What we talked about
Ken Pickering, CTO of Scripta Insights, joins Federico to unpack how his team is using AI and large-scale data to tackle the opaque, often unfair U.S. pharmacy pricing system. Ken explains why drug costs vary wildly person-to-person, how that opacity drives prescription “abandonment,” and where Scripta intervenes: ingesting messy plan documents, inferring benefits and conditions, modeling deductibles, and recommending clinically sound, lower-cost alternatives (including cash-pay options). He draws a surprising parallel to his work at Hopper: much like airfare, drug pricing is non-deterministic to consumers, so the real job is reducing ambiguity with clear UX and trustworthy recommendations.
Show notes
Today on the PreVetted Podcast, we’re joined by Ken Pickering, CTO of Scripta Insights, where he’s tackling the broken U.S. pharmacy pricing system with the power of AI and large-scale data. Over the past 20 years, Ken has led engineering teams through hypergrowth, platform rebuilds, and industry disruption at companies including Hopper, Starburst, Going, and Rue La La. Throughout his career, his mission has remained consistent: leveraging technology and data to make complex systems simpler, fairer, and better for the people who depend on them.
Full transcript
Federico Ramallo (00:00) Welcome back to the PreVetted Podcast where we spotlight extraordinary people and remarkable talent reshaping our world Our guest today is Ken Pickering, his CTO of Scripta Insights where he’s tackling the broken US pharmacy pricing system with the power of AI and large-scale data For the past 20 years Ken has led engineering teams through hypergrowth, platform rebuilds and
industry disruption at companies including Hopper, Starbust, Going and Rulala Through his career his mission has remained consistent Leveraging technology and data to make complex systems simpler, fairer and better for the people who depend on them Ken, welcome to the show
Ken Pickering (00:44) Hey, thank you for having me, Federico
Federico Ramallo (00:47) I’m excited to talk with you and learn more about your journey can you explain a little bit what Scripta Insights does in simple terms?
Ken Pickering (00:57) I mean, well, we summarize it as get people the right meds at the best price. But in the United States, pharmacy system here is pricing is very opaque. It’s an opaque problem for a of people. Like you get prescribed something by your doctor or the pharmacy to fill and you have no idea a lot of times what you’re in for from a cost perspective. And so one of the things that drew me to script that was to be able to use technology to understand what people’s benefits are and then actually try to find them.
alternative drugs or different dosing strategies for those drugs so can really optimize what they pay for medication. In United States today, we have a huge problem with drug prices going up like significantly year on year. And more and more we see what we call abandonment, which is people get a prescription, go to the pharmacy to fill it, and then don’t get the medication. So there’s people that are going untreated because they can’t physically afford what the drugs cost. they’re not aware of what their options are, right? They can’t.
Really kind of work through the system and figure out like, okay, but is there other alternatives or things I could do differently without talking to the doctor again is There’s usually a wait to talk to a doctor again about these sorts of problems and challenges. And so script is trying to solve that problem by Approaching it from a from a a from a machine learning and AI perspective as to how we can propose alternatives and get people the medication they need.
Federico Ramallo (02:15) Interesting interesting. Yeah, I mean I I’ve seen the over complex system of pricing in in the US related to drugs and pharmacies and There are a lot of offers for Non drugs that are you know Herbs and things like that that are borderline, you know, they’re technically not drugs but help people to get healthier, right? as an alternative, right and
And yeah, I’ve seen experiences of people where they get so varied pricing, right? So yeah In Mexico we have a system where you can get this generic medicine at a much lower cost so yeah, they say that it’s not as effective as the original drugs, but I think they say sometimes they say that for
because they want to sell you the higher price drug. So I don’t know how much that is accurate. I think there are some cases where could be.
Ken Pickering (03:15) Absolutely. mean, yeah, I think it’s I mean, the real problem in the US, though, is you go to the pharmacy in Mexico and the drug is the same price for everybody. Like in many cases, you’d go and it’s five dollars and it’s fine. In America, it could be five dollars for me. It could be one hundred dollars for somebody else. It could be thirty dollars for somebody else. Right. And nobody knows that. Like, that’s the kind of that’s thing that’s wild about our system here.
Federico Ramallo (03:15) So.
yes, yes, I’m from Argentina, moved to Mexico 17 years ago and yeah, every time I start doing the math of the numbers I’m realizing how old I’m getting anyway so in Argentina they have another system where it’s basically prepaid healthcare so here is, in Mexico it’s the same as the US it’s an insurance, like car insurance
In case you have an accident, then that cost is covered by the insurance, right? With you know, a lot of caveats and but anyway, that’s kind of the system. So basically There are no incentives to keep you healthy, right? Whereas in Argentina you pay a fixed monthly Cost and basically with that revenue they
able to distribute the cost of medicine for all the people involved, right? that way, know if you have some urgent care they’re going to cover but if you have some things that are not urgent they have this waiting time so after a year you can do, know things that are non-critical, right?
so yeah, dental care, have those type of things but anyway it’s a much better system because they are their incentives is aligned to keep you healthy, right? and once you’re into that system then they have when you go to the grocery, to the pharmacy you get a big discount so you get a 30, 50, 70 % discount sometimes
depending on on which plan it is right, but it’s a Philosophically different system, right? Yeah, anyway going going back to this How does AI play and data play a role in solving? You know the pharmacy challenges in the US
Ken Pickering (05:27) Yeah, well, so there’s not like a repository. A lot of times the places we can go to understand people’s benefits information. There’s usually multiple checks as to the process. There’s insurance company and the pharmacy benefit manager and the pharmacy itself. And then it’s what the drugs price cost. And there’s what is deductible is an other status tracking that occurs throughout the process. so for us, it’s really like, it’s, I think it’s like we have to, we have to input plan documentation, for instance, which is like a PDF or a file, right? And so have to
In the past, it be a human being reading it and typing it and putting in numbers, know, the automatic automatic documentation ingestion is a big part of understanding how benefits work for people. Right. And, you know, and then it’s also like understanding like beyond the condition that they’re treating what drug they could be on. Cause a of times, you don’t get conditions from these feeds either in different drugs have different, you know, dosing schedules and different ways to treat based on based on the person’s individual needs. And so it’s like all that kind of stuff is, is inference around those things.
really try to figure out like one, what should they pay for drugs? And then two, like, how do we recommend alternative strategies for somebody based on limited information sometimes? So yeah, and then, know, and it’s predicting things like deductibles, because, you know, if you meet a deductible, of a sudden, all your pricing changes for healthcare, so your recommendations might differ. And then there’s also the cash pay ecosystem in the US, there’s Mark Cuban and Amazon Pharmacy, where you can just
a cash for drugs, right? So there’s a lot of these elements around that. It’s actually reminds me a little bit of like Hopper, and that like, at Hopper, it was a similar problem in terms of like, people want to understand when they should buy airfare. Airfare to a lot of people is an ambiguous thing, like the prices change, and nobody knows why, and what’s a good price for a flight? When’s the best time to fly? Like I have suffix, you know, it’s like, so for me, drugs is the algorithms are actually surprisingly similar in those types of problem spaces, which is like, well, but how do you, how do you, how do you remove ambiguity?
from this complex ecosystem? Like how do you advise people, know, in a way it’s easy to understand for everybody as to what they should do. You know, and I think that’s one of the powers of like CleanUX and AI in our modern environment is like, you can take these complex pricing and problem spaces and reduce them to something that is manageable for somebody that is not maybe technology savvy, you know, that is elderly and on a Medicare advantage. And how do you actually give people their options in a way that is digestible in the…
and they feel confident in those.
Federico Ramallo (07:50) right, right, yeah I think that’s a use case because you have a non-deterministic data source messy unstructured, there’s so many layers of complexity there and then being able to use an AI agent to interpret and sometimes as you mentioned infer
the missing data, right? I’m being able to do that transformation and structure it in a much better way to make better decisions and recommendations, right? Which again, those recommendations go through a non-deterministic-ish scenario, right? Because all of that is changing dynamically all the time, right?
Ken Pickering (08:28) Yeah, Yeah, no, it’s it’s pharmacy drug prices go up and down. Formula is changed monthly. I would say a lot of the players in this space really thrive on the opacity of pricing. And then a lot of the reasons that people can charge the things that they do for them is that people are not educated on the problem space. You know, when you have like an educated consumer who has a rough idea of what things are and what things should cost, you know, you have a
you can drive more change with technology and adoption. When you have a problem space where people just feel like they’re constrained by the system itself and there’s not very many options for them, that’s when you get kind of like, they don’t know what drugs cause, they don’t know what their options are. I’ve been educated on different strategies and different ways to do things because there’s just too many people incentivized by keeping consumers in the dark.
Federico Ramallo (09:18) right, something similar happens with, as you mentioned, Hopper with flights, right? there are no incentives to keep a clear pricing structure so making it opaque is… I can see how that happens what excites you the most about your current work?
Ken Pickering (09:26) Mm.
Yeah.
Um, you know, well, one, it’s a startup. love working at startups. I’ve done mostly startups from a leadership perspective, uh, like be around to later stages typically. Um, but the one it’s a startup, but I love working on the problem that we’re working on. I think one of the things that I decided sort of the, uh, the, the second half of my leadership career or whatever is that I want to work on things that, that I feel like are making a difference and that are important to me. And I think important to.
society or culture, like I’m doing some sort of good with my knowledge and education background, you know, and at the end of the day, I feel good about it because I’m saving people money on drugs and that’s, know, they’re getting the treatment they need, feeling more educated about the pharmacy ecosystem. And, you know, I think there’s a lot of ways to make a living. feel, I feel pretty good about the way I make a living.
Federico Ramallo (10:33) Interesting, yeah. I mean, I think I talked about this some time before, but I haven’t graduated university, But I started my career in software engineer when I was 14 years old, 15 years old, right? So one of the things that allows us to code
without a degree is that there are no regulating bodies if you want to be a doctor you have to get the certifications and the logic behind that is well you’re putting lives at risk if you don’t know what you’re doing and with software you kind of not but eventually as you mentioned what you’re building is actually
changing and saving people’s lives, right? So I think that’s very powerful.
Ken Pickering (11:32) Yeah, yeah, I like it. do. really do. I like the team I work with. I like my boss. You know, it’s a good environment.
Federico Ramallo (11:39) So switching topics, talking about your career and background, how did you first get started in technology?
Ken Pickering (11:45) Um, you know, it one of those things, like, I think I always knew I was going to become an engineer. Uh, you know, I took apart my record player when I was six years old and almost, almost got it back together again, you know, but I’ve always been really curious about how things work, like understanding how things work and how things are built. and, you know, and then when I discovered like computer programming, the concept of building something, making a machine do something based on input, thought was hyper cool. So.
found the book on Basic and started working with it when I was really young. you know, I progressed. I grew up in the 90s. So like, you know, I copy and paste websites and build my own websites. And then, you know, and then it just kind of evolved from there. And I went to college, I started out as electrical engineering, but moved into computer engineering and computer science as I advanced. And yeah, I got my first job as an engineer. I was doing like hardware engineering for vehicles. So was actually working
I was a military project that was doing like tanks and future combat systems and stuff like that. did that for a couple of years and then they really got more on the software side of things and really invested more in like, you building software startups. I was really happy when I fell into consumer. I do like B2B 2C now, but I love working with the general public. I love working with like a consumer app with a lot of like selling stuff to people online.
Because it’s one of those things where it’s like, have to have a good product to be successful. Like I think it’d B2B, you can, you can have a good sales team. You can make an okay product and still be kind. If you’re filling a good market need, you can be successful. feel like consumer tech has always been really the thrill of the hunt. And that like, you can make an app that nobody has to download. Nobody has to use it. Nobody, you know, and you have to make a great product. You have to make a useful product. I think for me, as I’m volume to clear, like making something that people find useful.
and derive a use out of has been important for me. That’s where I get a lot of my energy from. It’s like, people using it? Are they loving it? Do they find value in it? Like, do they enjoy it? You know, and I think, so that’s what, and so really I think it crystallized, and you you’re in leadership, you’re in IC or whatever, but for me, always that fundamental act of making something that people like, that people are into.
Federico Ramallo (13:57) Amazing. I think that’s the ultimate goal for engineers, right? That whatever we build is being used by people, right? And it’s helping a little bit or a lot, but it’s helping people, right? And in that process, the ego of the builder is like, look, I built this. It’s so beautiful, right? Which is, it’s so nice to be able to say that, right?
Ken Pickering (14:21) Yeah. Yeah.
Federico Ramallo (14:27) ⁓
Ken Pickering (14:27) Yeah,
I mean, I also like it’s easy to consider is easy to explain like to my mom what I do like here use this app, you know, like if you’re working on like financial modeling for like insurance companies, it’s more it’s more difficult to describe what your day to day is, you know, but I think it’s easy to like, saw people flights or I hope people save money on drugs, you know, I think it’s so yeah.
Federico Ramallo (14:34) Right.
right, it’s much simple to explain when I started coding I’m very detail oriented so I was always trying to make the feature on the technical side the best possible and I went into overengineering
Ken Pickering (14:56) Hmm.
Federico Ramallo (15:08) eventually I shifted towards what we’re building is to add value to the user so it is important to understand the value to the user because otherwise we’re building something that is not going to add any value to anybody then what’s the point? so yeah, it took me… I’ve been doing software for 25-30 years so it took me a while to get into that
that mindset, yeah. yeah, it was a learning lesson that was very pivotal in my career, yeah. So what inspired you to move into engineering leadership?
Ken Pickering (15:45) you know, I, I, I’ve always liked working with people. and so even, you know, even, you know, as an engineer, just working alongside somebody and building a solution has always been a lot of fun. I’ve always enjoyed like the team teamwork of the agile construct or concept. but I found the leadership, you know, in one of those types of situations where you’re like the lead engineer and your boss leaves and like, I think you’re in charge now. And it’s like.
Okay, maybe, you know, like, guess, I can consider it. But that’s how I got my first step in management. It was always something I was, you know, maybe kind of interested in going towards. But, you know, I got the push when basically, you know, there was, you know, there’s just a bunch of engineers in this SVP of engineering who needed someone else to help step up and take more of an organizational role. And so I did. You know, and, you know, I think it’s, you know, and I think
I think that’s how a lot of us fall into it. I think that’s how a lot of engineering leaders kind of fall into it. As one day they’re an engineer and there’s a need of some kind and like, well, would you like to be, you know, and then, you know, you do it for a while and some people like it and some people don’t like it, right? And some people go back and some people stay. Um, but I think it’s, uh, you know, that’s, that’s how I felt it. I liked it. And it’s a, it’s a happy, I continued to develop on that pathway. Um, but you know, I mean, you didn’t get in engineering to be a manager a lot of times you got an engineering to be an engineer.
And so I think like, you know, some of us choose to kind of fork our career and go more of the management pathway, but it’s definitely like, it’s definitely, you know, it’s definitely, think a lot of it’s kind of fallen into that decision because we don’t really overly think about being a manager when we first start getting into the business.
Federico Ramallo (17:20) Right, right. Yeah, I’ve seen a lot of engineers that they prefer to remain being an individual contributor, right? And I can understand that. What I’ve seen happen to me when I start doing Engineering leadership roles is that the amount of interruptions that I will have throughout the day will increase, right? Yeah, and then that diminish how much you can actually
Ken Pickering (17:37) yeah.
Federico Ramallo (17:42) contribute individually, right? Yeah, and by the time you focus again to build something, you know and get back to coding, you get an interruption and you know the the day passed and we were trying to achieve that day coding, you couldn’t, right? So yeah
Ken Pickering (18:01) Yeah. Well,
I mean, that’s, you know, it’s funny, it’s, because you lose that flow state. A lot of times in management, you don’t have enough time to kind of achieve that, that flow state that you really need to do deeper work, know, to do deeper creative work. Because I find, you know, I need like 15 to 30 minutes to kind of figure out where I was, and then start getting back into it. And then you’re in the mindset for a while. And it’s, you know, but I will say like, I will say, I’ve done a lot more
Federico Ramallo (18:13) Right.
Ken Pickering (18:27) I mean, I don’t know you call it individual contribution, with like AI tooling and everything else, I find that I’m able to actually like fire up some rough ideas and then do a meeting and then come back and check output. I mean, like I’m able to actually get some intellectual property done during interruptions. Like I’ll try to queue up some stuff for like a meeting block and just fire it all off and then, and see what the output of it is when I get back. um.
Federico Ramallo (18:50) you
Ken Pickering (18:51) But I find it’s, I’ve actually been more successful that way, I think, than actually in terms of prototyping and exploring new concepts or constructs. It’s not production code for me at this point, but it is more like I have this idea that I want to implement and can I get a quick scaffolding and idea and still also do my kind of engineering leadership day job. It’s been kind of interesting transformative journey last couple of years around.
Federico Ramallo (19:13) Right, right, because if you stay in the ivory tower and you don’t get your feet wet or you don’t get the boots on the ground whatever analogy you want to use but if you don’t get into the coding and understanding how things work then there are lot of missed opportunities and being able to prototype and figure out what could work and couldn’t, I think that’s important
Ken Pickering (19:37) I think all technology leadership, this is an opinion by the way, and not everyone follows this opinion, but I do think people should stay technical. do think engineering leadership, I don’t think it’s purely about processing people. think part of the reason you’re in the role, I think all leaders need to understand what their teams are doing because by understanding what your team is doing, you can lead them better. And so I’ve never really agreed with the hands off, like not really focusing on the technology side of engineering management, even when…
I’ve been running really large teams. think it’s very important. you know, I, I maintain both technical and non-technical reports because I want to know what our senior most contributors are working on. Like I want to know what their challenges, want to know what the trade-offs are making technologically speaking on a regular basis. You know, some people don’t, teams get bigger. Some people just kind of go into the pure process management side of things. I just never found great results doing that. I find it’s hard to lead a team if you don’t
Federico Ramallo (20:30) right, yes, I agree. And I’ve seen that disconnect happens and then you have a human process, but the quality of the software diminish when leadership lose the technical touch, so to speak.
Ken Pickering (20:44) Yeah. Yeah.
Federico Ramallo (20:45) So I think you kind of answered the question, but I’ll ask it again anyway. What do you think is your favorite part about leading engineering teams?
Ken Pickering (20:50) Yeah.
Um, I mean, I, I love working with people, but I, if I had to pick, I am more of a completionist and that I love seeing stuff ship and I love seeing stuff get used. I love this getting something over the finish line and being successful. So I’m a very like objective based kind of leader, you know, and, you know, I think it’s important, you know, I think it’s important to inspire a team through that, but also like, like to focus the team on shipping too. You know, it’s important to fix down. It’s important to consider architectural issues, but like,
In the startup phase, it’s also important to deliver, you know, like you’re kind of, you’re kind of fighting and many times you’re fighting for your life as a business through the uncertainty of being a startup and delivery is a really important aspect of that. so for me, it’s like making sure that, you know, I build a great team of independent people who are passionate about delivering software. And so it’s easy for us to kind of, you know, work together and understand, understand each other. think it’s like, you know, it’s, it’s because I think it takes, I think it takes a special kind of mentality or
mindset to be successful in a career at a start. Especially when you’re like 20 engineers or less, things are still, everybody matters. Everybody’s output matters, everybody’s day to day matters. So working through environments like that and coaching people up as to why that’s important and why shipping is important and why always.
You know, it ends like end adopting new tool kits or not being afraid to bring in a vendor if we have to bring in a vendor to solve a solution for us, but really being holistic about the entire problem domain and building great software through that.
Federico Ramallo (22:24) Right, interesting. How do you help keep the team motivated during stressful times?
Ken Pickering (22:31) Yeah, I mean, I, you know, I think it’s one is one is building trust with your team. So if bad things are happening, like there’s negative things that are happening, there’s there’s mutual trust that they’re doing the best they can resolve the situation. And you’re doing everything you can to support them as a leader, right? I think, like, you know, we’re dealing with a lot of uncertainty right now, like the whole
generally I think is turning the industry on its head and the engineers are worried if they’ll have jobs in five years from all the media hype around it. There’s weird and challenging like, like, like, like, like, like, like, like, like, like, like, like, like, like, like, like,
Federico Ramallo (23:15) Thanks
Ken Pickering (23:16) You know, working through these things methodically and just being open and honest and building that trust with them so that they can come to you if there’s a problem in production that they may be caused that they’re not afraid for their day to day. If they made a mistake, they made a mistake. People make mistakes, right? Like it’s important we learn from our mistakes. But the end of the day, like building a culture where people can bring legitimate concerns and it’s not a retribution culture and it’s not a punitive culture. It’s just more of an objective and results based culture is to like, OK, we messed up. How do we fix this as quickly as possible? Like let’s.
let’s get over the guilt and get to the next phase of this process, which is how do we resolve this as quickly as possible? And I think trying to build an ecosystem like that where there’s like trust between executive leadership all the way down through the ICs is important because startups are stressful. And it makes the job harder if people are worried about things that they feel like they can’t articulate or express to their leadership. so, but that also requires a person that does have a-
and does want to give feedback and does want to involve and invest in the process of that kind of like communal culture that we’re building. If you just want to be heads down and just focus on your thing and not care about the large ecosystem or just want everything kind of handed to you in an ordinal fashion, those kinds of things don’t happen. It’s not a great cultural fit for a startup where it is chaos and we’re going to deal with disruptions and we’re going to have to clear the spring and we’re going to have to deal with.
P zero issue. Yes, everything’s on fire. No, observability is not where it needs to be. And yes, I understand this is a problem. And yes, we’ll fix it tomorrow. But right now we have to, you know, and so I think it’s been, but you need the right people and the right culture to build, build yourself so you can be resilient through these processes. You can be resilient through like all the kinds of fires and challenges that startups have.
Federico Ramallo (24:41) you
Right, right, in startups you have a much more chaotic workflow, right? And you have to adapt to the current situations and doing trade-offs, yeah. And what I’ve seen, this is what happened to me is that those trade-offs become more and more of a trade-off when we had a, it was on a lunch date, it was a demo day, right? Then you see the stress going up, up, up, up, up until, you know,
You launch as much as possible for that particular demo or launch or whatever. But by the time you go back to try to put everything together again, they announce another demo day, right? another. So it’s an interesting dynamic.
Ken Pickering (25:46) When I was, not to mention what start this is, but we definitely shipped an appliance once that didn’t work. We knew the updater worked. We knew the updater worked, but the appliance was essentially a brick that we were shipping, right? Like we knew that the code did not work on it. And we knew that we had two weeks from when it was shipped from, from Asia to the U S and they would put it in and they would update. had two weeks to solve the problem, right? Like, I mean, that’s, that’s the kind of stress that you’re like, you’re like, you, you, are on a hard clock. You are on a hard clock.
Federico Ramallo (25:52) Hahaha
Ken Pickering (26:15) We know the one thing that works is the update or we can get new software out. We can get invented and tested, but we have two weeks. You know, it’s I mean, it’s if you haven’t lived through those kinds of experiences, it’s really tough to articulate like like how you do it right. Like and how that how that works and what kind of team you have to have to like navigate the difficulties of that process and and to go above and beyond and deliver through those through those challenges and and you know and still and still you know and avoid burnout and still believe in the company afterwards. Like it’s it’s a.
It’s a weird, it’s a weird culture in ecosystem.
Federico Ramallo (26:47) yes, yes I had a very stressful moment once I was working at Microsoft, I joined there when I was 16 years old and I was demoing a feature I was part of the team that was launching Office so I was
maybe Sheraton, Hilton, some of these big hotels, right? we have the whole conference floor for us, 1,000 people, something like that, it was huge, right? while I’m walking towards the stage we have different people presenting different stuff so they call my name, I’m walking there and my demo laptop frees right? dies
So I had to restart my computer, I had to keep a poker face throughout the whole ordeal because I was on stage with everybody looking at me and I was just waiting for the time they would call me to do the demo.
Meanwhile, my computer was rebooting and I had to start everything again. It was the longest three, five minutes of my life. And I keep reminding that story because that summarizes what demo day is in a startup. It’s similar with more people where that level of stress goes up. And you’re at the last minute.
fixing something sometimes. So anyway, yeah.
Ken Pickering (28:18) Live demos are always, you know, it’s always interesting. Like it’s always a risk. you the amount of times I’ve, you know, it’s like, I think 80%. 80 % of the time it goes okay. But it’s, that’s a 20 % is a surprisingly large number for something that should work. But for some reason it just doesn’t when you start sharing your screen, you to show people. So.
Federico Ramallo (28:42) Right, right, yeah. And every time I do a demo or a show on my screen on a public talk, there’s always something going wrong. So you have to adapt to the situation and just move forward. I’ve seen people just do a video of the demo instead of just showing it to reduce that risk.
Ken Pickering (29:02) That’s a safer route.
That’s a safer route, 100%.
Federico Ramallo (29:07) yeah yeah yeah I and I understand why they do it but I’m thinking man you know this was a great opportunity just just you know risk it all and go for it right so yeah but it’s safer as you said yeah so so how do you think that the engineer engineering roles evolve you know from from work going from startup to beer corporations
Ken Pickering (29:28) I mean, I can tell about my own journey, right? find is so, cause you know, at Hopper, started about 20 engineers working there and I grew the org to about 270 people, which is, know, not, definitely not as big as some larger companies out there, but it’s the journey from, you know, in the same sort of journey at Starburst, about 30, about 150, 160 engineers. And it’s really your day shifts. I find that your responsibility, your core responsibility, which is like,
Federico Ramallo (29:30) Right.
Ken Pickering (29:56) Managing technology, managing engineering, managing the output of teams, making sure things are running on time is the same. The bullet points for your job remain the same, but really what changes for me is the ways and tools and things you have to do to accomplish those things. Right now, 20 person company, there’s very little management over here. work with lead engineers. have direct input on architecture and design and prioritization and trade-offs and all this stuff we’re making. I can be involved in that process.
day in, day out, it’s not a huge team, right? But, you know, a few years from now, hiring managers and directors, and now I’m managing through managers and directors, and then coaching them and working through them on how they do that sort of thing, or how they run that sort of process. Still the same, like I’m still responsible for overall the output. Now there’s more people, though, who shipping more things. There’s more product managers, more stakeholders. There’s more people in the field that have questions. And so it’s like, you know, I find that
I get wrapped more and more into process or building process as time goes on. Like how do you effectively manage your work with larger and larger organizations of people? But it’s still for me to accomplish the same task, which is like, how do we still ship great product? How do we still hit our milestones? How we still hit our revenue targets, right? How we still building and maintaining a great culture. It’s just that like, it moves from me doing that a lot as a human and being involved in that process to me working with a lot of other people.
a larger community of people who are now involved in investing in that process, but also bring their own input and structure to it as well.
Federico Ramallo (31:26) Right, right. And as you mentioned, every time you add a layer of management or a layer of abstraction, you have to reinvent yourself in the world, right? Because you have to build new processes, right? Yeah. And the opportunity costs go higher because you could build something, right? You could code something, you could research something, right? But
if the team that you’re managing goes in the wrong direction that cost becomes so much bigger than whatever contribution you’re doing and it goes both ways
Ken Pickering (31:55) yeah.
Yeah,
100 % example is like hiring right hiring. If you’re doing the hiring yourself easy right? You’re doing the interview. You’re the decision maker. You have a process you like. You’re evaluating the candidates yourself like. You hire to make a decision is great training people to hire not just in training like several different managers to hire and maintain the same bar and have the same decision making framework and bringing the same like caliber people wildly different.
Federico Ramallo (32:13) Right?
Ken Pickering (32:29) Right? Like you much larger problem and much larger cultural problem if it goes wrong, you know, it’s, one thing if you’re, you’re kind of the central person in that process. Another, if you’re, you’re trying to articulate a process that others have to follow that something like really high stakes, like the number of people and the people you bring into a company, you know, and then, and then, and dealing with inconsistencies in that over time and, and the, and the churn that those inconsistencies can cause that’s
You know, that’s, that’s, it’s like dealing with that becomes more of the issue than just, just, you know, working on a hiring process to hire great people. Yeah. And so it’s the level of complexity with just human dynamics. I’d say. Big challenge.
Federico Ramallo (33:05) Right, You mentioned human dynamic is one of the things that I I learned when going from individual contributor to managing teams that now You know, you’re not just focus on things now your focus has to shift our people and people’s process, right? Yes and and hiring it’s it’s a big big challenge and
And as you mentioned, it’s not the same when you’re owning the whole process and then when you try to delegate that. Usually what I do is I set my expectations low when I delegate something. That way people can exceed my expectations. Because if I expect people to do the same
output that I’m doing on terms of quantity and quality then I’m going to be disappointed, So I lower my expectations but I set them the expectations of this is what I’ve been doing, this is what we expect you to do, right? So that way they can, you know…
maybe they do 80 % of what I was doing but you know, if I set myself in so maybe this is a more you know, more of a internal conversation that I have with myself, right? Because as I mentioned, I’m very detail oriented and perfectionist in a lot of things then I know that it’s going to be difficult to find people that are going to be as perfectionist as me, right? So I have to give them that space for them to make mistakes, learn
And then eventually they’re going to do as good and sometimes even better than me, right?
Ken Pickering (34:33) 100%. And, you know, I mean, it becomes a job, right? Like, you can’t scale yourself internally to doing everything for 100 % org, right? Like, if you want to grow, you got to learn to trust and you got to learn to delegate and you got learn to build people up. you got to learn how to sample and figure out how to identify their problems inside of an organization and, you know, focus attention on, you know, I’d say like, you know, it’s, I think if you, but you know, one of the good things I think is that people are pretty introspective about how they spend their time.
kind of evaluate like as a leader, what phase are you in and what is the best usage of your time and being practical realistic about that and focused on like the highest efficiency thing you could be doing for whatever phase you’re at. I think it’s easier to deal with some of the kinds of cultural changes that come over time, right? Like, you know, as much as you might like working on technology directly, now you have
and principal engineers that work for you that are largely doing that. So how do you interface with them and still give them freedom and empowerment, but still feel like you’re connected to it, right? It’s like a thing or, you know, I have a ton of opinions on management, right? It’s been my craft for, don’t know how many years, a lot of years now at this point, right? have tons of opinions about how to manage humans and how do I incorporate someone else’s style of mind and we find common ground. How do you train and educate people so that you can build that kind of that trust back and forth and, know,
And yeah, and be comfortable doing it. Because I think a lot of us sometimes we get, I think a lot of engineers can be control freaks. That’s one thing that I find when I coach people. Sometimes we’re all control freaks at one point. We have to manage everything. We have to know everything that’s happening and know everything that’s around it. So that’s how we build our mental models of situations. And so dealing with now human beings in the loop and having to build relationships as opposed to systematic design, it’s a lesson, right? But I think like,
Federico Ramallo (36:02) You
Ken Pickering (36:24) But yeah, there really is no alternative if you want to continue doing more senior management roles at bigger companies. I think focusing on what really, really, really is important for career development and focusing on what actually is best for your company for you to be doing and sometimes sacrificing the stuff that you might not want to do is instead of how it’s played out. know, I was, that’s one thing I think that lot of engineers don’t know about their bosses like at companies is we would all probably just rather be coded and dealing with internal office politics. Like most of us,
love solving problems and would be heads down if we could be. It’s just not the path that we’re on right now. It’s not our journey right now. We’re with like dealing with tons of human issues and human challenges and deadlocks and you know, but that’s what we’re supposed to do. We’re paid to do. That’s what the company needs us to do and so we do it. But I think most people will be surprised at how often I would rather just be like focused on you know, being heads down on something.
Federico Ramallo (37:21) Right, right, I completely agree, I mean, when I was talking about my resetting expectations is basically because I being a control freak, I want everything to be right and perfect and when you’re working with a computer
You can do that, right? I mean, all the mistakes, all the issues are on your side. I didn’t give the computer the specific instructions. And once you do, then it works as you expect, right? But then that ethos doesn’t apply to humans, right? So that’s a learning lesson that, yeah, it takes a while to adapt, right? And as you said, eventually, on the management side, we want to go back to code, right?
Ken Pickering (38:04) 100
Federico Ramallo (38:05) one thing that worked really great for me on the hiring side was to get everybody on the team vouching for every new person that we screen and accept, right? that way there is lot of accountability and ownership for everybody involved, right? again, it was a change of culture and it took a while to figure it out, right? but we had a few
Missteps right that we think we’re thinking in the right direction and then we find some issues, right? and when we correct them, but it and also explain the people the importance of the ownership and What vouching actually means right? Because because it with the peer pressure it sounds easy to say well, yeah, if everybody says yes, and I will say yes, right so yeah, I
I got a lot involved into social psychology to kind of understand that, right? And there are great books about that, but anyway, it’s, you know, the peer pressure pushes to comply to what everybody else is saying, right?
Ken Pickering (39:08) I definitely, I like to get feedback in a vacuum. a lot of times I won’t let people see other people’s feedback in a process. so, like I want to, know, and I don’t let people give ambiguous answers. Like people are like, oh, I’m a soft, yeah. I’m like, there’s no soft yeses, there’s no soft nos. There’s yes, which is that you want this person to work here. You’re an enthusiastic participant in this process. Well, there’s no, and you don’t have to have all the yeses to work here, but like, if you’re a yes and you believe that, you know,
Federico Ramallo (39:18) Right.
Ken Pickering (39:37) that they are, it’s a strong fit and it’s a strong, know, because I think people, people don’t like, you know, it’s getting over people feeling like they’re judgment, laying judgment on other people is tough, is a tough part of my training for interviewing. And it’s like, well, but you’re asked to make a decision. Like you can say no, it’s not the end of the world if you say no, you know, I think, you know, one of the people I worked for,
Federico Ramallo (39:56) Right.
Ken Pickering (40:00) Especially for, for, and this is, I found this for hiring leaders is, is, is, is a good, it’s actually an okay viewpoint, even though it’s pessimistic. he, told me when I went into an interview process, I should just assume that the other person was a no hire. Like when you walk into the interview process, you walk into that person, that person should work here. And, and during the course of the interview, it’s their job to flip you to a yes. And that like your default is no, and they show you something that you believe, all right, this person needs to be here. You know, this person actually brings a lot to the table.
And I am converting now to being a yes for this person. And I found that walking into really like, because leadership interviews can be challenging because people are very polished. it’s, think, really trying to figure out if they got you over the hump to a yes, has made me make stronger leadership hires over the years. And so it’s like, you know, and I never liked it like, when I first heard it, I like, that sounds like kind of mean. That sounds really super judgmental. was like, but no, but actually, you know, if you’re hiring someone that’s crucial to you, crucial to you, you need to hire.
a really great leader for your organization, you’ve to be right about it because the challenge of hiring a bad leader, it it, reached havoc throughout the company, right? And so I found him in a bias of like, no, like they have to, in this process, in this 45 to 60 minutes, they have to get me over the hump to, to agreeing that they belong here has been, has been, has really helped me.
Federico Ramallo (41:08) Right.
Right, right, what I tell my team is if we say yes to a new hire and the person is not delivering and we make commitments on delivering whatever then somebody else on the team is going to have to work harder to compensate for, you know, so
There is a connection on that. once I explain them that if we do an ECS on the screening and hiring, then it’s going to affect everybody on the team in the future. And in particular, it’s going to affect you individual contributors that are participating on this. And when I shift.
shifted that way. At the end of the day, if we have an issue like that, would not assume that everybody else is going to do the work that that person is not doing. I’m going to try to detect that. But once I set that mindset, then they were able to be more comfortable saying no, because they know that that’s going to affect them in the future.
And as you mentioned, the natural proclivity is to empathize with the new candidate, right? And we want to say yes, right? It’s our nature, right? Yeah. And then the other thing that we did incorporate in our process is giving feedback. So candidates that we reject, we give them feedback to do better, which is challenging to do.
But the intention for that is a rejection doesn’t also mean we just let them die in oblivion. So we try to give them some value, even though we’re rejecting them. So that also helps people to be able to say no. We shifted from no.
to not yet, right? Yeah, not yet, and this is why, or these are the things that you need to improve. Read this book, learn about this. After you do that, come back in a year, six months, and apply again. So I feel it’s more humane, because we give them hope. We give them a north of do that.
Ken Pickering (43:05) OK, I like that. Yeah.
Federico Ramallo (43:28) 90 % of the people don’t follow that advice. Some people do, right? But at least on our side, they feel that we’re doing as much as possible to help them move forward, right?
Ken Pickering (43:40) great. That’s a great philosophy.
Federico Ramallo (43:43) Yeah. What is the hardest part of being a CTO that people might not realize?
Ken Pickering (43:50) I mean, I think.
I don’t think everyone understands the responsibility sometimes of being a CTL and managing a budget and managing a company and being directly responsible for the success of a company sometimes. People say, oh, it’s a great title, it’s a lot of responsibility, sure, but I think there’s a lot of, especially when things go poorly, there’s a lot of late nights and miss sleep and I think…
Like, I don’t think people realize that we feel directly responsible, like in many cases, I do. I feel directly responsible for the success of my company and my team. When things fail, like I take that personally, right? Like when we have to, like, you know, the SaaS crunch happens and we have to do layoffs and, you know, our business is down. mean, like those are things that, you I should be able to help address and fix and manage. And when those things happen, those are…
those are burdens I take on myself, and burdens I think that I feel directly responsible for. when I’m determining a hiring plan, I am concerned about it because I don’t wanna have to lay people off because I am responsible for managing to a budget. I am responsible for all of it. And I think it’s trying to balance all those concerns with trying to drive a strategy, but also knowing that you’re, what is the percentage of risk around this? If we miss it, like what’s the odds that I have to like,
reduce workforce in this day and age because like capital is not as easy to come by in this day and age. It’s not like VCs are handing out checks to everybody. so I think those are the things like those are the things I think are really, really hard about the job that most people don’t know. Like most people don’t see behind the curtain and to like the, know, the, the, the, budgeting and forecasting and business process stuff that comes with the role and trying to manage that successfully. Um, because, because that, know, after X number of years in this industry, seeing the cost of not doing it.
having to execute reductions in force. I worked for a travel startup during a global pandemic. I was working for a company that sold flights in 2020. We were just shooting up like a rocket and then boom, right? Went from 10x reduction ARR overnight. How do deal with that? How do you deal with that catastrophe? In those types of situations though, there’s not really a lot of people to help you with it either.
Federico Ramallo (45:56) Right
Ken Pickering (46:10) Like they’re just kind of, you’re just kind of the person asked to work out the plan and there’s not tons of tools in our industry to help people navigate these things. Like maybe you have a business coach that can kind of help you through some of it, but like all that kind of stuff and all that uncertainty and, and sort of the, I think the, the karmic debt that we feel we all accrue when we fail is, is think lost on people that want to actually get progressively further and ensure leadership.
Federico Ramallo (46:34) right and you can rationalize it saying well it was a market the situation but you you know in your heart you you feel in your heart that failure is your own right and yeah yeah yeah
Ken Pickering (46:46) Yeah, you’re a little
enough people I’ve hired worked with for years, right? Like, you know, you’re the one sitting there in the conversation with them, you know, you’re the one, you know, they just got married and bought a house, right? Like, you know, like, you don’t feel great about that, right? I mean, it’s just those types of things just kind of drag, drag behind you, I think a lot in this career. And so, you while I love celebrating my successes, I also learned a ton from my failures and
I think at the end of day, you just try to do better next time, but it doesn’t remediate the fact that you have to go through it.
Federico Ramallo (47:18) Right, right. The emotional toll is hard, And as you said, you had very few people that you can actually talk about that, right?
Ken Pickering (47:27) Yeah. Yeah, I my dog. Dog’s a great listener.
Federico Ramallo (47:30) And the firing is hard emotionally because the way that I see it is that person put their whole life, their whole well-being, their whole you know being able to pay their bills, they put their whole life and financial security in your hands, you know my hands, you know they I see it that way because it’s a
I feel that there is a big responsibility when we hire somebody because of that, right? yeah, yeah, yeah and that’s why I work hard to make sure that we’re hiring the right people, right? because that way we don’t have to fire the wrong people, right? yeah, yeah, yeah amazing so we’re running out of time do you want to share any…
Ken Pickering (47:55) 100%.
Yeah
Federico Ramallo (48:13) Last remarks before we wrap it up
Ken Pickering (48:16) No, I think this is great. think, you know, I encourage anyone listening, it’s an aspiration, engineering leader to give it a shot. You know, think it’s, I think it’s, I think it’d be a hard career. I think it’s a hard fork if you’re an engineer and then you become an engineering manager. But I think it can be ultimately rewarding for people if it’s the right fit for folks. And, you know, and so keep on listening to podcasts like this and learning from, learning from.
or if you watch from the people who’ve done it and failed and been successful and those sorts of things. yeah, but yeah, thanks for having me.
Federico Ramallo (48:51) Thank you very much for joining us today. I think you give us great insights and yeah, it was amazing. Thank you
Ken Pickering (49:00) Thank you.