From Microsoft Executive to Fractional CTO: Disrupting Traditional Leadership Models
Meridian Point Podcast - Episode Transcript
Host: Kumar Dattatreyan
Guest: Arunansu "Arun" Pattanayak, Founder & CEO of Tipsora
Date: July 29, 2025
KUMAR: Hi, everyone. This is Kumar Dattatreyan with the Meridian Point. Today we're joined by Arun Pattanayak, founder and CEO of Tipsora, where he provides fractional CTO and advisory services to startups and small businesses that don't have a dedicated CTO. After several successful years as a cloud and AI specialist at Microsoft, Arun made a bold decision to leave the security of big tech to build something entirely new. This approach challenges the conventional wisdom that companies need full-time executives for every C-level position, instead proving that fractional leadership can deliver enterprise-level expertise at a fraction of the cost. From helping venture capital firms modernize acquired companies to guiding traditional businesses through digital transformation, Arun is part of a growing wave of fractional executives reshaping how companies access top-tier talent. So without further ado, let me bring Arun to the stage. Welcome Arun, it's great to have you here on the show.
ARUN: Thanks Kumar, thanks for having me.
KUMAR: Of course. So you were very successful in cloud and AI with Microsoft, having worked there for quite a few years. What prompted you to start your own company and provide fractional CTO leadership? And maybe the follow-up question to that - what is fractional CTO leadership? So why did you leave and what is it?
ARUN: Yeah, sure. Corporate structure has its pros and cons. You get a big brand like Microsoft and you don't have to do the sales and marketing. You just show up. Your calendar gets filled and you just show up to the meeting and do the work. So that's easy. But the downside of it is that the corporate structures are very rigid. There are defined roles and responsibilities. So there are different teams that you have to coordinate. And a lot of times when I'm working with customers, I have a strategy in mind - how do we approach, how do we serve? And not all parts of my strategy are in my control. I can advise, but there are other teams, layers of management that can override and do things the other way. And I cannot change that. Then I have to work with it. That was one part of it that I wanted - more control of how do I engage and how do I serve. That was one of the motivations for starting my own company.
Now coming to the fractional part of it, another thing I noticed while at Microsoft is that Microsoft is a big company and they also like to work with other big companies. I was mostly working with financial services, so all the big investment banks or hedge funds, insurance companies - those are also big companies. And there were like teams of people at a given point, there were like five people in one account for just one customer. So I noticed this thing that there are these big companies that get whole teams of people to serve them. Anything they want, there are always five people on the call. But at the same time, I was getting invited to lots of conferences to give keynotes and workshops. And a lot of people would reach out to me after the call saying, "Hey, we need some help in our Microsoft implementation. Can you help us?" And I was like, "Okay, well, you should have an account team. I'm part of an account team where I'm working with multiple customers. Let me connect you to your account team." And it turns out that a lot of these smaller companies, they don't really have the dedicated account team that I was part of while I was serving other customers.
So then that gave me this idea that, you know, why not? And then I started talking to them. I cannot really help you beyond - I can try to connect you to other people who I think would be aligned to your account who might be able to help you. But if you want me to go in and implement the strategy that I talked about in the keynote, it's probably not going to happen in the way you're structured and I cannot help you because I have other accounts. So that's what gave me the idea that if I had a practice that I could just offer it to them right now. But at the same time, they have a very low budget. So they cannot afford the full salary and benefit that Microsoft offers. They just cannot compete with Microsoft in that way. But then I heard about this idea of fractional leadership.
So I was part of a group coaching program where they were talking about this idea that there were fractional CMOs, fractional CFOs, fractional product leadership, and then there was fractional CTO. So I said, this makes sense. So you cannot offer the full Microsoft salary, but can you offer one-fifth of it? Can you give me twenty percent, ten percent of that? Yeah, they might be able to. Okay, so if you give me only ten percent, instead of like five days a week, I might put one day a week for you. And if I get five other customers like you, that's together would exceed what I make through Microsoft. So that's a good business model for me. And that way I can really have the control that I need to implement my strategy and do all the things that I need. I can hire people, I can manage their people, I can create the technology roadmap that they need to align with their business goal. I can work with them in a strategic way. I can be part of their C-suite meetings and everything. So that's what gave me the idea.
And eventually, like I said, I have probably reached the highest level. The growth was starting to get stagnant at Microsoft. I said, this is the time to jump in and see how far I can take this because I had two customers already lined up to get in on this with my own personal delivery. I said, okay, I have two customers, let me get started with that. I will add a few more and I will make up the money in that way. And it's been going well. So I have a couple of customers and I have another customer in the pipeline where they're willing to pay more than thirty percent. So that would make up equivalent to having five customers that I was thinking about. So I'm all set now.
KUMAR: So is that your goal - sort of to replace your income or is it to further scale your operation in some way?
ARUN: Yeah, I mean, income is part necessity and part ambition, right? Firstly, like I have a mortgage, I have a family I need to support. It's a big risk to leave the security of a corporate job to do your own business. So I have to kind of convince my family that yeah, even with this I can still take care of family finances. So that aspect of that is a minimum that I need to maintain the standard of living and provide for my family. Beyond that, I think the money is also power. Depending on which tier of revenue income you are in, you get invited to different strategic groups where you get even better leads and even more engagement. For example, like Forbes is one of the big names in media, right? So they have - the lowest barrier to get into Forbes is the Forbes Technology Council and they have a requirement of half a million revenue that you have to show. So that's kind of setting the lowest threshold for getting there to kind of establish themselves. Beyond that, like you always hear this - top fifty under fifty, forty under forty. So to get into those lists and get that visibility, income plays a role.
KUMAR: Yeah, it makes sense. So you have to show credibility to be invited to those groups, those communities, if you will. And once you've established credibility, then, of course, there's a bit of a snowball effect where you get more customers, more clients, more recognition and so on. And I'm curious, maybe we can get to this later - so the idea of fractional has been around for a few years to your point. There's the fractional CMO, CFO and so on and so forth. And as companies, smaller companies can't really afford a full C-suite of people. And so it seems like there's a market for that. What's been your experience so far? It sounds like you're growing and you're seeing some results, right?
ARUN: Yeah, actually, just today, there was an article trending on LinkedIn that interim CEO - they don't call it fractional, they're calling it interim CEO. So it's still kind of the concept of a part-time or temporary CEO. The trend for interim CEO is increasing because a lot of the companies are kind of not decided. They don't want to commit to a leader and they kind of want to try before they buy. So they're using this idea of interim CEO to kind of test the CEO before they give them full time. And a lot of times this interim CEO deals are really pretty good for executives. A lot of executives are actually preferring to be interim CEO in multiple companies rather than just be full-time CEO in one company.
KUMAR: Are they, in that case, are they considered full-time or are they part-time in the interim?
ARUN: It's full-time for a fixed amount of time. Usually, CEOs span for multi-year. Interim CEO could be a few months to maybe one year. It's whatever time that the board thinks they need to convince themselves that we found the right guy, let's sign him for a multi-year contract. And the fractional thing kind of works the same way. So it's a low cost barrier. So cost is not an objection. And it's part-time for me. So I can have multiple customers to make up the money. So money is not an issue for me. Money is not an issue for the customer. But it gives them an opportunity to kind of try out - can he do this? Can he deliver on this? And if they see the value and the potential, they can increase it.
KUMAR: That makes sense. So who is your ideal client customer? What size company? What sort of problems do they face that you solve for?
ARUN: Yeah. So as I was getting started, my company is small. It's just me right now. And the market segment where I saw maximum demand, the market segment that's most underserved, I would put them into two categories. So there are these venture capital companies that are investing in startups. And even some of those startups, they are like somebody with a background in some industry. They are like non-technical CEOs, founders. They kind of understand technology. They know the capability of what technology can offer. And they understand the market that they're in, that what idea can disrupt the market and offer something that does not exist. So they know that there is demand for a service. They kind of know that using technology, they can achieve it, but they just don't know at the lower level how to implement it, like which cloud to use, which software stack to use, which hardware, should I do it on-prem or in-cloud? They don't have that level of detail. Those are the companies that I call greenfield development. In IT, we call it, there is greenfield and there is modernization. Those are greenfield development and those are ideal customers to have because if you are starting from scratch, I can lay out the foundation the way I think would suit, that would set us up for scaling in the future. Those are the first bucket of customers that I have. So I don't try to reach out to individual startup founders. I directly reach out to the venture capital who are working with multiple startups. So if I reach a partner of one venture capital, they can introduce me to ten founders. And out of those ten, two or three might want to work with me. So that's one channel.
The other side is even the same venture capital companies, they don't just invest in startup ideas. Sometimes they buy out companies. They buy companies that have reasonable revenue, reasonable business structure, but they have legacy infrastructure. So they know that if they buy this company, use technology to modernize their services, add some automation, then that same company can produce more output. It can be valued more. So they take a company with a legacy infrastructure, modernize it, increase its value and then sell it. That's their model. So I can use them to connect with those companies who are in that field. So I would technically still be working with some kind of CEO that the venture capital assigns to that particular company. So then I work with that CEO to connect and do that. Or sometimes I directly reach out. I have multiple agencies who used to give me contract type of work. Those agencies are now connecting me to these smaller to mid-sized companies who are coming to me with that same problem that they have been in business for fifteen years, but they have legacy infrastructure. Their database is going out of support. The infrastructure that they are using to run their app is bloated. It's starting to have performance issues. They want to change, but they don't know how. And they're afraid that new companies, new type of companies who are born in the cloud, they can be more agile. And they can grow faster and offer their services and they can be left behind in the competition. So they need help to catch up to the new players who are coming with the latest tech stack out of the box. So those are the other bucket of customers that may come through venture capital or may come through some other agency. But those are the two types of customers I have - one for greenfield development, one with legacy infrastructure that can be modernized to improve business outcomes.
KUMAR: Yeah, you mentioned this in our conversation last week - especially the greenfield companies and the transformation challenges that they have. Because founders, they have a great idea, but maybe haven't invested enough in technology. And so that being a place where you can really leverage your skills, your connections, your strengths to help them. There's a question that someone asked in advance of this broadcast. I'm going to just read it out. This conversation on fractional leadership and AI-driven transformation is crucial. How do you see SMEs scaling these strategies effectively while maintaining agility and innovation momentum? It's similar to what you just mentioned, but I wonder if you could kind of expand on that, especially the AI part, because a lot of large companies, the big players, the Microsofts, the Amazons and so on, they're investing billions of dollars into AI, not just for their customers, but for themselves too, right? So how do the small companies take advantage of this through the services you provide?
ARUN: Yes. If you talk about AI, there are two types of services in AI, right? There is one where there are companies who are coming up with these foundational models. And AI models have been around a long time. What's different today is with GenAI, the type of model we are using now, these are models that have millions of parameters. So to train these models, the type of compute power that's needed, smaller companies just can't afford it. So that's where there is this old saying that if you want to compete with the giant, you have to be able to use their weight against them. You don't want to compete with the big player saying okay, you are using million parameter, I am going to build a model with ten million parameter. You just can't. You cannot beat them, outdo them by just doing more of what they're doing because they have more money, they can do more. But where you can is - these companies are not just trying to do one thing, right? They are trying to cover a lot of use cases in one model. They are trying to serve everyone and they are trying to become the platform. So there is no point fighting that unless you are as big as them. It's better to join them, use those services, but then create startup ideas on very business-specific use cases. Like maybe you understand the insurance industry very well, right? Think about how you would use this model to automate the insurance workflow, simplify the claims workflow, and maybe do claims evaluation and fraud detection better. Because you understand the workflow that happens. You understand the process that's involved. And you know what AI can do. Once you use it, then that becomes easier.
There are a lot of startups who have come out since the LLM and the ChatGPT came out. And a lot of those, they are simply adding a value-added service. Like I use a service called Gamma, which is generating a lot of the social media I created using Gamma. I could do it in ChatGPT, but it would take a lot of work. They have created a platform designed for creating presentations, creating social media content, and it's just a lot easier there. I don't need to come up with creative prompts because they understand how to create this type of content. They have already built in all that into their app. So think about what process that you know that you can build into it. You can still use the LLM of the big players. Don't try to recreate your LLM. Maybe you can fine-tune it and add a few workflow automation. And nowadays you can create agents that automate that workflow. So combine that LLM with agents, with your business knowledge of how that specific business process works, and you offer that as a service. That's where you can compete with the big players.
KUMAR: Yeah, that makes a lot of sense. And certainly I echo that in the work that we do with companies. We also work with a fair amount of venture capital firms that are acquiring other firms and although our work isn't technical like yours, we're more on the people's side, using agile and coaching and things like that to integrate cultures, if you will, especially with companies being acquired and having to mesh cultures and things like that. But I see a lot of similarities in the work that you're doing. And what you just brought up with sort of a small company implementing AI, for instance, that makes a lot of sense is you can't beat the big players, but you can certainly use the products that they have created. And there's so many tools out there. The proliferation of tools is amazing. That allows you to sort of fine-tune how you would use it in your business or even to the extent of creating maybe agents or whatever to automate some processes and add some intelligence as part of it.
There's another question here from the audience, and I'm going to read this out from Kyle Ewing. In your experience, at what size does a company benefit most from fractional CTO services? There's a narrow window of opportunity between when founding employees can manage the work and when they can hire someone full time.
ARUN: Yeah. I mean, that is - I have worked with a few market research companies to kind of come up with a ballpark number. This is just the number because I have a marketing team that does reach out. They're like, okay, what should we use as filter to narrow down our target? So the filter that I use is less than a hundred million in revenue, up to hundred employees. Those are kind of the numbers I use to kind of create my marketing campaign. So I would say that's kind of the ballpark number that I'm going after. Those are usually the companies that can't afford a dedicated CTO or maybe they have a CTO who is also responsible for doing other things. So they are really not able to devote as much time they need to their technology roadmap. But that's it. And on the other side, like if you're going after startups, they're probably starting with zero employee. So they easily fall into that criteria. But that's the number I use. A hundred employees, less than a hundred million revenue.
KUMAR: Yeah. So Kyle, thank you for the question. We should catch up at some point, Kyle. I haven't spoken to you in a while. And if you have a follow-up question, Kyle, just put it in the chat and I'll be sure to ask Arun. You know, when we first met, we talked a bit about your speaking. I think you do quite a fair bit of speaking. And, of course, you still had your company, your CTO, sort of fractional services company. How do these align for you? And how do you leverage one to support the other?
ARUN: Yeah, actually, that's kind of how it all got started, that I was working full time. I also wanted to do something on the side, something that does not conflict with my regular work. And that's when I saw this ad and I met this marketing agency that specializes in getting paid to speak. So I went to one of their workshops, I understood what they are saying. First of all, the idea was very appealing to me that I didn't know that people get paid because I was speaking before as a part of my job at Microsoft, I was speaking at a conference, of course, I speak on the client side. And people, once you are in Microsoft, people invite you everywhere. Everybody wants to know what Microsoft is doing. So I was getting invited to all kinds of places. And I like speaking. But then I heard that you could get paid to speak. I'm like, really? Who pays to speak? I have been invited to so many places. Nobody offered me any payment. So they said, that is actually something called professional speaking. There are people whose full-time job is speaking. So there is this organization called National Speaker Association. This is an association of people whose full-time job is speaking. I'm like, really? So I joined them. I attended some of their chapters. I met other professional speakers who are getting paid. So we used to have a roundtable discussion, informal talks. And when I realized that, yeah, this is actually a thing. So then I hired that marketing agency. Okay, you're saying I could get paid to speak. Tell me, what are the gaps that I have that I need to do to really start getting paid? So they said, okay, you build a website. You create the speaker demo reel. You should also do a TEDx talk. You should write a book. I'm like, okay, I have kind of done half of that by now. I have a decent website. I write blogs sometimes. I have a YouTube channel. I am on this podcast. Other things in my to-do list is to do a TEDx talk and write a book. So those things are coming next.
So that's really how it got started. And now I'm being invited to these things called agencies and speaker bureaus, who are kind of the middlemen who manage the speakers who get paid to speak. So I'm finally into those agencies working with one agency to just talk about Ivy League colleges, students about how to get into a career in tech, how to think about creating a startup right out of college. So that's happening. But really, that's just how it got started. And while I was speaking, a lot more people came up to me saying, I like what you are speaking. I don't really want you to come and speak that again, but I want to do what you are saying. I want you to come in and help me do it. That's when - so the speaking, the way I thought my speaking career would take off, speaking did not go that way. But speaking led to the creation of Fractional CTO offering that I said, okay, I am speaking, but people don't really want to hear me speak more. People actually want me to come in and do what I'm talking about. And I said, okay. Speaking can be my top of the funnel that works as my marketing to warm up the crowd. And then CTO is going to be my core business. So that's how I have transformed my business now.
KUMAR: Yeah, that's brilliant. I love that. I love how one sort of led to this. And you obviously are a wonderful speaker. You express yourself really well. And so I can see where people are like, oh, we need to get this guy in here to help us with our problem. So that's great. I'm trying to pick from - we're running short of time, so I'm trying to pick from a question that will resonate with the audience. There's still quite a few people on LinkedIn watching. So I'm gonna go to the hybrid cloud strategy. I have a question around that based on our last conversation. So many companies are caught between on-premise infrastructure and full cloud migration implementation, right? And you speak about hybrid computing as a strategic middle ground. And so for companies that can't go a hundred percent cloud immediately, what's your approach to creating a bridge strategy that delivers value while managing risk? Then I have another question that came from the audience.
ARUN: It's not that companies can't go cloud, it's a question of should they? It's not a question of cost because that's all I did for the past seven years, convincing people that going to cloud is a significant cost saving. You convert your capital expenditure to operational expenditure. It's a really cost effective solution. It sets you up for future growth. That was my pitch for selling cloud for the past seven years. So that's still very much true. But even the big players, the big investment banks, the big multinational banks, even they don't want to go hundred percent cloud. It's not that they cannot afford it - it's actually cheaper, they can afford it - but it's really you have to understand that cloud is a managed service which means once you are in the cloud, part of the thing will going to be done by the cloud provider that you do today. So you are going to have to let go the control of how you want things done. You have to work according to how the cloud provider works. And that's why major big banks, they have a problem that they don't want to let go of the control. That's the number one reason why they don't want to migrate is because they are risk averse. They want to minimize the risk. If there is a cyber attack, if something comes up in the media and they need to change it, they want things in control that they can change fast and give people a good answer.
In terms of strategies, that is that middle ground that I talked about, the hybrid cloud. So you have to label all of your application, like what's very sensitive to you, like the payment processing, the core banking, maybe those are sensitive that maybe you are not ready to move that to cloud yet. But there are some auxiliary things. There are some ad hoc analytics that are - you are just training a model that requires a robust compute capacity that you don't really need to move the data. You temporarily, you give it the data to train and then bring it back. Cloud is really good for scalability. Some of your analytics applications especially that don't require you to move your sensitive data permanently to the cloud, those are easy target to leverage the cloud, and then bring it on-prem so it's always secure and you are able to leverage the cloud compute capacity. Some of the things that are not very mission critical for you, those are easy target to move it to the cloud so you get a flavor of how cloud works. You establish your cloud center of excellence, learn how to work with the cloud, and then gradually when you are confident then you can start moving your little bit more important critical applications into the cloud and maybe eventually one day you can be hundred percent in the cloud. But even that, there is another risk - do you want to put everything in one bucket? What if it goes down, right? So that's where this idea of multi-cloud strategy comes in that you can have multiple clouds. So your workload is distributed across multiple clouds. So not only multiple region, it's there in multiple clouds. So if one is down, your application is always on. So those are - and there may be companies that never want to go full cloud. They always want to have some of the most mission critical application - it kind of makes sense to keep it on-prem so it's completely under your control.
KUMAR: Sure. I have another question from the audience from Christopher Ed. I'm going to read it. I'm not quite sure I understand the question so maybe if Christopher you can clarify maybe in another note. So in terms of structures for these small companies when they're scaling aside from your pool of project leaders, when companies choose from other pools, how do you ensure the person is capable of completing the work? So I think what he's getting at is how do you choose the right people as a CTO? How do you find the right talent to do the work? Please leave a comment, Christopher, if you're still watching, if I captured the spirit of your question. Please go ahead and answer.
ARUN: As a part of a CTO service, part of the service is people training and people leadership. I have my own theory around how people hierarchy and selection of people should be done. It's kind of the same theory of how search engine works like Google came up with this PageRank algorithm. Before we used to use this portal type of thing like Yahoo where you kind of categorize people, so I would describe a lot of companies, the way their structure team kind of mimics that old Yahoo methodology that, okay, you are a product manager, you do this. So there are these different departments, different job roles, so they kind of get categorized around that. So that's how they form the team. I think now that we know that Google algorithm works, why don't we apply that to our workforce? So what I mean by that is you should have nowadays with social media, you have external presence. But if for sensitive reason you don't want to put it in the public internet, you can have your internal portal where people can post questions and others can answer and based on that you assign people an expertise and you kind of rank people's expertise. So somebody is expert in cloud - so maybe not all cloud, maybe only Microsoft cloud, maybe only AWS - so you know that person should be able to answer questions that nobody else can answer in the company about that particular topic. So whoever is able to answer questions that others can't, you know that person is the most expert. When you want to hire another person to work on that technology, you take whoever is the guru in that technology in your company, you ask that person to interview that person and get their perspective on how do they measure up. So that's how you kind of create that technical knowledge base hierarchy of who has the most knowledge of which category, who is SME in what, how in-depth knowledge they have in the field, and what are the job functions that relate to your business goal that they can perform. It shouldn't be that this person is a developer, so they should only write code. Developers can also do marketing. Developers can also go speak at conferences on your behalf and get you sales leads.
KUMAR: I love that. I love that. A way to democratize and open the company up to the talent that you have and not pigeonhole them into the role that they're playing, but really going a little deeper to see where their passions are and allowing those people to rise.
ARUN: Yeah, like a lot of times people just ask, what do you want to do? And then try to come up with it. Instead of asking, just open up everything to everyone. Let people decide. And you can put your weight that if you are able to show that you do this, maybe you get this much credit and those credit can translate into your compensation and bonus, whatever comp structure you have. So it shouldn't be that one person in one role only does one thing. One person could be doing twenty percent sales, ten percent marketing, other seventy percent app dev operation.
KUMAR: Yeah, it really leads to a lot more employee engagement that way.
ARUN: So it's kind of like you are internally creating your own fractional model of people and you let people choose what they want to do. If somebody wants to do less of a coder, more of a thought leader, they can reduce that time that they do in coding if they're able to offload it to somebody else. And take up more of conference talk or come up with doing more of the R&D, publish research paper. They can take up more of that work to make up for the time that they are not working on their primary responsibility. And if the combination of all of that should add up to how much impact they have on the business and their salary and the position structure and how much authority they have in deciding what the company strategy should be, should be all based on that.
KUMAR: Right. No, I totally agree. I love the model too. Christopher, thanks for that answer. Thank you, Christopher, for the question. And we're running a little short of time. So is there something I did not ask you that you'd like to share with the audience before we sign off?
ARUN: Yeah, I mean, I have this keynote speech is about this five step strategy where companies can go from zero to becoming a big business. So yeah, listen to my keynote. I think there are other podcasts where I have spoken about that in a lot more detail. But yeah, like that is - is there a link I can share with this audience here, your keynote?
KUMAR: Yeah, yeah. Not the entire keynote, but my demo reel should be on my YouTube channel. If you go to my website, arunansapatnaik.com, right on the front page, the demo reel loads up. So that gives you the highlight of what I'm talking about. So listen to that. If any one of those ideas strike you, you want me to come in and speak more on that, at your event or come in as a fractional CTO and implement some of those ideas, I'd be happy to do that.
KUMAR: That sounds great. I'll make sure that we add those links to the description of this show and it'll be on the podcast synopsis as well so that people will know how to get a hold of you. Arun, it's been a pleasure. I have so many questions I couldn't ask, so I'm wondering if maybe we could schedule a second, a follow-up at some point.
ARUN: I'm happy to get on this again. Feel free to email me, message me on LinkedIn. I'm very active on most social media. Happy to have one-on-one call, answer some questions by email or you can set up call with me and we can deep dive into any one of these things.
KUMAR: That's awesome. Thank you so much. And thanks to the audience for staying with us the whole time. I appreciate all of your questions and we'll see you next week with another guest. Thanks, Arun.
ARUN: Thank you.
