Product Management & GTM Today
January 17, 2025 | 49:24
Season 4, Episode 2
In this episode, Deepika Gajaria shares her journey from a background in mathematics and high-energy physics to product and GTM strategy leadership roles.
At companies like Tala, Zuora, and Securin, Deepika has held key leadership roles, focusing on aligning product development with GTM objectives to drive revenue growth and market expansion. She highlighted the importance of breaking silos between product, sales, and customer success teams, particularly by involving GTM leaders early in the product development process to ensure better alignment and readiness for market launch.
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Transcript Text
Chuck Brotman
All right, hello everyone, welcome to the Talent GTM podcast, your source for real conversations on hiring and building exceptional GTM teams. This so happens to be, I think, our last podcast recording of 2024, probably to be posted early in the new year, and today I am very pleased to introduce you all to Deepika Gajaria, who has agreed to join me from Palo Alto. Deepika, welcome to the podcast, nice to talk to you.
Deepika Gajaria
Thank you, chuck, excited to be here.
Chuck Brotman
Really excited to have the conversation. Deepika is one of our first guests. That kind of gets a little bit outside of conventional GTM, although I think she’s going to talk about some of the connection points between her work and GTM, which I’m really excited to get into. But to share a little bit more on Deepika with you all she’s a seasoned executive with a passion for driving business growth and delivering world-class products, and she has experience in industries that range from cybersecurity to high-energy physics. In industries that range from cybersecurity to high energy physics, she is currently the VP of GTM and Strategy at Securin, which is a cybersecurity startup, where she works cross-functionally to align on GTM objectives, revenue growth and market expansion. More recently, she was VP of GTM Strategy at Zawara, where she led the acquisition of Zephyr and played a key role in driving the company’s future growth and success, and prior to that, she has been a key member of the executive team at Tala, another cybersecurity startup that was later acquired by Intuit.
When Deepa is not working, she is very committed to giving back to her community and the environment. She currently serves on the board of Living Classroom and Soil and Water, and she previously served on the board of Loma Prieta Chapter of the Sierra Club. She’s also a founding member of FirstBoardio, a collective dedicated to increasing representation of women on boards, and when she’s not doing all this, she can be found spending time with her family, proud mother of two active boys and a die-hard Warriors and Longhorns fan. I don’t know how the Longhorns are doing, but it’s been a little tough for us Warriors fans lately, hasn’t it?
Deepika Gajaria
Absolutely. Longhorns had a decent year Until two weeks ago.
Chuck Brotman
Who did they lose to then? I haven’t.
Deepika Gajaria
The Cal Bears haven’t been great, yeah, so they won’t win the ACC, the conference final, but they just quite didn’t make it. But it’s been better than it was the past 15 years yeah you’ve all had a great run.
Chuck Brotman
Well, thank you for joining. I love to start. You shared with me earlier that you have an undergraduate degree in mathematics. You might be my first guest that has a degree in mathematics. We’ve spoken to folks with different STEM backgrounds, but I’m really curious to hear a little bit more about your narrative how you got interested in math and your education, and maybe what led you to pursue an MBA and ultimately to get into product management roles.
Deepika Gajaria
Yeah, no, thanks for having me, chuck. I think the math was a little bit of a default. Before I kind of get into the math role, I’ll talk to you a little bit about my childhood, and I spoke to you about this as well. I came from a family where everybody was either a doctor or some sort of a science background, right, so we were all sort of exposed to it early on, I’d like to say. But I think the pivotal thing for me was I had an amazing physics teacher in 11th and 12th grade, right in my high school years. I still keep in touch with her phenomenal lady and she made it easy. I know it sounds weird to say oh, made physics easy and math easy, but she really got down to the fundamentals and explaining the basics. That’s sort of when I thought, you know what, if it’s coming to me without too much effort, maybe I’d go and do a degree in this subject.
So, I applied to UT and this was, you know, the late 90s, early 2000s. There weren’t that many of us doing sort of physics degrees so I said maybe I should just be safe and apply to engineering anyways. So started off as an aerospace engineer. I think it was a couple of weeks in I realized that wasn’t going to go very well or not as well as planned, and that’s when I kind of moved to doing math and physics. Absolutely loved it.
I think it was interesting to see the world from a natural sciences lens, and what I mean by that is at the time in the early 2000s, and when I moved to California, it was Google had just started. You know, a few years prior it was all about the cloud. Everyone was talking about this and I was so far removed from all of that doing natural sciences that it helped me maybe learn more rather than take the risks I would have taken and join a startup in that Right. So I went back into being a fundamentals research and engineering scientist, work with folks who had a lot of that point right. So I went back into being a fundamentals research and engineering scientist, worked with folks who had a lot of that experience. So I think it came from the fact that I did it early on because I loved it, but I also got an opportunity to learn and have some of those foundational pieces that we’ll talk about later. That’s how I got into it.
Chuck Brotman
That’s great. I mean hearing you go through that I. I guess it’s a reminder that a big part of being great in the natural sciences really comes down to you know learning how do you process information and to think, and, like that first teacher in high school, how to communicate clearly and succinctly difficult concepts right oh, absolutely, absolutely, and it was all about community learning.
Deepika Gajaria
I think that I learned very quickly. If you didn’t figure it out yourself, that was totally fine in the science world. You always did it as a team, you always did experiments, and sometimes they were much longer than you had envisioned, and I think that also kind of stayed with me over the course of my life.
Chuck Brotman
And how did you initially get into tech to begin with? What was your first opportunity and what was the process you’re like, you’re coming out. Did you go back to school to get your MBA, or had you gotten your MBA immediately while in undergraduate?
Deepika Gajaria
No. So I graduated from UT, I started working at this company here in Palo Alto in the Bay Area, did high energy physics. I was in research. I had a phenomenal ride. It was a little over five years into that job I said you know what I feel like? I have the personality to be outside of the lab talking to customers. And that’s when I went back to business school at UT and in tech commercialization, because I thought that was a little bit of a blend of science, commercializing technologies and on the product side.
So went back to school then about seven, almost eight years after I graduated from my undergraduate and the first gig I took was at a company now Dell at EMC at the time where they were opening up their software enterprise software division here in the Bay Area.
And I started off as an intern. Because, number one, I wasn’t even sure about what I wanted to do, because when you’re a student, you know, and at least when I was in grad school, the whole idea was maybe we’ll launch a business right while we’re students. And I think being naive helps when you’re young in some sense, because there’s really it’s limitless the opportunities but you don’t really know what your guardrails are at that point, but I quickly realized that wasn’t going to go anywhere, and that’s when I took the internship, so I loved what I was doing, got exposed to different divisions within the company as well, so it was software there was obviously. They were then going through the transformation of moving away from being a hardware company to software hardware, something I felt very comfortable with, worked in it for years and that was my first gig, I would say, getting into the tech world, and that’s where I started as a product manager.
Chuck Brotman
Very interesting In deciding. Going back, even in pursuing your MBA, what got you interested, maybe earlier in your career, in sort of the commercial aspect of businesses? I mean, you’re doing high energy physics, obviously. I’m sure there are a ton of pathways that could take you deeper into the science side of things. Do you recall? Was there a specific moment when you became more interested in how businesses generated revenue, served their customers? I’m curious if there was a specific epiphany, or maybe just a general, as you mentioned. You called it naivete, but I think it’s healthy to have a perspective on recognizing we don’t know what we don’t know and wanting to just maybe broaden your horizons. How? did you end up going in that direction.
Deepika Gajaria
Yeah, and if I think back, I don’t think there was a singular moment that I went aha, this is what I needed to do. It was sort of that continuum right. I was growing as an engineer, as a researcher. I was presenting more outside of my team. I was starting to collaborate more and, like I said, science fundamentally is all about collaboration. I need folks to.
Not I was designing something on, you know, simulating a design. It could be anything. I needed certain engineers, I need chemists, I need material scientists and guess what? Very quickly, I needed to present to outside of our company. And I saw that very, very early on. I’d love to give a huge shout out to my mentors early on. My first manager was a physicist. I think that’s probably why he hired me, because when he met me he goes oh, I was a physics major 25 years ago and that’s when we clicked and he let me, I’d like to say, explore more than maybe other managers would a 20-year-old do. I was bored very quickly, like starting to do research and just sitting in my cubicle doing it. So I said you know what? Go to the machine shop, learn how you build things. Go to the material science lab, figure out what that is.
And then I said can I go visit some of these vendors? How do magnets, how are magnets made? It could be as fundamental as that, but when you see it, you touch it, you feel it.
Chuck Brotman
Right.
Deepika Gajaria
Let me do that right. So it came from the sense of being bored and being curious but also understanding what that entire in my mind, the supply chain of design, build and productizing something Right. I think the only difference in there sort of the parallels between how I enterprise that is, yes, it’s all quick and it’s three-week cycles of build and ship. It was probably three years in our case, right, and I worked on DARPA project that took years, that didn’t see light of day, to experiments that failed catastrophically, where power was shut down in Palo Alto for a few hours. That’s not a story I’d like to talk about much, but that was the idea, right.
Chuck Brotman
Right.
Deepika Gajaria
And we did big things, and we did it together, and failure was celebrated in a way that you didn’t fear it as much.
Chuck Brotman
Right.
Deepika Gajaria
So I think that was sort of the beginning of saying maybe there’s something more outside of these walls that I want to look at in creating something and shipping it or taking it all the way to market and maybe a shorter time span as well.
Chuck Brotman
Super interesting. I think it’s healthy for someone that doesn’t have a background in STEM to hear about the collaborative nature of doing scientific work and interesting how that kind of got you interested in other people’s silos versus, perhaps, an opportunity that others might take to just go deeper in their own. Really interesting, maybe if we can sort of pick up from here. So you’ve been in roles, deepika, that span product management, leadership and GCAM strategy. Can you talk to us a little bit about some of the historical gaps you’ve seen between GCAM or within product organizations? What are some of the gaps you’ve seen around understanding go-to-market? Actually, maybe take a step back. I’m very familiar with traditional alignment discussions between sales and your post-sales function, customer success. I’ve talked a lot with marketers about how to promote better alignment between sales and marketing. I’m curious, as a starting point, if you can share, as somebody who’s kind of been in both GTM and product leadership roles, what are some of the gaps you’ve seen in terms of the product side understanding go-to-market.
Deepika Gajaria
Yeah, it’s interesting. So I’ve been on both ends. Like you said, when I was in product, it was so easy to poke holes in all the things that were wrong with sales or why a product didn’t do well, and now, sitting on the other side, on the GTM side, the past few years, I go well. It’s literally a continuum right. So I don’t even see this as a handoff, frankly, as a product or giving something off and say, okay, go off and sail this ship. But I think it really starts early on chuck and I’ve seen and let me, let me just step back right so I’ve been in very, very small startups but it was seed funding and we were just trying to figure out what it is we were going to build if there was product market fit all the way to large companies where they run version four of the same, or they’ve already captured a market.
You’re not really there to create a category, if you know what I mean. You’re kind of you’re expanding right and each one does it differently in terms of. Obviously there’s the organizational structure of things when you’re a small company, where I led product, but guess what? I did other things as well, because for one, we didn’t have the resources or the people and two, we weren’t large enough to even hire those people to test certain things that we needed to test it. It was truly that experimentation.
Chuck Brotman
Right tested.
Deepika Gajaria
It was truly that experimentation phase and both ends. Small organizations and very large organizations do it slightly differently. They focus on things differently in terms of hey, are you focused on building something robust to go scale, or are you just building something to test and just say, hey, can we get our logos, Can we get those first 20 logos?
So it’s a very different mindset. That’s number one. I think you need to understand that and that takes time. I think if you see both, you realize that you’ve got to wear slightly different hats and also prioritize things differently early on versus when you are scaling, versus when you are at whatever that scale might be. So that’s fundamental. But when you are and let me talk to sort of midsize and larger companies that have some of this structure in place, because then it makes sense to actually put context to this right.
So I’ll tell you early on, when I was at EMC right Large company, it was sizable even at the time I was there. The team I was in was small enough, but there were a lot of changes where suddenly, within the span of a few months, I ended up being the lead product manager on this very, very crucial strategic product for my division. I in fact had to work with a very senior product manager in a different division Till today. He was probably one of the best PMs I’ve ever worked with right and I realized very early on how he saw things versus somebody who maybe I would have envisioned how product led the creation of a product. To me it was product went off, designed it. Yes, there was an iterative thing where you talk to customers. There’s this whole process, but the way this other PM did it was very different. He brought GTM in very, very early on. So I see that that’s not the common way of how people design products.
Chuck Brotman
I’m literally talking about the first phase of designing a product Can you talk about when you say brought GTM in, like what did that mean?
Deepika Gajaria
Yeah, and I’m talking about strategically. You have a sense of what you’re trying to build right. You’re never like the first. You’re rarely in that situation with the first mover. There’s nobody else in the market doing that. So most of us 90% of us are going to be in a position where you’re starting to expand on something that’s already there or optimize something right.
So he brought in the leaders, the sales leaders, pmm leaders meaning product marketers, because very quickly he realized and CSMs, customer success managers, who I honestly still believe that PMs do not utilize enough, because they’re the brains of any organization. He brought them in so early on where we just had a beta. We had a few customers we were going after, but he invited them to meetings very early on, without even telling them much about what we were trying to do and try to get feedback, and that refined his thinking. Did he take all the feedback? Probably not. Probably not even 50%. But what it does is it’s almost what AI is doing for us today Optimizes your thinking and gets you sort of the MVP in you. And he also brought them in very early on when we started to do sales training. So we had beta. We started to ship a few things out well before GA or when it’s generally available, which could be six to 12 months out.
He brought them in not just for oh, let’s figure out the pricing discussion. He brought them in so early on to say do we even have the skillset to sell this product today within our team? That’s the other lens I would have never thought about. You’re always thinking external. What’s the product market? What is the customer willing to pay? What is the product Hold on? Do we even know if we can sell this product to a particular ICP or the ideal customer you’re going after?
Chuck Brotman
Right.
Deepika Gajaria
And that changed the way we thought about. Do we go GA-based and roll this out the entire division? Do we have a small tiger team to test this out in a certain region? Because, again, there was a regional spread. There’s always a regional tilt to how you should product. So I think those are the sorts of things I feel like product kind of just takes for granted in a way.
They talk pricing, they beat up customer product market fit, all of that. But very quickly looking internally at what your GTM team makeup is and the team that is going to be going and selling the product is almost as critical early on before you move further along the process.
Chuck Brotman
Really interesting. I was going to ask you why many product leaders and product managers wouldn’t think to do that, but I think you kind of covered that in part, that they’re not really thinking about the considerations of like do we have the skills and wherewithal to sell what we want, to build kind of almost independent of customer pain points or demand or market sizing? But also, would you agree too that in talking to sales and as someone who comes from more of that sales background, you’re also getting more perspective on maybe some of the ways that customers articulate their pain points and challenges that might not be as self evident in trying to just go direct to the market to gain that data outside of a sales context?
Deepika Gajaria
right, Absolutely, and I think that’s outside of a sales context, right, absolutely. And I think that’s why I think of it like I said it’s a continuum, it’s not a handoff. Right, if you look at it, it’s literally circular, right? I might be building the product as a product manager with engineers and I’m always amazed. We have really tight relationships with the engineering org. We just don’t fill the other third puzzle in right, which is GTM, early on, right, we?
do all of this and then we kind of say, well, we’ve built it, we’ve talked to customers, but I think the lens product managers take is okay.
let me show you what I have rather than step back and say let’s figure out how much we can sell and when. Again, the timing is important If there’s a need, all of those aspects. I’d much rather do that sooner, right? So to answer your question yes, absolutely. I think a lot of people it’s just the training we get on, saying okay, you’re at the center, you’re the CEO of your product. No, I think it’s more, it’s teamwork.
Chuck Brotman
But why would the post-sales side be so often neglected too? And that seems like super self-evident right that when you’re building something. I would think that most product managers would know that we need to make sure that we have the services team or the CS team with the skill sets and the feedback to help determine implementation cycles and potential pitfalls. Why would that be often missed? What’s your perspective there, and maybe what have you learned in your career around the importance of post-sales as part of GTM alignment?
Deepika Gajaria
Yeah, no, that’s a great one. I mean, I saw that even when I was doing the acquisition of companies when I was working on the M&A side. Right, you’re looking at post-sales and going, ok, you’re just looking at the numbers and some revenues. But that ties so deeply back into what the product roadmap is, what you’re talking to customers and your customer advisory board and all of that. I don’t know if I have the magic, but I’ll tell you what I’ve seen work and not work, like when I was at Jasper, at Cisco, for instance.
Right and Cisco still does it, as far as I’m aware they break up product managers into sort of technical product managers and product line managers. I think breaking that up actually is helpful in a way, so you’re not trying to force fit all the technical skills that you need, all of the customer success skills that you need, all of the communication that you need back and forth between those two sort of pillars. And I think if you put all of the onus on a product manager or say the sales team to you know sort of communicate all of this rich data, because there’s so many different aspects you need to look at. Right, there’s the customer view what are you building Is your team efficiently building to scale and?
Chuck Brotman
all of these pieces.
Deepika Gajaria
I almost feel like having a little bit of that silo early on when you’re building and testing, actually helps. So you focus in on what you need to do or your task needs to be, and I’m talking sort of early on in your career, right. Obviously, as you move up and if you’re managing teams or managing product teams, it’s slightly different.
You need to have a slightly you know more long-term view of how things are going to go and things, and that’s where you see sort of higher level leaders interact with the sales team. But that knowledge is not always trickled down.
Chuck Brotman
So one of the reasons for having maybe product line leaders and technical product leaders is that you have a part of your product organization that has the competencies and the time to invest in being more of that. Liaison to GTM is what you’re saying, and then they ensure working internally. Is that right?
Deepika Gajaria
And I’ve seen that work and I think that’s what I’ve seen. So I think that may be something worth looking at, even when you have small teams, almost sort of you know, keeping the task list sort of finite, if you may you can do a better job at it but also making sure that there’s enough collaboration where you can get, or cross-functionally, you’re communicating on what matters. Because when you look at metrics, chuck, and there’s a lot of this right, there’s a lot of this untold stuff that goes in when you’re not attending customer meetings. You don’t know what they’ve said. You get their. You know the Cliff Notes version of it. How many of us are listening to Gong recordings? We’re not Right. We’re getting that summarized view. So maybe there’s somebody who’s attending all of those on the product side, but that person necessarily isn’t going to be working with engineers till 2. Am trying to figure things out so.
That’s the efficiency piece, that you cannot fit every skill set into one role, if you may, or one organization. But having enough metrics or shared metrics on what matters between post sales and product is also very important. That’s where I think there are still gaps, that I know. Tools are coming out now to say, ok, are we looking early on? And just stuff like that.
Chuck Brotman
So I think that’s where I think there’s a gap. Yep, on that subject of tools, I think we discussed like product and AI could be a discussion for a whole other session, maybe touch lightly on AI. I mean, do you see an opportunity for trends in AI to very specifically help product organizations to get up to speed faster on trends in GTM or the other ways that you think AI could both maybe help promote better understanding here and where also may set things back? What’s the opportunity and the peril associated with AI in this sense?
Deepika Gajaria
Yeah, I don’t think we are at a position to say it’s going to set things back. We’re moving, it’s here, so we better get on it. I actually love new and improved versions of everything we do, right why not?
If it’s, like I said, like a simple example of, like a tool that’s recording, or like the you know the Zooms of the world giving us a transcript, I think, where it still doesn’t the fundamentals still don’t change of how you need to communicate and how you need to transfer data. You know the analysis of the data. Yes, it’ll give you a summary. There are tools doing that, where I can summarize the conversation. Then look back at my CRM and tell me hey, who in our customer list is saying something similar? Is there an upsell opportunity? So on and so forth.
So I think the analysis time is shortened, which is great, but there’s no guesswork and there’s no, I think, or I feel there’s more. I know because I’m reading inward data, which is always great. And also, I think the second thing it does is the collaboration piece. That really helps is when we’re all looking at the same data. We can argue about what the data is saying, rather than where the data is right. So I think that’s the biggest unlock for me between, sort of, my product organization or my GTM. Automation Tools are also helping in terms of research right. So I always go back to hey, I need to know more about my customer before I go on to a call.
I need to talk to analysts. So I mean, there’s so many tools out there, right? So I can just summarize like four books or four papers and I go in there educated, and why not? You always want to go prepared, you always want to go prepared. So all of that, I think, is definitely helping take the guesswork out, and it also shortens the whole analysis that you need to do on your backend. Or most people are not even doing it and they just kind of go wing it. What improves it in that sense? And it also raises the bar of how well you should run your meeting.
Chuck Brotman
Right.
Deepika Gajaria
That, to me, is a great unlock.
Chuck Brotman
Right, because when you’re sharing all this, I mean ultimately and maybe this is what I meant by potential I shouldn’t have said setbacks but AI is powerful insofar as, in this sense, if it’s helping you know product organizations better, get to this place faster, right To be more prepared for those conversations, to understand data, customer context and to understand go-to-market. But if it’s being used as an alternative to seeking the understanding or as another kind of check the box exercise, that might be more of a problem, right. It’s ultimately got to be to help, as you just said, to raise the bar, right? Not as an alternative to achieving certain levels of understanding, right?
Deepika Gajaria
Absolutely. And the one other thing this is my favorite thing is being bilingual, right. So now the product team can’t say I have no idea what. Gtm is doing so, you’re almost like going to be bilingual, and I think there’s nothing better than being bilingual. We do that with our kids, why don’t? We believe in our careers. Whatever that is, it could be sales and marketing. It could be, sales and product.
So all of the sort of the structural organizational pitfalls are gone. Right Now you have these tools that’ll help you or enable you. Well, I think that’s the promise and I, I I’ve started to use tools that help me with, you know, just even just my understanding, not so much cross-functionally, but that’s what I think it’s coming to now maybe a good segue here from this.
Chuck Brotman
And what do you see when you think from a gtm centric perspective? What are some of the the common ways that um folks on this side misunderstand product and product organizations?
Deepika Gajaria
I think I touched on a few that in terms of just sort of where we each think we’re good at right, kind of like closing the deal or like, oh, I understand customers better, I understand the market better. I think the biggest misconception I’ve seen is and I think that’s partly again depending on where you are in the Valley a lot of engineers will grow up to be product managers right, so they’re like, oh, they’re so technical they can’t hold a conversation, and that may be true in some cases. That is absolutely not true in others. There are people who have no technical background who have been phenomenal product managers and vice versa. But also, just to kind of shorten that gap of understanding each other means spending more time right and neither one is putting in the effort to understand the other, and I’m not saying just leaders of the C-suite.
It has to trickle down, and I love the concept of tiger teams only because you go out there and you figure this out and then you think of scaling. So to me, again, it’s back to the fundamentals. You’ve tested, you play with it, you move on right. Csms will know more about messaging than marketing people in some cases, because they’re like this doesn’t make sense, it doesn’t resonate. But also, I will say this, chuck, depending on the size of the organization, again, it has to be a little top down, and the reason I say that is we’re all inundated with so much to do and our own metrics and our own performance metrics that we’re trying to chase. If it doesn’t come top down saying, okay, I need you guys to collaborate, I need the PM and the sales team to go and pitch to this customer, it doesn’t really happen, naturally, in a lot of organizations.
Chuck Brotman
Right.
Deepika Gajaria
Depending on how big or how you know how nascent the market is, right. So the biggest thing is yeah, they’re too technical. We don’t want them to be there. They sell. The other thing I hear is they’ll talk about the roadmap. That’s nowhere close.
Chuck Brotman
Right.
Deepika Gajaria
That used to happen a lot, don’t get me wrong. But I think again you need to have alignment with sales leaders and product leaders to say, hey, maybe you do need to test that in a smaller, safer, strategic customer.
Chuck Brotman
Sometimes I feel like just thinking about my own career. Sometimes it’s part of the problem that, as organizations get larger, you may have you’ve got your sales lead. You have your you know pre-sales and post-sales solution architects. You’ve got customer success trying to bring in. Sometimes the problem is just a sheer lack of imagination understanding when, specifically, you bring the product lead into the conversations and how to loop them in a way that will help you gain value out of them without having too many cooks in the kitchen.
Deepika Gajaria
Maybe, but I think that’s the reason I say leaders need to be involved, right? As a leader, your only job and your primary job is make sure you optimize what’s happening or unlock or unblock people, right? If you don’t see that cross-functionally and not just across your organization, then you’re not doing justice. You have to move the needle. Revenue is always one of those sort of those North Stars, right? Or like more logos, whatever it is, depending on what stage you’re in. But there’s also a reason why, again, larger organizations have these different pillars, if you may, or different teams, for a good reason, right? I, as a product manager, could not be sitting with my customer 24-7 trying to troubleshoot, right, so you do need CSMs in there. And also, I think when leaders don’t do that early on, it’s part of the culture, right? If you don’t do that, early on.
it’s just so much harder to do when you get larger. I don’t care how well the company is doing, you see cracks very early on and it’s just not optimized, right Right. So I do put that on as on leaders, frankly, and it’s a huge part of how you’re culturally built and how you build your teams as well.
Chuck Brotman
Totally, maybe taking the conversation from culture and maybe for this question to speak more to your experiences in kind of the startup and early scale of world.
I mean, I feel like in my career I’ve seen that company cultures tend to fall in one of two buckets. You have kind of the more product-centric culture and, by the way, if you think I’m oversimplifying, please shoot this down but I feel like you have generally and often often not always companies that have technical founders but where you have kind of product-centric thinking and the idea is that you build like a superb product and you know, with the right focus, distribution sales will kind of take care of itself right. And then maybe the other extreme might be like a sales centric culture where the idea is that if you really have, you know, the right gtm leadership in place, that you know kind of the product piece is never as hard as it as first appears. If you really understand customer pain points and challenges, like get the right, you know revolution in place and then your product follows. Maybe I’m oversimplifying, but do you agree? Do companies generally like I guess? Maybe my question is do companies generally follow one of those two buckets or is?
that in itself, like a sign of you know alignment issues that need to be solved, like, is that a healthy company culture maybe is never product-centric versus sales touch, but always a healthy balance of both? Or do companies tend to fall in one of the two buckets? And then the reality is that you’re you, whether you’re joining as a product manager, as a seller you kind of need to be mindful of that culture because you’re going to have to adapt to it versus getting the culture to change.
Deepika Gajaria
Yeah, no, no, that’s a fair point. And I go back to. I mean, you mentioned early stage companies, right, and that totally depends on where the stage is right.
Like if you’re very early stage, you probably, for one thing, organizationally, are not built where you have a large GTMT. We didn’t have large, we had like one salesperson, for instance, in the startup housing right, and that’s just again you have to prioritize. You probably have some seed funding or series A funding. Where do you invest? You heavily invest on the engineering side and maybe some product you know and the CEO is sort of the face of the company, the chief marketing officer, the CPL, the sales, whatever that might be. But very quickly you realize that you do need and to me I do believe that people who’ve done it and have deep expertise in it. There is value to add. Right, like, yes, I can go off and wing it, I can test it and do all of that, and rarely are you trying to do something brand new that nobody else has ever done. There is value in hiring somebody who’s had some of that experience. The second thing I would say is so that’s one thing Depending on where you are, you probably focus more on product versus sales.
Chuck Brotman
Where you are as a founder. Oh, the founder, yeah, okay.
Deepika Gajaria
Exactly where you are, as in the company size and things. But the second thing is also the mix of the leadership, right? So if you’re in an early stage tournament that’s what we were talking about you know it all comes down to the founders. If you like it or not, if you’re not part of the founding team, you don’t have that much say in who’s being hired and what position needs to be hired. Next, yes, there are boards that kind of. You know, I don’t want to say prescribe it, but will you know, kind of push their view. But I’ve seen boards that are awful, where they don’t really do anything but just sit there and listen. So you’ve seen good, bad and ugly and you go hold on, you should be pushing back on that decision. What was it that didn’t seem right? So I think so the mix of leadership, the mix of who you choose to be on the board also would kind of, you know, I’d like to say, steer you in the direction that they think is right.
But the third thing and undeniably I’m not superstitious on none of that, but there is timing, you know, if you’re at the market at the right time and it’s going bonkers, it’s hot, everyone’s trying to hire that CRO, hire the you know the sales team and go off like just go to the races. Right, timing is important. If you’re too early, too late, then you probably need to reset pivot. There’s absolutely nothing wrong in pivoting your product into something different or changing the way you sell. Right, maybe you need partners more or you go to market route. So I think all three of those have to align in a way.
But also don’t keep checking back every month to see if they’re aligned, because you’ve got to have enough of a runway to test. So I think it just depends on that. But I would not say confidently that when you look at a company at a point in time that you could say it’s product centric or something, because there always is that continuum or that journey that they’re going through.
Chuck Brotman
So early-stage company founders should know their DNA, their core skill sets, have great advisors guiding them and pushing back when needed, and be opportunistic when the market forces opportunity, to go after it Absolutely and absolutely.
Deepika Gajaria
And I think you have to be a risk taker. If you’re not an entrepreneur, you have to. I mean, you have to, and the way I think of it is I. I don’t like the word failure, because there’s nothing you you learn something from it, right, like maybe it’s a good thing that the timing didn’t work out, because maybe your product would you know. So there’s always something there. But when you really look at all of the, the data, and there’s an undeniable factor of going after it, your gut has so much to say about it. There’s so much research now I’ve just started reading about it. The gut has just as many nerve endings as your brain, and so the brain.
It’s just, it’s fascinating. I’m like, yeah, that makes sense. My gut told me this was in the right decision. And guess, what. You’re thinking about it too. So I think you’ve got to put all that in and have a great team. There is absolutely no substitute for a great team. You can do so much with the right founding team and the right core team.
And yeah, I spent nights and days with customers when things failed and things came to a halt, and they were all things that we kind of learned from and learned from, used on from.
6
Chuck Brotman
So, then, the lesson here from a talent perspective is, if you’re looking for new opportunities at early stage, whether you’re again on the sales or product side of things, worry less about like whether the company is product centric. This is a silly distinction. What you really should be focused on is you know what’s the caliber of the team in place, what’s the opportunity in the market, and are they aware of where they have gaps right, and are they committed to filling those to take the business to the next level right?
Deepika Gajaria
Absolutely, and the team matters. Interview the team as much as they interview you, especially if it’s in a small startup. There’s absolutely no substitute for that. And the one thing I found is very early on, you know, you know if this is working or not. Right, you may kind of suppress that sometime and say, okay, no, this is going, but reassess that. And somebody told me this recently. They said always reassess your life in quarters, right, like, okay, think of like, how did this quarter go?
Chuck Brotman
Right.
Deepika Gajaria
And how was your person life? And I just thought I was like hmm, that’s an interesting way. It’s not like you’re constantly-.
Chuck Brotman
Like fiscal quarters, I mean like four times a year. They’re saying Fiscal quarters, right, Reassess your life.
Deepika Gajaria
That changes the way you think. Maybe you’ve had a stellar quarter at work but you’re thinking, man, this team is really not there. So then you kind of assess okay, is it the team that’s making me feel this way? So you kind of reassess in your career how you’re doing, and those early wins do kind of make or break the team dynamic and the chemistry right. If you can get past a tough corner or a tough poc, guess what you can do anything right.
So you kind of you stay and you know very early on if it’s the right fit or not right, interesting have you been doing this?
Chuck Brotman
do you have once a quarter?
Deepika Gajaria
you know, I don’t know if I follow any of the stuff we gave you chun, but I’d love to. I mean, I think yeah, I think it’s being a parent. You’re reassessing your life, right? Let’s just put it that way, yeah for sure.
Chuck Brotman
Well, I I mentioned you, I with with um these podcasts I always like to kind of bring things uh around to hiring and I’d love to hear your perspective on hiring within a product org. And I obviously know how you hire will vary based on. You talked about stage of company, you talked about different product types and obviously you can break that down beyond technical and product line to seniority and hiring designers versus other product role specifics. But in general, I’m curious if you can talk about from maybe a common denominator perspective, what are some of the more common traits that you’ve looked for as a leader when hiring into your product orgs? And then maybe part two, what are some of the common fallacies you see being made by other product leaders hiring for their product orgs?
Deepika Gajaria
Yeah, maybe I’ll start with the second, just because I remember it now, but I think the biggest one I’ve seen as well, they have to have vertical experience right Like I’ve seen that a lot they’re like, oh, they have to have. It could be as broadly as SaaS, and I understand the SaaS thing. I know I read something that you said recently too. I get that If you’re selling fertilizer, can that be?
yeah, I’m sure there are a lot of similarities, but it’s just easier, frankly, and that’s fine. So it’s less of a policy, but that’s just sort of your foundational. Hey, I need X, y and Z, right. But I think more and more, you see, that as a lot of people who’ve moved between industries moved between sort of verticals, if you may, and have done just fine, right, because there’s a lot of those foundational things that don’t change industries, moved between sort of verticals, if you may, and have done just fine, because there’s a lot of those foundational things that don’t change.
Chuck Brotman
Like you yourself, right. Your career is an example of that right.
Deepika Gajaria
And I believe that right, and I think it does make you a richer PM or a richer GTM, and I think you think beyond just sort of those four walls of what’s possible, and I think that’s the key right, because it hasn’t been done before, can we not do it? Or, like I said, the word naive is actually positive to me because like, okay, can you actually do it this way? And they’re like, are you kidding me? But maybe it’ll unlock something. So being naive and audacious kind of go together for me, because it’s like I don’t have anything to lose. So but then you choose people outside your vertical or outside your you, you know. So that’s one thing, I think for part two, for part one, I think the biggest thing for me is people who can collaborate and can communicate.
The two big C’s for me. I don’t care how technically minded you are, how brilliant you are. If you’re a little bit of a jerk to work with, nobody’s going to work with you. I mean, unfortunately. Right, you do have to collaborate, you do have to be okay with asking the questions and being wrong, and also communicating is a lot of things. To me, communicating is being able to negotiate, being able to stand your ground, being able to shut up when you’re supposed to right like or to say you know what you’re right. This is a better route. So, and the third one is flexible. It’s hard to test that in an interview. I’ve done a lot of things that you know. I’ve hired people that were you know, didn’t work out longer term. But flexibility is also something you know very early on. It’s probably early on when you sort of talk to them about how flexible are they. You know, when you interview them, how do they change their thoughts based on some additional data you give them for instance whatever.
So there are little ways and there are books that go into this deeply. So I think those are the three big ones. Hire for collaboration, communication and have flexible and their eagerness to learn that never goes away. If you’re eager to learn, you’ll figure things out.
Chuck Brotman
And without getting too much into it, do you have like specific approaches that you take to like minimize the risks that somebody you think is a great communicator you know was simply like a great interviewer? Like, how do you, how do you, without maybe prolonging an interview process I know this can vary with large companies as well.
But how do you find those key skills you know in a way that you feel like is less likely to be gained by somebody who’s, you know, just getting really good at interviewing and maybe not as good outside of that context and those skills.
Deepika Gajaria
I know that’s a great point, and it also depends on what level you’re hiring for right, chaka, right, if they can find, like a golden nugget, you know somebody who’s just phenomenal but doesn’t have as much expertise and product, sure, I’ll hire you if you’re early stage. So it just depends. I think the big thing is actually it’s not just you, it’s the team they have to work with. I always do the first and the last interview just to sort of sandwich it, and it’s less me to judge them for the skill set, but it’s more on the soft skills. That’s how I’ve always done it, and then I give the hard work to somebody else.
So you have that little bit of a rubric right. So everybody has something that they’re specifically asking about or testing and then we all collaborate and do that Again. Like I said, have we not made wrong decisions? Absolutely, but I think we’ve learned from it and in hindsight you go okay, well, that should have been a flag, right.
Chuck Brotman
Well, in doing that, I mean that’s a great way for you to see, like what they have learned right from your first interview to the last, how well maybe they’ve collaborated across the process, a way to maybe see flexibility to an action there, right, oh?
Deepika Gajaria
absolutely, and it’s not just about them asking questions. Right, how have they dealt with it? Because I actually do tell people on our team. Tell them about our culture. Talk to them about the hearts.
Chuck Brotman
It’s not all, ms.
Deepika Gajaria
Honky, and we all know that you work more than a year in a life, know that maybe 30% of your work is mundane tasks. Guess what they have to be done right, or whatever that person did. So I think they need to understand that. And I’ve been told last year, you know what? I don’t think this is going to work. I’m like that’s great, respect, that I still think you would have been a great fit, but they refused. And I’m like, okay, that’s great, but you’d rather do that quickly, no-transcript, so you’re testing it out and looking for it.
What’s the other tip?
Chuck Brotman
We have a common connection. I won’t say her name. We’re going through an interview right now and I’m just so pleased with the company. Has a super tight process and they schedule out multiple interviews and, as a fan of this individual, I’m delighted to see such a streamline, rigorous and streamlined process being run right, it doesn’t have to be, I’m glad.
Deepika Gajaria
Yeah, it’s not always the case I think that we have a lot of work and you guys have a lot of work on the recording side.
Chuck Brotman
To help companies optimize that second last question here I am uh, you know we, as a recording time, like I’ll knock on my wooden desk here. I mean, the market does seem to be heating up. I’m um for a lot of the sales roles in particular, we’re working. What’s your sort of prognosis for product management hiring as we get into 2025? What? What do you? You know, not to put you on the spot here, but do you see things picking up like, are there certain role types think demand will increase for?
Deepika Gajaria
like I’d love to get your kind of general sentiment in the market yeah, yeah, I mean just you know, doing what I do, just even on LinkedIn and talking to people, I’ve seen a lot more roles open up. I do hope not everyone’s asking for five to 10 years of AI experience, because I don’t think that many people have AI experience on the product side. I’d be really surprised if they did. Having said that, I think this is the time. If you’re early in the in your career, whatever it is, if you have like more than 10 years left in your career, you kind of have to understand what AI means to you as a product manager. Right, these are tools you’re going to be using. Obviously, there are things that you can design for AI design with AI, design for AI but understand what that means and I think, I think it’s looking better than it did even six months ago for the types of roles that are coming of that right, but I just hope companies also think about it.
recruiters think about what it is they’re asking for for some of these newer roles that are coming. Maybe it’s just the foundational skills at plus plus, right, Okay, maybe you know how to use these tools, or would you be open to you know? That’s the way I look at it. So it’s both ends, yeah, and I think it goes back to the point.
Chuck Brotman
Yeah, and it’s. There’s no easy answer here, because companies at a certain level have to kind of think about, you know, tightening the aperture of the funnels and not have, you know, 10 million interviews to run, 10 million interviews to run. But the more that companies can be less, you know arbitrary and tense about, you know, the prerequisite piece and more rigorous and thoughtful about the assessment process and really vetting through these things in a streamlined but thorough way.
You know should mean less of the you know ridiculous requirements on AI experience and industry background and all the rest and more better hires, though I’m totally with you. Last question. I don’t know if there’s anything you want to share in terms of I’m very appreciative of all your commitments in terms of the boards and nonprofit work you’re doing, and your primary work as well. Anything else you want to share in terms of things that you’re reading or podcasts or organizations that you’re supporting now that you want to share with our audience?
Deepika Gajaria
Yeah, I think the final thoughts I’d like to say there are just some really interesting books out there just in terms of learning the new tools and things that are coming out AI in general but to me, psychology and science and how you work, just even just sort of looking at yourself if there was a cognitive bias or if you’re thinking about the world differently, I think that’s an interesting way, wherever you are in your career journey, to learn more about yourself as much as you learn about the organization, right? So I think that’s the one thing I learned over time. I wish I did that more, where I read more about psychology and how you work, but also how organizations work, because there’s so many layers to an organization. Yeah, it’s not always evident when your manager makes a decision. You’re going seriously. That didn’t make sense. Why didn’t they tell me this? And as you grow in your career, you realize that it’s just so much more nuanced than black and white, right?
Chuck Brotman
Yeah.
Deepika Gajaria
So I think reading more about that and just understanding fundamentals never change in, whatever you do. So always beef up on your fundamentals and you’ll be good to go.
Chuck Brotman
Totally Well, deepika. It was a wonderful conversation. I appreciate you being on the podcast. Thank you so much for your time. This was really fun.
Deepika Gajaria
No, thank you for that. I really enjoyed it. Bye Thanks.
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Despite so much innovation in HR tech and recruiting, hiring remains broken. As former operators with decades of experience hiring GTM talent, we wanted to start our own business dedicated to helping B2B tech companies across a range of industries do a better job at attracting and sourcing tremendous (and diverse) talent.
How do you charge for your services?
We have multiple services packages, depending on the needs of our clients. Please reach out to us for more information, and see our sales recruitment services page for a breakdown of our packages.
Do you recruit outside of the US and Canada?
What roles do you recruit?
- Customer Success: Standard, Senior, and Principal Customer Success Managers, Onboarding Specialists, Implementation Managers, Community, Customer Support, & Solutions Architects
- Marketing: Growth & Demand Generation Marketing, ABM, Events, and Content / SEO Marketing
- Sales: Sales Development, SMB, Commercial, Mid-Market, Enterprise, and Strategic Account Executives
- Account Management
- Revenue Operations and Enablement: Marketing, CS, and Sales Operations
- Solutions Engineering and Post-Sales Solutions Architects
- GTM Leadership: Front-line, second-line, VP, and SVP / C Level placements (CRO, CMO, COO)
I've worked with so many headhunters and recruiting firms. What makes you different?
Put simply, we aspire to be as proficient in articulating your business value prop as your internal employees. Exceptional talent does not want to speak with “head-hunters;” instead, they want to connect with educated ambassadors of your business and your brand about meaningful career opportunities.
We go deep on your business and into talent markets to foster connections that other recruiting firms tend to miss. And we work with our hiring clients to ensure excellence in their hiring process. Please reach out to us for more information!
Is SaaS experience important when hiring?
Hmm, what does this mean anyhow?! We recommend defining the skills and behaviors sought before running a search rather than using buzzwords or phrases from other people’s job descriptions. We help employees go beyond acronyms to ensure they develop robust job descriptions that tie to specific candidate profiles for targeting in the market. Need help? Let us know!