B2B technology is shifting at an unprecedented pace. As traditional sectors grapple with supply chain pressures, shifting workforces, and the demand for personalisation, new frontiers like hardware-as-a-service and physical AI are moving from peripheral concepts to essential infrastructure. For marketers, the challenge is clear: how do you build a category and drive adoption for a disruptive technology that fundamentally changes how the world works?

In this episode of the FINITE Podcast, Jodi Norris sits down with Caitlin Allen to unpack the mechanics of category creation and how marketers can spot market signals, tipping points, and growth opportunities within emerging tech. They explore the nuances of marketing robotics, how to structure a team to create FOMO (fear of missing out) while helping buyers overcome their fear of messing up, and the structural forces reshaping B2B go-to-market motions.

Caitlin Allen is a seasoned marketing leader who has spent two decades building markets for transformative technologies before they are part of a P&L. She has helped scale category-defining companies across venture capital, deep tech, and consumer platforms—including serving on the executive teams that led Lyft through its IPO and Happy Returns to its acquisition by PayPal, as well as advising ambitious startups as a Partner at Andreessen Horowitz. She is currently the SVP of Market and Chair at Simbe, where she is pioneering Physical AI and bringing “Store Intelligence” to the $28T physical retail economy.

Caitlin shares her refined methodology for taking complex, multi-threaded sales cycles to market. She discusses how she conquered narrative homogeny in the robotics space, the five questions every buyer needs to answer during a paradigm shift, and how she integrates an intricate network of AI agents into her team’s daily operations – from persona-specific bots and Reddit monitors to leadership coaching agents.

If you want to understand how to position disruptive technology and orchestrate a category-defining marketing strategy, this conversation is a must-listen.

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The FINITE Podcast is sponsored by Clarity, a full-service digital marketing and communications agency. Through ideas, influence and impact, Clarity empowers visionary technology companies to change the world for the better.

Find the full transcript here:

Jodi (00:00)
Hi there, and welcome back to the FINITE Podcast. This episode is a great example of just how disruptive technology can be, how it shapes norms and guides collective thoughts. And us marketers, we’re at the heart of it. We’re delivering messaging and positioning technology as a portal to the future.

Today’s guest is Caitlin Allen, a marketing leader who has sat at the forefront of category-shifting technology throughout her career, including time supporting go-to-market at Andreessen Horowitz. Caitlin has her finger on the pulse of technology, market and consumer shifts, emerging categories, and importantly, the signals marketers need to identify growth opportunities and sector tipping points.

She gives us some great examples of how she does this in her current role at Simbe Robotics, taking on a “fear of missing out” approach with an extensive and multifaceted product, brand, and demand strategy with automation. On top of all of this, Caitlin is such an articulate and analytical thinker, you won’t be disappointed. I hope you enjoy.

Jodi (01:05)
Hi Caitlin, welcome to the FINITE Podcast. It’s lovely to have you here today.

Caitlin Allen (01:09)
It is lovely to be here with you, Jodi. Thank you for having me.

Jodi (01:13)
Yeah, cool. Okay. So I’m so interested in hearing your perspectives. I know you have some really nuanced takes on market shifts at the moment and how marketers should be responding to them—technological shifts as well, never forget. So I’m excited to get into that conversation, but before we do, I would love to hear a bit more about your background. I know you have been on the FINITE Podcast before and your episode was super well received, so I know we’re going to get some great insights. If you could just tell us how you got into marketing, your areas of specialism, and things like that.

Caitlin Allen (01:47)
Yeah, sure. Absolutely. It is a delight to be back, so thank you for that opportunity. I got into marketing a little bit by accident, but have loved it and never left. That’s probably the highest-level way to say it. I’ve spent my career building markets for transformative technologies before they are part of a P&L and year-ahead planning. That’s taken a couple of different forms over the last two decades, scaling category-defining companies across venture capital, consumer platforms, enterprise software, and then most recently, deep technology like robotics.

I started and sold a small agency in my 20s, then worked at Andreessen Horowitz helping the portfolio with things like go-to-market strategy and messaging. And then the last decade, I’ve taken high-growth companies from small, early-stage to much more mature positions in the market. I helped take Lyft through their IPO as part of their leadership team. I was part of the leadership team that guided Happy Returns through an acquisition by PayPal—they’ve since gone on to be acquired by UPS. And then, of course, now I’m at Simbe. An area of specialty is really in category creation, which spans a lot of different marketing specialties, shall we say, but it really starts with understanding where a market is going and how to influence purchase decisions accordingly in a way that’s good for the buyer and the ecosystem.

Jodi (03:07)
Really interesting stuff, especially at Andreessen Horowitz, being on the front line of that emerging tech and deep tech. Just out of interest, what do you think is the most riveting and inspiring technology that you’ve helped market?

Caitlin Allen (03:21)
You know, we’ll get into a lot of examples today related to robotics. That has been the most challenging and most fun so far, if for no other reason than… you know, Marc Andreessen said that software was going to eat the world, and it very much has. The next frontier is Robotics-as-a-Service, right? The things that we see and how intelligence is surfaced from those physical places and digitized in a way that integrates across all channels. So that’s been a fun and interesting new frontier for me over the last two and a half years.

I would also say that something that was really interesting to be a part of was Happy Returns. They sell exchange software and also provide physical locations to drop off products that you’re wanting to return or exchange. That was a really big, really fun thing to be a part of because when I joined the company, the industry was thinking about returns as something to try to diminish, to try to pretend wasn’t there. Through the course of some of the work that we did, and other players in this space, we really changed the perception to understand the return moment as an opportunity to deepen a relationship with a shopper, create an exchange, and create brand loyalty. So it’s all about mind shifts, but both of those come to mind in answer to that question.

Jodi (04:40)
Great answer. And on behalf of all online shoppers, thank you. It’s really helpful having easy returns. It sounds like you’re really at that critical point of these huge seismic shifts. And you’re right, robotics—thinking about the future of technology and the future of domestic spaces and business spaces, and how those can be enhanced with robotics is super exciting, and I can’t wait to hear more about that.

So let’s dive in, let’s get to the meat of the episode. I want to set the scene a little bit, and I’d love to hear about how you think about the technology market right now. What are you seeing? What are the market shifts that you’re noticing? Any signals that you’re sensing regarding emerging categories or shifting consumer demands?

Caitlin Allen (05:31)
It’s a really interesting question, Jodi. There are a fair number of both tailwinds and headwinds that are driving a reprioritization in structural forces that are shaping industries. Traditional industries in particular right now—because of the highly manual, highly repetitive nature of some of them, like construction, retail, manufacturing, etc.—are ripe for disruption.

Maybe taking it through a couple of different lenses: There’s obviously the individual, which at the end of the day is the consumer that’s buying something, and this is the truth in both B2B and B2C go-to-market motions. We all know consumer preferences are converging towards personalization, and what that requires is an integration of digital and physical spaces. If you think about it, you might go to the store to go shopping, or you might order online. Eventually, those channels need to integrate with the smartwatch that you’re wearing, the voice assistant in your kitchen, maybe even what’s in your fridge. And that expectation—that the person or the company you are buying from understands that about you—is really changing.

The second piece, maybe more on the macro side of things, is that we’re all very familiar with the number of things disrupting the supply chain these days. Margin pressure has always been top of mind for businesses, but with tariffs and international dynamics driving new levels of scrutiny and new ways of managing supplier partners, there are a lot of dots that need to be connected in a new way these days. That is really shifting the way global businesses think about serving their shoppers.

And then another macro trend that we’re seeing a lot right now is more on the labor side. Attrition across industries has always been something that is top of mind. We have a shifting workforce, right? Newer generations expect more. They expect different things from their line of work, both psychologically in how they spend their time, and the tools that enable them. There are very interesting questions across different industries these days around what happens when you start to automate lower-level work. If you’re going to automate lower-level accounting, for instance, what happens when you need a mid-level manager when they haven’t been trained in that lower-level capacity because you’ve automated it? That creates open questions about how we train new entrants into the workforce. I think that’s part of what’s driving increasing respect for new roles.

For my part of the world, I think what we’re seeing is much akin to the moment where we all had our first time logging onto the internet, or the moment we remember using our first smartphone. We’re all entering an era where we’re going to share spaces with robots—be that delivery robots, robots in a grocery store, or robots at a restaurant that serve you your food. And that has big implications for the workforce.

The final thing that I’ll say in answer to your question is, because of the advent of artificial intelligence, the emphasis now for future-thinking organizations is on the quality and precision of data, and the insights that can be built on top of it. As we move forward into this new world where supply chains need to be invisible, self-optimizing, take into account the personalization that consumers want, and standardize across channels, we’re going to see a big shift. Whereas perhaps hardware was a differentiator in robotics, we’re going to see a trend towards full-stack solutions where software becomes the differentiator.

Caitlin Allen (09:36)
It’s safe to say, I think, that we’re entering an era where we as leaders and workers are not just going to be managing people, but also robots and agents. The information that all of those different constituencies have access to is driving a big change in retail operating models and operating models in other industries as well. Because of the different capture devices that surface that information—be it individuals, digital channels, agentic channels, social, or hardware and robotics—the way that information is surfaced and digested to drive prioritization of action across the organization is changing and will continue changing quite a lot. It’ll be really interesting to see what that means for the workforce, the supply chain, and how that’ll show up differently depending upon the amount of cash a business might have on the balance sheet, as it will influence the business models for the companies that serve those organizations.

Jodi (10:40)
Absolutely. I think the pace of change is quite unprecedented with all of these observations that you’re talking about. People try to compare it to when banks started getting ATMs—they didn’t think they would need tellers anymore, and in fact, tellers just upskilled. Then phones came along and wiped out physical banks. We had a long-standing, slow-moving paradigm shift there, but this feels different. You’re working at the forefront, you’re seeing the pace of the technology and the innovation in robotics. We could have robotic servers at restaurants in the next five years, who knows? So yeah, really interesting stuff. Thank you for sharing that.

Caitlin Allen (11:19)
It’s an interesting point. What’s been fascinating to me is our surveys these days show that shoppers actually prefer to go to stores with in-store robots. Their kids think they’re cute. They have a better experience with prices being accurate and items being on the shelf. We’ve also seen an elevation of the retail worker’s role because of different technology, be it robotics or otherwise, because that technology can automate away the things that they don’t like to do and that are really hard to do well because it’s boring, monotonous work. What I’m referring to there is things like going up and down aisles and checking to make sure that prices are accurate, that items are on the shelf, etc. As a result, we’re also seeing things like wage inflation because it’s higher-level work that’s more respected. So I think there’s actually a lot to be hopeful about that’ll be really fun to be a part of.

Jodi (12:12)
Absolutely. So let’s bring this a little bit closer to marketing. I want to understand how you track market signals and sense growth opportunities within emerging categories. When do you think you can come in and notice those tipping points in your role, where you can push over the edge and these peripheral technologies become mainstream?

Caitlin Allen (12:42)
Great question. At the end of the day, what you’re trying to answer is: do I have the architecture to create a new understanding of a problem and a new solution? At the core of that, to design a category, you need to be solving a problem that is rooted in very deep human impact. And to do that well, you need to have things like third-party proof, including client stories that can be told in a broadly applicable way.

Typically in my experience, if we’re talking about company stage and size, that doesn’t usually happen until a company raises its Series B round. Because that’s about the point that you have a couple of client data points, a couple of case studies that show you’ve got product-market fit. Then what you’re going to go find and look for after that is go-to-market fit, where you can go upmarket, go global instead of just regional, or go from a product to a platform offering.

So when I think about identifying growth opportunities and tipping points, it’s foundational to understand the human impact and make sure that there’s problem awareness. There is often not problem awareness in category design the way that there needs to be. So you have to shape that problem awareness at first.

The other thing that is often a signal when you’re thinking about designing categories is narrative homogeneity. When I started at Simbe, all of the vendors in the landscape were saying the same things. That’s a signal that someone needs to say something different, get out ahead, expand the category, and differentiate therein.

The third prong, beyond foundational human impact and proven traction, is how you can leverage an ecosystem of influential voices to tell your story. This isn’t just about, in my case for instance, selling to retail corporate. The store managers are the ones implementing and using the robot. So if there’s not adoption there, you don’t actually have the ability to realize value for the business. And then the shopper is walking around in the shared space with the robot. So there are concentric circles of audiences you need to influence. It’s about that end user, the buyer, the day-to-day person in the technology, and all the folks that influence them or that they influence—like analysts, experts, and partners. There’s a huge ecosystem of CPG partners and others that bring the product to the store.

And then there’s also the upside potential that needs to be thought about. In our case, putting hardware in a store means we often first work with store operations. But once the hardware is in the store and the data insights are being served up in a valuable way, there are a number of applications that provide value across the retail enterprise for new departments, new use cases, and new segments of the ecosystem.

I don’t just look at the pain, the narrative homogeneity, and the proof points—though you have to lay that foundation to begin with. Over time, I look at how you tell an incrementally larger story. It’s a long tale, but that’s the holistic way I’m seeking to understand market signals when I’m evaluating if I can help a company succeed.

Jodi (16:09)
Makes sense. So you’ve just highlighted those signals that show market maturity and category maturity enough so that you are primed to offer an alternative solution. And on that alternative solution, I loved how you mentioned it’s not just about having a new solution, it’s about having a new understanding of the challenge at hand. I think that’s really interesting. It’s driven by perspective and searching for that creative paradigmatic shift. I’d love to know how you think about Simbe in relation to this, and how you’ve applied this methodology to Simbe. How does Simbe understand their challenge in a new way, and how have you repositioned them?

Caitlin Allen (17:01)
It’s been so fun. Maybe to set the stage broadly before I answer your specific question: I started two and a half years ago as the first marketing hire. Over the last two and a half years, we have gone from selling just to small regional grocery stores to selling to Fortune 100 and Global 2000 organizations in 10 countries. We’ve also introduced new products. We now have a platform that we’re selling that’s not just hardware, but also insights-based. The new segments and ways we’ve needed to think have been complex and really fun. We are at the point where we’re recognized as the market leader in our current category, so it’s been very rewarding to have that journey, and we’re now repositioning again for the next era.

Getting back to your specific question—and actually, one more thing I should have said: our go-to-market is highly complex. Jodi, we’re talking like six to 24 months just to land a pilot. Then a pilot takes about six months. That pilot is generally about six figures and shows ROI in about a four-month timeframe. But it isn’t until after that pilot is complete that a retailer will decide if they want to work with us across their store chain. At that point, that’s when we start to make back the money we invested in acquiring the client. So, as you would imagine, multi-threading category creation is really important because this is a very long and complex sale.

How have we done it at Simbe? I think about marketing in terms of three time horizons.

The first and most near-term is demand. Do you have enough pipeline coverage, and are you meeting customers where their current understanding is at, while expanding it incrementally so they understand why they need to buy from you? In some businesses, that near-term timeframe is a quarter. In our business, it’s more like 12 to 18 months.

The second time horizon is brand. What do people think about when they think about Simbe specifically? That has a farther-out time horizon, maybe two or three years.

And then thought leadership is much more of a five-year period—where is the industry going in that timeframe, and how can we be at the front and center of it?

Our journey at Simbe has taken maybe three phases so far, and we’re not done. When I think about creating a category, there are five sequential questions we need to help buyers answer for themselves:

Do I have a problem?
Do I need to change?
Do I need to change now?
Do I need to change now with Simbe?
Do I need to keep expanding or changing with Simbe?
I would say we’re in the middle of answering the third question as a company. When I joined, there was not broad understanding around the problem that we solve. So the first year and a half was really focused on designing an understanding of that problem and its impact on the business. We worked really closely with our original ICP on the core use case where we provide value: store operations around on-shelf availability, which is a complicated way of saying, “Are the products that are supposed to be on the shelf actually there?”

There’s obviously the core narrative and figuring out what channels bring that core value proposition to bear. We made sure we had our core set of proof points and took that to market. Because it’s so complex in terms of the number of audiences we’re engaging, we had to be able to prove at the beginning that shoppers didn’t hate having robots in the store—that they actually loved them, and it caused them to buy more and be more loyal. We also needed to prove that store teams actually prefer jobs with robots, feel they have the ability to serve the shopper better, and, data-driven as it is, that store team members stay longer in their jobs.

Then we had to activate our ecosystem of partners across co-marketing, technology partnerships, and analysts. We developed the very baseline of bringing that message to market, largely through PR announcements and industry events, because that’s what influences retail.

Once we saw problem awareness shaping up—where retailers started to understand how much not having items in the right place, or on the shelf, or with the right price tags was costing them—the next question the industry asked was, “Great, how do I solve this?” That gets to the “why change.” There was a big enough understanding of the problem that they felt they needed a solution. There are many solutions available—do you go to robots? Do you go to fixed cameras? What hardware type do you use?

Our answer was to introduce new products so an either/or choice didn’t have to be made. We designed a platform that actually offered all of them. We tried to evolve the understanding that it’s not about what device type solves your challenge; it’s about how you achieve full store coverage so that regardless of where shoppers are, you’re serving up accurate prices with continuity.

With that phase, we got really into deepening our brand, because no one cares about your brand if they don’t understand the problem. Once the problem is understood, people start to care about who you are. So we spent a lot of time humanizing Tally, our robot, as the spokesperson of the company. That helped position the idea that regardless of the technology you put in your store, it needs to be founded on robotics, because that is the best data capture mechanism. We also started to champion a narrative around the broad applicability of shelf digitization beyond store operations to new use cases, regions, and departments within retail.

One of the most valuable things in that second phase has been the client forums we’ve developed. We introduced client advisory boards and a pilot health council internally, which gives us access to the voice of the customer. I’ve also started a strategic advisory board, which is very focused on how we architect the market to drive value for buyers and position Simbe as the winner in the space.

The third phase that we’re in right now is creating a new “aha” moment pointing towards the data foundation that a digitized shelf enables. The new questions we’re championing are: Now that you understand you need store technology, how do you sequence that? What do you choose first? What is the maturity model as you implement it? How do you set up change management? That’s the next frontier for us, continuing to position Simbe as the go-to choice for retailers today.

Jodi (25:57)
Great summary, thank you for that. Loads of detail and inspiring points for people to pick up on. It definitely sounds like, with disruptive technology, it’s particularly clear—but with all technologies that it can be applied to, there is this kind of friction in terms of adoption. There’s a gap between what people need and what will benefit their businesses, versus how much they’re willing to change and evolve their own assumptions of the store experience to get there. So you have to work on thought leadership, advisory boards, PR, and even product. It seems like you’re working really closely with product to elevate capabilities across the store.

I’d love to understand your team and how you actually achieve this. How is your team structure built to tackle this, and do you use automation?

Caitlin Allen (27:03)
It’s a great question. The way the team is structured really reflects the fact that we need to create FOMO (fear of missing out) in the market, and then help people get past their fear of messing up.

There’s Product Marketing, there’s Growth Marketing (which sits at the intersection of brand and demand and owns one-to-many demand generation), and then there’s Account-Based Experiences, which are much more focused on specific accounts, specific sectors, and the campaigns that bring people along that journey. And then we have the underpinning of Ops and Automation.

Product Marketing is focused on competitive positioning, commercial cohesion, and helping the team answer what it is that we do. In a very challenger-sales-style way, they help people broaden their understanding of shelf digitization. I find it harder and harder to empower a commercial organization to simply and clearly state what you do in a way that makes contextual sense, so Product Marketing is responsible for that. Uniquely in our business, they also own our website experience, because that is intimately connected with the buyer journey.

Growth Marketing manages our heavy investment in comms and PR, which drives about 27% of our net new business. They also own our real-life experiences at industry events and digital one-to-many tactics.

Account-Based Marketing comes into play once we’ve engaged with accounts in sales conversations. Our playbooks are really focused on stores projected to close within a certain time period, utilizing dedicated campaigns to help those stores join our customer base.

Ops and Automation is fairly standard in serving each of these constituencies. We as a marketing team are the service organization for the other commercial teams, serving up different agents and GPTs. Obviously, it’s a very human-in-the-loop approach, but we make sure the way we enable the commercial organization and ubiquitize insights is standardized.

Jodi (30:09)
Makes sense. You really brought that “fear of missing out” approach to light with those playbooks and reports. Gosh, it would be a scary thought to think your entire business is going to shut down in five years because you aren’t innovating your workforce and your automation. I’d love to understand in a bit more detail exactly how you are using automation. I ask my guests this all the time; I think it’s always interesting to hear different use cases and the specific agents people are building.

Caitlin Allen (30:43)
Yeah, and this is an area where no matter how sophisticated we get, I still feel like we’re behind! But we have a variety of agents and bots that we treat like they are part of our org chart. I think about them through several different lenses related to our team structure, as well as external relations and talent management.

Through our brand lens, we have agents responsible for specific content types, and then we have a master “editor-in-chief” agent. There’s a sequencing of how content is reviewed. We have one specifically dedicated to the personality and voice of our robot when we create content for that, as well as for some of our key executives as part of our speaker bureau.

Product Marketing is obviously a power user of agentic automation—collecting competitive intelligence, synthesizing it, and providing voice-of-customer insights. We have different agents designed for each of our personas and our buying committee. We also have macro agents that synthesize those sub-persona agents to reflect the whole buying committee.

We have channel-specific agents—like a Reddit monitoring agent that surfaces conversations happening online about the robot. We have agents that automate specific routines, like providing weekly updates to the leadership team or updates to the board. We’ve even created an agent for each of our board members, so when I create content for board meetings, I often get feedback through them first.

Finally, I’m a huge believer that work is an amazing way to extract and extend talent. I have different monitoring agents that take job descriptions, performance reviews, and recordings of one-on-ones and coaching sessions. They synthesize them and surface areas of opportunity that I might’ve missed for each member of the team, as well as myself.

Jodi (33:09)
Some really creative use cases, absolutely. It does take a deep understanding of where your audience is—for example, crawling Reddit—and the line between where they want to meet automation versus a human. We’ve only got time for one more question. How would you draw a line in the sand between things that automation can work for and where humans are needed?

Caitlin Allen (33:41)
I’m by no means an expert here, but I tend to think about this through a Pareto principle lens. I think automation can get you about 80% of the way in most use cases, unless you are literally automating extremely repetitive, highly repeatable tasks. So I’m a big believer that the human needs to be in the loop. It’s interesting—I just completed a course on AI leadership at Stanford, and I was expecting that course would change my opinion, but it actually just deepened it. So that’s my current thought at least. But we’ll see, I reserve the right to change my mind!

Jodi (34:16)
Absolutely. It’s all about hearing current predictions from diverse experiences and perspectives, because who knows what’s going to happen or what the next big paradigm shift will be. But it sounds like you’ve really got your finger on the pulse. Some really inspiring examples from your own work and a really refined methodology about technology disruption. Thank you so much for coming on the FINITE Podcast.

Caitlin Allen (34:43)
Thank you, Jodi. Thank you for this podcast. I love listening to the episodes.

Jodi (34:48)
Okay.

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