36 min read

Episode 17: Strategy

The strategy & operations exec with great advice for new ops leaders.
Episode 17: Strategy

Hopping on a "quick call" gets a bad rap these days.

We're all busy, we're sick of Zoom, we're trying to squeeze out more time in our day... I get it. And I feel it myself! But, occasionally, I'm reminded that it's good to leave room in my calendar for a little serendipity.

There's nothing like talking to cool folks with no agenda that allows me to spark new ideas and unlock old challenges. And this episode is proof of that!

I met today's guest through a mutual friend (hey, Caleb πŸ‘‹πŸ») who calls her his mentor. We hopped on a quick call and it was a total mind meld. I knew immediately that I wanted to have her on the show.

Our convo was enlightening in a lot of ways and I can't wait for you to hear it! (Or read it, if transcripts are more your thing. πŸ˜‰)

We dive into the difference between business strategy and operations strategy, what startups need to do differently in this market, and her advice for new ops leaders.

About Our Guest

Amanda Schwartz Ramirez is a strategy and operations executive who has spent her career incubating and scaling startups and business units in highly-complex and emerging spaces like fintech and crypto.

She spent almost a decade building new adjacencies at PayPal before leading operations and strategy at a venture-backed startup. Now, she advises founders and executive teams through the complexities of operational, people, and growth challenges.

She also writes one of my favorite newsletters, Thinking in Quarters.

About this Episode

In this episode, we chat about:

  • Amanda's unique trajectory at PayPal (and how it prepared her for fractional consulting with small startups)
  • Why she struck out on her own as a fractional COO and coach
  • The difference between business strategy and operational strategy
  • Overcoming the urge to learn to code when you're a non-technical person in tech
  • And her advice for new ops leadersβ€”including my new "don't lick the cookie" mantra πŸͺ πŸ‘€

Listen Now

You can listen to Opsy on your favorite podcast platform, including:

Show Notes

Stay in Touch

Mentioned in the Episode


Welcome to Opsy, a podcast for people doing opsy work in tech. I'm your host, Caro Griffin. Every month I dig into what Opsy work really is by talking to an operations pro who has something really cool to teach usβ€”in a traditional part of ops like HR or finance, or a newer specialty like no-code ops or marketing ops. Thanks for listening!

Caro 0:02

Hello, everybody! I'm here with Amanda Schwartz Ramirez, a strategy and operations executive and coach.

I recently connected with Amanda through a mutual friend. (Caleb, if you're listening, hello!) I was immediately impressed by her skills and experience and so enjoyed chatting with her informally that I knew I wanted to bring her on the podcast.

Amanda spent almost a decade at PayPal in numerous roles where she learned the ins and outs of of working at a large, complicated fintech company.

These days, she has shifted her focus to fractional consulting and coaching, primarily within emerging tech like Web3, AI, and of course, that has its own complications.

If that wasn't enough, she also has my new favorite ops newsletter. It's called Thinking in Quarters, which I think is just such a good name. I really resonate with it.

So, thanks for joining me, Amanda.

Amanda 1:15

Thank you so much! It's so fun to be here. Hi, everyone.

Caro 1:18

We've obviously chatted a little bit before, and I've done my share of internet stalking and sleuthing to read up on your background and projects. [Laughs] But why don't you share with everyone listening [about what you are up to].

Tell us a little bit about your consultancy, Garden Labs, and what kind of projects you're working on. What made you strike out on your own?

Amanda 1:40

I'm happy to, and thanks for the opportunity.

I'll give you the origin story in a second, but Garden Labs is a strategic boutique advisory firm. And, in that, I spend about half my time working with COOs and CEOs, lots of first timers on both sides, and really do what I think of as advisory and coaching, but also drop-in COO support.

That might be in the form of projects where I'll help them tackle some company building thing, like undo some weird knot, or some side-by-side action where I'll actually come in more as a fractional COO.

That's about half the practice. Then the other half is more on the strategy side. That is a bit of insights work.

A lot of time I'll be working with more emerging tech startups that are looking for a large market to kind of serve up their technology too. Or, I'll be looking at a large existing company and help them think about how they leverage technology. So, it's this bi-directional insight and strategy development piece that we help with as well.

Caro 2:50

Okay, very cool. That's a lot of different things. Why don't we go into the origin story? How did you end up running that ship?

Amanda 2:53

Yeah, it is a lot of different things.

Caro 2:54

I'm mixing metaphors. Steering that ship, running that game, I don't know what you want to call it.

How did you end up doing this?

Amanda 2:58

I'm notorious for mixing up metaphors, so let's do that through this conversation.

You know, it was a bit out of necessity. So maybe taking a quick step back, my entire career has been at this intersection of strategy and operations.

And it's always, I'm the person in the room, like you are as well, asking, why are we doing this? Why does it matter?

And how are we gonna make it happen? And then what? And one always goes hand in hand with the other.

I was at this point after 15 years of really intense heads down operating roles where I wanted to be heads up for a minute. I wanted to be able to see all these emerging spaces for what they are. And I wanted to diversify a bit across multiple companies.

And then, if I'm really honest, I really wanted some flexibility because we just had our third child and my life is completely run by these three little maniacs. I am not at all in the same place where I used to be, where I could just take 200% of my life and hand it over to a CEO and say, "What are we doing tomorrow?"

So, you know, this setup is as much about me taking control of my own destiny a bit and my own schedule while learning fast, and hopefully offering something up to COOs and CEOs to help them along their journey, I'm gonna choose something I just love.

Caro 4:33

I find it really interesting that you were at a company, first of all, as big as PayPal, and were also there for so long. And then now you're working with these smaller companies in shorter engagements. It feels like a really different skill set, but am I projecting that? Do you think it is, or do you think it's pretty similar?

Amanda 4:49

It depends on what you're doing in a large company. PayPal is massive. And I was there for a decade, which is a long time. [Laughs] I didn't actually expect to stay there for almost 10 years. But when I started, I was on this really interesting Labs team. And I was just surrounded by these really smart engineers that were trying to figure out how to translate their ideas into a working code and then get other people to care about them.

I spent the first five years at PayPal doing thatβ€”working on the kind of fringe of the business, never within the core, and always thinking about how to extend the business in different directions and iterate and test ideas. And it was always product-level incubation.

The last five years was much more like business building and scaling. I was at the business unit level standing up units, but it was always from, again, outside of the core. So, it was always, what new thing do we want to get into now? And how are we going to make that happen in a way that builds on the existing business, but doesn't break it?

It was always like these things that I do feel are transferable from a skills perspective, but also [in] my DNA is that I grew up in my dad's business. I'm very connected to the entrepreneurial journey and all the things that go into building something from scratch. It felt very natural to me to just go earlier stage and kind of keep my sleeves rolled up and just do stuff. So I did.

Caro 6:23

Yeah, absolutely. And I think when you put it that way, it really does show how much overlap there is. Because, like you said, you were standing up business units, you were off on the side doing these mini startups underneath a bigger startup.

Judging by LinkedIn, you did everything from Chief of Staff to Director of BizOps work while standing up these functions and special projects. I would love to hear about some of the projects you're proud of during your time there. Is there like one or two that come to mind and tell us about?

Amanda 6:50

I was just reflecting on that recently. I was talking to somebody who is still at PayPal and looking for something to kind of sink their teeth into...

I think where I really like lit up, and this might be like psychotic, is like the things that are incredibly complex and seem totally impossible at their face, but behind it is some team that actually really trusts each other. I find that both of those ingredients have to be in place or else something feels off. And so there's a couple of examples.

In, gosh, what year was this? 2015. PayPal was still very much a part of eBay Inc. and needed to really quickly spin off into a separate publicly traded company. So, it was a complete spin-off situation and I was lucky enough to help with that.

Caro 7:47

Lucky is one word for it, for sure. [Laughs]

Amanda 4:50

Perspective of every day there was a new problem, right? But there was also a really strong team on it and we're all blood bonded at this point because we kind of went through that together. But it felt like we cycled through problems really well together.

It was not the situation where something would happen and then you'd spin on it for three months and then just like relent and move on to another thing. That really hurts. That's not the complexity most people are looking for, but this was very much - see your problem, hoard, basically jump on it together as a team and then address it and then move on. And, of course, there's another one right there.

I loved that. It was fun, it was intense, the hours were grueling, but it was definitely a time where I learned the magic of working across functions and just keep going, like don't stop.

I don't know, I'm proud of it. It was exciting and that opened up some interesting doors to go into different functions after that and help rebuild those as a new company was forming and so on.

Caro 9:04

Yeah, that makes sense. I think what I hear you speaking to is the difference between... there's complicated, but there's also challenging and tricky. And then just like hard for the sake of being hard.

There's a Venn diagram of all these different things and sometimes it's hard to figure out where a problem sits. But trying to spin off PayPal into its own entity... I imagine doing that with an org that large was definitely challenging. It sounds like you had fun doing it though.

Amanada 9:30

I did!

Caro 9:31

I'm proud of you for doing it. I'm glad you're proud of yourself because it sounds hella cool and impressive.

The Challenge of Building a Startup

Amanda 9:38

Yeah, it was a good time, but you hit the nail on the head. The question of like, is this hard because we're getting in our own way? Or is this just challenging?

This pops up all the time in my advisory work now. Everything you do when you're building a startup is really challenging. None of it is easy. If it was cut and paste, everyone would do it. There's nothing simple about it. But there's lots of times when, as a team, you're just getting in your own way and you're making it harder than it needs to be. There are some things that you need to diagnose that are preventing you from really making progress.

And, in other times, it's just hard. And you need to accept it and just keep working.

The latter is great when you're somebody that is just eager to contribute and learn and you've got a lot to give. I found myself in that place over and over again at PayPal, which was great because it kept me there for a decade.

Caro 10:35

Yeah, absolutely. I feel like that was a really good example of like... I don't want to get too off track because I have more follow up questions here [laughs] but you just perfectly summed up the like, "Is this complicated because it's hard? And is it challenging because it's hard? Or is it challenging because we're getting in our own way?"

I feel like you have an ability to really succinctly put those things into one sentence, whereas sometimes I feel like it would take me like 45 minutes to be like, this is the scenario that I'm facing... and you would be like, "Yeah, you're getting in your own way." That's it.

That's like why I love your newsletter. I feel like you so skillfull at exactly that. You're like, "Pick which boulder to roll up the hill." "Are you licking the cookie?" We're gonna circle back to all of these guys!

So I feel like that's a nice little... stay tuned to hear what licking the cookie means! [Laughs

Amanada 11:25

Please do! I wanna talk more about that.

Caro 11:27

I'm already working that in the same way that Molly Graham's "building your Lego tower" and "giving away your Lego tower" is very much part of my professional vocabulary. "Don't lick the cookie" is my new give away your Lego tower.

Amanda 11:43

I love it! And I'm a huge fan of Molly's, so I agree.

Caro 11:49

"Don't get in your own way" is a commandment that should probably be on the startup or ops, like tablets...

But I guess going back to to these nitty gritty, you know, challenging problems that you faced at PayPal... All of your roles sound like they were very related for sure. And they really required this common skillset that I think you're kind of speaking to... but I wouldn't call them traditional or linear jumps. Like, you weren't going from like ops manager to ops director, you know?

How did you decide when to make a pivot or take on a new role?

Making Pivots and Changes in Roles

Amanda 12:26

Yeah, they definitely all had their own focus. And certainly they were never in the same organization when I made these moves. But there is this through line.

I think maybe it's worth taking a step back again and just saying like, I spent probably seven years at PayPal not really knowing what I was doing and how to talk about it.

I found myself in these rooms where there were all of these really brilliant product and engineering people that I really respected, but I was like, "I don't do that."And I noticed everybody kind of wanted to be in product. And I was like, I don't, I don't get it. It doesn't appeal to me. And I complimented them, but I didn't understand the value I was bringing.

There was one point I remember, a few years into PayPal that I was like feverishly trying to learn how to code. And I was taking all these product classes because I was just like, "Oh, what do I do? Like, this doesn't make any sense to me."

Caro 13:18

I feel like so many of us go down that path, where we're like, "No, in order to contribute, in order to be valuable, I need to learn how to code. I need to take these classes."

I totally did that thing too. And I'm so glad to hear that also you, as someone who is so badass, also fell down that rabbit hole. My guess is that there are people listening who are finding some reassurance in that.

Amanda 13:45

I hope so. It's like unfortunately common.

I still am like a little bit embarrassed to this day because one of the smartest engineers on our team at that time was asked by our boss to teach me how to code. [Both laugh] He was sitting across from me and I felt so bad for him. I mean, I'm looking at this guy and I'm like, you could be doing so many more important things right now, but here we are.

I was pulled aside by a mentor at the time that said, "What are you doing?
Do you understand that we're on this entire floor of like 800 people and everybody here knows how to do that already. Are you gonna become better at that than they are?" And I was like, no, I'm barely gonna become adequate if I do this for three years. Like, this doesn't make any sense to me.

That was when I started to figure out, what should I be leaning on here? And at that point, it was really collaboration skills. And I really do feel strongly that that's been one of the superpowers I've honed across all of these different roles, startups, or large company. At the end of the day, it's all collaboration skills.

How do you actually sit across from somebody and figure out what they're amazing at, bring that out of them, build on it together and turn something around that's better than either of you could have done separately? That's a skill. And you build on it over years, and then you become adequate at it at different levels of an organization.

There were times where I was on teams, and I just couldn't achieve that with the team around me, and I just wasn't able to unlock that piece. And I kind of felt maybe I was in the wrong room, maybe I'm just not able to break that barrier of trust or mutual respect or like alignment on vision. There's something that's blocking it.

Instead of me banging my head against the wall, I was able to turn around and go to previous bosses or sponsors of mine that really understood that I had this soft skill and what contexts it was better in. I was able to do that a few times. And there were a few times along the journey that I was like, maybe I've done that enough. You know, this is now not making sense on paper.

My background is so... all these jobs [were] now just appearing to be odd jobs to me. I don't know that this is going to resonate down the road, and I did worry about that at some point. But I also got to a place where I started discovering that this is called strategy and operations, and this is a discipline. And that was this big unlock for me. And then I found myself on one of my favorite teams, which I ended up, you know, staying on for a while and standing up business units with and sort of doing some of the most impactful work that I'd done at PayPal.

But it wasn't until I was able to like really crystallize that for myself and say like, what is this thing?

Caro 16:40

Yeah, totally. I feel like so many of us end up in ops one way or another, and then we're like, "I don't really know what I'm doing." And we kind of either follow the path that's laid out for us, or we kind of follow our interests and intuition. And it's only when looking back that we're like, "Oh, I can see the common thread there."

In the moment, when you're in those jobs, it can feel so stressful. Like, "I don't know what I'm doing." There's no path, especially if you're thinking in quarters, right? Like, what are my quarterly goals? What are my annual goals, my career goals? And you're like... I don't know.

Tou have to have three or four roles to find the common thread, right? Like, you can't find it when you only have two or three.

That's something I talk to a lot of mid career people about quite a bit. And so, yeah, I guess I say that just to be like... so many of us hit that and I'm so glad when people talk about it because it can feel so lonely when you're in it.

Amanda 17:30

Yeah, and it helps to have those sponsors in your corner, not just the mentors that are going to give you good advice, but the people that really will advocate for you to take on jobs in other parts of the business and get other people to take bets on you. I had a few of those bosses and they made the biggest difference in my career and in my life.

Transitioning from Fintech to Emerging Tech

Caro 17:50

Love that. Okay, so, obviously you were at PayPal for a while, really in the fintech space and the PayPal space, specifically. Now, it seems like you're pretty focused in emerging tech and that that's something you're really interested in. Tell us more about that. What drew you there?

Amanda 18:05

Yeah, I mean, I think I've always been the person that has been really curious and really drawn to new and exciting and creative things.

I started my career in the music industry and I was always surrounding myself with musicians that were doing things that nobody around them was doing. I was just a fly to this, I was a magnet. You know, there's the bad metaphors again. [Laughs]

I couldn't stop myself, you know? And I think of the same thing in tech.

There's the existing market, you know, the mass mainstream market. And then there are these emerging markets right behind it. And this is where a lot of experimentation is happening. And lots of failures. And lots of really interesting glimmers of hope and insight. And that's just where I'm just excited by it.

So, when I joined PayPal in 2011, I was on this Labs team. And we were talking about QR codes back then... They were this really exciting thing. [Laughs] But, you know, text to pay...

Caro 19:15

The comeback of the 20s, you know. [Laughs] Who would have been able to predict back in that room, right? Like Amanda back in that PayPal room being like, "No, actually, they're gonna be big, but not in a way we expect, unfortunately."[Both laugh]

Discovering Cryptocurrency and NFTs

Amanda 19:30

Yeah, and I just loved it, you know. Not all the things are equally exciting, but I did discover cryptocurrency at that time. And it was quite an eye opening experience for me because I was in this space where I was probably the only person in the organization that cared about this weird thing.

I wasn't able to really do anything with it for a few years. But then I started helping with hackathons, I started bringing in speakers, and just finding ways for it to become like a thing that hung off my desk.

And then, finally, it was kind of like right place, right time. In 2020 ish, I was on the global business development team. My boss at the time was asked to spin this meaningful partnership into a separate business unit. And that created the crypto business. Finally, it was my full time job. And it was like, you know, the lights turned on and I was thrilled. I still am so proud of that team and everything that they continue to do.

That was also when I was like, "Wow, there's also this world of NFTs. And holy cow, what are these like other things that are happening, like zero knowledge proofs? And how does that relate to cybersecurity or identity or risk and compliance?" There's all of these offshoots of these kernels of technology that I just started becoming really curious about.

When I decided to leave PayPal, I went into a startup that was fascinating in many ways, it was a complete scale-up situation, but firmly planted me in this emerging space of all things Web3, and I couldn't stop there. It was just a matter of, okay, I'm gonna have to just keep this going because it's just too fun.

Caro 21:15

Yeah. Oh, I love that for you.

I think earlier you said something about this challenge you had early in your career of like, how do you find the common thread? How do you explain your work and kind of these series of random jobs?

I feel like on paper, maybe yeah, 10 years at PayPal in FinTech and now working in emerging tech and consulting... I feel like you do such a good job of bringing it together, like even on your website. Shout out to anyone who needs a website - GardenLabs.xyz has some great inspo.

Amanda 21:45

Aw, thank you.

Caro 21:35
I feel like you do a good job of really succinctly summarizing the strategy and kind of the thread between the two. It's these like complicated emerging problems... and I guess like I don't know what my question is other than I'm just like interested to hear you like tell me how you arrived at that, right? Like, do you have 15 versions of your website before you landed at that? What helped you really tell your story?

Amanda 22:13

Yeah, version number 16 in development right now, actually. [Laughs] Because the story evolves. I'm always trying to figure out, you know, what are the projects that I love doing.

I always find, and I think this will always be true, is that there's teams that are struggling with operating clarity, or operating practices are off, or there's something going on that's creating an environment where people aren't collaborating correctly or in a way that feels right... Most of the time, you should go upstream and look at the strategy and figure out: do people understand what it is and does it make any sense to begin with?

And then, also, you know, if somebody's like, "Hey, I've got this strategy issue, we have no idea what markets to go into," or, "We're in a market, but we're just not seeing the results that we felt were meaningful." Typically it's like some execution issue or some operating thing is off, whether it's talent or practice. And so I immediately knew I needed to keep those things together.

I've been experimenting with different ways to deliver that service, which is why I'm iterating on the site. Because one is, I started this thing as like a solo advisor coach person. You get Amanda. And that still is the case today. Like, I'll come in there and I'll spend a few hours a week with you and we're gonna work really hard on something together.

But then I started realizing like, oh, wait a minute, there's also lots of needs for like HR practitioners. And that's not me, I'm not an HR practitioner, nor am I a marketer, nor am I a payments person. And so I started really slowly building this bench of really incredible, entrusted advisors around me. And now I'm trialing this thing called COO in a Box.

It'll be fun to see what happens, because my hypothesis is that there are companies that believe they need a COO, but they may just need these other domains to come in and debug something and then get out of the way. And this would be the answer for that. Or one answer for that.

And then, you know, ongoing, coaching and advisory would sit alongside it. But, but that's, you know, that's kind of the experiment here. Because COO is very amorphous. And it's sometimes all these things, and sometimes none of them. So we'll see.

Caro 24:45
Absolutely. Yeah, it's different with every person that sits in the seat in every company with different needs, right.

Amanda 24:54

That's right.

Caro 25:55
Yeah, I love the COO in the box. Something that I think is a common thread between COO roles is the ability to like get in there and figure it out, like to help diagnose a problem.

Sometimes I think companies are like, we know we have a problem and we can't solve it so we should hire a COO. And I'm like... You're so early stage. You just need like a really great, motivated Ops Manager or Head of Ops. And then you need someone like Amanda to come in and help diagnose the problem to be like, this is a payments problem. Here's the payments expertise that you can plug in, and your ops person is smart enough to figure it out. They just need a hand.

Amanda 25:38

You nailed it. They need a little box. That's right.

Caro 25:30

I love that you're building that and I love having something to point people to. If y'all are listening and you're like, "Oh, we have that problem." There you go. It's the COO in a box. It's ready for you. Garden Labs.

Well, I look forward to version 16 of your website coming to a browser near me soon. [Both laugh]

Let's talk more about this work. So you're working on a number of projects, plus coaching, and I feel like there's so much to unpack here. How do you structure your day with so many things going on? Not to mention your three small minions or whatever you call them. [Both laugh]

Structuring the Day with Multiple Projects and Clients

Amanda 26:10

I wasn't as nice.

So, I'd like to say I have this perfect structure to my day. I did attempt to have one, but, yeah, it doesn't work.

I truly structure my day around nursing my daughter. So, that's the blueprint. I have a detached office, and I run in and out of the house throughout the day to see how she's doing and tend to her needs. And then I honestly structure my day around my energy levels.

The morning is when I'm freshest. And when I say and think some things that make sense. And so I will use that to the best of my ability, whether it's through writing or just doing some heavy lifting for one of the companies I'm working with. That's the thinking time.

Then the afternoon for me is mostly just chit-chatting and like meeting with people. And that's when my energy is a little lower. I'm not as insightful in the slightest, but I'm an extrovert and I can just connect. And so I'll take my meetings as much as possible in the afternoons.

And then, you know, I try to structure my weeks so that the context switching just doesn't like brutalize me. But, most of the time, it's really hard to do because I just want to be available when I need it. But I will attempt something resembling like dedicated days as well.

Caro 27:38

I feel like it's like impossible to do, so I guess I'll just set that bar. It's impossible to like perfectly protect the time and put everything in neat blocks, in part for the reason that you're saying, right? Like you want to be available, but like even if... I don't know, I'm not as nice as you, Amanda [laughs] and even then I'm still like... It's so hard to like get people in. Everyone has their own schedules, their own preferences, you have time zones to contend with.

Have you found anything that is working for you in terms of carving out dedicated days or or blocks with different clients?

Amanda 28:15

Yeah, so I do really like to preserve Mondays for just priority deadlines.
So if I have something like the most important thing that week, like I wanna do it on Monday. I'm not gonna be the person that waits till Thursday to give you something on Friday. I'm gonna do it Monday. And that gives me the headspace to get as close as possible to done on something, let it marinate, and then turn it around after I've had some more time to think about it.
So I try to attack the big rocks early.

And then Tuesdays, I will leave fairly light. Just to see what hangs over from Monday.

And then Wednesday, Thursday, I like to dedicate to like a specific company or space. So whether it's, geez, like zero knowledge proof on Thursday or payments on Wednesdays. There's a certain amount of completeness that I can achieve if I only think about a company on a certain day. And so I do like to do that.

And then Fridays, I preserve for writing and conversations like this, where it's just like reflection, connecting, new business, things like that that I wouldn't kind of bring in the regular course of the week.

Organizing One-on-Ones for Better Impact

Caro 29:30

Okay, I mean, that sounds pretty organized. I'm just gonna say it. [Both laugh] Sounds like you're doing a pretty good job. I'm like, even if you're hit, right, it's only like 50% of the time, or like 40% of the time. I'm like... that sounds pretty good. I need to take some cues.

The best I can get is like my one-on-ones in a block. That's like about as organized as I get these days.

Amanda 29:56

That's a good unlock. It's a good thing to do.

Caro 29:57

Yeah, I like to put manager brain in where I can. Otherwise, I feel like I do that like Cardinal Sin of turning 1-on-1s into action items and stand-ups versus like professional development and coaching. I have to consciously turn that brain on and off. Or it's just, you know, not as powerful as they could be.

Amanada 30:18

I can relate.

Caro 30:19

Well, I'm glad. [Laughs] And also sad that you can relate... but let's take a little bit of a right turn here. I would love to hear your more general thoughts about ops.

You know, tech has had a rough year. And I would say, just by nature of your work, I feel like you probably have an interesting perspective and position on what's happening across these early stage scaling startups.

What are some themes you're seeing right now? Is there any advice that you find yourself like giving over and over?

Amanda 30:43

Yeah, so I think I'm seeing probably what everybody is feeling, which is more of an unrelenting focus on impact and picking your bets. Whether that means companies shifting more to a focus on profitability versus just growth at all costs, that's something you hear often in the VC world. But in the space that I operate in...

Looking back 18 months ago when I first started this, the engagements were a lot of... how do we explore this new market or how do we do more? And how do we think about these adjacencies to just kind of drive, drive, drive to growth and acceleration? There were a lot of really good questions being asked and those are good questions, but that was the flavor of what the engagements felt like at the time. And, of course, I was very focused on web3 and there was lots of experimentation going on. New channels, new engagement methods, et cetera.

Now it is... the teams that are very convicted on those bets, like they went well so they're continuing. And I am still seeing teams building a lot of more emerging and very interesting things, but I'm finding that the engagements and the conversations are now shifting. The questions are becoming much more about, how do we know that this direction that we've chosen is the right one? Or how do we refine our focus to do fewer things but make sure that they're more impactful? And those are also very good questions. So I find that one is probably not better than the other, in all honesty. Like, of course, the market is moving in cycles, and you have to adapt.

I think that there's time for this divergence and blossoming of creativity. And then there's also this time for convergence and focus. And I feel like that's the period we're in now.

Mitigating Risk in Early Stage Tech Startups

The advice that I give most often is... I think I wrote an entire blog post on this, which is about going back to your core thesis, if you're early stage.

What are the big assumptions that you've been making all along about why this thing will work and be massive? And what can you do right now to mitigate the risk of a false assumption? Like how do you de-risk your guiding thesis?

I can give some examples, but I think those are some of the questions now versus like, how do we 3X growth and do more, more, more, more, more? I'm not seeing that.

Caro 33:23

That makes sense. And, like you said, I think that's so consistent with what everyone is feeling a little bit. And I think it's an important call out that the shift isn't really good or bad or better or worse. It's just different.

I would love to hear some examples of like, do you risk gain the main, I guess like value prop there? I think that's like a whole interesting thread I want to tug at a little bit.

Amanda 33:45

Sure. Yeah. So, you know, every emerging tech bet has one or two things that they're just assuming customers will do to adopt this new technology. A lot of these things are sweeping assumptions. "We're building this great thing on a blockchain and people want it because they care about this one core value, and they will jump through hoops to adopt this thing. And we're going to be massive." There's lots of those.

The Risks of Assumptions in Blockchain Technology

Sometimes those assumptions are right and things work. And sometimes they are risky. And so there's a couple of companies that are in this space, of thinking about putting things on blockchains that reside on paper today, and, of course, like the reason is, to me, very clear. You know, it's digitizing things, making them transferable, making them trackable. And all of these things make sense to me from a very pragmatic perspective, but there's all sorts of assumptions like, that all of these organizations that are using paper today are just going to move over to this new thing and we're going to be massive.

In this new market, I'm seeing teams just say, "Okay, let's just assume that that's not true now." Let's assume that the hype cycle has run its course and the drive to adopt new technology has lessened in many ways. What are the ways that we can actually ensure adoption? Are there any partnerships that we can put together that drive adoption behind the scenes of this technology so that we don't have to push the user so hard? Are there any things we can do to lessen the barrier to entry?

This is getting slightly into the weeds of like now, just general strategy, but these are some of like those fundamental things that I think are important to revisit at this point in a market where you may be 18 months in on something and may need to go back and say, does this make sense? Are we still doing this?

Caro 36:09

Did we like miss a key piece here? Is there like a pillar that we built on that's like really... to continue our use of problematic metaphors... Like, you know, is it going to fall? Is it going to buckle under the weight of these assumptions and this whole thing we're building on top of?

No, that's super interesting. And I think something I would love to clarify for for listeners here and really for myself, too, is like you talk about strategy quite a bit. And I think there's like operational strategy, and there's business strategy and I have my working nebulous definitions, but I would love to hear how you think about this.

Do you think they're the same? That they're different? Tell me your thoughts.

Amanda 36:56

Yeah, yeah. So I see them as distinct but related. For me, you know, the business strategy is derived from some proprietary insight that you've developed from either really in-depth knowledge of a market and it's landscape and composition, or just through activity in the market you've kind of unlocked something. And that proprietary insight will help you decide how to prioritize efforts to win. What does winning look like? And how are you going to get there? What are the three things that you're going to do that gets you to win?

I think of that as like business strategy. And so it's not just here are the three things, but why do [those three things] matter? And how are we going to do them so that we really increase the chances of exploiting that proprietary insight that we have? And that's a really nice strategy when you can get there.

The operations piece of it becomes really interesting when you say, okay, great, we have these three things. What's the best way for us to achieve those today? Do we want to build all these functions in-house? Do we want to outsource a piece of them? Do we want to acquire and integrate a business?How do we want to structure ourselves so that we can attack this most optimally?

A lot of those questions of like where focus meets talent and how people work together. The ways that you swarm around problems and solve them - that's the way I think about operations strategy.

Caro 38:50

That makes sense and, you know, as always, a super, articulate, formulated way of putting something that's my brain like, "I don't know I'll know when I see it." [Laughs]

Let's talk a little bit about you about your innate ability to do this to do this great... I don't want call it summarizing, but like putting your finger on the pulse.

You have this great newsletter that I've made it clear I'm a fangirl of, and you've somewhat recently started a great series called Dear Ops Leader, where you share these big, important fundamentals that new ops leaders should know.

What inspired you to start this series?

Amanda 39:29

I was told to just write the thing that I have to write, the thing that every time you sit down and write something, you just got to get it out before you could move on to something else. And, and that's what I that's what got me started on this Dear New Ops Leader thing.

I don't know if it was like therapy or something, but I kept getting into this space where I'm like, if I don't say this here, I'm never going to be able to move on. I think because I've been in that situation so often. I know what it's like to bang my head against the wall and just not get anywhere. And I was like, I wonder if there's a way to crystallize this for people that I care about, which are new ops leaders. Like I really respect the role. I feel like it's so hard. And there's all these non-obvious reasons that make it hard that are less about, do you have like the skill like to do it?

I know every ops leader has the skill to do it. Like there's so many incredible ops leaders out there, but there's all these things that kind of stack up against you. And it's really important to know what they are and make sure you traverse the landscape. And so I've been like really inspired by the idea that I can just write to these folks right now. And it's kept me writing, which I think is the goal for me at this point. And I'm having a blast.

Picking Your Boulder and Licking the Cookie

Caro 41:06

Well, love it. Let's dig into one. Maybe I'll let you pick between picking your boulder or licking the cookie.

Which one do you wanna dig into a little bit more and maybe explain to people who haven't read it yet?

Amanda 41:23

Yeah, I mean, I think picking your boulder is a good starting place. Because if you pick too many, then you end up licking the cookie.

So, for everyone who hasn't read my blog, I'm writing for you. Like if this resonates and you're like, "I would love to hopefully have a chuckle with somebody who definitely knows what makes my role really hard," then find me.

This idea of picking your boulder is born from, I think... Like all ops leaders, we've probably all done seven habits of highly effective people, where you have, you know, you start with your big rocks and you prioritize your week. I've taken that class multiple times now.

Now, in the ops world, there are boulders everywhere. So it's not about your personal big rocks anymore. It's these big things that you dig a little below the dirt and all of a sudden you're like, whoa, what is that? And at first you're like, am I the only one that sees this? And then you realize, no, it's just that this isn't getting done. And sometimes there's a reason.

This post is really about, you know, as a new ops leader, you come in hot most of the time and you're like, how can I just make this place work better. And you want to, with all the best intentions, knock as many things off the list, but one trap is finding yourself pushing multiple boulders up a hill and having them all kind of roll back and splat.

Caro 43:13

So, this piece is about how to not let the boulder kill you. [Laughs] Very, very important.

Importance of Buy-In and Following Your Interests

Amanda [43:05]

Yeah, truly, truly.

The kernel behind it is, you know, a lot of what you do as an ops leader requires buy-in across the entire leadership team, like really true shared ownership, not even just buy-in of, "Yep, sounds good, Amanda. Good luck." But really, "I see the problem. I'm invested in the solution. I'm gonna own this with you."

If you don't have that, you probably are in a boulder pushing scenario, depending on the complexity of the thing. And sometimes it's worth it, sometimes it's not. And so that's the kind of setting.

Caro 43:42

To learn how to pick your boulder and how to successfully get buy in and push it up the hill, definitely check out the show notes for a link to Amanda's Thinking in Quarters.

And actually, on that note, though, I want to ask a follow up question.

You were talking about your role at PayPal, specifically becoming kind of the crypto person at PayPal. You talked about it "hanging off your desk," and I'm interested how you think differently about that.

When is it okay for something to hang off your desk, and when is it like a boulder you're pushing up the hill that no one else cares about? Or when is it a cookie that you've licked? To really mix all of our metaphors here!

I think we all have those passion projects, you know? And I guess how would you recommend people think about those things that hang off their desk.

Amanda 44:32

Yeah, I'm a big proponent of follow your interests, but don't prevent other people from doing the same. That's the thing.

I've never been the de facto crypto person in any room. I've always tried to find myself in rooms where people are exploring the bounds of what is achievable at the company. That's when I'm happiest. It's like, what could this be?

For a while, that was about, how do we bring crypto into the company and get people excited about it? And it was never my job to do that. But there were a few roles that I was able to say, "Well, what if we did this?" and partnered with other people internally to just kind of get people into it. And, when I saw other people working on things that were related to to crypto, that was a success for me.

Now, I feel like the issue, and I get into this a little bit in the lick the cookie article, and I've seen this a lot where people go, "I'm in charge of our data and analytics company wide. And so, therefore, if you're working on anything related data analytics, you come to me."

That's kind of the anti pattern, especially in a large organization, but also in a scaling organization where there's new needs every day, and it's impossible for one person to keep up with it. Eentually, you'll no longer be able to serve your customer, which is the entire company, if you give yourself such a broad mandate. And, you know, this ever expansive ownership, it ends up not working in your favor as an ops leader. And it also just, you know, hamstrings the company. I think that's maybe the nuance.

But I'm all for, you know, explore things that are interesting to you, because then you might end up in a new role altogether, which is a good thing.

Caro 46:30

Yeah, totally. It's the difference between, "I have an interest in this." If you're interested in it and you want help, you wanna talk about it, come find me. It's not like you have to go through me and hope that I have availability on my calendar and that my priorities align with yours and all of those things.

We've all been there and been like, why are you slowing me down? I could be halfway down the field by now, you know?

That shared sense of urgency - a company works best when people can capture that, right? And when they can, they're not being held back by someone who's licked their cookies.

Amanda 46:55

Yeah, that's right.

Caro 46:56

And now that we've really made everybody go want to both read all of your newsletters and also maybe go lick (and hopefully eat) the cookies.

Amanda 47:05

Please do. It's Friday.

Caro 47:06

No matter when you're listening to this, bring some Friday spirit to it, right? Eat a cookie!

Advice for Someone Considering Consulting in Operations Leadership

Caro 47:13

Well, on that note, I usually like to ask guests kind of what advice they would have for ops leaders. But I feel like you have a whole newsletter series about that. Maybe a different question to ask here is like, what advice would you give to someone who is maybe considering a branch out on their own to more of a consulting state?

I think this is something we're seeing more and more with operations leaders. And so maybe we'll narrow it a little bit there. But what do you wish Past Amanda would have known?

Amanda 47:40

I love this question. I keep urging people to explore this because it's risky. And I have the benefit of health insurance through not my own business. So, there's different privileges I have that I'm able to kind of do this and it be sustainable for me and my family. But, if you're able to, I mean, goodness, there's no better way to learn incredibly fast and be of service to multiple companies and ideally share back a perspective that enables them to move faster.

Starting Slow and Building Balance

The advice I would have is to start slow. I was lucky in that I was able to start with like two meaningful projects with teams that I just really loved being around. And that's a really good starting point because you're excited and then you have a little bit of bandwidth to think about, what do I love about this and how do I crystallize my value prop, and start to build this thing if I really am enjoying it? Versus like saying yes to everything and then having no time to reflect and no time to build.

I think you need to preserve some balance for yourself. And also I do think, if you try this and you end up going back into a leadership role, good on you, like great. That's a great outcome, there's no failure here.

This is not for everyone. It is a little bit of a different lifestyle to not have like the stability or just the sole focus of a single company. And so if you try it and you're like, not for me, that's also great as well.

Caro 49:28

Yeah, I think I would say that it's just as powerful to know what you don't like to do. Because then it's one less thing that's hovering on your peripheral vision of, "Oh no, what if?"

As someone who did fail consulting, same thing. I started consulting and became employee number one and now I run the damn thing. So maybe you'll fail just like I did and end up running the company. [Laughs]

Amanda 49:55

And still have multiple focus areas! I mean, look at you. You're still well diversified across a number of things. So, I think, you know, everyone's life takes different shapes.

Caro 50:06

Totally. I like that variety. Clearly, as do you. This was great. Thank you so much for coming and sharing all of your wisdom with us and just nerding out with me.

Amanda 50:10

Thank you. Great to chat with you again. This is wonderful. Thank you so much. I had a great time.

Thanks for listening to Opsy. You can find resources and links from this episode in the show notes at Opsy.work.

While you're there, I hope you'll take a second to join our free community, where, we share resources and opportunities that help us all level up in our ops careers. Again, that link is Opsy.work. Until next time, stay opsy, friends.

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