00:00process by definition is variance
00:03reducing like you're introducing it
00:05because you worry that the variance in
00:08your org is too high like you want
00:10people to sort of meet a certain
00:13and the cost of that is obviously while
00:15you're reducing the standard and
00:17bringing Folks up to the average you're
00:20also bringing other folks down to the
00:22average and oftentimes the folks are
00:24bringing down are your highest
00:27performers your most creative thinkers
00:28the folks who like you know I think
00:30actually don't really need process to do
00:35that I think is always the tension that
00:38you have with process and obviously like
00:39one of the reasons why companies
00:41introduce process much more and more as
00:43companies get bigger is because it's
00:44just it's harder to sort of like get all
00:46these folks who kind of don't need
00:47processing you actually want to reduce
00:52welcome to Lenny's podcast where I
00:54interview world-class product leaders
00:56and growth experts to learn from their
00:57hard-won experiences building and
00:59scaling today's most successful
01:00companies today my guest is AKA
01:03demilliano Aika is head of product at
01:05retool prior to that she was a long time
01:07piano at the stripe she was actually one
01:09of their very first PMS where she helped
01:11build some of their foundational
01:12products like stripe checkout stripe
01:14connect stripe radar and stripe
01:16chargeback protection I had a total
01:18blast chatting with Tika we covered
01:20Stripes internal culture and what makes
01:22it so unique and Innovative how to
01:24Foster and protect Innovation at your
01:26own company what is the right amount of
01:28process by stage of company how to build
01:30a talent portfolio and so much more I am
01:33really excited for you to hear this
01:34episode and with that every bring you
01:36AKA de Emiliano after a short word from
01:38our wonderful sponsors
01:41today's episode is brought to you by
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01:54love for me to have on in 2023 and while
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01:59shared space to work closely with your
02:01colleagues to capture ideas get feedback
02:03and iterate quickly and easily on
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02:08strategy by brainstorming with sticky
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02:32get the picture head on over to miro.com
02:34Lenny to leave your suggestions that's
02:41this episode is brought to you by notion
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03:29today again at notion.com Lenny's pod
03:36hey welcome to the podcast thanks so
03:39much for having me Lenny it's absolutely
03:41my pleasure a bunch of people have told
03:42me that I need to have you on this
03:44podcast and actually a big thank you to
03:46sneer kodesh who I believe is a
03:48colleague of yours who gave me a bunch
03:50of interesting questions to ask you so I
03:52hope you're ready awesome very ready uh
03:54sneer is the best so yeah excited so
03:57you're currently head of product at
03:59retool but before that you spend a lot
04:01of time at stripe you spend six years at
04:03stripe and so before we get to retool I
04:06actually want to spend a little time on
04:08to set a little Foundation could you
04:10just talk about some of the things you
04:11worked on at stripe and maybe some of
04:13the things you're most proud of during
04:14that time yeah so when I draw stripe I
04:17joined stripe in 2013 it's pretty small
04:19the times around 50 people and stripe
04:21didn't have any product managers at that
04:22time and I think struck is kind of
04:24famous for that and it really wasn't
04:26because you know we were anti-pm in any
04:29way it was mostly just because we're
04:30building this product for developers we
04:32had a lot of really talented Engineers
04:34who were essentially doing the PM job so
04:37I actually joined stripe as the first
04:39account executive which I think is
04:42pretty funny now that I've seen you know
04:44real account Executives do their jobs
04:46because I really just had no business
04:48doing that job but it also really wasn't
04:50your typical sales job and that most of
04:52Stripes volume was inbound so I was
04:54really just spending all of my day
04:55talking to customers helping them figure
04:57out how strike might work for their
05:00particular business flows and payments
05:02models and a lot of it was I think you
05:04know what PMS do it's just like talking
05:06to customers understanding their pain
05:08point and really help them figure out
05:10how the product might do that so and to
05:12this day when people ask me hey like
05:14what's your advice for going into
05:15product management I'm like well you
05:17should go get a sales job I think it's
05:19like pretty pretty valuable
05:21but it's kind of a long story uh to
05:24explain that at the time there were uh
05:27there's this one sort of business model
05:28this did the two-sided Marketplace
05:29business model that was really it was
05:30just becoming huge and yeah like you can
05:32even remember you sort of imagine that
05:34now but like back then like Airbnb Lyft
05:36Uber all those marketplaces it was quite
05:39a new way of of doing business and so I
05:42was talking to all these customers and
05:43they had like pretty complicated
05:46payments needs so you know if like one
05:49putting in funds and it's getting paid
05:51out to a recipient so an Airbnb guest
05:53and an Airbnb host or multiple payers
05:56putting funds in and it's getting paid
05:58out to one recipient like a GoFundMe
06:00campaign or one payer putting in money
06:02in it going out to multiple recipients
06:04like you know with class tasks where you
06:06get a subscription and then it gets paid
06:07out to a bunch of a bunch of Studios so
06:10and then on top of that all these
06:12platforms and Marketplace has started
06:13having all these pretty complex
06:15Regulatory and compliance requirements
06:17that were pretty different country to
06:18Country so it's just this like really
06:20complicated Financial infrastructure
06:22problem and stripe actually didn't
06:24really have the right solution for it
06:26and no one else in the market did either
06:28so at this time this stripe engineer
06:31Brian Krause started pokering around in
06:33this problem because I was talking to so
06:35many of these customers we started
06:37talking about this prom together and
06:38poking around and that actually resulted
06:40in us launching this sort of evolution
06:43of this product that we had at the time
06:44called stripe connect that was easily I
06:47think you know one of my favorite
06:48products I worked on on not only it
06:51ended up actually being really quite
06:52significant for Stripes business but
06:54also because you know it was the first
06:55product and I think that's always always
06:58and then the the second product that I I
07:01think of very fondly during my time at
07:03stripe is this product stripe radar so
07:06you know stripe obviously processes a
07:07lot of payments wherever there's money
07:09fraudsters will kind of follow and there
07:12were certainly some Merchants who were
07:14just particularly vulnerable to payments
07:16fraud so someone's using stolen credit
07:18card information to since she purchased
07:20the good and if you're not in payments
07:22that this is gonna maybe sound kind of
07:24shocking but if a merchant processes a
07:29payment from a customer and that
07:31customer used a stolen credit card
07:34the merchant is ultimately on the hook
07:36for those funds so it can be yeah it can
07:40be detrimental like the merchant who's
07:42trying to you know run a real business
07:43is just losing all this money because
07:45they're all these fraudsters who are you
07:46know buying stuff from them online so I
07:50really like working on that product so
07:51that the product of stripe was
07:52essentially uh we built a bunch of
07:54machine learning models to try and
07:56predict when a payment was fraudulent
07:57and then we built a product on top of
07:58that to help customers understand why we
08:01were blocking payments and help them
08:02sort of write their own rules around
08:03that too that was really fun both from
08:06like anthropological perspective because
08:08we were kind of hanging out in corners
08:09of the internet where you wouldn't
08:11usually go if you were doing only legal
08:13things so you're trying to understand
08:14who these frosters were but it was also
08:16really cool from a product perspective
08:18because of all the I think kind of
08:21complicated product questions around how
08:23humans should interact with AI and
08:25models and yeah I imagine a lot of the
08:27folks in the sort of latest movement in
08:29AI are thinking a lot about that too
08:30it's like how do you explain a model to
08:32humans how do you let them interact with
08:33it so both those things were really
08:37I actually use stripe for my newsletter
08:39it's how you know folks subscribe and
08:41when I log into my strike Dash stripe
08:43dashboard and there's so many products I
08:45don't even know what many of them do but
08:47I've often seen radar been pitched to me
08:49as a something I should pay for uh nice
08:53yeah I feel like I should probably turn
08:55it on that sounds really useful
08:57um one thing that I want to dig in on so
08:58you said when you join there were no PMS
09:02how many PMS were there when you moved
09:04into products at stripe that's a great
09:07question I want to say maybe like three
09:09or four wow incredible and I know you
09:13said stripe is kind of known for being
09:14really late 2PM and kind of like I don't
09:16know if I want to say anti-pm but there
09:18was like a lot of sense why do epms we
09:19have amazing Engineers who can decide
09:21what to build is there anything you can
09:24share around just that General
09:24philosophy of stripe and was it
09:28effective was it good because a lot of
09:30companies are anti-pm and I think they
09:32always point to stripe and snap is
09:33another example of like we don't need
09:35PMS look how far these companies got
09:37with ipms is there something unique to
09:39stripe that allowed them not to fpms I
09:41think it was like 200 employees probably
09:42by the time they had their first pm I
09:44think we actually had our first payment
09:45I want to say it about 100 employees
09:47okay um but but yeah I know it was it
09:49was late in the game and actually maybe
09:52just sort of to pattern match ritual
09:54also didn't really have PMS for a while
09:57and I I think actually both in the
09:58stripe case and the retail case the the
10:00thing that both of these companies have
10:01in common is you're building for
10:03developers the people who are building
10:05the product are the customers in a lot
10:07of ways so like they get it you know
10:09there's there's really no no reason why
10:11you should have sort of some in some
10:14ways like a middleman trying to figure
10:15out like hey who's the customer and what
10:17is it that they need and whether they're
10:18pain points and I think the the moment
10:20at which it became clear like we really
10:21do need PMs and stripe and I think we
10:24felt the same way retail is your
10:26customer base starts expanding you start
10:27having different kinds of customers you
10:29need to understand sort of the whole the
10:31whole Market all of all of the icps that
10:34you're going after and the organization
10:36gets more complex I think stripe gosh in
10:39particular it's just an extremely Matrix
10:41organization in business because every
10:43time you launch your product you're
10:44having to think about well how do we do
10:45this in other countries it's different
10:47Financial infrastructure how do we think
10:49about the legal side the compliance side
10:51Etc and I think PMS could really kind of
10:53bring that whole story together and make
10:56the whole machine move and you know in
10:58addition to sort of understanding the
11:00customers and and the value prop and
11:02like what the overall strategy was
11:03it's a really good reminder of
11:06engineers and designers can do the work
11:08of a PM but often they don't want to
11:10it's like there's a lot of non-fun parts
11:12to it they're like I wish we could have
11:14someone here to do these things npms
11:16enjoy that work they're good at it and
11:19So eventually engineers and designers
11:21realize okay I see I see why maybe we
11:22should hire PM I say this often actually
11:24to folks who are thinking about going
11:26into product management it's like that's
11:28awesome just be really really sure about
11:31what you're signing up for
11:33it's kind of the same like eating a lot
11:35of people want to become a manager but
11:37just so you know like being a manager is
11:39like hey you're like you're doing
11:40performance reviews a lot and you're
11:42like you're in one-on-ones a lot and
11:43like you have to really love that kind
11:45of work and I think the product
11:46management case also like you're just
11:47you're constantly working across a lot
11:49of different teams you're trying to
11:50influence a lot of people who don't
11:51report into you directly to do a bunch
11:54of stuff and if you love that that's
11:56great but like you know you've got to be
11:58sure you you know you're signing up for
12:00it yeah that's a really good comparison
12:01I when I first became a manager I was an
12:03engineer actually and I was managing
12:05engineers and then when I moved on to
12:07something as an IC engineer again I was
12:09like I will never manage again that was
12:10no fun at all why but I want to do this
12:13and I imagine people get into product
12:15thinking they're gonna have all this
12:16control Power influences and they're
12:18like oh my God this job is so freaking
12:19crazy what did I say it's so hard yeah
12:23that reminds me something that I heard
12:25you did at stripe is you wrote their
12:27internal culture guide it was like a
12:29quick start guide to culture at stripe
12:31that I think was maybe shared with early
12:32employees and if that's true I'm curious
12:36what it is about Stripes culture if you
12:38could just I don't know briefly share
12:40just like what makes Stripes so special
12:41clearly it's one of the most successful
12:43companies in the world in history I know
12:45there's been a you know slow down with
12:46the market everyone's slowed down a bit
12:48but it feels like stripe has been
12:49incredibly successful continues to
12:52it hires incredible people people that
12:55are starting amazing companies so I
12:57guess back to my question what is it
12:58they think that makes Stripes culture
12:59unique and special yeah the quick guide
13:02to Stripes culture I think we wrote it
13:05um maybe we were around 150 people or so
13:07and we actually wrote it to share with
13:09candidates because we yeah the idea was
13:12like look we have like we're kind of
13:13opinionated about how we do things here
13:15most companies struggle to to describe
13:19what their culture is like how does a
13:20fish describe water but it's worthwhile
13:23getting a sense of sort of the things
13:25that that we feel opinionated about and
13:28that you might like or you might not
13:29like and actually when we when we put
13:32out the guide our metric of success was
13:36that more of the right people would
13:38apply to stripe and fewer of the wrong
13:40people and there was you know there was
13:42a whole section in there I was like hey
13:43look we work pretty hard here and that
13:46is certainly not for everyone and and
13:48you know hopefully you're excited to
13:49come and work really hard with like
13:51really with colleagues who really care
13:52and that's kind of the reward but
13:54um so that's maybe one example
13:56on Stripes culture and and what what's
13:59made it so successful I've I've really
14:01been thinking a lot about were there you
14:03know one or two pivotal points or
14:05decisions for stripe that it really set
14:09it on its its path to success
14:11and I don't think there are actually
14:14like every time like well if this hadn't
14:16happened I can always sort of like
14:17reason my way into like I think these
14:19other things would have happened and you
14:21know strike would have kind of ended up
14:22in the same place so I think what stripe
14:25was actually particularly good at and by
14:28the way you should take all this with
14:28the humongous green assault because I
14:30haven't worked there and you know since
14:312019 but at least my experience when I
14:34was there with stripe was really good at
14:36was just making not just like one or two
14:38big decisions good decisions was like
14:40making a lot of really good decisions
14:42all the time big or small and that I
14:45think was quite cultural like there was
14:47this just humongous respect and
14:50enthusiasm for thinking like it was just
14:53just like a it was such a part of the
14:55culture that was you know one of the
14:56values was think rigorously like every
14:59meeting was very much like Hey how do we
15:01how do we think about this thing from
15:02first principles no one would ever say
15:04for example it's a best practice to do X
15:06like people be like well why like you
15:09know you you have to kind of go a few
15:10levels deeper so that was that was I
15:13think one piece the other piece and a
15:16lot has been written about this already
15:17is stripe had a very strong writing
15:19culture all communication was along from
15:21writing business reviews strategy memos
15:24product reviews there's just there's a
15:25lot of writing that happened and I you
15:27know I I very strongly believe this I
15:29don't think you can be a good writer
15:30unless you're a clear thinker
15:33um and if you couldn't write well I
15:34think it was actually pretty hard to be
15:35successful at stripe at least in the
15:36early days so I think stripe just
15:38cultivated a lot of really good writers
15:40and you know by sort of by sort of input
15:42into that a lot of really good thinkers
15:44and then I think the last bit stripe is
15:46really good at was not overthinking
15:48decisions because that's kind of the
15:49flip side of of this sort of like really
15:51rigorous approach is that you like lock
15:53yourself into a room like can't come out
15:55for five days and you have to like be
15:57good at making a lot of decisions and
15:59write decisions quickly and one of the
16:02things that that we would always sort of
16:04kick around a lot was this like idea of
16:05is it a trapped or decision which I
16:07think is a an Amazon concept it's like
16:09the one if you make the decisions is it
16:11like one door or is it is it two doors
16:14um like can you come back from this
16:15decision and I thought stripe was
16:17actually really good at being rigorous
16:19you know back to the rigorous point
16:20about what actually was a chapter
16:22decision so like I think a lot of people
16:24for example think pricing is a trapped
16:26but actually like it's really easy to
16:29grandfather your existing users into
16:32some existing pricing model and change
16:34pricing for future users and if you
16:36believe that the product is going to be
16:37successful your early users are only
16:39going to be a fraction of that pricing
16:40model and yeah the product's not
16:42successful then you know who cares if
16:44you change the pricing model so I think
16:45I think that's a really good example of
16:47like people think that's a trapped or
16:48decision but actually you can move much
16:49more quickly on that decision than you
16:51think and then decision that was
16:53definitely felt to us like very much
16:55like a chapter decision they think
16:56stripe took a long time being really
16:58rigorous about was titles anything
17:00Stripes kind of famous for not really
17:04I think it was right to be rigorous
17:05around that decision because you can't
17:06like once you've given someone a title
17:08you can't really take it away so you
17:11know you better be damn sure about you
17:13know the title you want to give someone
17:15yeah the titles are hilarious I uh put
17:18together a career ladder doc of all
17:21leveling names across all the big
17:24companies and that's like a lead product
17:27manager product manager product manager
17:29product yeah and there's like a lead
17:30here and there like yeah like VPS are
17:32basically product manager or product
17:35leader something like that yeah
17:36hilarious you talked about this idea
17:39first principles people talk about that
17:42often as we want to be first principle
17:44thinkers we're going to think from first
17:46principles how did stripe actually
17:48operationalize that Implement that was
17:50that just like founder top down continue
17:52questioning people and that trickles
17:54down was there anything else they did to
17:55kind of instill that mentality I
17:57definitely think it's founder top down
17:59they were really good about hiring
18:01people who thought that way too so it's
18:04just all that stuff it just really
18:05really trickles and actually to this day
18:07when I'm preparing like a memo or like a
18:11board deck or something I imagine in my
18:13head I'm like what if I had to present
18:14this to Patrick and and like my ideas
18:16just get so much better because it's
18:19just like sort of I know like you can
18:21kind of think about sort of the
18:22questions they would ask so I think that
18:24was one you know I think the other one
18:25was just to Surf this writing culture
18:27piece like people would just like once
18:28you start writing things down you
18:30realize like hey that actually doesn't
18:31make a lot of sense and then I think the
18:33the third thing actually was there was
18:36just always a lot of questioning about
18:37like the status quo so if something had
18:40been done in an industry for a long time
18:42people would always be like well why was
18:44it done that way and I mean I think this
18:46kind of actually how stripe got its
18:47start right like I think when Stripes
18:49started if you want to set up a merchant
18:50account it could take weeks and everyone
18:52just assumed like that's that's what it
18:54took and yeah of course John and Patrick
18:56were like well it doesn't actually make
18:58that much sense why it should take that
19:00you shared some of the values I don't
19:02know if they're just called values core
19:03values at stripe but is there other ones
19:05you can share you said one is think
19:07rigorous or don't ever think yeah I
19:10think rigorously was one and
19:12they might have actually sort of updated
19:13these on the on the website recently so
19:15my recollection is is very likely out of
19:18date and the stripe would call them
19:20operating principles actually which I
19:23think is actually better because values
19:24is almost like you can't really tell
19:25people what to Value like everyone has
19:27their own value set but you can tell
19:28people like hey here's here's how we
19:31operate another one that I loved was
19:33move with urgency and focus
19:36it was just really this idea that you're
19:39kind of your your biggest compatriot and
19:40your biggest I think enemy as a startup
19:42is time so like you just you have to
19:45move like really really really fast on
19:48it and customers first was the other one
19:50or users first as the Zeo stripe would
19:52refer to customers as users so those are
19:54some of my favorites when I think back
19:56to what made Airbnb special in a similar
19:58way the values we call them core values
20:00I think we're actually really really
20:02important and turn the company into what
20:05it ended up being and it's actually
20:06there around the time they created these
20:08values I'm curious at stripe do you have
20:11any recollection of just how they came
20:12to these operating principles because I
20:15imagine Founders are listening really
20:16how do I how do I come up with these for
20:17our company I'm pretty sure Patrick
20:21um yeah I think they came from Patrick
20:23and John wrote them the other actually
20:26the other value that I love I don't
20:27think they have it anymore but so go to
20:29the operating principles micro
20:31pessimists macro optimists wow yeah it
20:35was just like this idea that like look
20:36long in the long term we expect the
20:38curve to go up like we believe like you
20:40know we very much believe in the upward
20:41trajectory of just about everything but
20:43like on the surf day-to-day decisions on
20:46the magnesia we're like we're quite sort
20:47of critical like we'll like how do we
20:49make sure this thing works and like you
20:51know we think about all the ways in
20:51which it doesn't work so zooming out a
20:53little bit we've been talking about
20:54stripe we told also is a very first
20:57principles Innovative company something
21:00that I think of when I think of retool
21:01is during the wild Market Days of long
21:05ago last year I know retail is very
21:08conservative in how they raised money
21:09and the valuations they raised at which
21:11looking back ended up being a really
21:13good idea while everyone's raising it
21:14like 100 billion dollars I think their
21:16last round is a few billion and it's
21:19like a very reasonable conservative way
21:22to think about fundraising and so I
21:24guess just thinking about innovation in
21:26general why do you think some teams are
21:28able to run like Innovation machines
21:30continue to put out new products disrupt
21:32Industries while other companies kind of
21:35plot along stay conservative is there
21:37anything you've seen something you bring
21:39to teams you work on to help Foster
21:41Innovation and big thinking yeah I
21:43actually think about the the extremes of
21:45that question so so not you know why are
21:47some teams Innovative but like why isn't
21:49every team Innovative like I think no
21:52one wakes up in the morning and thinks
21:53like yeah today I want to work on like
21:55boring incremental stuff but most teams
21:59do end up working on like pretty
22:00incremental stuff I always wonder like
22:03what is it that's stopping folks from
22:05being creative and and thinking bigger
22:07and I think it comes down to like a
22:09couple of things that you know companies
22:12sort of unwillingly or not even sort of
22:14realizing it and one is this fear of
22:16failure like I think leaders want the
22:18upside of innovation but they're not
22:20really willing to deal with the cost of
22:23innovation which is like look if you're
22:24gonna swing big you will invariably
22:28so you know I think if you want to
22:31mitigate that you have to start Shining
22:33Light on failure that's that's really
22:35the only way like you have to start
22:36normalizing it a little bit and
22:38obviously like if an individual or if a
22:39team is like consistently failing and
22:41not learning that you need to you know
22:44you need to sort of deal with but I
22:47think sometimes it's it's good to fail
22:49so you know like and and when when you
22:51do feel it like use it as an opportunity
22:53like don't squander that moment to to
22:55not learn but yeah I think like one one
22:58example is you know instead of calling
23:00something a postmortem called a
23:02retrospective so that it's kind of a
23:04positive thing like hey we're learning
23:06and then I think the other way to kind
23:08of mitigate the feel of failure is like
23:09you have to figure out how to give folks
23:11more at bats because like obviously
23:13anything that takes one year to ship and
23:15you like haven't gotten any customer
23:16feedback like the stakes of that are
23:18just gonna feel so so high like any like
23:22if you get it wrong it's it's gonna be
23:24devastating so you have to figure out
23:26how to lower the stakes and I honestly I
23:28think that's in some ways it's kind of
23:30easy it's like look don't put too many
23:31resources against these kind of like
23:32bigger swings like have them be small
23:34teens and then also like just get
23:36customer feedback as quickly as possible
23:38like don't wait until the thing is
23:40perfect and that way you can kind of
23:41yeah like limit the limit the risk so
23:44yeah I think that's fear of failure
23:46that's that's definitely one thing that
23:47stops teens from being innovative
23:49there's kind of a like a I think a very
23:51practical one like sometimes teens are
23:53just getting bogged down by like really
23:55urgent work like there's just too much
23:57Tech debt there's too much product debt
23:59bugs instability it's like massive
24:01hierarchy of needs like there's just no
24:03way that they're going to be able to
24:04focus on the like you know the
24:07enlightened like bigger creative stuff
24:09if they're just like heads down dealing
24:10with incidents all day so if that's the
24:12case like yeah like yeah
24:14diagnose it and and get your team out of
24:17that and then I think the the last
24:19reason why teams aren't always that
24:22Innovative is because I think thinking
24:26and to some people it comes pretty
24:28naturally but for most of us sort of you
24:31know mortal Souls it's it's just really
24:34really hard and it's it takes time and
24:37when you're at a startup and you're just
24:39grinding day in day out you're just like
24:41you're just trying you're treading water
24:42you're just like trying to make it
24:43through the day like
24:45taking the time to really think about
24:47you know the strategy and like where
24:49things should go and and get creative
24:52it's pretty hard so I call this you know
24:54you have to give teams permission to
24:57so create these moments in your company
25:00culture in your overall business
25:02processes where you're asking people
25:04you're literally saying like hey this is
25:06part of your job to to think bigger so a
25:10ritual we have these team Charters and
25:11we do Team Planning and at the bottom of
25:13every team charter we have a section
25:14called think bigger with you know 20
25:17more time what would you do that isn't
25:19on this list already
25:21and then another thing really neat
25:23tradition that we had at Stride we have
25:24a retail now too is this uh idea or this
25:28this thing called crazy ideas so at the
25:30beginning of every year David will send
25:35like a blank dock to the org and it's
25:38titled crazy ideas and the prompt is
25:41crazy ideas are ideas that we shouldn't
25:44obviously do there's a 90 chance that
25:47they make no sense but in the 10 chance
25:50that they do they will make you know 10
25:51to 100 x difference for the regional
25:53business and then it's just it's
25:55literally just a call a request for
25:56crazy ideas and the org loves it it's
25:59it's amazing the energy around it is so
26:01cool and it's it's not just product
26:04ideas it's different ways of of how we
26:07should run our organization or like so
26:09it's like really cool marketing ideas in
26:11there so it's just that Doc is awesome
26:13and whenever I have like a down day I
26:15just like scroll through that dock I
26:17know that you launched three different
26:19products this year which I want to talk
26:20about which maybe came out of this big
26:22thinking but a couple more questions
26:24just to dig into some of the stuff you
26:25just shared one is this big Dock Of
26:27Awesome ideas what's come out of that
26:29because you know I think of like
26:30hackathons and people have all this
26:31energy and it's exciting and then I get
26:33all these cool things and then they
26:34don't go anywhere do things come out of
26:36this there's Elite actual ideas that
26:37people yeah yeah yeah every so every
26:40year that we send out the dock we look
26:41at the past year the doc from the past
26:43year and we're like okay like did what
26:45did we do anything on this list and like
26:46consistently we do anywhere between
26:48three to things on the list wow yeah is
26:51there an example a product that launched
26:52that came from that list that comes to
26:54mind actually probably at least one if
26:56not two of the sort of three products
26:58that we launched this last year were on
26:59the crazy ideas list at one point like a
27:01year ago if you'd ask me what is
27:02Rachel's product I you know I would have
27:04told you ritual helps you build internal
27:06front ends really really fast
27:09but you know if you were trying to like
27:12schedule a query to run at a later point
27:15in time or have something Trigger or you
27:17know uh run an ETL task like you
27:20couldn't do that in retool so that was
27:21actually one of the crazy ideas and and
27:23that ended up becoming ritual workflows
27:25which you know we launched just last
27:26year November okay we're definitely
27:28going to chat a bit about that I want to
27:31go back to the two other suggestions you
27:32had one is Embrace failure make it okay
27:35to fail and then two don't let people
27:37get sucked into urgent stuff and have
27:40time to focus on important stuff
27:42is there an example of just like how to
27:44help people Embrace failure you talked
27:46about retrospectives is there anything
27:48else just like that you found works
27:51either as a tactic as a process as a
27:54framework just to like help people get
27:55out of it because you know I hear that a
27:57lot like Embrace failure and then people
27:58like oh but I failed and you suck so
28:00yeah is there anything else along those
28:01lines you found effective to create that
28:03feeling to me it's always in the
28:05follow-ups so like you know have people
28:08talk about the failure in like these
28:10sort of public forums where usually you
28:11talk about the successes so like have
28:13someone actually like write a note
28:15that's like hey here are all my
28:16learnings from this thing that we did
28:17and send it to the org at every tool we
28:19have a shipped at email list like if you
28:21ship something you know you'll listen to
28:24that have them send that email to the
28:25org and it's it's just kind of an
28:28awesome way to celebrate or have them
28:29present at all hands and share what they
28:31learned and it almost always sort of
28:34results in I think a really positive
28:36twist at Airbnb there was I think for a
28:39period there's an award for the biggest
28:40failure like project really that's so
28:43cool you like a trophy or something yeah
28:44it was like a short-lived yeah yeah yeah
28:47and then on the second bullet point of
28:51urgency creating giving people a chance
28:53to think longer term is there anything
28:55there that you found to be actually
28:56effective to create that culture and
28:58give PMs and product teams a chance to
28:59think longer term and not just be stuck
29:01in the fires that they're dealing with
29:02there's a couple of top-down things that
29:04I think a couple of Bottoms Up things on
29:07the top down I think sometimes you just
29:09have to be willing to fund some someone
29:11with something like they come to you
29:12with an idea and you're like look yeah
29:13like take an engineer and and go do it
29:16and you just have to kind of give folks
29:18that that sort of organizational buy-in
29:20like actually I was thinking back to
29:22that that engineer Brian Krause at
29:25stripe who started you know kind of
29:26poking around on these on this
29:27marketplaces model and
29:29I was thinking like I can't remember a
29:32moment when someone formally said to him
29:33this is now your job like I think he
29:36just kind of went and looked and and
29:38went and and dug into and then at some
29:40point I think a manager was like all
29:41right this is now your job but yeah I
29:43know I I think you have to be able to
29:44sort of like fund fun folks's time and
29:47and give them that hackathons I think
29:49are like pretty good for that stuff it
29:51is kind of a moment for folks to to take
29:53a step back and then you know I think
29:56more than anything in people's planning
29:57processes like I really like asking
30:00folks you know like this or the 20 more
30:02time question or the other question is
30:04like look like if you doubled the team
30:05today what would you do that shows up in
30:07our planning processes as well and I
30:09think it really helps people kind of
30:10break out of this like I think you kind
30:12of end up planning towards the surf the
30:15team that you have not the team that you
30:16should have so I like how folks can
30:18break out of that process
30:20awesome I really like to think bigger
30:22bucket in your planning docs just like
30:23what would you do if you had more
30:24resources just maybe a quick question
30:26there is there like a bunch of detail
30:27that you asked them to put into that or
30:29is it just like a bullet point of Big
30:31just yeah folks can just go go crazy on
30:35it it's however they want to take it
30:36like yeah I've seen folks actually sort
30:38of like create entire demos but I
30:41actually think the trick is like less
30:42structure in those cases because you
30:44don't really want to pigeonhole or or
30:47make it even that intimidating for folks
30:49like if someone just wants to write down
30:50a few bullets that's great
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32:01your experiment velocity
32:03okay so you launched three new products
32:06this year usually companies are lucky to
32:08launder one product a year a few
32:10questions one just like tell us what
32:12those three were in case people are
32:13interested and want to check them out
32:14two is was that a good idea is it good
32:17to launch three new products in a year
32:19and then three what did you do
32:21organizationally to allow for this to
32:23happen because that feels really
32:24ambitious and rare and I'm curious what
32:26you learned from that so the three
32:28products we launched were women's retail
32:31workflows that you know I I talked to
32:33you a little bit about it's like if you
32:35want to be able to sort of essentially
32:37create a workflow like schedule an alert
32:39run a task you can kind of do it in the
32:41retail way where it's this visual sort
32:43of easier builder of creating these you
32:46know different sort of workflows but you
32:48can write your own code on top of it as
32:50second product is Rachel mobile so you
32:53could pretty easily build you know
32:55credit web apps with retool but there
32:58are plenty of folks who don't sit behind
33:00their laptop at a desk all day and you
33:03know for those folks who had a lot of
33:04companies who were like I want to be
33:05able to like a mobile native app and so
33:07we launched that product and then the
33:09third product was a virtual database
33:11um so yeah until very recently like if
33:13you came into retool you could connect
33:15your data you know via your apis your
33:18database directly into retool but what
33:20we found is that actually a lot of folks
33:22like either don't have access to their
33:24database or they're actually just like
33:25they're trying to build an internal tool
33:26and they don't necessarily want to store
33:27that data and their sort of production
33:28database so we built essentially like we
33:31spin up a postgres database for you and
33:33you can just access it via really nice
33:35UI and and manage it directly in retool
33:38amazing okay back to the other two
33:41yes okay so I think your second question
33:43was was this a good idea right
33:49you know what I think in hindsight if I
33:51if I were to do it again
33:54I think maybe sequencing it would have
33:56maybe been slightly better
34:00just because I think what we end up
34:01doing is we kind of ended up launching
34:04or launching the idea behind all three
34:05of these products at around the same
34:07time and they all ended up maturing at
34:10around the same time and that was just a
34:13lot of headspace from the org even
34:15though actually the teams themselves
34:16were not that big like it was just like
34:18you know we had all these products we
34:19were just waiting for them to launch and
34:21waiting for them to launch whereas like
34:23maybe if we sequenced it I think that
34:24would have felt probably also just more
34:26satisfying to the whole organization but
34:29I mean it ended up working out that's I
34:31think that's kind of the crazy thing
34:32it's like you know we we kind of were
34:34able to pull off launching these you
34:36know these three products and by the way
34:38I should caveat that you know the sort
34:40of the the further I get along my career
34:42the more I realize I'm just kind of
34:43building on the shoulders of giants and
34:45a lot of these ideas Etc were very much
34:46in the works and and were happening
34:48before I came along but um yeah it was
34:51really neat to see how he we got that
34:53all over the Finish Line in here
34:55and then the last question there is just
34:57what do you think you did to allow for
34:59this because it's pretty rare you can
35:01build so much and I know the team's not
35:03huge right like how many people work at
35:04retool roughly today we run 300 people
35:06yeah so how do you structure an orc to
35:10build three and launch I didn't realize
35:11they launched around the same time it's
35:13like I'm picturing uh Elon Musk
35:15launching three rockets at once how do
35:17you uh how do you allow for that to
35:19happen yeah I'm sure a product marketing
35:25yeah a couple of things we we started
35:28really small with all these initiatives
35:29so yeah I think I mentioned we really
35:31had one or two people working on on each
35:34of these products for like the first six
35:37um so it was like one engineer and one
35:38designer or one engineer in one pm and
35:41they really didn't get funding until it
35:44was clear that there was something there
35:45so they just those teams just they spent
35:47a ton of time with customers it's been a
35:49ton of time building a ton of time
35:51prototyping and it was kind of the
35:53moment where I was like okay like
35:54there's a there that that we started
35:57sort of bringing more people onto the
35:59team so it's the first piece the second
36:01piece is that we really treated them
36:03like startups where like rituals the VC
36:05and like ritual funds with like
36:07resources and Rachel's existing customer
36:09base which is obviously quite valuable
36:10because you kind of have all these
36:12customers you can can Market to and
36:14promote to but then the teams really had
36:17to prove out Roi either in engagement or
36:22in order to be able to move forward and
36:25then the third thing and this one
36:28it can be quite controversial is we were
36:31really deliberate about keeping these
36:33teams separate from the rest of the org
36:36especially early on and now a lot of
36:38them are they're very much kind of a
36:40part of the overall organizational
36:42processes very early on they were kind
36:45of they're running on their own they
36:46were you know meeting quite
36:47independently it was like one or two or
36:49three folks from a leadership team and
36:52they were also just quite separate from
36:56like I think retail mobile is actually a
36:57really good example where we had a lot
37:00of debate about whether or not we should
37:02build retail mobile out of the core web
37:05app builder because a lot of The
37:07Primitives are the same
37:08and we eventually decided that we were
37:11going to run it as a separate team
37:12because we wanted the team to be able to
37:14move really really quickly and we didn't
37:16want it to get bogged down in what are
37:19just the realities of running a product
37:20that has product Market fit like you
37:22know bugs yada yada Etc and
37:25I think that was absolutely the right
37:26call because retail mobile actually has
37:29Target customer which we only really
37:31realize maybe like halfway through the
37:33project and I don't think we would have
37:34been able to sort of really understand
37:36that or even like sort of like Get
37:38broader in that kind of thinking had we
37:40sort of been been stuck in the the core
37:42retail product but yeah there's a cost
37:44to that too which is like okay now we
37:46have these two products and we have to I
37:47think obviously the strength will be how
37:49do all these products interact with each
37:50other and how do they build on top of
37:51each other so we have to go and invest
37:53in that now but I I think it's totally
37:55worth it because your team can just move
37:57more quickly be more independent and
37:58think more independently too
38:00in the time that you've worked at stripe
38:02and retool I know we chatted before we
38:05started recording you think a lot about
38:06what is the right level process for
38:09companies at different stages and I'd
38:12love to just hear your thoughts because
38:14I know I know that's a challenge a lot
38:16of companies face how much do we put in
38:18now do we get inspiration for big
38:20companies do we try to stay lean
38:22something here maybe actually run into
38:23I'll just mention briefly that there was
38:25a huge resistance to process for a long
38:27time and so the product team was just
38:29kind of a little crazy for a bit and
38:31then we're like okay we need product
38:33development process we need deadlines
38:35and just specs and and that helped a lot
38:39so yeah so let me ask again just how do
38:41you think about the right level process
38:43for stage of company and what have you
38:44learned there what I would really love
38:46from companies is sort of like this time
38:48capsule where you can see what their
38:50processes were when they were like 20
38:52people and 50 people and 100 people and
38:54500 people because when we were at
38:57stripe we were trying to figure out our
38:58planning process we actually talked to
39:00like Amazon and atlassian and apple and
39:02like all these companies that we really
39:03really respect and look up to and I
39:08remember you know taking down notes from
39:09these companies and being like yeah like
39:11this is awesome but there's no way that
39:13this will work for strive like stripe
39:15was so much smaller than any of these
39:17companies so yeah they were showing us
39:18where we had to go but no idea how to
39:20get there and so like yeah Lenny maybe
39:22you can you can help us figure out time
39:23capsules for companies what processes
39:26make sense I'm working on that roughly
39:29Company by company by how they think
39:31process and a bad process and then maybe
39:33I'll check in every every couple years
39:35cool I love that um but yeah to answer
39:38your question directly uh
39:41process yeah it's it really gives people
39:43a bitter taste in their mouth I think
39:46process by definition is variance
39:50like you're introducing it because you
39:53worry that the variance in your org is
39:55too high like you want people to sort of
39:58meet a certain standard
40:00and the cost of that is obviously is
40:02like while you're reducing the standard
40:04and bringing Folks up to the average
40:06you're also bringing other folks down to
40:09the average and oftentimes the folks
40:11you're bringing down are your highest
40:14performers your most creative thinkers
40:15and the folks who like you know I think
40:18actually don't really need process to do
40:22that I think is always the tension that
40:25you have with process and obviously like
40:26one of the reasons why companies
40:28introduce process much more and more as
40:30companies get bigger is because it's
40:31just it's harder to sort of like get all
40:33these folks who kind of don't need
40:34processing you actually want to reduce
40:38this is actually a little bit of an
40:39aside but it's kind of relevant so I'm
40:41just gonna mention it you can feel free
40:42to let me know if it's too much of an
40:44aside let's get into it
40:46I I was I was just listening to this
40:48awesome podcast with um with Russ
40:51Roberts who's at Professor he hosts econ
40:54talk I don't know if you listen to it
40:55and he was in interviewing this guy Ian
40:58Leslie who's just this great writer and
41:00who's just getting written this article
41:02that's basically something along the
41:04lines of like what it means to be human
41:05in the age of AI and I thought he just
41:08articulated this idea so well which is
41:10like we're all really like so impressed
41:11when we see like jack chat gpt3 like
41:15spit out this this sort of piece of
41:17writing that feels very human-like but
41:20what we're kind of forgetting is that
41:22over the last you know 10 20 30 years
41:24we're actually like asking humans to be
41:26a lot more robot-like and that like
41:28we're really asking everyone to like
41:29standardize in a lot of ways and like
41:32we're making people a lot more formulaic
41:33like if you think about how we ask
41:35people to or how we teach people to
41:36write it's like well there's five
41:38paragraphs and there's your opening
41:40paragraph and like there's you know you
41:42state your topic and so anyway I think
41:45like the point is like we actually I
41:47think you know the more formulaic the
41:50more sort of like mass produced you're
41:51trying to make something the more you
41:55quench people's creativity and I I think
41:58sort of the further away you get from
41:59like the really really high highs and
42:01that to me is kind of the cost or
42:02process and and rules and templates so
42:05like if you're going to introduce it
42:07be really really sure that you're okay
42:09with that cost and give folks Escape
42:13so I've started referring to this as
42:15like the the MVP the minimum viable
42:17process so if I give folks a template
42:19I'm like look use the template but if
42:21you want to break out of it please
42:23absolutely do and like start writing
42:25this at the top of templates now it's
42:26like if this doesn't work for what
42:28you're trying to explain like don't use
42:31it but like just know that this is the
42:33minimum viable thing like this is kind
42:34of like we're setting the bar here but
42:36like go higher if you can please so
42:38anyway that's that's my sort of like
42:40long day trip on process with all that
42:42said I do think that companies yeah
42:45there's just a set of documents that are
42:46like really really valuable that every
42:48sort of like I guess level of the
42:49organization should have
42:51throughout its life cycle
42:54and then you know I think a house or
42:55involved it is or how like long term it
42:58is really depends on you know how big
43:00you are but you know those those
43:02documents to me are the charter so uh
43:05what is your mission your vision and
43:08the goals what are you aiming to do and
43:10how are you going to measure success and
43:12then the road map what is the thing that
43:15and I think the whole company needs
43:18these the whole function so like a
43:20product like you need all three of these
43:22and then within each team you need all
43:26and I've kind of like noticed two things
43:29about this surf this framework for
43:31myself like one I've actually noticed
43:33that teams often work their way from
43:35like the bottom up versus top down like
43:36they start with a road map they're like
43:38what are all the things we're gonna ship
43:39especially early on and then like they
43:40kind of work their way into a charter
43:42but I think it's really really worth it
43:44to like start from the top down
43:47and then the second thing that I've
43:49noticed is that like your time Horizon
43:50really shifts as you get more mature so
43:52like you know if you're very early on
43:54you don't have pmf like you should have
43:55a charter but your Charter should be
43:57like three months in the future because
43:59you can't look that much further and you
44:02know if you're you're kind of a company
44:04that's humming and going your Charter is
44:07the horizons like maybe a decade so
44:10wow there's there's so much there uh I
44:13could go into so many different
44:14directions one thing I wanted to follow
44:17up on a little bit is this idea such a
44:19great point that process
44:22brings the best people down and kind of
44:25address averages them out to kind of
44:26create consistency and
44:29I'm curious if there's anything else
44:31you've seen succeed in allowing the best
44:34in most Innovative brains to just do
44:37their thing you know I know part of it
44:38is probably hiring amazing people but
44:40yeah is there anything else that's like
44:42Escape Hatcher or just like oh yeah this
44:43person just go go figure this out yeah
44:45to me the unlock for organizations is
44:47managers for this because like you need
44:50managers to both detect the high
44:52performers and be like this person
44:53doesn't need the process and that you
44:55need managers to give that person air
44:57cover to be like well honestly because
44:59what you're doing is you're giving them
45:00some special treatment and you need to
45:01be kind of okay with that and you also
45:03need to be okay with the organizational
45:04costs for that like Claire who used to
45:07be the the CEO of stripe would obviously
45:09like are you willing to break the org
45:10for this person and I always thought
45:12that was like a really nice Framing and
45:14you kind of need to decide who you want
45:15to do it for too but yeah like some
45:17people are just that good that like yeah
45:19of course will break the org for them
45:21they like you know they're gonna break
45:23the org in the best way possible so I
45:25love that term uh I think Claire's
45:27coming on this podcast you just wrote a
45:28book right is that the same person
45:32all right we just booked her coming well
45:35maybe we'll spend some time that's
45:37do you have any other product building
45:39philosophies that you found especially
45:41useful in your time at striped retool
45:45I have like a couple of I guess mental
45:47models I use the the first is
45:50um build for your best user not your
45:53and what I mean by that is I think it's
45:55actually really easy to kind of get
45:57or to sort of focus on like what if
45:59there's abuse of this product or think
46:02about all the ways in which the product
46:03won't be used well and then you kind of
46:05end up sort of shaping the product in
46:08these like really weird funky ways to
46:10make up for that whereas like in reality
46:13the worst users are always like they
46:15should be a fraction of your users
46:16anyway so like you shouldn't really
46:18really be building for them I think a
46:20really good example of this is like
46:21onboarding processes where you know
46:24you're you're probably going to be
46:26building an onboarding process where
46:28you're trying to like maybe sort of
46:29collect a lot of data or try like figure
46:32out like Hey how do I help this user who
46:34like maybe isn't sort of well suited for
46:35my product be successful like really
46:37should just be building an onboarding
46:38process for the user who's like gonna
46:39jump into your product and get it
46:40immediately because I was thinking about
46:42this actually just the other day because
46:43we're in this product review and we're
46:45talking about this other new product
46:46that we're thinking of exploring more
46:48products we're going never yeah exactly
46:51and we're kind of going down this path
46:53of like oh well you know if this gets
46:54really big like there's going to be all
46:55this abuse of the product and um Anthony
46:57or founder was like wouldn't that be an
46:59amazing problem to have we're like yeah
47:02that's a really good point so
47:04we kind of you know put that on the back
47:06that's an interesting approach because
47:08usually you're trying to optimize the
47:10flow get more people through it which
47:12are the least good users you're saying
47:14you found more success just like focus
47:16is this more initially focus on the
47:18users that will understand this and be
47:19excited about it and make that work
47:21really well and then kind of over time
47:23build on that yeah totally yeah sure if
47:24you really get the end you're like
47:25trying to optimize Etc absolutely but in
47:28that sort of early product development
47:30stage it's like that's just not worth it
47:32to to be too focused on that sweet
47:36um the the other the or head of design
47:39Ryan I think always kind of reminds us
47:42um build the scooter not the axle so you
47:45know if you're trying to build the
47:47minimum viable product for a car like
47:48don't sort of build just you know the
47:50wheels and the axle like build a scooter
47:52first and then from there you build the
47:53bicycle and the motorcycle and then the
47:54car and it's always just such a good
47:56reminder like you always kind of want to
47:57start building the whole thing like
47:59really try and think about like the
48:01slice that gets the customer to like
48:03complete value on a smaller thing first
48:05so with virtual mobile for example like
48:08there's just so much you could be
48:10building there and we decided very
48:11specifically like Hey we're only going
48:13to build this for companies that have
48:14field workers and like you know they
48:16would need to do inventory management
48:18and it's like it's a very specific slice
48:19but it helps kind of get through from
48:22you know something that was actually
48:23like viable beginning to end got it so
48:25it's it's an approach for MVPs basically
48:27make something simple and functional not
48:29just something barely like not actually
48:33working but getting you to some dream
48:36product eventually yeah and then the
48:40this idea of 70 2010 split Investments
48:43like I I really think that a lot of
48:45product management can sometimes be
48:47reduced to funnels and portfolios so the
48:51the 70 2010 Investments model in my head
48:54is just like 70 of your building time
48:56should really be going to your core
48:57product that has product Market fit 20
49:00of your time should be going to
49:01strategic initiatives that aren't core
49:04but like they're strategic to the
49:06company that you know you have to do
49:07them and then 10 of your time should be
49:09going towards bets that's actually
49:11exactly the same heuristic I've always
49:13used one question there is how do you
49:15think about maintenance and bugs within
49:17that yeah to me that falls like squarely
49:22um so yeah like core product Tech debt
49:25sort of the the stuff that you kind of
49:27the maintenance mode type stuff and core
49:29projects obviously you're also doing a
49:30bunch of new stuff there too but yeah
49:32like no more than 70 of your resources
49:33should be going there what did you say
49:37strategic initiatives that you know
49:39aren't your core but you just know based
49:42on your strategy like you have to do
49:43these things got it so the way I break
49:46it up is 20 I think is where I put bugs
49:49and maintenance and then 10 was like big
49:51old big ambitious bets so similar ratios
49:54but different things go into the buckets
49:56come on but let me ask you a similar
49:59question how do you just add retool and
50:01maybe even at stripe think about finding
50:03time to do maintenance and bugs do you
50:05build it into road maps do you set off
50:07time to just fix all the bugs I know
50:09it's probably an evolution and goes back
50:10and forth but yeah this I think is it's
50:14it's really one of the trickiest parts
50:16of product management in my mind we
50:18don't have a company-wide sort of
50:21process on this it's pretty team
50:22specific some teams do like Friday bug
50:26bashes other teams are just kind of you
50:28know as products roll out will kind of
50:31work on them as they go I was actually
50:34speaking to a product manager at a
50:36different company who mentioned that
50:37they just spent the last 18 months doing
50:40basically just product polish in bugs
50:43and yeah I think they landed in a place
50:45where they just they had to do it
50:47because they just had so much
50:49debt but you know luckily we're not
50:53there yet but right now we let most of
50:55the teams just kind of do it do it
50:56themselves and figure out what makes
50:58sense for them okay awesome
51:00I wanted to go back to something that
51:02I've heard about retool that you all are
51:04really good at which is PM's being
51:06really close to customers and I'm
51:09curious what you've done there or what
51:11the team has done that it's been really
51:12effective well I do think every good
51:15product Team figures out how to get
51:17close to customers but just based off of
51:20my observations from Rachel and what
51:22I've seen at other companies there are a
51:23couple things that are more pronounced
51:26at retold than I've seen in a lot of
51:27other places the first is we have a lot
51:30of PMS who used to be in customer facing
51:32roles at retools so yeah I I obviously
51:36am a big fan of that I think it's
51:38there's just nothing like really
51:40understanding the value of your product
51:42at the moment where a customer actually
51:44has to put money down and so I really
51:46like that about you know PMS who have
51:49had those conversations with customers
51:51have been really really get it second is
51:54because the virtual product is so
51:56Technical and I do think this just
51:57depends on what product you have like
51:59our PMS are really very technical like
52:01everyone has you know either a CS degree
52:03or has done some sort of Engineering in
52:05the past third is we use slack very
52:09heavily to to talk to our customers and
52:13interact with them so we get this
52:14binding of hundreds of slack Channels
52:15with customers every time you know we're
52:17testing a new product or you know we're
52:20we're kind of a new customer who's
52:22somewhat large comes online like we will
52:24work with them in slack to to get there
52:28off the cut feedback just back and forth
52:30it's really nice and just have this
52:31direct line to them which is awesome
52:34and then the fourth thing we do is we
52:37use retool to build retool so
52:40um our product roadmap lives in a ritual
52:43app and the app that we use to you know
52:46to have feature flags for particular
52:48features is a retail app so PMS are just
52:51in the product all day long every day
52:53they're their own customers in a lot of
52:55ways and that that really helps as well
52:57wow I didn't know that that is very cool
52:59so you built like a task management
53:00product by using retool oh yeah well we
53:04build many basically all of our internal
53:06tooling happens in Rachel like our PMS
53:08all their team dashboards are in retool
53:10all of their you know all their yeah so
53:13their task tracking is in retools
53:15submitting uh linear requests or bug
53:17requests happens in retool and then goes
53:19to linear so it's just uh yeah it's how
53:22we run the company you haven't been able
53:24to replace linear yet that's cool a big
53:27fan of linear okay two more questions
53:30and then I'll let you go one is around
53:33product like growth which I don't want
53:34to get too into we talk about it a bunch
53:36on this podcast but it's interesting
53:38that stripe was very product-like growth
53:40it was just self-serve
53:42PM's Engineers however just started
53:45using it it grew and became Enterprise Z
53:47down the road retool on the other hand I
53:50think people think it's product like
53:51growth I imagine it's actually sales LED
53:53mostly and so I'm just curious what
53:56you've learned about the difference
53:57between Building Product and leading
53:59product teams within a sales.org versus
54:03I have a couple of insights on that one
54:06one actually I think interesting Insight
54:07is that uh teams that have one always
54:09want the other like whenever whenever I
54:13talk to to candidates I feel like you
54:15can always tell what you know their
54:17company has because they'll be asking a
54:19lot of questions about the opposite like
54:21they're probably like broke up and
54:22they'll be like well how are you guys
54:22thinking about Enterprise and then if
54:24they are like more of a sales LED Growth
54:26Company they're like well how are you
54:27guys thinking about you know your
54:28self-serve motion or your product-led
54:30growth my main takeaway just you know in
54:34in sort of and and I I don't know if I'd
54:36even sort of use the dichotomy of
54:38product like growth or cells and growth
54:39with ritual like I think we do have a
54:41lot of product growth but we have we
54:43work with a lot of Enterprise customers
54:44and a lot more Revenue comes from
54:45Enterprise customers and we have like a
54:47fantastic sales team
54:49and I I think the the main thing is that
54:51you just have to really figure out your
54:54like interaction mechanisms with with
54:57sales and that that just has to be so so
54:59tight and it goes in both directions
55:01there's obviously like how do you get
55:02feedback from them because they are so
55:04often on the front lines talking to
55:05customers more so than product managers
55:07even but it also goes the other way like
55:09if you are going to ship something or if
55:13you are going to you know put out a road
55:15map like how do you make sure that the
55:16sales team has everything that they need
55:19the sales and you know and Rachel's case
55:20the success team and the support team
55:22has everything they need to accurately
55:24talk to customers about that and I've
55:27always actually found that really hard
55:28because it's really hard to figure out
55:29the right altitude if you're giving a
55:31presentation on the road map people are
55:33either going to feel like it's it's too
55:36high level or it's you know too low
55:38level for folks who maybe are new so
55:40this year we're actually trying
55:41something different we are doing a
55:44science fair where each product team has
55:47a little booth and they get to sort of
55:49stand there and anyone who has questions
55:50about the product can come you know from
55:52the go to market so I can come and ask
55:53questions and get demos and go like as
55:56deep as they need to so I'll let you
55:58know how that goes but I'm excited to to
56:02to experiment with it okay are there
56:04going to be foam core boards and will
56:07there'll there may be prizes who knows
56:10oh my God to see a picture of this
56:13final topic you have this concept that
56:16you call the product Talent portfolio
56:19what does that mean and how have you
56:21found that useful in your product
56:23leadership life yeah yeah it's back to
56:26the like all aquatic management is
56:28portfolios and funnels I think it's
56:30really tempting as a manager to build a
56:33team in your image because you
56:35understand their skill sets and you
56:38value those skill sets and you're going
56:39to be able to detect and assess those
56:41skill sets better but
56:44the best product teams in my mind have
56:47really figured out how to balance the
56:49you know the talent portfolio so instead
56:52of sort of having a bunch of PMS who all
56:54spike in one particular area figure out
56:56how you can you know have a great
57:00complementary skill sets for the whole
57:02PM team so the whole is much stronger
57:04and one way in which I like to do that
57:07is I really like to balance product
57:08teams with homegrown product managers
57:11who really get the product they've you
57:13know probably been in it they're amazing
57:15cultural carriers often they really set
57:17the tone but they may not have seen
57:19product management at other companies
57:21and they may not have some of the sort
57:22of more conventional traditional product
57:24management skill sets so I want to
57:25balance that with product managers
57:27who've come from other companies and
57:30have done it and can bring a little bit
57:31more of that product manager rigor even
57:34though they don't have that sort of you
57:35know the core and you know the retail
57:37cases of the core ritual product
57:38management you know Vibe so that's one
57:42example I think there's like others as
57:44well well like some PM's incredible
57:45execution machines other PMS are like
57:47amazing Visionaries like you kind of
57:49want a little bit of all of them and you
57:52want to also balance within all of your
57:53different pillars so you know we have
57:56three different product pillars at
57:58retool and there's kind of needs for all
58:00those pillars and I always push the
58:01leads to sort of hire people who don't
58:03look like them so that you know we have
58:06balance everywhere I love that do you
58:09actively as you're hiring like hey well
58:11you're strong in these areas here's the
58:13person we need here we want like the
58:15specific super strategy mind person is
58:18that actually how you think about this
58:19yeah yeah I I do a little personal
58:22exercise for myself every six months
58:24where I like sit like sort of chart out
58:26the team that we have today and like
58:28write down all the strengths that we
58:29have all the weaknesses that we have as
58:31a team and then I try to sort of hire
58:33specifically for those weaknesses
58:36any last pieces of wisdom or thoughts
58:39before we get to our very exciting
58:43okay we got through everything I was
58:45hoping to get through so with that we've
58:47reached our very exciting lightning
58:48round I've got six questions for you are
58:52what are two or three books that you
58:55recommend most to other people
58:57Bird by bird instructions on writing and
58:59Life by Anne lamott it's incredible so
59:03touching really great also I think
59:05product managers should be great writers
59:06so love that and then the other book
59:09that I was going to say but I'm glad you
59:10mentioned Claire is Claire's book
59:12scaling people which is coming out I had
59:14a very small hand in ghost writing for
59:17her a little bit in the first draft so I
59:19use a lot of the early chapters from
59:21that book still in management and I
59:24still recommend you know recommend sort
59:26of the tactics in there so I'm excited
59:28for her to to get it out wow I've been
59:30hearing about ghost writing as a career
59:32recently and it feels like it could be
59:34the option for you down the road and I'm
59:36excited to read the book I haven't
59:37gotten a copy yet and I think you can
59:39pre-order it now and we'll link to it in
59:42what's a favorite other podcast do you
59:44like to listen to other than maybe the
59:45one you're on right now yeah this one's
59:48I can't choose between these two one is
59:50um Lex Friedman and then the other is um
59:53econ talk by Russ Roberts I I really
59:54like that both of them are like their
59:56agenda is like curiosity which I love
59:59totally resonate there what is a
01:00:01favorite recent movie or TV show that
01:00:03you've enjoyed is it too basic to say
01:00:06White Lotus cool that's like the most
01:00:08mentioned one which is says a lot right
01:00:10that just says how good that is because
01:00:12I I love it too but that works that
01:00:15works uh season one or season two oh
01:00:17season two all the way yeah same I'm
01:00:20excited for season three
01:00:23no spoilers favorite interview question
01:00:25that you like to ask candidates to what
01:00:28do you attribute your success and you
01:00:32interesting because most people look for
01:00:34do they believe it's Luck versus like
01:00:36their inmate skill so you don't even
01:00:39allow them to say luck interesting yeah
01:00:41because you know I think humble people
01:00:44will always say luck in some way and you
01:00:46know I always kind of wanted it like did
01:00:48you like how self-aware are you
01:00:49basically and I think and how curious
01:00:51are you and I think people really sort
01:00:52of gone back and reflected on
01:00:55why why are they where they are today
01:00:57really really says a lot about how they
01:00:59think about the world I love that what
01:01:02are some SAS tools that you love or use
01:01:04often at your current company or
01:01:07anywhere else yeah well first and
01:01:09foremost the retool
01:01:11um and then the other satchels that we
01:01:14use a lot slack gong linear and full
01:01:19favorite new product that you found
01:01:22maybe in life maybe at work
01:01:24uh have you heard of rewind
01:01:27yes I have it running right now
01:01:31yeah I I mean I think it's really
01:01:33incredible what they've done maybe
01:01:35describe it briefly just so folks know
01:01:36what that is it basically records
01:01:39everything that you're doing on your
01:01:41computer and then makes it really easy
01:01:42for you to search it
01:01:45which is it's just incredible like I
01:01:47like I don't I I don't know if if you
01:01:50work this way Lenny but like I feel like
01:01:52nowadays I don't really go to like tabs
01:01:54anymore or like I like I kind of
01:01:56directly like search for the thing that
01:01:58I'm searching for and I think rewind
01:02:00just like fits that user Behavior so so
01:02:03well amazing Aika this was so much fun
01:02:06we got through everything I was hoping
01:02:08for and more two final questions where
01:02:10can folks finding online if they want to
01:02:12reach out learn more see what you're up
01:02:13to and how can listeners be useful to
01:02:15you definitely find me online on Twitter
01:02:18it's a good DM and how can they help us
01:02:20try out the retail product and uh and
01:02:23give us some feedback amazing ritual.com
01:02:25right yes awesome thank you again for
01:02:27being here thanks Lenny
01:02:30thank you so much for listening if you
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01:02:50see you in the next episode
