From Microsoft leadership to startuplandia with Romi Mahajan

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Episode Outline

[00:50] Romi’s shift from Microsoft to the startup space

[02:04] The transferable skills Romi gained from Microsoft and what he had to learn and unlearn

[04:23] Where Romi is at in his current company

[06:20] Why Romi’s company split off from their parent company to become an independent entity

[07:35] Romi’s growth thesis and how his thesis evolved as his company grew

[09:24] How Romi structured his shift from direct sales into channel selling

[11:54] The strategy that Romi’s company plans to formalize in the next few months

[13:38] How the Pacific Northwest startup community has changed

[17:40] How tech companies can become more involved in the communities that support them

[22:15] Romi’s favorite community projects and thoughts on how tech can help drive meaningful change

[25:12] Romi’s inspirations

Connect with Romi



Alright today. I'm really excited to have Romy Mahajan on the call. Uh, Romy is the chief marketing and revenue officer at . And before that did a very long, almost a decade sprint at Microsoft. So Romy, welcome to the show.

Thank you. Well, so I'd love to just. You know, I'm always curious when people make a big shift from big company stuff and, and, you know, rising through the ranks in the, in the large company, like Microsoft to the startup world. I mean, obviously it's a, it's a big shift. What's that been like for you? Yeah, that's a good question.

I mean, you know, I did two stints of Microsoft, um, the last one ending in October of 2011. And so it's been a while and I think the. The shoot really is one of ours is more about mindset. It's about your ability to control outcomes and control your day. Um, you know, as opposed to being part of a larger machine that operates some, it's a logic.

So, you know, my story there is, I accidentally, in some ways, got into Microsoft though. I loved it. And then I sort of all my freedom, loving instincts and desire to fly, like a bird pick over. And I just sort of went into my own. It kind of into my own world of advising small companies and then finding a few that I really liked and wanted to be taken off pretty well.

So there's really, for me, it's not even a, it's not a moral judgment thing. It's just a question of how I like to spend my day more than anything. And so within that, like what. What has transferred over really well. What's become from your experience there over those 2 cents, what has become really an asset to you and something you've been able to leverage.

And then maybe what's something on the flip side of that, that you've had to relearn or retrain yourself on so that you can be effective within the small company. By the way. That's a fantastic question. I mean, and Microsoft, and I guess I learned a few things very profoundly from a couple of the people there and then just.

It's part of the middle, you in general, what, you know, you think about speed and scale when you're, when you're, when you're part of an edgy, I mean, you're dealing with things that were so much larger than you could've ever imagined in the, you're talking about billions of dollars in audiences of a hundred million.

Um, you have resources and assets at your disposal that are, that are phenomenal, but you have to use them well. And so really speed and scale. Um, and the notion of compromise. No really comments. How do you compromise with other parts of the company to get to a better? Right. Um, and I, you know, I think I learned a lot there, although I had some hiccups, um, it, you know, in my earlier years when sort of, I thought I knew how to do things and I realized that I really needed other people's help all to really be able to scale up and, and, and, and, and have the laws to be.

Career into the, into the value add we were on from the marketplace. I think so. So I learned those there and how to think in a grandiose fashion. I think the things you have to unlearn and relearn, or when you go on your own, you no longer call. Someone or email someone, you know, from the perspective of Microsoft, right?

You don't have people jumping up and down. You have some recall call and try and laughing at your jokes and pretending, right? Because you are absolutely small, you're not being any. And it's, you have to unlearn that kind of privilege. And you have to unlearn the fact that you had resources at your disposal, um, that could make you yourself.

Almost just a traffic cop is supposed to do. So you've got to sort of relearn your discipline as well. Again, these aren't negative or positive statements. They're just statements of fact that have to do with the size scale grandiosity and the amount of resources that you spend. What wa where are you in the sprint?

Right? Yeah, we, the, you know, the show we focus on either the one to 10 millionaire, our sprint attended 20 plus sprint. What would make the most sense for us to focus on based on where you are? Um, at your current company, one period, you know, you know what, here at work, we're an AI company that's focused on residential real estate or B2B company.

Now that we're making some plays into B to C for much of the company's history. We were a part of another, a large wreckage company. And as such, we were not. Um, out in the commercial world, sort of, we'll try to sell our products and services with that said, um, 2019 last year was our full year as a kind of commercial entity entity.

And we did, uh, just over 7 million. So, you know, where did that early part of the sprint, um, as you, as you point out, we believe that there's incredible things in the future, but we're also. Very knowledgeable that with, um, the changes in the business world over the last five, six minutes over et cetera. Um, and that coupled with the other hand, some tailwinds in the market, that number from seven per, you know, it could go much, much higher.

Really in the next 18 to 24 months. So we are, uh, we're extremely optimistic as a company and we've been given incredible feedback in the marketplace from all manner in all parts of kind of a mortgage and real estate ecosystem. So we're feeling very, very good about our future. Although like anybody who carries the title, I do.

Um, you know, more would be better sooner, but one has to be patient in these sprints. So in some ways they're sprains in some ways, the marathons too. It's the LG. So when, when you're thinking through, you know, the last year you split, you just said you split off from another parent company last year. Right.

Why did that happen? And what was that process like? Yeah. So I think it happened for all the right reasons on both sides and the process was. Um, it's always somewhat painful, but in our case also very amicable the pair company, nation star bank, family nation star, man. No, mr. Cooper and it's in Munich, brilliant company.

Um, they are, uh, incredible company based out of Dallas. But they are not an incubator of it, right? They are, their mortgage company made a lot of acquisitions, very, very talented people, but you know, an AI company we're based in Seattle, et cetera, it's just a different culture and a different places. And as such, um, we felt mutually that it was time to move on for us to see kind of an independent existence and for them to continue to be well-wishers in customers.

Got it. And so what, what, it's been the driver, I mean, the first year as an independent entity, that does truly exciting times. Like what, what is your thesis on growth men to date? And then a lot of stuff has inherently changed at a macro level since then. So what gets you excited about the next call it six to 12 months on the growth side.

What are you thinking about there? So our thesis in the first kind of year was that direct selling would be our core lever. Um, we have some incredible people from the real estate data industry, um, when we connections. And so we did rely a lot in this, in this first year, this been a first 20 months, right.

Um, uh, on, on, in connections we have. Conversations that had taken place over the last five years. What would gentlemen call kind of roller mixing? We have moved that motion into much more of a structured connected sales and marketing channel led a process whereby. Um, you know, we're getting inbound leads and then we're going through a process.

And so the lever of growth early on was kind of people in the concentric circles of network. And now it's, um, any, and everyone who can realize value from kind of our data streams are automated valuation models or analytics models. Or propensity models and sort of portfolio optimization, AI solutions for mortgage real estate, you know, banks, insurance things.

So the thesis naturally changes as, as you grow and as the motion that you set up in the company changes, and we're sort of in that amazing cleaner period where we're still, um, direct selling, we're also leveraging and expanding food channel. Um, as well as connected sales and so exciting time, certainly for me as no CML.

Um, and for the sales team from 11. So tactically speaking, I'm curious how you structured your shift, your transition from this, you know, it's not fully abandoning direct selling by any means, but as you made that transition into, you know, channel, how, how did you choose to structure that transition? Yeah.

And part of this was, you know, we can flame, so that everything's by is only right. But at the end of the day, you also feel you went through. And, um, we realized that, um, that given what we had done last year in terms of adding on customers, um, in creating what we call sockets, right. And, or sockets, or potentially.

I'm taking the customer a longer journey where they just start with us that we, we need not only to sell to them, but also they're really nurture too. Think about customer success as, as any sense. And so we have an amazing person, um, who sort of looks after. What percentage we called up sell, but in reality is basically helping your customer longer journey for help them avail of different products and solutions that they need as they, as they themselves in nature.

Um, and so we, you know, we, we felt our way through that and realized that that kind of farming and not hunting was also a good thing. But frankly, with the holding world kind of hitting us and, you know, Depending on where you are in the world from November to March and then ongoing, there's been a lot of interest in automation, AI based solutions, and what is kind of a no touch economy, contactless, um, and, and better collaboration between sort of the government and what we call the GSEs and the mortgage companies and consumers.

And so that has called for kind of a channel model where there are companies out there that. Like how relationships are going to be as, and provide data. And as an always said, You know, if you want to meet money is what you should go to the bar where they hang out, don't trying to build your own bar. All right.

So sometimes you, you said at work with established channels and sort of educate them on what you're doing and that's kind of a proven, so, you know, from a Microsoft background, again, direct selling and channel selling are both fundamental parts of the company's business. So now forward thinking, I mean, what, what sort of things in a I'll call it revenue gen, since I know you straddle both sides of that coin, what, what has you most excited about the future?

There? Are there any kind of new strategies or tactics that you haven't yet tried, but that you're seeing out in the market and you're excited by, you know, we, one thing that has worked for us that we haven't said. Is a, what I would loosely call customer advocacy, which is that as our customers onboard, they have massive ecosystems and they are increasingly say, look, Hey mr.

X, and this is why you've got to think about here. And we use them. They're amazing. We're not going to get this type of either. Uh, kind of average, but also this type of service level of agreement from any other company in the space. So customer advocacy sort of, um, them being our biggest advocates and biggest.

Vectors of revenue is just an incredibly new area for us. And, uh, in terms of formalization and is one that has really become very fertile in terms of, in terms of our ability to grow. I think that's kind of the next thing, six months. That's a huge concentration in that. Yeah. Um, and, and, and then there's these, this beautiful Bluebird.

Of inbound, right? Which is people are finding us and, and, and, and hitting us. Right. And we feel very fortunate to be positioned in such a way that a company like ours is really spent very little money on marketing, just given our size, um, has been able to be, um,

Now totally a question I wouldn't normally ask, but yeah, I'm curious. So my last company was founded in Portland, Oregon, and I know you're in Bellevue. I'm curious how you feel the Pacific Northwest startup community has changed. If it's changed at all. You know, back, back in the day, there was always this kind of big.

Yup. Not a debate, but it was yeah, just like, Oh, you're not in Silicon Valley and kind of establishing Pacific North, the West startups as, you know, a viable path for companies to grow and see the same level of scale as the Valley. And then now we have this interesting thing happening where there's this in some sense of a mass Exodus occurring out of Silicon Valley to places like.

Seattle and Austin and Denver and these other kind of what used to be. Well, just not the Valley. Right. I'm curious if you're seeing or feeling any of that, is that out there and what that is like now that remote so much more? I think that's a great question. And I will say that, you know, I have a lot of strong opinions on this, so please, excuse me.

I sound constrainted, but um, almost stopped the Valley and Silicon Valley. You know, I went to school at Berkeley, right. Which is part of that area. But in my wife, um, you know, I am very fine to some system area, but I do think Silicon Valley kind of a force field. Created this view in the world that everything is tech and tech only.

Um, and that is if you haven't done a startup  and so on and so forth. And, you know, I think that's not super healthy for you in Seattle, Microsoft, Amazon. Yeah, you name it, right? I mean, punches of new unicorns, um, in some ways, explain drive Seattle's home to three of the rich tech people in the history of pack or, or actually four, right?

Although one of them recently passed. I mean, my point is, Seattle is no longer can no longer be considered even sort of secondary in the background. Um, that said, I think Seattle has its own issues. Right. Which is there's some big companies that. They do offer a lot. And then there are startups and then midsize companies and everyone's fumbles as to which one is right thing.

Right. And, uh, and so Seattle's in some sense in microcosm of, of what was thought of as that kind of Valley fever or another, that valued degeneracy earlier. Um, you know, all of this, all of the stuff that's going on with the massive growth of that comes with consequences as well. Right? In social unrest, economic inequity, Rachel, and justice, et cetera, all these things are part of, you know, one area of growing  and at one sector dominating.

So, so whereas I've, you know, my bones and pack and whatever, listen, send somebody, my queries. Uh, I think we need to look at each of all of these cities as, as much more than just kind of an incubator for, for new tactic. So we have to think of them as holistic. We got the systems for everyone, from teachers to people, to drivers too.

Homemakers to detect protect exists. So Seattle, I think is as good as any place to be if you're a liberal tech in the tech world. Um, but I think, uh, it's also facing some of the consequences of that room and I really hope that there's a balance. That's right. And fight for, right. In, in, in some of the value to Seattle and Austin Jersey say Denver, other cities that are sort of really

big in Boulder. So I really liked the direction we're headed right now. I'm curious, how do you think. Tech, this is going to be a little too general, so I'll try to make it less general, but like how, how do you think tech can push to be more involved in those other aspects or to help create more balance?

And I don't know if accountability is the right word, but you know, just interconnectedness between technology as its own. Microcosm and all of these other facets of a healthy community that. You know, can be ignored if this monoculture is, is left to just grow on its own, without some sense of balance, that question might not have made much sense.

So it made perfect sense. I really, I sort of have three answers. Um, it's weird because we think about that on hearing a lot. Right. As a small company, number one, and number two in a, in a very poor area of the economy, which is housing. I don't just mean quarter of the economy, but also, or area of quality.

Right. And let me see. Housing is self is not a very equal industry. And so technology to housing gives you a lot of insight insights into what are the things we can do better as a technique. So, first is I think people involved in the tech community. Whether you're working at Microsoft or Amazon, you're an executive.

You're not, , we've got to realize that your other world is, is not the hermetic Matsu. Um, there's a big world out there. Not everyone's making the money. You're making that everyone has the benefits. Not everyone has the freedom to kind of randomly work from home or go to the office and you, you know, and so on and so forth.

So I think we would know the language of. And the feeling of insularity and privilege is not to be, it's not to be dangerous. And so I think that's pretty cool. And if it's not going to happen just naturally, then I think technical is  where people can go work in the community for a year or two years or three years and maybe get a pet salary or whatever, but really do something that's creating Buddhism.

So that's the one. The second is I do think that. Um, even though this sounds very strange for anyone who's involved in business, I think there's not any less of a focus on. The insane profits, right? Yeah. That big tech and the technology companies in general, I think there's not a, be a leveling of that and more spending on the community infrastructure, permanent housing, um, public works, you know, parks, that sort of things that.

You know, if I think about my area, I live in Bellevue near Redmond, you know, I'm very lucky that I can move in surrounded by green, et cetera, but you know, um, the traffic, so traffic is increased because of all these nobody's been successful. These companies need to do something to mitigate that maybe, uh, you know, have better, uh, you know, pay for transportation, subsidized, public transportation, you bill parks, you know, subsidize the local businesses that.

Renters heart, et cetera. So I think there's an organic connection that has to be made between these companies in the communities that support them, which starts with getting out of the thought bubble and to start to connect with, maybe reduce your profits for awhile and pick up the third thing I think would be the big companies, et cetera, sort of gently agreeing with community.

You know, activists, doctors, urbanists, sociologists, anthropologists, run big projects that can be working together and really to throw their resources and capabilities. So for instance, let's say there was a project around, were you saying air pollution is right. Okay, great. Let's all work on that together.

Things that are better the lives of everyone and not just, you know, the people informed it and with the same figure salaries and some. So I think those three things can really forge bones and, and reduce the negative impact of what is for many, a very positive, you know, the impact of growth and so on and so forth, but really not.

Everyone's sharing. So as we wind down, thank you for that. By the way, I love it. When we can combine a conversation about, you know, high growth technology companies with community and, and some of the bigger things at play in the world right now, um, I'd love to close by. You know, if you have, do you have any favorite community projects, you know, in, in Seattle or even more broadly that you're really passionate about that you'd be willing to share with our audience and those who might also want to get involved.

Yeah. I mean, you know, I mean, I don't know how, uh, vulnerable these are others. I mean, obviously these answers are very specific person, but you know, very, very, I, I do think that we, you know, we're faced with an existential crisis and technology can play a big part in number one, stopping. The further pain and then actually adding to the solution.

So we've gotta be very smart about intersecting with technology, with all our data centers and Bitcoin and the standard that we're adding, that we just, uh, you know, not just using technology to solve that. I do think second week. Absolutely. Um, We do use technology to increase community engagement. You know, people need to get out there and vote this year.

They need to be, it's much more involved in, I mean, we still live in and that we'll have, well, I think stating and wonderful facts in bold. You know,

racial justice, gender justice, you know, all that stuff that really requires engagement and requires an ability for meaningful change that come about as a result of demographic. So I think that's kind of the second thing. The third thing I would say is, and this one seems a little counterintuitive, but you know, we have to support.

Not just the STEM professions. We have to support even as a tech industry or an anthropology and the science and wall and environmental studies and so on. It's not all about creating the next wave of amazing engineers, but really much a balanced. Um, and full society in the technical roles. So, you know, there's a lot of rhetoric out there that we're now seeing.

And I really, really hope that it's backed up with really, we all know that sometimes the rhetoric locates and I'm a marketer sometimes. I myself use my rhetoric, you know, to say things that it can appear disingenuous. Right. But I think we need to get to the point where we're letting our ingenuous most as disingenuous and really come together as, um, and as an industry.

In which even if we compete with each other, ultimately the goal is with the C. So Rami, as we wind down, uh, you know, you you've had an amazing career thus far. I'm curious if there are any mentors or even friends and colleagues who have inspired you along the way and helped you get to where you are today.

Know there are, and I'm gonna, I'm gonna sort of be a bit of a, let me call her and keep them nameless. They know who they are. Career wise, there are five or six people that I can point to that gave me, gave me options. They made choices that on me, when I really wasn't ready to do what I was taking on. Um, and, and I will say though that most of my mentors and people from whom I seek advice are not in the industry.

They are. People who keep me stuff outside of the industry, eat me active in those things. And increasingly also a 60 year old dollar who is social activities, to be honest, every day, it was very uncomfortable. So with that, I, you know, I won't name names. They know who they are. Or, I mean, thank you so much for having this conversation with me.

I really enjoyed it. And I think there's a lot in here for our listeners as well.