March 17, 2022

The Thrill of Being a B2B Startup CMO

Are startup CMOs gluttons for punishment? The CMO role is tough enough these days, but strap on high expectations, limited resources, and the pressure of a low life expectancy for startups, and you’ve got yourself a real challenge.  

For CMOs Allyson Havener of TrustRadius and Ajay Khanna of Explorium, startup is a way of life. They don’t see their roles as punishment; instead, they see an exciting opportunity to build something great in a fast-paced environment, with a close-knit team of others who are like family. Tune in to this fascinating episode to hear how both CMOs navigate their roles, standing up the marketing function while building a team and a brand with an eye towards long-term success. 

What You’ll Learn in This Episode

  • What’s so exciting about being a startup CMO
  • How to create a strong employee culture at a startup
  • How to market effectively with a limited budget

Renegade Marketers Unite, Episode 284 on YouTube

Resources Mentioned

Time-Stamped Highlights

  • [0:00] Cold Open: This is Renegade Marketers Live 
  • [1:43] Allyson Havener’s Career Journey: From Abu Dhabi to LiveRamp to TrustRadius
  • [9:40] Ajay Khanna, Four-Time Startup CMO 
  • [17:59] Recruiting, Retention, and Employee Culture at Startups
  • [26:19] On CMO Huddles
  • [28:26] Building a Foundation and Experimentation as a Startup CMO
  • [31:37] How to Increase Impact with a Limited Budget
  • [36:00] Being a Purpose-Driven B2B Startup 
  • [38:06] Top Three Marketing Challenges at B2B Startups
  • [42:30] The Benefits of Startup Marketing  
  • [45:38] Tips for CMOs Looking to Go Startup 

Transcript Highlights: Drew Neisser in conversation with Allyson Havener and Ajay Khanna

[0:00] Cold Open: This is Renegade Marketers Live 

Drew Neisser: Hello, Renegade Marketers! Welcome to Renegade Marketers Unite, the top-rated podcast for B2B CMOs and other marketing-obsessed individuals. You’re about to listen to a recording of Renegade Marketers Live, our live show featuring the CMOs of CMO Huddles, a community that’s sharing, caring, and daring each other to greatness every day of the week.

This episode is homing in on what it means to be a startup CMO, with Allyson Havener of TrustRadius and Ajay Khanna of Explorium, two—you guessed it—startup CMOs with a whole lot of insightful things to say about a marketing challenge that is entirely different from CMOing at an established company. 

Tune in to learn what makes CMOing at a startup so exciting, how to build a winning team and marketing strategy, and so much more—let’s get to the episode. I can’t wait for you to listen. And of course, if you enjoy this episode, hit me up on LinkedIn and I’m happy to share at least on chapter of my new book, Renegade Marketing: 12 Steps to Building Unbeatable B2B Brands. And here’s the show. 

[1:43] Allyson Havener’s Career Journey: From Abu Dhabi to LiveRamp to TrustRadius

“When you find yourself at a really great company that's also investing in you and your growth, it's really easy to stay.” —Allyson Havener @trustradius Share on X

Drew Neisser: Hello, I’m your host, Drew Neisser, live from my home studio in NYC. Whether you’re in Silicon Valley, New York City’s Silicon Alley, or in Israel’s Silicon Wadi, new companies are hatched literally on a daily basis. 

Most of these die before their third birthday and before reaching 100 employees. Those that do get this far, set their sights on new milestones aiming for, say, $100 million annual average revenue, otherwise known as ARR—an important word in all this conversation—enabled by large funding rounds. 

Being the Head of Marketing at this stage is, in a word, “challenging.” The expectations that marketing can work miracles are high. The resources marketers are given are low. It’s a tightrope that takes courage and skill to cross successfully. 

To truly understand the perils and joys of being a startup CMO, we have two special guests who have taken very different paths, but now find themselves in similar positions. 

With that, let’s welcome Allyson Havener, Vice President of Marketing at TrustRadius. First off, Allyson, you are the only marketing chief I’ve ever interviewed who spent two years out of college teaching dance in Abu Dhabi. 

Allyson Havener: Yeah! 

Drew Neisser: There’s got to be a story there.

Allyson Havener: I lived out in the UAE for two years dancing out there and teaching ballet, tap, and jazz. And so, it was really fun, really great experience. But knew eventually I would come back to California. I’m originally from the Bay Area, so I knew I was always going to come home eventually.

Drew Neisser: All right. Very cool. So how did you make the transition to LiveRamp?

Allyson Havener: I moved back to San Francisco; I knew I wanted to start getting into the tech scene. It was really blossoming back in 2013, so I randomly got placed at LiveRamp. 

I was hired as a kind of swiss army knife, and I was doing anything from front office work to working with our recruiting team. Pretty much anything that needed to get done, I was kind of that person. And then we made one of our first marketing leadership hires, and she brought me on to the marketing team where I really started to hone my skills and learn from her. 

So, it was a different path and I’m really happy… I started there when it was about like 40 people, so kind of the early days. 

Drew Neisser: Was Rebecca Stone there?

Allyson Havener: Yeah, Rebecca Stone was the leader that brought me on to marketing. 

Drew Neisser: Got it, got it. No, and she’s terrific. It’s funny, we met when she was still at LiveRamp and so it’s been—you were there, you’ve been there almost eight years, which is really unusual in Silicon Valley. I’m just curious, what kept you there for so long, and then what made you decide it was time to leave?

Allyson Havener: So, I think there are two things that just happened in parallel. I think LiveRamp was going through hypergrowth, we went through many stages as a company, right? 

So, I started, about nine months later, we were acquired. Once we were acquired, we were a subsidiary of a larger company. We were able to acquire companies, have this hyper growth, and then we actually divested our parent company and IPO’d, and then continued growth. And so, this whole interesting trajectory of the company, and then I was given a ton of opportunity to learn and grow under Rebecca Stone. 

I think I found myself in this perfect pocket of growth in the company, and marketing was a huge component of that. And so, I think when you find yourself at a really great company that’s also investing in you and your growth, it’s really easy to stay, and then all of a sudden eight years kind of flies by and you’re like, “Whoa, what happened?”

Drew Neisser: And it’s interesting because in CMO Huddles, we’re talking a lot right now about retention. I know a lot of CMOs would love to be able to keep their staff that long and so it sounds like a combination of they just kept throwing new challenges at you, so you were learning the whole time. 

You had a good relationship with your senior executives, and they were in some ways looking out for you. And the other part of it is—since you were at a startup and it had so many iterations, I feel like you went through a lifetime in eight years of the different kinds of startup experiences, which is kind of crazy.

Allyson Havener: Yeah, yeah, I was really lucky. And you’re right, you learn so much along the way. Not only did I have a great relationship with the executives and given a lot of opportunity, but I feel like the team that surrounded me was also just very, very impressive. 

Everybody at LiveRamp was and still is very, very intelligent people, but also very humble, very collaborative. It was all of those things combined, so it kept me there for a very long time.

Drew Neisser: And one thing I would imagine, because you really learned the tech stack, you really learned demand gen because that is one thing that, you know, Rebecca really takes a lot of—when she talks about her LiveRamp experience, building up that muscle, if you will, for LiveRamp was her key accomplishment, right?

Allyson Havener: Yes, yes. The demand gen function was something that we built from day one, right? We really started with the fundamentals, we had a lot of investment or marketing operation, we had a lot of investment in making sure we had all the fundamentals to build the demand gen engine. 

And she did a really, really good job, so a big part of my job now, right, is taking that demand gen functionality and taking it to another company. I have a lot to owe to Rebecca in teaching me all that goes into a really good, sound management strategy.

Drew Neisser: So, what made you decide it was time to leap?

Allyson Havener: I think it was a combination of my desire to lead an entire marketing team and to continue to grow. I think that at LiveRamp, even though I had tons of opportunity, I was ready to go back and lead an entire marketing team because I only was managing a portion of it. So that was one thing. 

And then I also really missed the startup life, I missed the days that I was in the trenches with the sales team, I knew every salesperson’s name. I really missed that kind of camaraderie, so it was a combination of my own personal growth that I was looking for in my career, but also the type of company that I was looking for as well.

Drew Neisser: So, you seek out the smaller company, the startup mode, and some might describe you as a glutton for punishment, but it’s important in this conversation to know what you like. 

Just give us a quick window into what’s going on with you at TrustRadius, how far are you into that? We’ll dive deeper in a bit but, you know, just give us a picture of the landscape for now or your challenges.

Allyson Havener: So, I was brought on to the team to really rebuild marketing. I’ve just made it through my first quarter, which is really exciting. It was really about honestly turning on the lights, like we did very basic database marketing, we were working with the BDRs, doing some very basic paid media. 

The main thing is rebuilding the whole team, so we’re still in the process of that, but we have some core function in terms of our demand gen engine that are actually working right now that give us that breathing room—not even a quick win, right? It took us a whole quarter to build that. 

But we also, now we have that breathing room to, one, build off of and to continue to grow our team, continue to kind of grow our contribution to the company because I really want this marketing team to be a growth engine for TrustRadius. That’s really what we’re working on right now. But we’re definitely in a building phase. If I had one sentence, that’s what it would be.

[9:40] Ajay Khanna, Four-Time Startup CMO 

“This is the fourth time I'm building the marketing organization… Exciting is the overall speed and the pace that you work with, and all the learnings that come along the way.” —@khanna_aj @Explorium_ai Share on X

Drew Neisser: All right. Well, building it is then. Well, let’s bring on Ajay Khanna who is the CMO of Explorium. Hello, Ajay! 

Ajay Khanna: Hey Drew. 

Drew Neisser: How are you? 

Ajay Khanna: I’m doing fantastic. How are you? 

Drew Neisser: Good. Thank you for waiting patiently in the semi-green room. 

Ajay Khanna: Yes, yes. 

Drew Neisser: So, you’ve worked at a number of startups from Savvion, Veeva, and Reltio. What keeps attracting you to this world versus a big company like Oracle, which only got a year of your time?

Ajay Khanna: [Laughter] Yes, yes, of course, there’s a real story behind that. But as you said, a glutton for punishment, right? But no. You can call me a builder at heart, right? I think that is where the crux is and that’s what I really enjoy doing. 

So, this is the fourth time I’m building the marketing organization, and this whole idea of like, building the teams, building the processes, building and experimenting with the new and latest tech stacks, that is really, really exciting. 

Exciting is the overall speed and the pace that you work with, and all the learnings that come along the way. That is really fascinating. And then you get to start with this empty canvas; you write the whole story. So overall, I think that is the place that I always wanted to be. Then I have done that thing again and again and it is where I belong and it’s really exciting for me.

Drew Neisser: Well, it’s good to know exactly what you’re good at and what you like. There’s no doubt about it, because it’s such a challenge anyway, so you know exactly what you’re getting into. 

I’m curious, you’ve done this four times, but I’m imagining at Explorium, it’s a bit different than it was at some of the others. Talk a little bit about how you’re looking at this one. 

Obviously, you’re bringing a great deal of confidence into this. But how do you make sure like—one of the things where CMOs often struggle is setting expectations with their CEO and getting those sorts of, “Here’s what we can do in year one and year two and year three.” Talk a little bit about how you’ve approached this job maybe in a way that was a little different than in the past?

Ajay Khanna: Absolutely. Because throughout this journey, you learn a lot of things and then you become wiser and then the whole idea is that we want to bring in focus within the company. We want to make sure that everybody is aligned. And then the way I started this particular role was just to speak with people, more and more people. 

I spent my first month, month and a half to speak with as many people as I could. I spent like one hour listening to people from each and every person in sales, each and every person in solution side, each and every person in your customer success teams, in finance, so that you can really make sure that you are getting input from all sides. 

You have enough information to really understand what this company is about, what are the focus areas, where you want to bring in alignment as well as start building that whole message and story about that company. So, spending that time just to have that conversation. I had like 40+ conversations before I started doing anything. 

Have a method around that structure of discussions that you’re having with the product teams and everyone so that you can take your notes and then start building your plan which is right for that company. There is no cookie cutter, there is no like one size fits all approach in marketing, and the initial phase of this knowledge capture, knowledge gathering, that is really critical.

Drew Neisser: I love this. Forty interviews is a lot. What you’re also saying to your employees and your associates is that: “You’re important. I need to know what you know in order to be able to be better at what I do.”

Ajay Khanna: What works, what doesn’t work, yes

Drew Neisser: All of these things, you bring a certain framework and a frame of mind as a marketer having done it. What do they call that where you’re searching for the answers that will fit into your model, a certain bias? What do you do to make sure? And I’m not very good at that, by the way. I am really good at getting the research to confess, but how do you go into this and make sure that you’re having 40 interviews, but you’re really hearing with fresh ears and a fresh mind?

Ajay Khanna: Exactly. I think that is the whole idea of doing those interviews in the very first days before you’re actually part of the system so to speak, right? So, where the biases are not already there. 

You want to make sure and ask the right questions, right? What is this company about? What are the things that are working? What are the things that are not working? What are our challenges? What are our opportunities? What are our threats? Who our competition is? Who do you think our buyer is? How do you speak about this company? 

These are like very basic questions, but when you start diving into these, you start seeing that, “Okay, maybe there is a little bit alignment here, maybe there is a little bit disconnect here.” So, you start building your marketing plan to find those right gaps and start from there. 

Doing that right away when you start this new role is important because if you do this thing like six months down the line, that, “Okay, I’m starting a project of new positioning and I start asking these questions.” Then there will be bias in what you’re asking, what you’re listening, and what you’re building. So, it’s important to do this upfront.

Drew Neisser: Yeah, I remember the term. It’s cognitive bias, which is not a buzzword, by the way, just in case they’re playing buzzword bingo at home. Okay, so we’ve done the tour, which is really important. 

But I can also see the sort of CEO tapping his fingers or the head of sales tapping their fingers, saying, “Okay, great. You’ve done 40 interviews. Now, when am I going to see results?” I’m wondering how you manage expectations in these scenarios.

Ajay Khanna: In my particular situation, it was kind of like guidance from our CEO as well as our management team as well as that, “Okay. Take your time. This is a marathon. This is not a sprint. Don’t try to do everything on the day one. Don’t try to make all those changes.” 

There are some guidelines—books like “Your First 100 Days” kind of a thing. It gives you some kind of roadmap, even from your last company. When a new executive joins, there is an expectation that they will be spending their first 30 days, 45 days about learning. They are not going to take any action. So first you set that expectation right up front, it makes it kind of easier for everybody to get aligned with those.

Drew Neisser: The First 90 Days is such a good book. And by the way, I think it’s a leadership book. I don’t think it’s about 90 days. I think if you follow what they preach, it’s really some smart stuff in there. And of course, I’ve recommended it a ton of times to CMOs who are getting started. 

I’m wondering if the fact that Explorium was founded in Israel, but is now headquartered in Silicon Valley, I mean, this is your fourth startup. Does it bring a little different spice to the table?

Ajay Khanna: So interestingly, Explorium was not the first Israeli company I’ve worked for. My first one was Amdocs during my career actually. Kind of where I started with like product design and then user experience design and moved into product management. Before I moved into marketing, I spent almost five years there. 

That was one of the largest IT companies—it still is, I think it is like $10 billion plus revenue. It’s like a really large IT company. But now the startup scene is really so vibrant. There are so many interesting and fascinating startups coming from there whether those are data startups like Explorium or startups around like MS, startups around security, DevOps, FinTech. 

There is so much happening and they’re like, much more closer to Silicon Valley than traditional older companies like Amdocs. I really like, love, the passion that they bring to this whole startup scene, the speed and the pace that they work with, and this whole, I would say, the hyper growth mindset. That is so, so fascinating. I really enjoy being part of that kind of environment.

Drew Neisser: Yeah, we had the good fortune at Renegade to work with Riskified, which went public, but I got to go—when it was our first 30 days, I got to go to Israel pre-pandemic and interview not only the leaders but also their customers. It was just a great experience, and you felt the energy. It’s really incredible. 

[17:59] Recruiting, Retention, and Employee Culture at Startups

“When you're at a startup, your time to impact should be really short. You can get in there, you can sink your teeth into projects and take ownership and have an impact in a short amount of time.” —Allyson Havener @trustradius Share on X

Drew Neisser: Let’s bring Allyson back. One of the things that I wanted to get into is, you both started after the pandemic began. And that changes things. I mean, it really is—you don’t meet your team. So, all these interviews, Ajay, that you described, you did virtually I’m guessing?

Ajay Khanna:  All of them. 

Drew Neisser: So, first of all, have you met all your team members?

Ajay Khanna: Very recently. A month back, I did my first team meeting here in the Bay Area. And right after that, we had our first management meeting, which was face-to-face. Otherwise, everything was virtual. But yes, finally!

Drew Neisser: Amazing! And how about you, Allyson? 

Allyson Havener: Yeah, I’m actually in Austin right now. So TrustRadius is based in Austin, and I’m based in San Francisco. I’ve been out here I think three or four times and I usually come out for about a week. 

I’ve met the rest of the executive team, a lot of the team members, and then the marketing team as well. I’ve been really lucky. I feel like, we’re starting towards, hopefully, the end of this pandemic, right? Hopefully, people can start going back to their offices and stuff to continue that building that camaraderie.

Drew Neisser: Yeah, it’s sort of funny because in our huddles conversation, I only know of one company that brought everybody back, or asked them all, and they ended up losing a huge percentage. So, I don’t know. I don’t see necessarily folks coming back to the office en masse anytime soon. Yeah, there’s a good chunk of people who like working at home. 

Anyway, let’s talk about, you both had to build teams and hire people. And we’re in the middle of a pandemic and now we’re in the middle of The Great Resignation, talk about how this changed the nature of your challenge and what you’ve been doing either to keep employees or to go find the new ones. We’ll start with Ajay on this.

Ajay Khanna: Yeah, I think we have had this discussion a few times during our huddles as well, right? This is on top of mind for all marketing executives around building the teams, especially during this kind of pandemic phase. 

I think it is about continuously looking for talent, continuously seeing what are the types of people that you want to really bring on board. And having very clear ideas and definitions around the people, the culture, the fit, as well as the skill set that you want to bring in. 

The more clarity you have about the kind of people you want, the better they will be successful in the organization and they will be happy, and they will stay longer. I think that is starting from having a very clear idea on what are the kind of people that are skills that you want to bring when you’re building the marketing team. I think that is very critical.

Drew Neisser: I’m hearing you talking and at the same time, I’m listening to all of these CMO saying, “Yeah, but you got to get offers out there quickly.” And this other part of the question that I keep asking is: What is culture without office? 

Allyson, I’m just curious—because you’re building a team, what kinds of things were you doing during the pandemic and now you’ve been through the first quarter. You have to hire people and you’ve got to get them excited. What is culture right now?

Allyson Havener: When you think about culture, I think about the values of the company. One thing at TrustRadius is that we have very clear values and what that means. When you start a company and you align yourself to those values, and those resonate with you, that makes it much easier to buy into the mission and the vision and what you’re really trying to accomplish. 

I think specifically for my team, because we’re rebuilding and TrustRadius was without a marketing leader for some time. When I came in, I came in with a very like clear like, “This is our goal, this is what we’re going to accomplish, this is what we’re going to do together” and kind of rallied around that. Because at the end of the day, people want to see that North Star, they want to get to that goal, and you want to keep them really focused on that. And that really motivates people. 

So, I think two things: If you have those values and people really align to them, then it makes them want to stay at that company, right? And they also have to see a clear path to like, “Okay, I’m going to achieve these goals.” That’s also personal growth for themselves. I think if you have a nice combination of that, this kind of hybrid work situation is going to be successful for companies. 

Drew Neisser: All right, so we’ve got clear values, a very clear goal—maybe a single-minded goal—and showing the path and the contribution that individual can make. Ajay, anything else that we can do in this area to build culture? 

In the old days, yeah, you could say, “I want this kind of talent, I have this kind of budget” and you could see 10 candidates and you could interview them, get 10 people to interview. Now it’s like, you got to meet the one you want, and you’ve got to make an offer really fast. That changes this situation a little bit, and your team wants huge raises.

Ajay Khanna: It is, and it’s not as well, right? I mean, culture, first of all, is how close you are with your team and making sure that you are speaking with your team very often. I mean, you have face to face meetings, whether it is on Zoom, you need to have them often. 

You need to make sure that, as Allyson mentioned, that there are clear goals defined and why do you believe that you can meet those goals and why have you defined those goals? What is the math and what is the reasoning behind those goals? 

Once the team understands that, for me, that builds the culture. That builds the transparency and the belief that, “Okay, we are going to meet those goals, right?” So that is really important. 

And on the second part around the hiring part, you want to make sure that you are getting the right people in, right? That is more important. Yes, you need to move fast, so the whole process needs to be more efficient. 

But that does not mean that we don’t have the right descriptions, right skill set, everything defined, and we can pull the trigger just because we have a warm body coming in. I think that can be more harmful than doing good. 

So, make sure that your hiring process is very efficient, but make sure that you clearly know why you’re hiring this person, what is the gap they’re going to fill, and what is the role they’re going to perform?

Drew Neisser: Okay, so I think my takeaway from that is, it’s the same basics that we had pre-pandemic, only accelerated which is kind of a little, you know, a little tricky wrinkle. But I would guess, and I wonder if this is true, that there’s still kind of some sex appeal to being at a startup. 

I mean, Allyson, you specifically like that, like being at a smaller company. And I imagine the people that you’re hiring also get excited about that. Now, here’s the question that goes with that. Startups are not famous for work/life balance. 

Gen Z are famous for asking about work/life balance. What are you doing in that when the startup is like, “Oh, all in, all consuming” and there is a generation here that says, “Yeah, that’s nice, but how many hours a week do I really have to work?” I’m just curious how you’re thinking about balance on your team, Allyson? 

Allyson Havener: So, I think it goes back to what I was saying like, “Hey, here’s our clear goal, this is what we need to get done.” And letting people have the flexibility of how are you going to achieve that, right? 

You would actually be really surprised with your team and the creative, innovative things that they could come up with. I think it’s like, you know, you have a clear goal, but you’re letting people figure out how to get to that goal and helping them along the way, coaching them along the way, getting out roadblocks. 

It’s their time, so they have to figure it out, and I really leave that up to my team and give them that flexibility. That’s why also you join a startup, right? Because you have that flexibility to create your own path to reach that goal. 

But I think the other thing too is that when you’re at a startup, your time to impact should be really, really short. Because you can get in there, you can sink your teeth into projects and take ownership of that and really have an impact in a short amount of time, which I think, if you think about that, a lot of the millennials and Gen Z, right? That’s what they want to do. They want to have an impact in the shortest amount of time.

Drew Neisser: I love that. That’s a great way of thinking about it. Time to impact, and that is one of the things that is truly a benefit of working at a smaller company because, you know, you do one good thing, it can have a huge impact. 

[26:19] On CMO Huddles

“It is just invaluable what you get out of these connections.” —@khanna_aj @Explorium_ai on @CMOHuddles Share on X

Drew Neisser: Alright, we’re gonna take a quick sort of break, but not really, because I’m going to plug CMO Huddles for a second. Launched in 2020, CMO Huddles is an invitation-only subscription service that brings together an elite group of CMOs to share, care, and dare each other to greatness. One CMO described huddles as timely conversations with smart peers in a trusted environment, while another called it a cross between an expert workshop and a therapy session. 

If you’re a B2B CMO that can share, care, and dare with the best of them, visit or send me an email,, to see if you qualify for a guest pass. Ajay, Allyson, you’re both relatively new to CMO Huddles. How has the experience been so far for you?

Ajay Khanna: Oh, it’s been it’s been amazing. It’s been amazing. This is like some of the most fascinating people that I’ve met where you can really discuss your challenges, discuss what are the different tactics or strategies. 

Your peers and colleagues are taking in their companies. And it is not just about the frequent huddle meetings, I have been contacting them off those huddles and having one-on-one meetings with them, kind of picking their brains around organization, around marketing stacks. And it is just invaluable what you get out of these connections. It’s amazing.

Drew Neisser: I love that. And Allyson, I know you’re just like almost as soon as you got this new job. But tell me, any thoughts so far?

Allyson Havener: Actually, it’s been really nice the opportunity to meet people one-on-one because I do think like, in the group settings and chatting with others it’s, one, nice to know that people have the same problems as you do and you’re not alone, right? It’s easy to feel like that, especially as a marketing leader. 

I really like being set up with people that either have expertise in a certain area that I want to learn more about and having that one-on-one time with them, or if I can provide that expertise and have that one-on-one time with them, I think that’s just super valuable, that matchmaking with CMOs to exchange information.

Drew Neisser: I love it. 

[28:26] Building a Foundation and Experimentation as a Startup CMO

“Trying to make things perfect does not work in startups. You need to show the progress day after day, week after week, month after month, quarter after quarter.” —@khanna_aj @Explorium_ai Share on X

Drew Neisser: Startups have, I think, this fail fast mentality, which gives you the marketing chief—this is, in theory, the latitude to experiment. Is that true?

Allyson Havener: I think I would say yes, but in moderation, right? Like, I think you need to have the fundamentals in place before you start doing a lot of different testing. That’s something I think about a lot, that: “Hey, let’s just get the fundamentals right, and let’s start proving that those things work.” 

Once that gets going, then you need to start testing of how you are going to keep feeding that demand gen engine, how you’re going to keep widening the top of the funnel, how are you going to think about the bottom funnel, all of that, etc. 

But if you don’t have the fundamentals in place, you really shouldn’t be doing too much testing and hopefully not too much failing either, right?

Drew Neisser: Interesting. Ajay, what do you think? 

Ajay Khanna: Yes, so I think I do agree that we must have those fundamentals right around the processes and some of the basic things that we need around integration and the stack. But yes, I think experiment will be key because if you see that so many tactics, strategies, as well as technology available, the tech stack, if you see there are like 5000, maybe more marketing technologies available… 

There is no one size fits all, right? So, you need to find what is the right thing that you need for that particular company for product, for that marketing, for that market, as well as for the marketing motions that you’re using, right? Whether it is like a waterfall or is it like ABM or is it like PLG motion? You need to say: “Okay, what will fit best in this situation?” 

What I believe in and I really, really encourage my team to think like is that it is about progress over perfection. Experiment, move on, but you have to move on, right? Trying to make things perfect does not work in startups. You need to show the progress day after day, week after week, month after month, quarter after quarter. And as long as you’re moving in the right direction, experimentation is all good.

Drew Neisser: I love that expression: “Progress over perfection.” And I’m wondering, what’s that look like for you, Ajay? I mean, what does that really mean? Is it all about opportunities in pipeline? What is progress in your case?

Ajay Khanna: At the end of the day, it is opportunities in the pipeline. It is about the revenue. It is about the ARR, right? And then how are you driving the overall marketing motion, your channels, your mixing, your programs, your GTMs to that end goal do that is always there. 

The progress is definitely seeing at the end how it is impacting the end goal. But even at a smaller level, you want to see that, “Okay, what is the progress on your website? How is the progress on your lead gen? What is the progress on your SEOs? What is the progress you are making along your even AR and PR kind of a thing?” 

Everything needs to be moving along, right? They need to like move along, move along in the right direction, and then the end goal is that you are measuring the end impact on the pipeline and impact on your sales. That needs to show. That’s what progress is.

[31:37] How to Increase Impact with a Limited Budget

“You're not going to win by this feature vs. another feature because your competitors are just going to build that feature. Where the ingenuity really comes from is the story that you tell to the market and doing it in a really… Share on X

Drew Neisser: I’m curious, because both of you describe sort of a demand gen motion, if you will, that is very common in Silicon Valley. And it’s sort of: “This is the playbook.” And I’m just wondering, at what point is there a little bit of ingenuity to make up for the small budget? Because you’re not dealing with a lot of dollars is my guess. 

I’m just wondering if you have an example that either of you could share that’s delivering for you in a way—and I know, Allyson, you’re only in it three months. But where’s the ingenuity here? Or is it really just about, you know, blocking and tackling?

Allyson Havener: I think the ingenuity comes from the messaging and the narrative, right? If you have a really strong narrative—and if you even take a step back, right? 

A lot of technology, if you’re coming from a SaaS business, a lot of that’s being commoditized. You’re not going to win by this feature versus another feature because your competitors are just going to build that feature. 

Where really the ingenuity is coming from is the story that you tell it to the market and doing that in a really consistent way and how you get that message out there, right? Everybody has the same channel mix. You know, the B2B playbook is pretty straightforward, so I think really the ingenuity comes from the messaging and the story that you tell.

Drew Neisser: Interesting, interesting. Okay. That’s music to my ears and I’m believing it. Ajay, what do you think of that?

Ajay Khanna: That is definitely really, really important, right? Having that narrative, making sure that your messaging is resonating. Everybody is able to articulate your position, your messaging. And then it flows through various pieces in your content from your sales site, from your messaging site, from your website. That is really, really important. 

Then when it comes to the budget, look, I mean, you will never have enough budget, right? Because whatever budget you get, you will be asked to do more than that budget can do. At that point, you need to understand how different motions work, how different channels work, because tactics and the channels, they will bring in things with a different quality. Things of like, they will convert at different ratios, they will convert at different paces. 

Once you start understanding those levers that, okay, this motion will either generate more on generate better quality or generate faster or convert faster, then you can pull those levers and maximize whatever your budget is. Getting that understanding is really important. And it is always like, I mean, you are like building to deliver today, but also grow tomorrow, right? You have to maintain that mix and use that budget so that it is not just for today, but also you are building for tomorrow as well.

Drew Neisser: I’m curious with your situation because you did the month of listening. At some point you said, “Okay, here’s what we’re going to do.” Where are you in terms of—when do you get the chance to say, “You know what, I don’t think we’re talking about our business quite right. We need to really think through what our brand stands for.” 

At what point at a startup—because both of you talked about building this muscle of demand generation, which is what investors are looking for, which is what maybe the CEO and the CFO like. But there is this story that you both talked about that needs to be on the top. 

When do you get the chance to have that conversation at what point? And Ajay, you’ve been at Explorium longer, so you could talk about that.

Ajay Khanna: It is at Explorium, as well as in my previous companies, right? And what I’m trying to say here is: It is never done right. You will always be asking that question. What your messaging and positioning and branding is today, two years down the line, you will have to rethink that. Four years down the line, you will have to rethink that again. Because the market has changed, your customers have changed. Maybe you have pivoted to a different vertical, maybe your product has evolved, right? 

You have to ask that question regularly, like I mean, every six months and every year and maybe every year, year and a half, you will start thinking that: “Okay, do we need to reposition ourselves? Do we need to rebrand ourselves? What is marketing looking for?” 

At even my last company, we did like three times—or at least two and a half times—to keep pace with the market. Or not to keep pace with the market, to outgrow the market, right? Because that’s how you do it. It is a regular iterative process.

[36:00] Being a Purpose-Driven B2B Startup 

“The fact that I've only been there for a quarter and I can clearly articulate our purpose means that we're very purpose-driven.” —Allyson Havener @trustradius Share on X

Drew Neisser: Are either of your companies what some people would call purpose-driven? Is there a clear articulation of purpose in terms of why the company exists? Allyson—I mean, again, three months, it’s very quick.

Allyson Havener: Yeah. But I think that we have a clear purpose at TrustRadius. The way software is bought today is not the way it’s going to be bought in the future, so when you think about the future of review sites that are really turning into these research tools for buyers, so our purpose is to really aid the buyer to make the best purchase decision they can when it comes to technology for their business. 

The fact that I’ve only been there for a quarter, and I can clearly articulate that, that means that we’re very purpose-driven.

Drew Neisser: And Ajay?

Ajay Khanna: That kind of brought me to this company and really attracts a lot of people and the new employees to the company, this whole idea around that we are bringing the whole world’s data together, right? 

We are connecting the data and building this platform, which is an external data cloud where you can get the world’s best data. So, what we are building is like what Google is to Internet; Explorium is to data. 

That whole value, that big goal that we have, that aspirational thing that we are the ones who are going to bring all this data together into a single platform, that is massive and that is so exciting.

Drew Neisser: Wow. Okay, that’s a big purpose. That is, because there’s a lot of data out there. Everybody has it, and they don’t know what to do with it. 

That is a perfect transition because in this show at about this moment I ask, “What would Ben Franklin say?” I know that’s random, but there’s a reason. He was America’s first Chief Marketing Officer. He sold a revolution to a king. What you’re talking about is easy compared to what he had to do. 

Anyway, here’s what he would say: “We make these times better if we bestir ourselves.” And that in one way is why we wanted to talk about purpose because that is really what “bestir ourselves” means. 

[38:06] Top Three Marketing Challenges at B2B Startups

“It is you and maybe like two other people. If it bombs, it bombs, right? You start all over again, so don't be scared of failure. You can learn from it and come back stronger.” —@khanna_aj @Explorium_ai Share on X

Drew Neisser: We are getting closer to the end of this conversation. For some folks who are thinking about going to the startup, give me three top challenges, what it really means to be the head of marketing. The three top ones. And we’ll start with Allyson. 

Allyson Havener: All right. So, when I think about the challenges that I’m facing, it’s really balancing the short-term goals and long-term goals, right? There are things that you need to do right now and achieve to keep the lights on, but you really need to make sure that it’s laddering into that long-term goal that you’re trying to accomplish. We’ve talked about this a lot, but the biggest challenge also is around prioritization, right? 

Everything needed to be done last week, the month before. You’re always kind of working at a deficit, so it’s really hard to make sure that you’re prioritizing properly to reach those goals whether they’re short term or long term. And you’re also aligning on those as well across the company because you don’t want people going in different directions, right? You really need to align on the prioritization across departments. 

And then the last thing that we’ve been also talking about is resourcing properly. You just don’t want to throw warm bodies and money at problems without really good process in place, really good clear goals, clear action plan, etc. 

I think resourcing properly with a strapped budget, with strapped headcount, all of that, you really want to make sure that you’re investing in the right areas.

Drew Neisser: Those are such great points. I wish I’d started the show with those. We’ve got the challenge of balancing short and long term, makes total sense. I talk a lot about in the book that, as a CMO, when you get that job, you need some quick wins. And so, there’s that short-erm, and that quick win will buy you the long-term. 

The prioritization, man, I mean, and making sure that there’s an alignment against priorities… I would say, the CEO needs to help there. It’s hard though, because startup CEOs are often better engineers than they are leaders, so that’s a challenge. 

And then resourcing properly, obviously, you’ve got to have the right players, the right team underneath you to make this work. Ajay, what did we miss here in the challenges?

Ajay Khanna: I think a lot of them are same, right? I mean, like building for delivering today and building for tomorrow, that is a big one. I always say that you are coming on like this rocket ship, right? But you will be building the rocket ship while you’re flying it. So, make sure that you understand that and this whole idea of progress over perfection. Make sure that you understand that you are delivering something today and then building for tomorrow, right? I think that is really important. 

Second thing, challenge, is that things will change. Things will, for sure, they will change. Your messaging will change, you will uncover new things, your product will evolve, your market will evolve, you will change directions around verticals, your user persona will change. So, make sure that you have that mindset to pivot fast. 

Don’t get really paralyzed by that, okay, things are changing because that’s what a startup is. You will find your story as you’re writing that story, so understand that part. And then the third one is, don’t be scared of failure. 

There will be failures; that is given. And by the nature of the business that you are getting into, there won’t be much safety nets, right? It is not like 300-person marketing organization that there are like, people and people who are checking and cross checking the work. 

It is you and maybe like two other people. If it bombs, it bombs, right? And you start all over again. So don’t be scared of failure. The thing is that you can learn from it and come back stronger.

Drew Neisser: Live to fight another day. I love that. And you know, people talk about building a plane, but you’re talking about building a rocket ship. And I think if you are at a startup, you really are thinking about how we get to that unicorn status, so that’s important. 

I love this notion of flexibility. I was thinking of the days when I was a tennis player, and you approached the net, and you’d do it in such a way that you land—like your toes can go right or left at any moment. And I feel like that flexibility being able to pivot feels really smart. 

At the same time, as you’re talking about that, you’ve still got to have a core strategy, right? You still have to have a clear objective. So, this pivoting is tricky. And then there’s no safety net. Yeah, yeah, I get it. That’s an upside and a downside and I just want to make sure we’re driving this clear picture. 

[42:30] The Benefits of Startup Marketing  

“If the focus is cashing out, you will be even more stressed… That thrill of building just for the reason of building something new, I think that is more important.” —@khanna_aj @Explorium_ai Share on X

Drew Neisser: What’s the best part of all this for you? Is it that moment where they IPO and the stock goes out? I mean, what’s the upside for being the head of marketing at a startup? 

Allyson Havener: I really think it’s about the people. I love knowing everybody by their first name, so I think there’s that human element of it that makes it all worth it. I do think that there is that level that I was kind of talking about of that time to impact is really short. If you really like that, like this is the place to be. 

A startup is exactly where you can take on projects and really run with it. And also, I think, if you really want to grow, right? There’s so much that I’ve learned in the last quarter that I wouldn’t have learned if I had stayed at LiveRamp and stayed in my—I had a really great role, but it’s getting yourself out of that comfort zone and really pushing yourself and challenging yourself. 

So, you get to grow, you get to have a ton of impact, and you get to be really human. You get to know everybody by their first name and something personal about them and create some really long-lasting relationships.

Drew Neisser: Cool, I love all the humanness of this. Ajay, give us some of the—I mean, are we cashing in here at some point? I got to believe that you’re not putting in these kinds of hours over and over again, because the stress has got to be high…

Ajay Khanna: I will tell you, Drew, that if that is the focus of cashing out, you will be even more stressed. I think that is not something that I really think about, but it is that whole journey, right? That thrill of building and just for the reason of building something new. I think that is really more important. 

If you keep up thinking about that, “Okay, when is there going to be an exit? Is it going to be an IPO? Blah, blah, blah.” Then things become like much more miserable, I would say. You need to enjoy the whole journey itself; I think that is really important. You need to enjoy learning new things, that is really important. 

And what Allyson mentioned, this whole idea of building these long-lasting relationships, you become like sisters and brothers in arms, right? It is not about colleagues; you are like a band of brothers who are going to war and having scars to show to each other. And those are lifelong relationships. 

All the companies that I have joined in the past and all the startups, I mean, they are still friends. We still meet at Christmases and Thanksgiving and exchange gifts. They’re for life, and that’s the best part.

Drew Neisser: Yeah, as you’re talking, I’m thinking about something that came up in a huddle. That if you really—and this may be the answer to a question I asked earlier—when you’re looking to build a culture and you have this remote thing: Give everybody a really hard challenge. Even if it’s nothing to do with the company, but that they have to do together. 

There’s something about overcoming a hard challenge, even if it’s a nonprofit, off-hours activity. If it’s really easy like going on a sailboat, they’ll have a good time, but they won’t bond the same way than if they had to sail the sucker, right? Yeah, I mean, if they really had to do something challenging. So, I think that inherent in being at a startup is you have these things. 

[45:38] Tips for CMOs Looking to Go Startup 

“Align your marketing strategy to the company goals and continuing to communicate that and the progress that you are making.” —Allyson Havener @trustradius Share on X

Drew Neisser: Well, we’re getting to the point where we need some final words of wisdom from you two. I’ve been doing this Allyson first, so Ajay, other words of wisdom? We’ve got a CMO audience, help them feel good about this. And here’s the scenario, they’re about to leave a big company where they had a big staff and a big budget. We know some of those CMOs, and they’ve left that to go to 100-person startup. Give them some advice.

Ajay Khanna: Keep learning. You will learn a lot of new things. Be open to that. There will be failures, you will recover from them, you will move forward, so don’t be scared of that. And then, again, progress over perfection. 

Drew Neisser: I love it. Yes, we’ve come back to that. “Progress over perfection.” Okay Allyson, last words.

Allyson Havener: I think it’s really aligning your marketing strategy to the company goals and continuing to communicate that and the progress that you are making, right? I think one big thing that CMOs forget is communicating out all the amazing work that you’re doing. 

Even one thing is worth communicating to the company because everyone’s so excited about it and they’re so excited about marketing, so if you align it to the company objective and you clearly communicate how you’re making progress on that, it’ll really help you.

Drew Neisser: I’m so glad you mentioned that because that’s one other thing in the virtual world. And I think that came up in a huddle where a CMO started to send a weekly, almost water cooler-like conversation of things that they had heard from the executive team. 

It’s a way of communicating and bringing everybody together because you’re not together. All right, well, thank you Allyson and Ajay, you guys are great sports. I really appreciate you being on this. Thank you, audience, for staying with us. 

Show Credits

Renegade Marketers live is produced by Melissa Caffrey. Our botanical expert is Nicole Hernandez. Our intern is Alex Smith. For show notes, past episodes, and the latest on my new book, Renegade Marketing: 12 Steps to Building Unbeatable B2B Brands, please visit I’m your host, Drew Neisser, and until next time, keep those renegade thinking caps on and strong.