Latest / Growth After Headcount / CRO 2.0: $25M To $100M From The Terminal — Omar Ismail (Ascend) #003

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CRO 2.0: $25M To $100M From The Terminal — Omar Ismail (Ascend) #003 · Growth After Headcount

• Haris Odobasic: Today we are talking with Omar, the Chief Operating Officer von Asset, and he calls himself the Chief Revenue Officer 2.0, which means he runs the whole commercial org from his terminal. Let's find out how he does it. Haris: Hey Omar, how are you doing? Omar: Hi Harris, yeah, very well, thanks. Haris: Perfect. So you are the chief operating officer at Ascent. You guys are so very heavy on AI. And can you maybe first tell me a little bit about yourself and Ascend and your role within the company? Omar: yeah, sure. I mean my background pre ascend I would describe it as a generalist, about as generalist as they come. So I actually started out not in tech in investment banking for the first three years of my career in in London and Amsterdam. Then I had a stint in in venture capital, which was my first kind of foot in the door in tech and startups, and then really the vast majority since then has has been on the operator side. so initially joined and kind of started the growth function within a series A helping them to use data to basically inform their product and commercial decisions, a company called Mixcloud, and then I actually went and started my own company called Temple shortly after that. Temple was basically a digital marketing platform for the music industry. and the the core insight was music artists, managers labels, both big and small. did not enjoy using tools like Meta Ads Manager or like you know LinkedIn Ads Manager or drafting email campaign sequences on HubSpot. And so our vision was to kind of package what the ideal growth marketing stack would be in an abstracted way and verticalized and focused on music artists. and so I did that for four years, got to work with incredible managers and labels, the likes of Warner Music and AWOL and a lot of the big companies in the space and we sold it in 2025 to a company called Groover and it is still going and and now part of the overall Groover offering. And I joined Ascend in August as chief operating officer. And yeah, Ascend was was really, really interesting, very different business. I'd never worked in the travel space, so that was interesting. But what was more interesting about Ascend was it was a very organic growth story. So it got really from zero to twenty-five million in ARR purely organically through word of mouth, through referrals, and through a very small number of partnerships. And it had some tech, but not really. It had built up to this scale through just incredible people and incredible process that they built around it. But it had coincided obviously with everything happening in AI that they were now really seriously taking, you know, both the expansion ambitions to take this from 25 to 100. in a short space of time and also the the plan to really integrate and embed AI and tech across the organization. So that was a really like fun and interesting new challenge that I wanted to pursue and I joined in August. So it's been about eight months and that's what I've been doing there since then. Haris: Right, so you see it's so it seems more like a transformation from more or it was also AI from the beginning apart, or is it now accelerating or transforming it? Omar: I'd say yeah, it's tr it's transformational. So it's not it was it had an ex a very successful existing business. but rather than I'd say layering on bits of AI here and there, the the stated goal really of of the company is to become, you know, the best and most AI native travel tech company around. And that is not only on the kind of internal and product-facing sides, but also in go to market and across the organization in how we do everything, how we structure our meetings, how we communicate internally. we've really kind of embraced that that transition. Haris: Okay, all right. Can you walk me through those that transition and what is your role in it? Omar: Yeah, I'd say but you can split my role into into to two angles. So one is actually not what a traditional COO would be doing at all. and that is actually kind of leading and owning the the go to market stack and and and process. So we don't have a growth team. It is it is just me. we have account executives who We'll take on the calls, but we don't have, you know, a growth marketer or, you know, anyone running our ads or our email campaigns. really, I mean, part of the reason for that is we are a scale up, we've been very lean, primarily bootstrapped. We we have raised a reasonably small round for investment venture partners, of about three million, but relative to you know, our size in twenty five million ARR, it's not big. And so, you know, we we are always looking to be as lean as we can. and so that is a big part of my role as doing the go to market, which isn't your typical COO kind of stuff, but it's what I do. The other side I'd say is more kind of COO two or COO in in the land of AI, which is how can we be always thinking about what the next evolution of our processes and systems looks like in this massively changing world. So that's working with the product and engineering teams to really reflect, challenge, and put pressure on them to be thinking about, you know, what does the evolution post agile look like? And are we are we how much of our process and code is now written by Claude Code? And are we really feeling the velocity? And are we educating everyone in the team about how to use this safely and setting the say the the guardrails? Similarly, operationally as well, it's encouraging and incentivizing. different team members to be able to like have a shared context layer that can allow us to create documents and marketing assets and stuff more efficiently. so yeah, it's it's two very different things, but all very much centered around this kind of AI native vision for the future. Haris: Okay, I mentioned a few interesting points. CRO Chief Revenue Officer 2.0. Omar: Yeah, yeah. Haris: For that, I've never heard that before. I find it very interesting. And what skill set do you think the Chief Revenue Officer 2.0 is gonna need to have? Omar: I think the the things I love about the current moment we're in and I think the skills that I love seeing love having the more space for is when you don't have to worry about the super time com consuming parts of the job, the manual execution, the manual meta like ads, audits Haris: Mm-hmm. Omar: and exports, the like connecting super complex nurture sequences on HubSpot for your CRM, when you've freed up the time and headspace to build and execute on those things, you have much more time for strategy and positioning and creativity. And I think that has become more important than ever in an age where there's just so much content and so much noise and so much stuff. I think the the best leaders, whether it's a CRO, whether it's a CEO or a C can spend more time like really articulating the vision, the positioning and and then building out the infrastructure to streamline the execution of that and do the kind of things that you you can automate and can streamline. Haris: you're freeing up time and you have time to think because yeah many people are just going from meeting to meeting to meeting to meeting or doing something manual and in between there's no time to even think strategically do you use primarily Claude? What other tools are in your stack stack? Omar: So my personal for my personal use case it's it's primarily clawed code. and so if I if I look if I zoom in on one aspect of our operations, I'll talk about our go-to-market. That whole execution from end to end was clawed code. So when I joined Ascend, it was actually called Fly Flat. and this was in August. So it was a very different looking and sounding business kind of visually. and really we didn't have a a growth system as I I mentioned, it was very much organic word of mouth. And so, you know, I can walk through the process I went there, but in summary, everything was orchestrated by Claude Code, which was incredible. So being able to analyse thousands of transcripts of sales calls and you know do deep research on Great marketing frameworks, some of which I'd never heard of, some of which I had heard of and used before, things like four forces and jobs to be done and like, you know, taking a bunch of these frameworks and methodologies for analyzing the transcripts, and from those transcripts drawing really, really good insights, creating personas, you know, doing all of this really deep discovery work that is completely doable in a manual way, but would be so, so unfeasibly time consuming for a one person kind of growth team, or even a big team to be honest. And so Claude was very much the orchestration layer from zero to one in terms of this this big transition we had and this big rebrand and this big launch of our of our growth stack. Haris: How can you make sure to trust trust Claude, Omar: so y I mean, firstly I think hallucination has just got a lot better as the models have evolved. The accuracy has just improved and continues to improve. And so I think hallucination as a partic as a specific point is far less of an issue than it used to be. however, d h how do you trust it? How do you I think the biggest from a go to market orchestration perspective, the biggest issues around trust on or or errors are not actually from hallucinations. In my experience, they're from things like when it's building like an attribution engine, it having gaps in it that don't become apparent until you find attribution errors. And then you prod it and probe it and get it to analyze the script it's built and it says, there was a bug here that has meant this. So actually the the trust issues are becoming more like software bugs. And I think this is where to come back to kind of your point, CRO two what does it mean for the future of Teams? The the gap between technical and non-technical people is shrinking. And I don't think there is a world Haris: Mm-hmm. Omar: in which you have a go-to-market team that isn't becoming inherently aware of software processes, you know, AI agents, building harnesses. you know, doing all of these building software and scripts for their go-to-market team. Historically, go to market and products and engineering are kind of two completely different things. But now the crossover and and the kind of connection between the two is becoming really big because a lot of what we're doing is just code. It is software scripts Haris: Mm-hmm. Omar: that run overnight. And so yeah, to your point on trust, the better and more robust and resilient and the less fragile that these things are, the better your overall operation. And so to that point, one of the next hires I'm really excited to do, and I think half the world is very excited to be doing right now, is a is a go-to-market engineer. someone who is maybe a software engineer, maybe not necessarily a software engineer, but someone who's kind of technical enough, has spent enough hours tinkering and using Claude Code or Codex building automations on N and kind of is aware of how to create these interconnected systems, but also has us a lens of understanding what the growth stack is and what the different tools are out there and being able to build a system, not just a campaign. And so yeah, that that that line between technical and non technical in go to market I think has really disappeared. Haris: you're processing a lot of data, How do you store data? Omar: I'd say I mean in terms of our stack, the core the core backbone of it is right now we use HubSpot and we try and centralize everything as an engine in HubSpot. However we build a huge number of custom interfaces around Hubspot. So HubSpot is, you know, I would describe it as far from being like a seamless user experience, especially for kind of non go to market people. it's not a nice thing to actually work on and it's very kind of constrained. However, it's an incredibly Haris: Mm-hmm. Omar: powerful kind of at least for our use case and our size, engine to store and kind of coordinate everything. And it's very easy, easier than ever now to build even temporary interfaces on top. So to give you an example, we we might have a meeting where which is being transcribed where people are asking, have we ever actually looked into, you know, the number the the percentage of people who end up converting who how long it took them to do their first booking when they were on a trial. Some random question which might be a significant data point and that leads us to start optimizing our operations around. Historically we would have gone away, someone would have had to go and either do some kind of crazy SQL query or go and figure that out in a very convoluted way on HubSpot. Now, because we've spent so much time on kind of this really, really intense HubSpot backbone, it's very easy for anyone to just quickly go and and query that with natural language via HubSpot API and present that in a very clear interface that anyone can see and see the charts of and say, actually this is a really useful dashboard. We should add this to this other place. And I would love to add these data points onto it. And so because it's so easy to build this visual layer on top of HubSpot now. Haris: Mm-hmm. Omar: we're seeing s a much bigger excitement and curiosity and interest across the organisation in data. Haris: Which task do you still wanna focus our people to do it, versus what do we really wanna say, this is AI. Omar: I think there's always going to be a really, really important element of taste and judgment and creativity in campaigns. And so, you know, if we were to let AI query our whole data set of of transcripts and information and context, etc., the first time we did this, it produced, let's say, 20 kind of hooks or ideas for static creative that we could use as meta-ads. I'd say from that 20, probably about nine or eight were like usable and good. However, as we've evolved and fed in feedback and ensured that feedback is contextually stored within you know the overall context generation workflow, that's gone from let's say eight or nine out of twenty to fourteen out of twenty. And I think over time that we'll probably get to sixteen out of twenty. I don't I think it's very hard to imagine a world where it's twenty out of twenty. I think there's always an element of just human taste and human judgment with you know what will land and how can we be different and how can we separate ourselves from the norm because also AI is kind of normalizing towards a very common and increasingly cluttered space of how it speaks and how it positions. So I think the role of humans will be how you can create differentiation, creativity, taste and judgment within all of that. I think the areas as well that I would love to see more progress in it is definitely exciting seeing some really great products coming in, but I still think we're quite far away is really, really high quality video creation. Haris: Mm. Yeah. Omar: I think you can do it now, and there's a bunch of incredible AI native video people who can build incredible marketing content for you. But I'm imagining a world where this can be truly orchestrated with your clawed code or your orchestration layer. And I think that's where things will get really interesting, also quite busy and scary for our social media feeds. But I think that's where the gap is right now in in, you know, truly elevating Martin. Haris: how do you see then the role of marketing, evolve? Will marketing become more important, less important? Omar: I think I think good marketing will become more important. I think the brands that find the ways to stand out will have a platform because it will be so refreshing in a feed and an age of so much noise and so much slop, frankly, that I think the ones who still manage to find an edge and a differentiation and who spend time crafting these different experiences for leads will will get the recognition that that deserves because people will find that refreshing. I think equally there will be a move towards, you know, when everybody is doing email outbound, what's the like thing that everybody can't physically do themselves? And, you know, some really tangential things I see here. Like I see a world in which actually physical marketing sending mailers out to people might actually start to become more trendy again because you know historically it felt less programmatic. Probably we can make it a lot more targeted and programmatic now. And when you're getting fifty cold emails a week, but actually you get two kind of cold things in the post, maybe you're more likely to read those things. Equally I think the kind of value of like in-person conferences and in person sales and human relationships will become more important than ever because people will naturally gravitate and seek that human connection that can't be replicated at scale on email and LinkedIn. And so yeah, I think people will gravitate towards what's different as the abundance of of AI marketing and AI outbound increases. Haris: Yeah, going back to Analog. The history keeps repeating. Omar: It's always a cycle. Exactly. Vinyl and C D. Haris: nice. well AI is changing how you are working a lot. So it's pretty much changing the future of work. So anyone who would like to start the marketing, what skills do they need Omar: I I think the most important skill and way of gaining that skill is is experimenting with agentic tools. I I personally have a very strong preference towards clawed code. Haris: Mm-hmm. Omar: but Codex is great and you know there are there are a bunch of others that you can do, but my my main advice would be if you are interested broadly in marketing would be to say, I want to go and create a an end-to-end marketing campaign for the company I work at or a company I would like to work at and then go and do it. There is nothing stopping you from doing everything end-to-end for the first time in history. And the process of just doing and trying and pushing the boundaries of what is possible with these agentic tools is is the best way to learn. you know, what drove me to write this This growth engine post I did was actually just a a bewilderment and shock at what was possible to orchestrate with Claude Code. Because despite the fact at this point I was using it, you know, 10 plus hours a day, every every basically minute outside of meetings, I have my terminal window open and I'm doing Claude Code. Like that's my my new workspace. But despite Haris: Mm-hmm. Omar: all of that use, I was still shocked every time I would think, I wonder if. I can connect it with HubSpot and get it to build our nurture flows. And you know, no one has necessarily done some of these things before because it's so new, but once you realize this is this is like having a digital teammate who can access any APIs and can read and write things and if you provide the harness and the context around it can be incredibly powerful and reliable and resilient. And so yeah, my main advice is to just go and do it, experiment, try, fail. give it some real use cases and learn through using agentic tools first and foremost. Haris: for your company in the coming years, Omar, What are key areas you wanna work on? Omar: Yeah, for for us the key areas is we you know, we we are very we wanna go from, you know, the the twenty five or kind of so million ARL we're at now to get to at least a hundred million and we wanna do so without scaling headcount. already scaling headcount in a meaningful way. we we think there's always gonna be a very strong need for people, in the business, given what we do is very kind of high touch and white glove and people based. We're not a An AI only travel concierge service. Haris: Mm-hmm. Omar: but we want to basically empower every employee with with jetpacks. And so really the the the main area of focus for us right now is our core concierge offering. It's how can we provide the best possible travel booking experience for customers that feels the most effortless, seamless, human, personalized, and do that at even more four or five X the scale we have now without adding people. And that's really the core challenge we are optimizing around as a company. from a growth and go to market perspective, it's very much doing what we're doing now, which is, you know, how can we get to a perspective very soon where we we feel really, really, really solid unit economics, payback periods that we can feel we can go either raise some money or just keep pumping money in and kind of have that as going from five percent revenue contribution a year ago to being, you know, sixty percent revenue contribution and driving that four or five X growth I've just talked about. Haris: Yeah. When looking in the future, what do you think will be the number one business KPI where we're gonna measure a business on? Omar: I I think probably the same as what it was before, which for most businesses I think as a personal preference should always be some kind of retention measure. How much are you you know, I think the ultimate fit of have you built something people really want and and need can be measured by are you retaining people? And so in a world Haris: Mm-hmm. Omar: of people getting to, you know, one, two, three, ten million error in in weeks or months I think it is easy to get lost in like growth above all costs, but I think for us always as a company personally and I think for many companies in an age of such hyper competition, knowing that you are retaining customers either through a combination of incredible product market fit, customer experience, and also probably essentially through really strong votes and defensibility, are things that won't change in the future. and should continue to be the the metrics people optimise around. Haris: Yeah, still the same holy grail. Omar, Omar: Yeah, exactly. Haris: amazing. Thank you for this and much appreciated your time here. Omar: No, thank you, Horace. Good to chat.