From CIO to CBO: Lenin's Journey Through Tech Evolution and the AI Revolution

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Challenge for these existing organizations by

next decade, most of these will become obsolete.

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With AI, there's just so much opportunity on the

table, which comes with a little bit of risk

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taking. So now we're at the point of creating

superhuman capabilities. Is AI actually driving

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some business values? What AI is giving right now

for people is to really rethink about the

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opportunity. It's the same old problem, your

solution. And that's what tech debt is. You're in

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the right era with the right time. If you're

building something now, you're building for the

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future. Hi, Lelein. Really nice to have you with

us. We're doing this for the first time, but you

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know, the idea is that, you know, like you've seen

the world in a lot deeper ways than we ever could

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have in terms of your experience across so many

different companies, including startups,

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across functions all the way from data analytics

to IT to now in your role as CBO of Atomic Work. And as

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a startup, we're just now trying to enter that

world, right? So we want to see the world from your

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perspective in sort of like quick, short 10

questions, right? We'll, Harsh will try to keep

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score to 10 so that we can manage time. But that's

sort of the idea. Yeah, no, thank you for having me.

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And I'm very excited for what it is that Trupea is

doing and happy to be here to engage with you guys.

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Great. I think, you know, the first question that

we all had on our minds is that yours is actually one

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of the most interesting career trajectories

we've seen, like in how your roles have evolved.

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And, you know, you've seen the IT side of the world,

and now you've seen the business side of the world,

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right? So what are some misconceptions that these

two sides of the world have about each other? Oh,

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great question. I think when I was in IT, in the

olden days when we first entered, it was not about

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business, it was more about technology. So we

wanted to make the technology work because, you

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know, everything was always about how to make

technology function for the business. But it was

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predominantly core is IT is segregated in its own

space. It was always thought as IT always have to do

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something. And and and the business is always

looking for IT to do something. So it's more like an

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enabler to some degree. So for the last three

decades, when the first time IT has become, you

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know, an important part to drive technology in the

organizations, it was not meant for employees to

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become highly productive or anything like that.

The idea was just make it work. Technology should

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work. That's the idea. And CIOs and others, all of

the people who are always building things and

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making things work. And if these things don't

work, they were like, okay, that's all I can do.

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Right. So there's a limitation. But what's

happening now that the tech is advanced, we as

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humans have matured, adopting to the changes,

learning faster, it's becoming more business

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driven. So that means if you bring a technology, it

has to be business friendly. It has to be employee

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friendly. It has to be justified for what it is

worth in the organization. Why do you need it? So

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that maturity also came with the technology

adoptions and also the evolution of technology

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itself made us really see the value of why we need

something in the organization to begin with. So

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I'm kind of seeing the trend of evolution of making

technology work to now making business with the

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technology to run. So we kind of went from crawling

to walking to now running. So eventually we'll

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also be flying with technology. So I think that is

where we are in the AI age, I would say as a maturity.

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Got it. And I think the other interesting angle

here is that you've also seen both sides of the coin

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in terms of you being a CIO as a buyer of technology,

which is now you are CBO of a startup and you need to

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sell technology. So what are you seeing in terms of

evolving vendor relationships and how has your

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understanding changed about that? Yeah, so even

though I was a buyer and on the one side now I am on the

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other side to sell, the concept for me was the same

in the sense that you need to understand the buyer

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and if you're selling, that's important for you.

But if you are a buyer, you need to understand the

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seller because a negotiation of whatever you're

buying starts from the get go of why you need that

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and all of that stuff. So me being on one end really

helped. So I was only worried about why I am buying

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it for the organization. I never cared about the

other side because initially it was all about a

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transaction. But then when you start building a

relationship with people who are actually

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building those, the perception changed. So when

you are a startup and you've grown into a larger

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organization, your understanding is a bit

different from people who are actually

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entrenched themselves in a larger organization

might not be thinking what the other person is

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really going through. Why are they selling? Your

opinions might be different. I think why I'm

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advocating buyers now to spend more time with the

sellers, not for the transaction purposes, but

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building a relationship that is going to help them

understand why they're building something and

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how what they're building is actually going to be

useful to you, not now, but into the future. See the

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problem when you're buying a matured software,

you don't actually care about how it is built, who

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built it. Nobody really cares about it because you

just go and buy it and then use it and then that's it.

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There is no relationship. But when you're buying

software now from a founder in early stages, you

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now have to do a lot of scrutiny and understanding

who the founder is, how much money they have,

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viability, sustainability, growth and why are

they doing it, can I rely on them. So the CIO's

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tendency is typically, it's just risk covers.

Nobody wants to really buy something risky. And so

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now coming on the other side, I'm actually now

applying what I used to think in trying to work with

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CIOs, why it is important for them to build a

relationship with the founders and so that you

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don't have to really wait until the software

becomes better, where you're only doing a

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transaction. But if you now build that

relationship, you might also become an advisor.

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You could also help them grow and the credit will

become where you're giving back something and you

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could also grow with it. Also, there's a

satisfaction that I used to have whenever I used to

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help a founder before and going on the other side

now I'm expecting the CIOs to have the similar

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thing and that's something that I'm advocating

through my being a CBO and doing this start

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leadership and sitting down with the CIOs and

explaining to them why they should give time to the

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founders and learn a little bit more about why

they're building it and how that is going to help

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you. Absolutely, I can completely attest to that.

Like Lennon has actually been that conduit almost

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for the startup world to actually interface with

the CIO world and them getting to understand each

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other like you're saying. I think one of the things

like you mentioned, the CIO role is typically

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meant to be risk averse but with AI there's just so

much opportunity on the table and they obviously

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have to be open to innovation which comes with a

little bit of risk taking. So how are you seeing

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CIOs actually tackle that? Like is there actually

still a lot of risk aversion or are they open to? So

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what happened two decades ago when everything is

installed on the computers, there was nothing

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really leaving very small network controlled.

You do not have these many problems because the

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maturity or opportunity for anyone to really

penetrate those type of networks was hard. Once it

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has become open web, open network, global, we've

also opened a lot of doors that we didn't know open.

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So when the organizations are now introducing

technology, it's not about just use of the

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technology, it's also protecting your own

organization because by introducing that

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technology now you're introducing certain risk

that you don't know and that's why CIOs are more

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cautious around not just because they don't like

it, even if you like it sometimes you can't employ

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it, you can't deploy it and that's not because they

don't want it, it's just because they can't

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because of the restrictions, certain

guidelines, governance, compliance, so many

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things that needs to be part of the ecosystem that

is really why the CIOs are more methodical,

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conscious around why they should introduce

certain technology in the organization and

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that's really the thing but that is by nature

because their jobs are on the line if they

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introduce certain things, they have to justify

and that's one of the other reasons so many things,

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policies, other things were introduced to help

the CIOs to make those decisions not by taking

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ownership of all of these things on their own,

instead they're bringing an whole ecosystem to

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support them so that's where procurement comes

in, security comes in, the infrastructure teams

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come in, everybody is evaluating the viability of

a solution in so many different things,

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eventually the decision is going to be made. Makes

sense, makes sense and like when it comes to like

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viability, right, like that point around, you

know like there's still a lot of conversation

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around okay at the enterprise level is AI just good

enough for pilots or is it actually driving some

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business value so what are you seeing? So I was as I

was mentioning earlier the maturity is really

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critical, the maturity of both is critical, the

buyer and the seller, what is important in newer

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technologies is trust, trust that it works, trust

that it is secure, trust that it is reliable and

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also is going to make things better than worse and

that takes time, there is going to be hesitation,

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there is definitely going to be some sort of good,

bad and ugly situations of people taking the risk

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that didn't pay off, again if you make those

decisions with certain bad rails then people who

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are in that process protected on both sides,

otherwise things can be worse, right. So yeah I

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think more about what use case is because of early

stages and then what return on that investments

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that you're making then not everything is about

ROI, so that's why sometimes people talk about

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ROI, is this really a growth driver? How are you

going to justify employee empowerment? How are

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you going to justify something that is not

tangible for you to measure at this early? Are you

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going to sit out or are you going to try? That all

depends on the organizations and that's why I

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think startups need to understand that if a buyer

is hesitant not because they don't want it,

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potentially they just can't and what is that

factor is really important and that's why

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choosing the right ICP or in this case your ideal

customer and also product market fit what you're

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trying to work with, making it easy for them to

experiment, making it easy for them to use is

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really really critical and then learn fast and

then deploy fast. Like understand what matters to

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them and then deliver backwards. I'd like to

switch gears a little bit because there's this

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other side of you which is also very fascinating

about pulling together so many different people

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from different spheres of knowledge expertise

and just bringing them together on shared goals.

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So what's your vision for this global CIO circle

and how did it come about? I've always had this

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notion of bringing people together. I like

socializing, I like networking. So when I started

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interacting with founders, when I became an

investor, an advisor and I thought opportunity

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came not because somebody asked me, it's just

because I asked people like how can I do this and how

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can I become an investor, how can I advise. So same

thing is happening for people who did not have that

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opportunity to do and they didn't even know that

there is an opportunity exists for them to become

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an advisor to startup, they can invest into

startups. There is this notion of investing

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startups is a VC's business, let them do it but then

you are sitting out and everything else is

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happening around the world and how are you going to

get involved in some of these things and so I think

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there's a way to do that and so I wanted to really

understand what that is. So once I figured that

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out, I wanted to bring it to the people and that's

how it started. Initially we were just doing with

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one or two founders, it looks like this butterfly

loves the conversation that we're having here.

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She wants to be a part. So what happened is that

network started to create around me and once I came

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out from quotient I've kind of decided to go into it

just as a hobby in front of mind basically said

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let's start a syndicate and to bring and then start

helping startups and I was doing one-on-one but

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now it had become a movement and that picked up and

we started investing, advising and it picked up

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further and then you know then I started

syndicating it and now why not just create a circle

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and like-minded people that want to engage

founders and become advisors, angel invest and

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those are all the you know circle formation was. We

did it in a smaller way last year and there was

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significant interest so then I decided to create

the circle, why not bring all of them together and

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bring the portfolio of companies and VCs and who

share the same interests to come and that's what

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Global CIO Circle is. Yeah like we are also really

excited about being a part of this like we keep

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looking for such platforms right like where we can

actually tell people about what we're doing and

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how we're already helping CIOs so like 200 of the I

think 200 of the world's biggest companies CIOs

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are coming together here also it's really really

really interesting. So you know like one thing

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that the team was also really fascinated about was

the fact that you seem to know everybody and

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anybody right like you have such a wide and deep

network so what's the secret sauce there like how

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is it that you're able to build such a sustainable

relationships with so many different people?

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Yeah I mean it's not easy so it's a lot of energy a lot

of time goes into it but I did put it you know as part

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of my thing I always like to have it and I feel like

sometimes I'm not actually doing enough

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networking but I think what is important when you

when it becomes part of you you don't feel like

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you're doing it and it just naturally happens and

that is really what is going on now I think it's the

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LinkedIn ecosystem read you know had this vision

that the network impact from your first degree to

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second degree to third degree and that is really

where we are right now in LinkedIn evolution is

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really now paying off because all of those decade

to two decade old people who have been on LinkedIn

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that have not done anything with it are still the

same but those who understood how networking

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really works reaching out to people and offering

them help is the first thing to do and I always

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offered my help and I basically said hey you need

anything I never sought out anything else and

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that's how I started building my network

obviously the payback period will come where I

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could really ask for when I need something as a

favor but usually it's what's most important

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thing about this is when people understand you you

don't have to explain too much right the purpose is

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very simple the reason to network is very simple

and at some point they also see the value and

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self-explanatory yeah and I think that is the

reason the circle is evolving and that is the

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reason people are wanting to come to the network

and also to these events for me it's all about

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founders and I tell the same thing to all of the

executives joining we're here to just make sure

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that they benefit from us because we've seen it

they haven't how can we give back and in return you

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advise and you get to an opportunity to invest when

there is an opportunity to invest if not we'll

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continue to grow and open the doors and open the

opportunities for them because they're doing so

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much if we can speed up that acceleration of growth

by doing a little bit it goes a long way yeah

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absolutely and you know we also noticed that you

have an open calendar like anybody can just come

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and talk to you is there a reason why you did that so

the reason is because if you people don't know how

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to reach out to you then they're like waiting like

how am I supposed to talk to this guy what to do and so

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why not you know if you really want people to reach

you there's no point in keeping the calendar

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closed so one of the reasons I started doing that is

so that you know people can reach and then I'll find

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out you know what the purpose is and there's a

notion like you know you know within the five ten

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fifteen minutes is this something that you're

going to continue further or that's the end of the

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road And so I think it's important for them. And I

also know that rejection is another thing nobody

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wants. So if you reach out for a connection on

LinkedIn or you know, somebody that you want to

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talk to and they've never paid attention to you.

But if you do the same thing to others, they might be

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feeling the same way too. So I have this notion that

if I know somebody is doing this to me, I don't want

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to give the same thing to somebody else. That

doesn't mean I'm actually accepting everybody.

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It's also very deliberate and that's important

because at some point you want to make sure the

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quality, important conversations and time. So I

think why people tend to restrict themselves is

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they dedicate certain time of their calendar for

networking or doing things when they have, but

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then they're busy with other things. And so

eventually that takes over and you won't be able

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to. So give an example when I was just doing

investments and I was not really doing anything

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else. I was playing golf. So now I don't. It's just

because you're so busy with everything else. So

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you just have to give up something. So I think

people give up their time because they have to do

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other things. And so I think that is one of the

things naturally happened. Obviously this is

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open route, but eventually it probably won't.

Yeah, I guess a lot of people will just grab the

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opportunity after hearing this. But I think just

sort of like looking a little bit into the future,

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and we were just starting before this that you've

seen all the shifts in technology all the way from

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on-prem to the cloud, even social as a way with

gaming and now with AI. So what excites you the most

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about this and what is different about this time?

Yeah, so I was one of the luckiest in terms. And I say

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lucky. So there's a definition for luck is that you

need to be at the right time on the right place. Then

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things happen, then you ride the wave. So I think

that is exactly what happened with me. You know,

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obviously there is some work involved in it. But I

think the three decades that that I've had in my

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career, I think I've seen how I've matured. I've

seen how organizations matured. I've seen also

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the employees have matured. And then I've also

seen how technology matured, and also how people

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who build companies have also matured. It's just a

natural evolution. It's just because when you

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have nothing, you're ended up being a lot of it. But

when you start putting the reinforcements around

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repeatability and simplification, automation,

and then ultimately reusing the resources that

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you already built. So we've become much more

efficient as humans in doing what we're doing. And

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that is actually what is helping us go faster. And

we're always looking to improve. And this is by

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nature. And now technology is enabling that. And

now we're at a point where we've laid the

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foundation of chips, which actually propelled

processing capabilities. Then we use them to

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build the compute so that we're processing more.

Then we understood how important data is in order

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to process the information. And now we understood

how important it is to have intelligence. So that

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means you have data, but now you need to build

intelligence from that information or that data.

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And that's where AI is. So now we're at the point of

creating superhuman capabilities, where human

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capabilities are limited. We're adding and

augmenting with AI. Now we need to learn how to use

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that. So this is the new power that is in your hands.

So or in your reach, how do we then use it for the

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better of the world and better of the society and

organizations and for people? And now the

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responsibility kind of shifts from not from

innovating, not from just inventing and just

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deploying, but how to use it to make it useful. And I

think that is really what I'm excited about is that

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there's so much changing now. The third era that I

was talking about this decade is where it is

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creating so many opportunities with AI,

disrupting the existing architectures. It's

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creating new categories. It's creating new

opportunities for existing players to either to

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go into it. I strongly believe most of the existing

incumbents will understand that AI is a

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completely different beast of architecture.

They won't be able to really take what they have.

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They have to augment also. At some point, they see

that it cannot really sustain and M &As will happen

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just because they needed that new blood and new

innovation, invention, so that they can move from

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here to the new ones, rather than trying to

basically change the existing one. Because at

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some point, you can't remodel a house. After three

remodels, I'm like, I'm done. I'm done. I'm tired.

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And you're breaking things then, you're actually

fixing it. So that's when the new things will come

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and extensions and other things. And so that's how

acquisitions happen. Smart entrepreneurs and

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executives are making those M &A decisions. And I

tell all of these startup founders now, be very

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positive around and have that attitude that

they're building something completely new and

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opportunities will come. Actually, that was

going to be my last question just to wrap this up.

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That as founders who are actually building in this

space, what would be your likey actionable tips

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for them to actually make the most of it? And

especially from an enterprise perspective,

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there's just so much opportunity, but there's

obviously like a gap in terms of their

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understanding of that opportunity. Yeah, so what

everybody's worried about, and I think there's a

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reason why we're all worried about it is, is that

when cloud and data and capabilities came in the

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last decade, we've started creating a lot of

applications. Obviously, everything is use case

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based and people start building these apps and

applications to solve one certain problem. So

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that created a swath of applications that are

sanctioned, unsanctioned usage is happening in

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the organizations. There's some maturity came in

towards the last end of the decade to this new

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decade is that the sprawl of these applications

created a lot of risks. And that risk averse that I

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was talking about in the organizations is

continuing. But with AI, it's becoming 10x, maybe

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100x more. It's because number of applications or

apps and agents that we're talking about

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deploying is multiplying. And now, if you're a

founder building these small, agentic

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applications that aren't necessarily

sustainable, then you need to think about it. Yes,

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you can build something, but is it something

sustainable, longevity and ability? And that's

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what investors are looking at. The other

important thing is, are you building a category

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defining product? What problem are you trying to

solve? Because opportunity for building

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something like this is not going to come for every

time. It's a generational thing. What AI is giving

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right now for people is to really rethink about the

opportunity. It's the same old problem, new

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solution. Every organization, see, the thing is,

is that problems already exist. We've already put

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a solution to it. But if that solution isn't

evolving, as businesses evolving and the people

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are evolving in the organization, new

opportunities get created. That means the

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problem didn't go away. The problem actually

perpetuated into a different state. And that's

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what tech debt is. Everybody thinks tech debt is

somehow magically and nobody cares about. The

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tech debt happened is because you had a problem,

you deployed a solution. The solution didn't

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evolve, but the problem evolved. The business

evolved. And now how are you going to solve it? You

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can't solve it in an existing problem solution. So

that's why you're finding a new solution. And the

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newer solution happens to be with a newer

architecture, more capabilities, much better

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efficiency, able to do a lot more. And that's why

there is an opportunity for founders to go. So that

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is exactly what happens every decade. I think that

is why this is a decade where opportunities are

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plenty. And I think if you're building something

for an existing problem, this is the time to do it.

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Because this is going to really transform the

following two decades because we're in an

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intelligence era. Up until now, we're in a

foundational era. We're only in the first era was

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compute being better, networking being better,

communications being better. Then came the usage

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of those, processing of those. Now the byproduct

of those two is data. Now you're using the

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intelligence of how to use that to become that

intelligent beings. I think that is why this is

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going to be even more interesting. Because now

we're rewriting the chapter. See, we kind of came,

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now we're going to make a full circle to go back and

fix everything that we did with this new

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intelligence that we got. To say, oh, did we, oh,

now I could do this much easier, much more

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efficiently, then why not? So now the challenge

for these existing organizations, these

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existing solutions and technologies is what is

their lifespan look like? By next decade, most of

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these will become obsolete. And the new ones come

in and they will become now primary systems. These

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becomes the secondary. Right. Right. That's

exactly what is going to happen. So that's why I'm

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telling every founder, you're in the right era

with the right time. If you're building something

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now, I think you're building for the future.

Absolutely. Like the patterns will just repeat,

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but the scale and complexity will just be another

level. Yeah. For me, so the question is like, how do

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I see TruePair in this ecosystem of new

opportunity and why is this going to be better for

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you guys? What I liked about TruePair when I first,

you know, saw, first of all, Pratish reached out to

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me after the CIO event that I had and he loved it and

he said, like, I really want to talk to you. I

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ignored him for almost two months, basically,

because I didn't know much about it. I didn't have

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the time, not to, it's not because I didn't have the

time and that was the reason I was traveling and

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whatnot, but he was persistent. And so I was able to

meet with him and do and I think I encourage every

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founder, if you, if people are ignoring you, not

because they didn't want, I mean, they want to

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ignore you just because they didn't have time. So I

think what I liked about it is that the ease of

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product use is number one. See, the problem could

be there already. I think what is important is, is

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the solution easy to use? That's number one. And

number two is, is the adoption of that solution is

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viral in nature. Yeah. Right. And three, is the

capability scalable in the sense that whatever

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you built as a platform and as an architecture as a

solution, is that going to amplify the use in the

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organization? That means you land and then you

expand into places where that is opening more and

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more opportunities for organizations to

leverage that capability and that use. And I think

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these are the three things that I saw as an

opportunity and then that's why I'm excited about

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it because the product does something unique. And

that's why I was telling British that, you know,

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the, when we were having, I think I also shared with

you, is make it easy to use, make it simple for

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growth and scale and then start seeing the scale

with adoption and then you can adapt to the use and

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then build the pricing, build the product

capabilities because I think when you're doing

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something new, it's always like you don't know

what you don't know and you will only build what

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customers are asking and that's the best thing for

founders is that list that you have is by seeking

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that from the customer, seeking that from the

experts and build it into the product. I think

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having talented team is really the one of the other

attraction and why I'm confident that you guys can

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do it. So yeah, these are the four things like, you

know, I would say team, the ease of use, the

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problem, expansion capabilities. I think these

are all very, very attractive key elements for

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Truepeer. So my philosophy is you always have to

punch up. You don't know what you don't know. It's

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important to try, but trying should have some

method. Why do you want to go into that? So that

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means you do some research to figure out, is this

the market segment that has the pain? Are they your

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primary? Because everybody wants to go to the easy

route. There are certain problems you could solve

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easiest way, but then is that, you know, you don't

want to get addicted to it because then, you know,

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as you're growing, eventually you'll hit the

wall. And because your focus was only uni

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direction, you didn't figure out how to set

yourself as expansion. So then by the time you hit

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the wall, you have no capability to expand

anymore. And I think it's very important to know

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that as a founder, to try and create that expansion

capabilities as you're growing so that you can

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pivot as you build when things hit to a wall. And

that means you've reached a capability that does

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not have much market fit or a category fit or a

customer fit. Then you need to change the

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direction to figure out what that would look like.

So I think this is important. So that's why you

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build work-alive solutions and horizontal

solutions, what play you are in. And the most

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important thing is really making sure this

understanding of who your ICP is and also

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constantly checking that and evolving. But you

need to know where you want to be and how are you

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getting there. Right? And if your only target is

Fortune 10,000, not Fortune 100, then you need to

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build from a Fortune 2000 to 5000 rather than

building it for 10,000 because then you can go up.

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So always target the middle of the ground.

Otherwise you will end up building something of a

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smaller capability that is requiring a lot more

velocity and a lot more scale. By the time you spend

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a decade, you would only reach the mid-market. And

you get tired and you run into a situation that you

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hit the market penetration problem. And I mean,

that's okay. If that's what you targeted, it's

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fine. But if you want to become a bigger company and

longer, you need to start punching yourself from

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the middle of the ground to up. And that only comes

when you make that pivot very quickly. You enter,

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but don't spend too long in market. You need to kind

of be able to adopt that and then just go from there

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to the mid-market and then stay there to mature the

product, then start punching up so to go. So that's

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important for this strategy. Makes sense. I have

just one last question. So from a CIO perspective,

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how do you see, like you've seen, through peer

closing, right? Like what we are doing. So how do

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you see through peer fit into the CIO agenda? Like

in terms of how CIOs look at digital

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transformation, change management, adoption of

software at the deepest level? See, with AI

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products, the organizational maturity has

already came to a point where CIOs are now become

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shepherds of technology. There are only three

main buyers of technology in the organization.

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CIOs, CISOs, CTOs. I mean, predominant in their

teams. The CIOs are in the CISOs right in the

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middle. The business technology,

customer-based, customer-facing technology,

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and security being a byproduct of both, and those

are the three. True peer can fit in all of them. And

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the idea for you to build a product that has the

usage in every department, that has the

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capability to have an impact across the

organization, has a huge potential. And it's very

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difficult to have that. In an enterprise that is

even more difficult, because you could do, you

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could see this in the B2C and start somewhere small

and then scale in customers and all of that stuff.

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But in the B2B, you're labeled already, and you

have a limited scope of what you can do. But I think

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true peer being a content, creation, and enabling

capabilities of what you have to offer to your

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customers, or what you have to offer to your

employees. And because that is where the product

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fits. So it's fitting for employees. It fits into

the systems, applications. It also fits into the

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products that are actually being shipped by the

organizations for their customers. So that's why

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true peer has broader potential. And I think, and

that's one of the reasons why you, the CIOs, have

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being the shepherds in this area, then can

transition into security products and

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applications, or even to the technology and the

product of products that are being shipped and

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where you could also use true peer for that. I think

that's why I'm excited about it. It's a broad swath

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of organizational use. Great. Thanks so much,

Levan, for doing this. I know you've been, you

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already had a long day, but like, this has been

super insightful and lots of takeaways for us. And

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hopefully, whoever is watching this. So thank you

so much. No, no, I'm really having fun and I really

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appreciate you guys having me here. I'm actually

very excited for what you have and meeting all the

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team. And I'm really, now part of the success for

you and I would love to be. I'm looking forward to

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it. Absolutely. Awesome. Thank you.