Meraj Imani on Refounding: How Product Leaders Navigate the $10M ARR Inflection Point (Part 2)
So I'd I'd love to to shift gears a little bit. We talked a little bit about getting from a, you know, a pre a $10,000,000 ARR mark or, you know, at least not being the line in the sand to how do you scale from there. I'd love to talk about more about the the people side, which I think you referenced earlier as well. Right? I think there's there's two aspects to this part of the conversation to be at least right.
Brian Root:One is, as you said, you have you have people who are you know, let's call them legacy employees. Right? They've been there for a long time. They're very familiar, arguably comfortable with the way that things have been operating. A lot of that now has to change in in subtle or overt ways, you know, depending on what the the changes as you continue to scale up.
Brian Root:So part a of my question is kind of how do you manage those people? Right? How do you do that assessment of, you know, at a at a very kind of crass level almost, can these people scale with us? Right? Mhmm.
Brian Root:I I think that's frankly math that a lot of investors are doing about the executive board and, you know, the executives need to do about the the employees that work for them as well. But two, how do you know, when you're looking at bringing in new new members to the team as well, what are you looking for in terms of the general criteria that will help a person be successful, you know, going along that journey from, say, 10,000,000 to to a 100,000,000 with you?
Meraj Imani:Yeah. Yeah. When you're sort of sequencing as a product leader, the different steps that you need to take to help scale the company, you know, first is vision. We talked about it. We didn't talk about big bets that much.
Meraj Imani:It's just your strategy, right? Like, you you know where you're trying to get to, what are the sort of big bets you're trying to make in order for you to get there, sustain short term growth, and also set you up for long term success. Really, the third is team architecture, and combining the people that you need with the way that you have them organized. So probably the situation that you're walking into as a product leader at a company, something like that, at that stage is, yeah, you have people who are grown, sort of homegrown people, they probably didn't have product, any sort of product experience, they were in supporting roles, or engineering roles, potentially even, or implementation, and they had opinions about the product, they didn't understand the customers really well, and they sort of adopted that role. It's how I got into product.
Meraj Imani:I was in support, I started voicing that, hey, I actually care about this, and they hired me into my first product role. Great, there's definitely a inherent knowledge that they have, what worked, what didn't work, They know the customers really, really well, sometimes on a first name basis, and and that there's a ton of value there. What starts to happen is you're scaling. The biggest change that I've seen, and I'm gonna Brian, I'm gonna ask you the same question as well, just curious what what what you saw. But the biggest thing that I started to see is you kind of move away start to move away from generalists into specialists.
Meraj Imani:Like, for example, if I early on, you know, was looking for to bring on somebody on board from a technical, like a technical PM or an integrations PM. And that's not something that you want to teach to somebody here. Like, no, I want opinions grounded in market demands. It's the same for mostly everybody. I'm going to bring in a specialist.
Meraj Imani:So that's that's one of the big changes that I saw, and I've noticed in through the two, three scaling journeys that I've done is sort of the need to start moving away from generalists. That's not to say that they don't have a role, to start sort of bringing in specialists and really explaining it to the team. Like, look, the reason we are bringing this person is, A, we have, we need the expertise, and B, we don't have time, for example, to train this expertise to somebody. So at least your team sort of understands the what and why behind the change. And then the things that I look for in in the people that are there, you know, performance and potential always kind of this matrix that I try to benchmark everybody against.
Meraj Imani:Are they fulfilling the roles of a that you would expect in the market at the stage that your company is at for somebody who has that title? Because, you know, bloated titles is a problem, especially for early stage startups because, you know, you're not paying a lot of money. So, you kind of give people big titles, but then you sort of bring in a specialist, a principal, a senior PM, and so on, and they're kind of at the same level, and they're like, what's going on? Right? Like, it's what what's happening there?
Brian Root:Yep.
Meraj Imani:So certainly that's something. And then potential, it's you are as a product leader, you're going to be implementing a rhythm. You're moving from gut check to data driven, and those two extremes that that's a journey that doesn't come naturally to a lot of people because they had to be sort of quick decisions, and hey, I need to get this ball rolling, unblock this customer, and so on. But now you're looking, asking them to actually see trends and assess market feedback, and then make decisions based on that, and then sort of try to prove it down the line as well. Hey, do we do we achieve what we said we'd achieve?
Meraj Imani:And the third one is I look for system builders, especially in a b to b SaaS environment, not looking for feature builders. I need somebody to see the bigger picture, and has a potential to see the bigger picture, and see their role within it, and in making it work, and in expanding it as well. Yeah. What what's been your experience?
Brian Root:Yeah. I was gonna say, mean, I I think a lot of what you said, I I would also second. Two other things I I would add kind of as as complementary experiences I've had. One, I I tend to look at you know, I'll focus this on on product managers just for sake of argument. Like, the way to be a good product manager is not to be exactly the same profile, you know, copied and pasted from person to person.
Brian Root:Right? I think there's dimensions in which you need to show strength. You know? I probably could list a lot of them, but industry knowledge, technology knowledge, you know, specific company know how. Right?
Brian Root:Just, you know, understanding of tribal knowledge. Right? There there's you know, as long as you are over indexing on arguably at least one of those, I think you have the foundation to be a good PM at a lot of companies. So that that's kind of thing one that I've I've learned to look for. Right?
Brian Root:Is there something that you're exceptional at? If you're, like, okay at everything, you know, arguably, you can go and find a specialist, you know, to your point to to give you more outsized value. But if you if you can at least demonstrate, you know, exceptional ability in one of the areas, that was helpful. And then but going along with that, the the second thing, which I think is nonnegotiable to me, particularly in the scenarios that we're talking about of, you know, growth and cultural changes, are you willing to change? Like, some people will call that, you know, a growth mentality.
Brian Root:Right? You you can be an exceptional PM, but if you are not willing to take feedback to anything differently, grow with the company through its growing pains, like, it's just not gonna work. Right? So I I think the people that I've seen a lot of success with are really good in at least one thing and really, you know, excited to to, you know, learn more, do things differently, change their skill set, maybe even change their their job title in off cases. Mhmm.
Brian Root:The the other thing that I I think about, and I'll I'll use bit of an oddball reference here, but they're really I do I do think about this a lot genuinely. I don't know how familiar you are with the, like, the mid nineties San Antonio Spurs basketball teams, but, you know, they championship teams at least several times over if I if memory serves. And and they had Dennis Rodman on the team who was, you know, notorious weirdo. And I recall reading an interview with Greg Popovich, their coaches, to, like, how how do you win with this, you know, weird character on your team when the rest of the team is so, you know, straight laced and even keeled and whatever it may be. And and his response effectively was mix.
Brian Root:Right? We can get away with a Dennis Rodman because everybody else is very straight edged and, you know, plays within the team rules. But if we had two Dennis Rodmans, we'd be in big trouble. Right? And and I I kinda think about that as well.
Brian Root:Obviously, I'm not usually hiring Dennis Rodman onto my team, but to me, it is it is about mix. Right? What can I you know, this person isn't great with interpersonal skills, whatever? Fine. I can't have a whole team of people that are like that.
Brian Root:I can have one person, and we can make up for it, you know, from a combined team cultural perspective by having people who reinforce that skill. And then, ideally, you know, as a leader, you put them into the same room, same situation so that, you know, the Dennis Rodman character can learn or at least be held in line by, you know, some of the other people. But so I, know, I think there's a lot of dimensions on which that applies, but, it's hard to get that right. But I think, you know, the the sense of do we have a, you know, a a core of what defines our team. Right?
Brian Root:We are San Antonio Spurs in x y z ways. Yeah. Some people don't, you know, 100% comply with that. Some people don't have exactly the same skill set, but Mhmm. They at least have enough reference back to that core that there's a connection point, and we can we can grow with them.
Brian Root:So maybe that got a little too obscure, but I think No. No. No. I just yeah. Go ahead.
Meraj Imani:I thought I thought it was great. I mean, I'm I'm more familiar with Dennis Rodman during his North Korea friendship days than his his first date. That's the whole other thing. We we won't get into that. But I think what what you said is, especially really, a, I agree with everything that you said, and b, I think it's for your listeners who may be in the job market right now, like a senior PM, for instance, and they're maybe discouraged about not hearing back or going in pretty far in an interview round and not getting selected, and they're like, why?
Meraj Imani:You know, I'm a senior PM. What's what's what's what's the what is it that I'm missing? And I've spoken to a lot of them over the last few weeks and months, and a senior PM is not a senior PM is not a senior PM, just as you said, right? Like it's I'll use an example at from an enable perspective. When I joined, the company was doing six week planning in terms of product.
Meraj Imani:There was no visibility beyond that actually. So if the story I tell people is if we've if engineering came and said, hey, this thing that we thought is going to take six weeks is actually two weeks. It wasn't good news because we're like, are we going to replace it with? Like, there was no work really to sort of have it filled up with. So one of the two senior PMs I hired very early on, one of them was extremely market focused.
Meraj Imani:I said, I need somebody who is, yes, senior PM, but really great at discovery and market validation and so on. Don't need them to be great at delivery of product. It's not the persona that I want. Right now is right now, I need runway. I need to help create runway, basically.
Meraj Imani:And then the other senior PM that that I hired, maybe within a week of this person was complete opposite. Like, here, I have an area that I do have. We have a very good understanding of what we're trying to make, but I need execution excellence. Like, I need somebody who sits down with the customers and does the design validations, works with engineering, and is able to hit deliverables that we set out and learn from them and kind of move on. So, yeah, really read the job description and see what it is that the company is looking for.
Meraj Imani:And I couldn't agree with you more on the core that brings everybody together. The thing that we had was we had a set of team values. Actually, company had its own values. We had a set of team values and we said, you know, we are a big diversity of team members, regions, experiences, backgrounds, and expertise. But the things that we care about as a team, really the values that we sort of try to find, that trying to coalesce around are these core values.
Meraj Imani:And sometimes you do need a Dennis Rodman on your team to just kind of shake things up and bring a different opinion on it. But, yeah, as long as that the core value is the same, I think the team can be high performing and cohesive.
Brian Root:Yeah. I I think you're talking to a level of awareness about, certainly, nuance of skill set and and and capability within a role, but also just a deeper understanding of how do you compose a team thoughtfully, right, which I tend to get a lot of my inspiration on on that topic from sports. Right? Because I think, you know, you have defined different positions that have, you know, ways of of interfacing, and that is something that, you know, coaches and general managers talk a lot about, you know, think a lot about. I I find that it is discussed, for whatever reason, far less in business, or maybe I'm just not exposed to the right, you know, people and books and what have you.
Brian Root:But I've I've inherited so many situations over the years where, you know, hiring has gone on for years in a lot of cases with the perception that, like, there's only one job profile for a PM. There's only one job profile for a UX UI designer. Right? Everybody must look the same. Often, it's, you know, templated off of whoever the person that was successful, you know, in previously years looked like we need to hire more of that person.
Brian Root:Right? So just go get five more of that person. And then often, it becomes very counterproductive because, in a lot of these cases, the person that was successful, particularly at these, like, early stage companies when things were chaos, was somebody that kind of was smart enough to skirt around the rules, you know, find ways to just, you know, get shit done. And then you hire five people that are just getting shit done. Cosmic turns into absolute chaos.
Brian Root:Right? Like, you need people to enforce structure and scalability and, you know, think about the long term. Right? Again, you can have a couple people thinking about, you know, how do I just get shit done? But, like, you do not organically move from that into, you know, a a a mature composed, you know, sustainable company, in my experience, at least.
Brian Root:So I I think I can't even think about how many conversations I've had with with, you know, c suite executives, CEOs, just to say, like, by the way, there there is like, there's such thing as a growth PM, for example. Right? Mhmm. Don't We have anybody on the team who has that skill set. Here's what that looks like.
Brian Root:Here's what we need to hire for. And it's just like this but we already hired PMs. Why why do I need that? Like, I find that to be a a very essential, but often often a bit head scratching kind of on both sides conversation to be had. It it's curious to me, you know, a lot of it feels like it's maybe boiling down to just obscurity of job titles.
Brian Root:Right? If they had very different titles, maybe it would be a lot easier for people to wrap their head around.
Meraj Imani:And PM, just in general, it's just an obscure role to begin with. Yeah. Couldn't agree with you more. And then there's this I'm gonna just add another layer just kinda going back to the scaling, right? Like, you're 10,000,000, you have like a bunch of generalists, and they own maybe different different modules probably of your product, and kind of doing their own thing, and dealing with customer requests, and so on.
Meraj Imani:So we talked a lot about how the profile might be different, and how what you look for might be different. But the thing that also kind of just to borrow your sports analogy, it's how your the the topology of your team really matters as well because, yeah, you have different players, some of them are more physical, some of them are, you know, kind of game builders and so on. Some of them are great at defense. You play, you set them up differently. Mhmm.
Meraj Imani:Depending on the type of a team that you're facing. Product teams as well, you set up your organization in a way sometimes it's usually it becomes kind of portfolio based. Hey, you own these products, you three own those other products, and so on. And that's certainly how I've set up teams as well, because a portfolio model made sense at a certain point.
Brian Root:Mhmm.
Meraj Imani:But what what organizations, kind of scaling organization and product leaders need to be aware of is that, guess what your architecture is gonna look like when you have a the three different groups that own three different things, that's what your architecture is gonna look like. Your architecture is gonna end up mirroring what your organizational structure looks like, and how these teams kind of work together and talk to one another. So really, setting up these groups in a way to kind of mimic the architecture that you want, really, whether it's value streams, whether it's like a platform and kind of solutions kind of a model, or something else. And and then setting them up differently. Right?
Meraj Imani:Like, you talked about a growth PM. A growth PM may may not need a team of 10 developers and, like, DevOps, like, of built into it and so on. No. You want an experimentation, agile team, two, three devs, maybe one UX designer and so on. So I see a lot of CEOs, acting CPOs, you know, kind of and so on who are like, no, I wanna be able to take this person from this group, and put it in that group, and I want them to be successful right away.
Meraj Imani:Yep. There is definitely merit to that, but in order to get the best out of your groups and what they're trying to achieve, you gotta make sure that the team's apology actually supports the outcome that they're trying to achieve as well.
Brian Root:Yeah. I yeah. I mean, I think if you're operating in that mentality of interchangeability, I don't know how to navigate that personally, at least without having to accept some level of, you know, decreased standards for Exactly. Which, you know, if situations like maybe hiring is a, you know, a really complex challenge for your organization, maybe that makes sense because the, you know, the cost of going out and trying to get a specialist is, you know, exorbitantly high compared to just shifting somebody in and, you know, accepting the the lower standards. But yeah.
Brian Root:I mean, it's, to the point of this conversation, I think very difficult to scale your company dramatically with, you know, with people who are not truly experts in in their roles. I'd love to to leave with a couple of wrap up questions. We're we're coming up on time here, but really great conversation and insights from you so far. So if you can sum up a little bit for any product leaders that are stepping into, you know, the the situation that we talked about, you know, you're you're at a give or take $10,000,000 ARR company. Mhmm.
Brian Root:What are the, you know, two, three things that you would really urge them to to focus on, right, over, you know, let's call it the the next 90, you know, hundred eighty days?
Meraj Imani:Yeah. I think, first, try to understand the company, and the dynamic, and the market, and the customer. Try to speak to as many people as you can within the organization, and as customers, and prospects, and so on. Then, in terms of kind of starting to put the steer the ship in the right direction, a, be aware that this is a marathon, this is not a sprint, and it's actually never ending marathon, because once you get to a particular place, then it's a whole other set of things that you need to do. Yep.
Meraj Imani:But the the sequence that I like for product leaders to think about and follow for their organization, and each of these steps might be at different stages for their company is the vision. Do you have something compelling? Is it dormant? Meaning, is it just in a slide deck, or is it something that actually is a root of decision making or not? So Mhmm.
Meraj Imani:Divisions. Assess your big bets. What so this is your product strategy, basically. It's like, hey, what are you trying to achieve over the next six months, one year, eighteen months? Your team architecture.
Meraj Imani:We talked a lot about this. Do you have the right players? Are they set up in a way that they can be successful as people, and for your organizational products, and so on? Process and tooling. Do you have the right processes?
Meraj Imani:And put processes after people because you want, don't want to design processes for your sort of weakest people within the organization. You want to set it up actually for your for your success, for your strongest players to be successful. And then finally, the roadmap. That's really the sort of the last things like, hey, what are okay? Based on vision, big bets, architecture, processes that we have, how are we gonna deliver on the products and outcomes that we want?
Meraj Imani:So that's what I would recommend the most, and it does take time.
Brian Root:Yep.
Meraj Imani:Hedge your bets on smaller wins to just get the ball rolling, get the flywheel moving, and, yep, don't forget to bring people along for the journey with you.
Brian Root:Yeah. Well put, and I think very, very, very practical. I'll leave you with one last, maybe a little bit provocative question. What's one thing in product leadership that you feel like you haven't yet figured out or or that keeps you up at night?
Meraj Imani:That's a good question. The thing that always I don't have I've never found a good answer for this because I don't and I'm more and more, I'm thinking there may not be a good answer for this, and I'm gonna I'm gonna ask you this question because maybe, Brian, you'll give me the good answer to this question. When you're in b to b SaaS product leadership, you will have a big account that will come along.
Brian Root:Mhmm.
Meraj Imani:And there is a set of things that they need that they will derail the roadmap. And it's there is no math for you to say a definitive yes or no on should we proceed with this or should we not proceed with this? Yeah. There's just gradients. So you're like, hey, do I sacrifice short term sort of successes?
Meraj Imani:Mhmm. Maybe hitting the quarter quarterly numbers, which then kind of has the board kind of pushing down on you. It's like, What's gonna happen? Or do I kind of sacrifice or delay this strategy or division, which has a projected kind of outcome that you're trying to achieve? But I would love for there to be a formula, you know, that you just plug in and get an answer out, and, you know, yeah, there are there are ways of figuring out how much the cost is gonna be of maintaining this customer and whatnot, but it's always it's never black and white, at least that I've seen.
Meraj Imani:And, yeah, I think that's just one area that I would like to be better at, and what I've personally started doing is just getting closer to sales and learning more around Yep. The sales methodologies and so on and what that persona kind of thinks about and tries to operate as. But, Brian, do you have this answer for me? Is there a formula?
Brian Root:I I don't have a formula for you. If if I have any shred of insight on this, I think it's this, which is I spent the initial years of my career out of college as a business analyst, primarily doing a lot of efficiency work and contact negotiation, things like that. So in that capacity, was dealing with a lot of clients or suppliers that, you know, wanted things from us, not product, you know, enhancements, but aspects, you know, of of their contract to be changed, for example. One of the things I learned during that time with that experience was it is often very obscure to external people external to your company what's easy for you or what's hard for you to do. Right?
Brian Root:I think either in the context of, you know, adjustments to a contract, but also, I think, in the context of building software. Right? Things that seem immensely difficult are often very technically easy to do and vice versa. Right? So if we're looking at this from the lines of just to some extent, how do I keep my my client happy?
Brian Root:How do I make sure that we, you know, appropriately, for lack of a better word, to use internal company resources? What are the kind of tricks there? And I I think it is a trick on some level, but really was to kind of present everything as almost equivalent. Right? This super easy thing internally.
Brian Root:Gosh. I don't know. I'll I'll have to go, you know, do a lot of work and figure out whether we can do this and, you know, escalate up to the CEO and blah blah blah blah, you know, and then a week later, come back and say, Oh, gosh, I can't do the thing that's actually really hard for us internally. But I really, you know, wet the bat for you and did all of them, blah blah. And guess what?
Brian Root:I could do this thing that for us is five seconds of work. Mhmm. But I'm gonna position it to you as, like, I'm I'm really, you know, I'm I'm doing my absolute best for you. Right? And and often, my experience there was, the company would be like, oh, wow.
Brian Root:Thank you so much. Like, we're really appreciative of you doing this. Right? And I don't think you can get away with doing that, like, as your default way of business. That's a little bit deceitful.
Brian Root:But my my point being, like, I think there's a time and a place to use kind of the obscurity to your advantage there and to make sure that, you know, you buy yourself the time to thoughtfully plan the requests that do have value, but are immensely difficult to execute on and, like, not put yourself in that time crunch while, you know, know, still positioning the things that are super easy for you to get done, like, as as, you know, gifts. Right? Very very, you know, nicely packaged difficult things that that are actually pretty easy. So I don't know. That's that's the best insight that I have for you there.
Brian Root:It's a good advice. Trick your customers. That's that's no. That's not what I'm saying. Well, Raj, thank you so much.
Brian Root:It's been a a fantastic conversation, a lot of insight. I I really hope that everybody gets something at least from this that they had not thought about before. And would you like to share with everybody where they can find you if they if they would like to?
Meraj Imani:Yeah. Brian, it was a great conversation, and, yeah, I'm sort of starting to focus a lot more on content. So my Substack, my Medium profiles are both available. You can search my name, and they should come up. Add me on LinkedIn, and I'm always curious about what's happening in this space.
Meraj Imani:Just drop me a message, if you have challenges, you just wanna bounce ideas, always always curious what's happening in the market, and if there are ways I can help, I'd be happy to. Great.
Brian Root:Rajivani, thank you. It's been a pleasure. Thank you.
