thousand and then you know ten thousand and millions of users from there that is crazy I have never heard a story like that where the team that is building your product ends up being the source of
initial growth I know pretty crazy yeah so many nice things happening in the history of calendly I know and wow Ukraine so I'm actually from Ukraine and so nice that's pretty cool yeah they're great rails aware yeah and it's also interesting that it's rare that you hear
a successful business starts with contractor Engineers it's often like I think YC's like do not do that so that's a cool counter example if it can actually work out especially if they're your first users you know they are we also we still work with them and they're fantastic and they
have incredible Engineers so they're still part of our culture which is great so Kelly got big in Ukraine sounds like initially there you go there you go what's something that would surprise people in terms of how calendly grows today or grew through its history
most people probably think about countley as a drilling link and really for individual users to reduce the back and forth of email and scheduling right so they think of that one-on-one use case and I think people would be surprised to learn that our team's business so multiple users in an
organization who want to collaboratively schedule together is growing much faster as in our solo user business and 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 facing roles and selling
into departments and supporting multi-departmental deployments with Galilee across you know an entire organization so I think it's still really well known as this sort of solo user tool to eliminate the back and forth of email but the growth of what we're seeing or where we think it's
going to go is actually more teams of users and Departments of users and and then multiple departments in an organization it's interesting when you hear the story of accounting that just has so many good things happening like basically for free it's just gross so well I think people
don't realize you eventually will that'll slow down it'll taper off eventually you'll need to drive growth very actively in these new ways that you're describing and I think people don't often realize that they just want to find something that was viral and then you know things are going to go
great but taper's off yeah you I mean you get to a there's only so many people who you know solo users who are going to pull out a credit card and I think once you also get to you know hundreds of millions of dollars of Revenue scale just the law law of large numbers means
that growth will slow and so you kind of have to figure out where's that next growth curve going to come from I think the the beauty of calendly is that while we certainly have built features of functionality to support teams and and departments we got pulled there right it
wasn't one of those things where we sort of said we need to find our next growth lever let's go you know build X our customers really pulled us there by the way that they were using the product and so again a very fortunate position to be in but when you can kind of see in the
data and see how customers are using it that they want to be working on you know scheduling with their teams that was you know how we sort of sort of Saw early sign that that's kind of where where the business was going to go in the future I don't think I mentioned this I went
paying user of cut of cattle it's what I use for booking these podcast episodes you got me I think I started when it was totally free and I I was like how do these how will they ever make money this is too late too much power and then now now you you learned that um it was free
almost by accident yep I was like yeah please take my money this makes my life easier what are some fun or unique traditions and cultural kind of components of the calendly product team the ones I thought we could talk about one we have a meeting called oppa which
stands for opportunity problem opportunity slash problem uh assessment and so what this is is a meeting where basically PM's I don't even go to it it's a meeting for PMS to really debate and discuss with each other and kind of Spar around you know either areas and problems that they want to go
investigate or after they've gotten data back or research back from evaluating an opportunity deciding whether we actually want to move forward and go try to develop a solution so it's really really in the product development life cycle of letting product managers really get into
a room with each other on a frequent basis and just think there are things debate discuss and I know that that they all get a lot of value out of that reminds me of something just like a bad version of that I had a friend who's a PM at Zynga and he said there's a
meeting where PMs present their plans to all the other PMS he's like it was like it's like you're like like in a shark tank where everyone's coming to destroy you they just point out all the problems that's all that ever is in this I would say on this one it's kind of the
opposite where I feel like everyone really needs the meeting you know they're like oh I really need to take this to Oppa because I need to I'm working through these problems and I really want to bounce it off of other people so I think I could imagine a world where it would be like that
actually part of the reason I don't go to the meeting is that I really want everyone to be able to be open and transparent and provide feedback and not feel like there's any sort of judgment from me or any sort of needing to act a certain way because I'm in the room so
that's sort of why I intentionally don't go another fun one we do is something we call competitive work aiming so you know on a some sort of time interval at times has been quarterly we'll have assigned people into groups for the quarter to own a competitor and their job is to
essentially you know spend a lot of time immersing themselves into the product of the competitor really trying to think through the lens of do a SWOT analysis really try to Think Through the lens of where's this uh competitor going and you know how she can only think about that
and as it relates to our strategy and so we spent a quarter doing that and then we have sort of the competitive wargaming day where every team comes and presents and there's prizes and it's a lot of fun but it's a really great way to stay on top of what's Happening
across the market uh without you know sort of requiring every product manager designer to be deep in the weeds of a lot of different competitors we can kind of bring all of that knowledge together through what we call competitive work gaming that is cool it's really impressive how you do these exercises
and they're seemingly positive and friendly and constructive it sounds like it's kind of a there's a pretty unique culture accountantly I'm curious if there's anything else that's kind of core to the values or the way that you think about the principles of building
product they can only what I touched on earlier is really core to how we build product which is honing in on this target user and honing in on our target market I do think it's it's quite rare I think most organizations that I've seen I think there's a desire to do that but
I think again when it push comes to shove it's really hard for executives to make decisions that say no to things one of Kelly is actually core principles is focused wisely it's pretty deeply embedded into our culture and so I think it you know one of the reasons that I've
been successful in being able to create the clarity around who the target personas are is because I think it's embedded into the culture of calendly to focus wisely so I don't know that would work in every organization I think many organizations really struggle to say no
and they're kind of you know always adding more onto the plate versus taking off but I do think if you you know from an ethos perspective there is something around focusing and the ability to focus to therefore deliver the highest quality of product that you can to your Target
customers that is unique and I think it starts with you know some of the broader cultural paradigms that exist at the company and then we've now embedded that into the way we think about how we build product is there anything else you do to instill that sounds like it's a core value
do you put posters around the office so how else do you keep people focused we're a fully remote company okay so now you've got my brain going on are there you know some sort of virtual sticky notes that you could get people to put onto their uh to their laptops to remind
backgrounds yeah exactly yeah it's embedded into a lot of the documentation right so it's embedded into the the templates that I talked about in terms of when you know even everything from sort of the way we structure that Opa uh document that folks are are going to be
you know working on and debating to when they go to create the actual sort of PRD you know when teams come in to present as part of you know sort of our our product reviews you know we sort of we have a we have a template that sort of keeps reinforcing who's the Target
customer who's the target user within that customer base what are their needs and how are we going to solve their needs you know better than any alternative that there is on the market so I think there's lots of different kind of reinforcing uh mechanisms to to that Focus I feel like sometimes things
like that come from like a big problem the company had and then it like yo you index way the other side like Focus here's the four people we will build for it becomes like instilled in the culture and I think you're right right I mean because Cal only started as such a
horizontal product which was amazing because that's how it grew so virally right and so it had the entry the wedge into scheduling and how we sort of our first horizon and becoming the best horizontal scheduling automation platform was because we had that horizontal focus and so it was it was a
blessing but as we think about sort of transitioning to Horizon 2 which is really about deepening our support for these you know teams and departmental users as well as verticals that's I think the inflection Port where we said in order to to shift us from Horizon one
to Horizon two we need to be making some some real trade-off decisions and we need to create this Focus so that we can actually allow teams to go do that so I think it's actually it's a really good point we sort of had to create Clarity around Focus because we were trying to
make shift from broad horizontal platform serving lots of users to a deeper investment into specific users and specific teams of users within departments before Gallery you were at box before that you're a glass door I'm gonna ask two different questions you can pick which direction you want to
go what would you say are kind of the biggest differences culturally between these three like if you had to bucket here's how I describe plaster box countley or what did you take from those two places that kind of that you bring with you to calendly and future
opportunities I love this question so they're all different um which is why I just feel so fortunate to have had experiences that were we're all quite different so starting with box maybe I'll take your second question box when I joined we were in the process of
moving up market and trying to capture as much Enterprise market share as possible and I was on the Enterprise product management team so I spent a lot of time as I mentioned earlier talking to customers in in my first year in particular trying to ramp on the business and I'd say my biggest learning
during that time was around how to ask the right questions to really understand the why behind what a customer was asking for and then figuring out how to build a solution to their problem that would also meet the needs of a broader swath of customers it became very clear
early to me if I would just go build what customer a wanted and what customer B1 and a customer C wanted Not only would that be you know wasted effort to do it three times but more importantly what they wanted me to go build was going to have a negative impact on the
end user experience and preserving that end user experience was so critical so you know learning how to ask the right questions to understand the actual problem and then build the solution that's going to be most scalable to that problem set across lots of customers was
probably my biggest learning from box moving to a Glassdoor totally different business model right Glassdoor is actually really more of a consumer business and you know 60 million unique users go to Glassdoor everyone then it's a it's a Marketplace between job Seekers and employers and it's highly highly
dependent on the consumer engagement right growing traffic getting that traffic to come and engage and apply to jobs and so during my time as CPO there I was responsible now for both sides of that marketplace right the consumer business and the B2B and so I learned
all about you know sort of how do you build consumer products how do you think about optimization of a funnel how do you think about building up a growth team and and growth as a discipline how do you use data and a b testing to make decisions so I think that kind of
consumer mentality and how you approach product I then have brought with me to Cowley which is really a blend of both right uh calendly is first as we've talked about a plg business and it looks a lot more like a consumer business like glass doors and then it's got this
direct selling business that looks a lot more like boxes Enterprise business so I think I've been able to take kind of lessons learned from both box and Glassdoor and kind of apply them together to calendly but a cool set of experiences I'm trying to imagine using all three in the same day sending
accountantly storing your files in a box looking at reviews and recruiting and recruiting yeah yeah not looking for anything new okay final question you're part of something called the skip Community which I believe nikhil and a few people run and so I'd love to just hear a little bit about that and maybe
how folks can join if they uh might be a fit yeah as you mentioned about about two years ago nikhil uh who is the former CPO at Credit Karma and is now a vpa product at meta got a small group of cpos together who were all kind of going through similar phases of companies
growth right late stage growth companies and you know we all were facing the same challenges in our roles and and he kind of formalized this community as a way to help us kind of gather advice from one another you know talk through how to manage challenges we're facing and just
make us more successful in the roles and we always joke you know we're like the support group we meet on Sundays and it has been incredibly valuable as I've sort of you know gone through the last couple of years in my role at calendly since then we've grown the group to
about 23 heads of products and cpos and expanded the charter a bit which I think is interesting to kind of help product leaders not just be safe successful in their current role but also how to think about setting them up for success in the role after this right and so we're
experimenting with a couple different interesting ways to help product leaders grow one of them is you know we're actually partnering with some companies right now to experiment with how can we help them as they're looking to make their first head of product higher or
their first CPO higher really hone in on what they're looking for and partnering with some Talent Partners we know to really have to try to increase the success that they find the right candidates that's something interesting we're doing uh we also launched a recently launched a podcast covering
some topics like you know how do you manage the next job search how do you avoid burnout breaking down things like equity and other kind of you know timely topics and then also we just have a we have an active Discord server where we've got all sorts of channels from
topics like how to you know manage the CEO CPO partnership compensation uh you know even sharing planning uh even sharing some advising opportunities or other CPO roles that you know kind of come across our radar so it's been a really really really cool kind of
experiment to see how the power of the community I know any of you do a ton of stuff around Community you know how that has helped all of us I think is just more effective in our roles and feel like we have a group of people who are behind us supporting us during you know what is a very hard role
I love this I imagine when people look at a CPO they imagine they just like know everything already they have a bunch of friends in the same role but I think in reality it's like kind of a lonely role a lot of times and so I could see the power of something like
this just to help people understand who who would be a good fit for this how do they go find it and yeah what's like the site and the best thing to do is just follow the skip community on LinkedIn and then you know we're you know sort of targeting sort of head of products that
you know call it series BEC and Beyond up to you know late stage growth companies and up to cpos so I'd say start by kind of following the skip community and if you see folks in there who are in the group you know reach out to them to get a sense of what it's like and what it would be like to join and
then it sounds like if you're a company hiring a CPO maybe reach out to or yeah that'd be great that'd be great yeah okay and they do that by going to LinkedIn also and looking for the skip Community yeah that'd be great okay cool we'll put all the links in the show
notes as well well with that we've reached our very exciting lightning round I've got six questions for you are you ready let's do it what are two or three books that you recommend most to other people playing to win so I I referenced that one earlier good to
Great uh and hooked awesome what's a favorite other podcast that you enjoy other than maybe this podcast I think I got introduced to you by Harry from the 20 BC I think but if not either way I'll cross promote his podcast uh which is a great one yeah Harry is responsible for this podcast I was on
his podcast and he's like Lenny you gotta do it I love it he's the Godfather of this podcast yeah that's great what's a favorite recent movie or TV show and you cannot say wait Lotus I have two young kids so whether I like it or not sing too uh it's a great movie
especially if you have young children sing too so it's like the second of sing it is it is distinct from sing one sing two is better it's better okay cool I haven't I haven't seen them I I would hope you haven't okay cool favorite interview question that you like to ask
people you interview talk me through your biggest product flop uh what happened and what did you do about it what do you look for in an answer what's like a sign of something good in their answer people being brutally honest around how bad it was and why it failed
you know the rest of the interview they're trying to tell you all the wonderful things they did and all the accomplishments they had and so I think the RAR the answer in terms of how bad it was and why the better awesome next question I think you might have answered voter's top five SAS products
used day to day either at work or home whatever slack Miro Loom pendo and Confluence awesome and these are like actually unlike other people's answers so that's really interesting kind of a unique stack you got there I love it final question what's your best calendly pro
tip yeah so 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 fly to like an event type and tweak things like title or duration or you know override a date uh based on the person you're
actually sending it to without having to go create a brand new event type just to make one small change based on the recipient so it's kind of that you know one-off use case where you need to make a little bit of a change on the Fly depending on who you're sending it to
but you don't want to go through the effort of creating a brand new event type so I'm loving it and you should check it out that is awesome I even need that I find that I need to block dates out and change times and I just like go do that on my calendar versus accounting
there you go okay all right Annie this is amazing we learned a ton about Callum Lee growth product building two final questions where can people find you online if they want to learn more and reach out maybe ask some questions and two how can listeners be useful to you
finding me best place online is LinkedIn and then in terms of uh being helpful to me one we're hiring at calendly so explore open roles on the product team at calendly if you're interested share any feedback for me on this episode at a DOT Pearl calmly.com and then as we
talked about would love to have you follow the skip community on LinkedIn as well awesome we'll have all those links in the show notes Annie thank you again for being here so which Lenny hi everyone thank you so much for listening if you found if you found this valuable you can
subscribe to the show on Apple podcast Spotify or your favorite podcast app also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at lennyspodcast.com see you in the next episode