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2026.10.06 | TB | Software | Upland Software AI Portfolio Refocus

原标题：Upland Software – Refocusing the Portfolio Around AI-powered Growth

#software

Third Bridge · 2026-10-06

Analyst-led • 22 Sep 2026

Companies: UPLD US

Samantha Middlebrook (SM) Co-founder at Fndry Ventures Pty Ltd

Dylan Koehler (DK) — Third Bridge Sector Analyst

Agenda

Key Insights

Introduction

DK [00:00:02]: Welcome to Third Bridge's Interview entitled Upland Software – Refocusing the Portfolio Around AI-powered Growth. I am Dylan Koehler, and I will be facilitating today's Interview with Ms Samantha Middlebrook, former VP, Product Strategy and Marketing at Upland Software.

Before we start today's Interview, please state I agree or I disagree to the following statement: You understand the definition of material non-public information and agree not to disclose any such information, or any other information which is confidential, during this Interview.

SM [00:00:29]: I agree.

DK [00:00:30]: Could you start with an introduction to yourself and your roles and responsibilities during your time with Upland?

SM [00:00:40]: Sure. Previously, I was Vice President of Product Strategy and product marketing at Upland Software. I looked after the, at the time, it was the contact centre portfolio, which was made up of a combination of knowledge products, so three knowledge products, Panviva, RightAnswers and BA Insight as well as InGenius and at a point in time, Rant & Rave as well. My responsibilities really sat over the product strategy roadmap, direction and vision of those products as well as the product marketing aspects. How we position competitive wedge, sales enablement and all of those kind of things.

Questions

00:01:31] Could you walk us through how Upland Software's business has evolved over the past couple of years? What are the company's biggest challenges or changes in its positioning today?

SM [00:01:59]: I think over the years and the way that I started working with Upland is I came through acquisition of one of the products, Panviva, during that time, Upland's business model was really focused on mergers and acquisitions. Purchasing products that were a fit within their ecosystem and then working alongside them. That work had slowed down by the time that I left Upland Software. The focus has really been on maintaining and growing the products that the business had.

DK [00:02:52]: As Upland shifted away from acquisitions towards managing those existing products, what has changed in how the businesses were run? Were there more investment in product development and sales, or was the priority more about cost reduction and generation?

SM [00:03:27]: For the changes, financially, I probably can't comment on those things. I would say definitely focusing on the different pockets of the business was something that was part of the strategy, and I think remains part of the strategy. We're really locking into those growth areas seen by Upland. That was probably the biggest change. There's also a lot of growth in some of the offshoring teams as well, I would say.

00:04:11] Under CEO Sean Nathaniel, Upland has shifted away from the historical acquisition-led model to focus investment on knowledge and content automation. How meaningful do you think this reset is? What does this mean for the company? What needs to happen for it to succeed, and was this the right decision?

SM [00:04:44]: Yes. I think that knowledge is definitely a growth area in terms of what we see happening in the SaaS market with AI. I think any product that has a strong foundation and a lot of great data that can be leveraged by other AI products are quite popular at the moment, and we'll see that in the market through other acquisition strategies that are happening with some of the larger tech companies. I think in order for this to be successful, the ability to focus funding and effort and strategy in those areas means that you can easily balance away from the other products that you still own as well. I think that, that is something that maybe still needs to be solved for.

DK [00:05:36]: How much of the company's existing portfolio has a credible path back to sustainable organic growth?

SM [00:06:12]: I think when you work with large enterprise customers, which is what Upland does, there's always opportunity for expansion in those accounts generally depending on how the sales cycle is working. I think with the addition of AI features, lots of products in the market are being able to commercialise on those add-ons. Rather than a feature being absorbed in a per user per month pricing, we're seeing a lot of pricing strategies completely change. That's where lots of growth is happening. If we follow that methodology, we would think that, yes, there should be organic growth in those accounts. The other thing, though, to think about is there's a lot more competitive threat in enterprise software than there has been before. It's less about direct competitors now and more about, I would say, comparative threats. If we think about the likes of Microsoft, as an example, who are working more closely in the contact centre space and really offering many resources to those large clients in a bid for them to build their own products, that poses a risk that hasn't existed in the market before.

00:07:38] Regarding the comparative threats, and specifically, you mentioned how Microsoft is enabling the enterprise, which Upland products do you think are most exposed to that threat? What would make a customer choose to build that rather than continue to use the Upland products that they have been using?

SM [00:08:09]: Yes, it's a great question. I think any of the clients who have had a long-standing relationship with any software vendor, whether it be Upland or not, who have technology that's been around for quite a long time. There's always this fear of missing out. I would say in the industry that something shinier may come along. I think that, that fear has expanded more rapidly with the resurgence of AI in the market. I think that some of the large tech vendors have quite loud strategies and a huge market presence. I think that any of those enterprise clients that already have long-standing relationships with those larger techs, there is always that promise of simplifying things like billing by having a single bill with a line item around knowledge management for an all-in-one provider instead of having lots of different solutions, that problem has been around for a long time. You see that a lot in some of the competitive content or competitive analysis content that you have around with all-in-one providers vs bespoke providers, I would say that.

DK [00:09:50]: Are there specific areas of the portfolio that are particularly exposed, or is this more of a broad-based concern you're highlighting?

SM [00:10:16]: I think that I haven't worked with the business for over 12 months now. I wouldn't be able to give an up-to-date view on any of that exposure. What I would say is from having a look at what is publicly available on the website and things like the announcement of features or recent case studies, there doesn't seem to be much moving in that innovation space, which would, I would think, raise a lot of red flags for some of those large organisations that are very locked into a forward-thinking AI strategy at the moment.

00:11:01] You mentioned the appeal for a customer of consolidating with a larger vendor such as Microsoft. When evaluating that option, what keeps them with a specialist product such as Panviva? Is it implementation complexity, transition cost and risk or building an in-house solution?

SM [00:11:48]: Yes. It's a really great question. I think a lot of Panviva, RightAnswers and BA Insight, when you have a look at the target market is they heavily focus on compliant industries and what the products do really well is to manage those industries, and they have a lot of experience specifically in those spaces. Panviva, if you have a look at, it's healthcare and it's banking. That historical data that comes with those products is what makes it very appealing, I think. Also a lot of those customers have been around with the vendors for many years. There's also the change management aspect to consider, especially if you're thinking about use cases like the contact centre, pulling out software that impacts every one of your frontline agents is a huge feat that you need to consider.

00:13:01] Upland is clearly concentrating on its highest potential businesses while managing the rest of the portfolio for efficiency. What do you think should be prioritised, and which products would be most important for investment today? Are there any products that you would consider divesting or selling off?

SM [00:13:41]: Yes. I think divesting and selling off, I wouldn't have an opinion. All of my information is quite dated now, I would say, in terms of the performance of their products, I think knowledge management remains a pretty key focus. AI needs great data to be successful and knowledge management products have great data because of the way that knowledge is structured in them. It's easily consumed by human agents or AI agents. I think those bets are right. It's just how quickly you can commercialise those bets.

00:14:32] Regarding knowledge management, which is well-positioned for AI, commercialisation is critical. What would Upland need to demonstrate to show its AI strategy is working? What capabilities must the company offer to justify a price premium over customers using existing data with a different AI provider?

SM [00:15:14]: Yes. It's a really great question. I think that it's really the proof points still in. Having real-life customer testimonials, case studies, content showing those live use cases. Again, if you have a look at Upland's website vs some of their competitors and the content and case studies that are being highlighted, they're quite different. That, I think, should be the biggest priority because when a buyer is looking, they want to make sure, especially in the space of AI, that someone's already done it before and that they don't necessarily want to be the first one when a software vendor is releasing features. I think that having those clear use cases and video content and clear content about the AI features that is easily accessed for a shopper online or whether they're engaging on the social channels and things like that that needs to be front of mind.

00:16:34] Which specific product segments or software categories of Upland do you think face the steepest competitive headwinds or lowest growth potential? Looking at the broader portfolio, what are the primary structural or market factors that make certain areas of the portfolio less viable long-term winners?

SM [00:17:27]: I think with the portfolio, the biggest thing is it's really hard to focus on multiple products at any one time successfully. That's across the board. You've got to think about marketing spend. You've got to think about where to put your best salespeople. You've got to think about which analysts you're briefing. I think that, that needs to be considered. It's very different before there was so much rapid change in the SaaS industry before AI, I think maybe that could make more sense, but now I would question you can't be everything to everyone. If you have so many products, how do you prioritise what should happen?

DK [00:18:25]: Upland's Q2 2026 revenue declined 8% YoY with prior divestitures contributing to some of that decline. How much of the pressure is the company under? How much of that is attributable to these portfolio changes vs underlying weakness in the core business?

SM [00:19:03]: I think it can definitely be a combination of things. I think the market has changed quite a lot and the overall business strategy needs to meet that market demand. I think it would be hard to say.

00:19:24] Given that Upland reported that its revenue declined by 8% in Q2 2026, what do you expect to see in terms of revenue decline or growth over the next 12-24 months? Is there a realistic range for the company to achieve this?

SM [00:20:28]: I'm not sure if I know of a range. I'm just cautious of what I'm saying also. I think that making bets on the product, they need to see some significant evolution of their product to see that uplift of revenue is what I would say.

DK [00:20:50]: Do you expect to see further revenue declines, or could the company return to growth?

SM [00:21:04]: It's a great question, and I think it sits on the point that you made before, whether it's about focusing on just a small number of products, which is what Sean is saying that they want to do and then what happens to the rest of those products. I think it plays on to that. I think it's around what retention rates look like and it's total retention, not partial churn. I think it's around commercialising those AI features as well. All of those pieces need to come into place in order to see that growth.

00:22:13] Upland experienced revenue declines of around 20% in 2025, following a steady downwards trend over the past couple of years, where declines stepped up to the 6-7% range. Current consensus expectations project another 10% revenue decline in FY26 before the company returns to flat growth of less than 1% in 2027. What is your assessment of these numbers, and do they align with your own expectations for the business? What are the primary driving forces behind these projected declines and the subsequent flat growth?

SM [00:23:18]: Yes. Okay. They're interesting. Decline at the moment, decline for one more year and then levelling out the year after is what you're saying.

DK [00:23:29]: Yes, it was declines in 2026 of around 10-11% and 2027 was the flattening.

SM [00:23:43]: For me, the flattening of the estimates, the prediction there would be that something drastic has changed or a strategy has come into fruition. It's a longer burn, it sounds like from that. I would say that in the market, we would need to see a really key indicator that something has changed with Upland. Whether it is some large customer acquisitions or some really innovative new product features or maybe integration in between the products that they have, those indications, I think, would be what starts to level it out or even move it back into the growth space.

00:24:46] You mentioned that Upland needs a clear catalyst to return to growth. What might those catalysts look like which could realistically move the needle over the next couple of years? Do you think the company needs a major new product or customer win to return to growth, or is this more a play on cross-selling and better execution overall?

SM [00:25:32]: Yes, it's a great question. I think if we look at the executive team of Upland, it's quite an interesting mix of roles. There is no Chief Marketing Officer. There's no Chief Sales Officer. There's no Chief Growth Officer in the business. The Chief Product Officer and Chief Operations Officers' roles are split. If we think about fundamentally, those two roles are almost at completely opposite ends of the spectrum. You've got operations, which is very black and white, process-driven, being in the weeds of what's happening now and then looking at improvement in efficiencies. Then you've got a Chief Product Officer, which should be visionary strategy. I think that the structure of that executive team isn't really set up for that growth strategy. Does that make sense? If you think about the roles that they have in there. I think that, that's a really interesting out in view of how the business is structured and then how could it execute on future growth plans. Does that make sense?

00:26:52] What are your thoughts on Upland's leadership and its leadership structure? Are there any executives that would be important to highlight, and how is the culture of the company?

SM [00:27:27]: Definitely, I don't think I can get into highlighting any of the executives. I think that what I would say is that some of those innovation style roles when you look at the executive list that's available for Upland, there are those standard roles. If we compare to some of the other large technical company… Tech companies or even some of their competitors, there's a lot around having a Chief Innovation Officer or a Chief AI Officer, and there's a lot of thought leadership coming out of those areas of the business when you look at what Upland is publishing and their websites, that for me is a real gap. What is the product strategy? What is the direction? What does knowledge look like in 2030 and beyond? All of those kind of points of view, I don't see coming out of Upland.

00:28:48] Do you think Upland's lack of product vision and thought leadership translates into uncertainty within teams about the products' vision? How could the company execute on the strategies internally?

SM [00:29:35]: I think that whenever there is multiple products within that have the same label, knowledge management, it can cause confusion to the market and internally as well.

DK [00:29:52]: Upland added 81 new customers, recorded 200 account expansions in Q2 2026. What do these figures tell about the underlying demand environment? How do you expect new customer acquisition to continue to trend over the next couple of years?

SM [00:30:17]: Yes. The 88, was there information on how they were split across the product lines? How many products does Upland have in total now?

DK [00:30:52]: Quite a few between knowledge management, the document and workflow products and sales enablement. The company did not highlight exactly how it were broken down.

SM [00:31:21]: Yes. For me, it would be around… I'm looking at this as over 20, it says. If we divide that by, what did you say, 88 without knowing the split, I think it would be… Does that align to the forecast? I'm not sure if all 88 sat in that growth portfolio that they're talking about, then they might be feeling quite good about that. I think the thing is around expansion as well. I'm not sure if it's published or not, but an interesting question to consider is, is it growth on licence count, or is it growth on ARR because of new features that are being commercialised? Does that make sense because those are two very different key indicators for how a product is going?

00:32:23] Upland reported 96% core net dollar retention for 2025. How do you characterise the health of the company's existing customer base today? Are the net dollar retention trends in line with that, or do you see it ticking up or ticking down?

SM [00:33:12]: I would say that sometimes, net dollar retention, that indicator is looked in isolation. Then when we look at things like, as we mentioned, feature uptake or buy into the newer strategies, when those things aren't aligned, I think you can see quite often that one year, you will have the net dollar retention, but if the customer is maybe working in something in the background really rapidly in the following year, you can start to see churn, if that makes sense. I think that sometimes the numbers in isolation may not tell the whole picture. It's hard to say with that number that they give.

I think that for the contact centre industry, in particular, there has been a fear of shrinkage because of the concept that human agents will not be necessarily needing the same numbers that we've had before. There's a lot of push to see how can pricing structures be reimagined in a world where it's not a human that needs to access the knowledge. If you think about, yes, shrinkage in that account, that's something that you need to consider as well because if we think about banks as an example, which is a target for a lot of those Upland products, we're seeing a lot of banks move away from having human customer service and having augmented AI experiences. How do you commercialise an AI workforce, leveraging your data?

00:35:19] How do churn and expansion rates differ across Upland's knowledge management, content automation and more mature software products? Are there particular areas where customer losses or competitive displacement are becoming more pronounced?

SM [00:35:48]: Yes, it's a great question. I think a general statement on customer churn in this space would be that a lot of customers are thinking that they can build things on their own or partnering up with third parties or the large tech vendors to build bespoke solutions, and that is posing risk, I would say that.

00:36:30] Across Upland's portfolio, it competes with a range of software vendors. Where does the company have a competitive advantage, beyond knowledge management products?

SM [00:37:05]: I think it's quite interesting to have three unique knowledge management products that's quite different in the market. I'm not sure if anyone else has that. I think there's lots of knowledge management solutions in the market. I think that's definitely a differentiator to have three within one business. The follow-up question I would say is how is that being leveraged by Upland? I think looking online, I can't see anything about those products being integrated. It's not like there's one big knowledge product to rule them all. Yes, that is interesting to me. I think differentiation and how you appear in the market is all down to your messaging and positioning. I'm not seeing a lot in that space. Based on what is publicly there to see, it's hard to see any huge competitive wedge, I would see right now, given how much innovation is happening in the space.

DK [00:38:24]: Given what you mentioned about product integration, do you think there's more value in integrating the products into a unified platform, or is it better to keep them as standalone solutions?

SM [00:38:47]: I think that the market that we're in, platform play is a really strong play that's happening. If we think about Salesforce, as an example, their strategy is integration, being able to connect into other parts of the business. I think when we look at enterprise, there are clear differentiation of use cases, front office, back office, front of house, sales, service, all of those things. I think that being able to service those specific use cases with a set of defined features is really powerful. Being able to connect those use cases in a platform is equally as powerful and sets you apart. Makes sense. I think that gone are the days of being able to work independently. If a product doesn't have a strong integration strategy, it is very hard for it to stand its ground, I think, and to be able to survive procurement rounds YoY. Yes, that's what I would say.

00:40:08] Upland is concentrating investment in knowledge and content automation as enterprises deploy AI. Where do you see the strongest opportunities across the company's product portfolio?

SM [00:40:46]: I think AI fundamentally changes the management of knowledge in an organisation. If we think about knowledge follows a cycle in an organisation, it's the creation of it, it's the management, it's the discovery of it. Every single piece of that process is completely being reimagined by knowledge. If we think about some of the challenges organisations historically have gone through with implementing a knowledge solution, the first part is always implementation. How do I get my knowledge in, so I can actually start using the tool? AI has removed those barriers. That's the first part. How is knowledge being created using AI within an application? When you look at knowledge management solutions across the board, that's the first tick.

Then we think about the management and maintenance of it, knowledge becomes unusable when people aren't keeping it up to date, when there's not metadata attached, when it's not constantly enriched and ready for other channels. Again, AI gives us the ability to do that fairly seamlessly without needing a huge army of knowledge managers to do that in the business. Then, of course, there's the discovery piece. Going away from things like standard search, we're seeing AI discovery, conversational searches, all of those things and the integration is what's happening in the space of knowledge. When we think about that, we need to think about, essentially, the products as they were at a point in time need to fundamentally change in order to keep up with where the industry is going.

The challenge whenever you've got legacy software that's been around 10-plus years is you've got a customer base who is very used to the old world and then you've got a market that's expecting the new world. That foot on both sides of the fence, if you will, is very hard to manage.

00:43:13] You talked about AI fundamentally changing Upland's knowledge work and what customers expect from knowledge management. Does that create a bigger opportunity for the company to upsell the installed base, or do you think it's more likely a risk that customers are going to bypass the legacy products and adopt newer AI-native solutions instead? What's going to determine which way that goes?

SM [00:44:02]: I think that knowledge management software across the board has always had those same problem statements, where the knowledge is… It takes a lot of time to maintain. People can't find it. It's been in here a long time. The users aren't using it. That happens with all software across the board when it's been in a place. I think the difference now is that the market is showing that AI can do all of these things around knowledge management. If the Upland products do not have those features already or they're not quickly coming or it's not clearly marketed that they're available, then it becomes a very interesting discussion at renewal time because now it's easier than ever to find another provider that claims to be doing these things.

Before knowledge management was a bit of a niche. Now because of AI, people are getting close enough, I guess, to doing lots of the moving parts. For an uneducated buyer who is really focused on innovation and a shiny new toy that fits in really nicely in the tech stack or a portion of a product that they already have, then that feels like an easy buying decision.

00:45:43] Looking at some of Upland's products –RightAnswers, Panviva and BA Insight – seems to help enterprises organise and access knowledge. You talked about modernising those products. How difficult would it be for the company to modernise products while continuing to support customers who rely on those existing workflows? Do you think it could introduce AI capabilities within the current platform, or does delivering the experience customers expect require a more substantial rebuild of what's already there?

SM [00:46:59]: Yes, it's a great question. I think that in the market, we're seeing that a lot, where it is just a point in time, that architecture is built at a certain point and is it ready for some of the newer AI features? Maybe yes, maybe no. If that's the case, that modernisation needs to occur. The fact is that many products have a singular pool of developers that can work on the product. Then if you're thinking about splitting the prioritisation of a new product or a new stream of work and an older stream of work, that's a challenge as well as competing demands of what's happening in the market, customer requests coming in, it becomes a very interesting position to be in.

Change management is such a huge piece of this puzzle when you're working with enterprise customers because if we think about contact centre and every metric being measured, every second measured, every click measured, putting in huge changes is risky. There's always the change management side and how do you roll out that change? How do you test it? How do you give the confidence to your customer to take that on as well? It's a real balancing act that needs to be managed properly. I think you need to have strong conviction of where you're taking the product and then how you bring your customers along for the journey. I think you can't be trying to cater for all of the scenarios. There comes a point in time where your strategy has to be visionary enough that the customers are bought in and that you understand natural attrition will happen, but this is the path that you're going down, and that's how it's going to work.

00:49:10] Regarding rest of Upland's portfolio, beyond knowledge management, how much opportunity do you see for AI to drive growth across some of the other products? Are there specific use cases that have real opportunity and potential, and are there others that aren't as good of a fit?

SM [00:49:38]: As part of the analysis that the team are doing, you would think that there would be a bit of an AI blueprint put over all of the products to understand the feasibility. I also wouldn't discount, the internal use of AI. How is the business changing the way that they operate around product management, sales, marketing, how AI-native are they as a business to make sure that they're getting the efficiencies in the other area. It's not just about the end product. I think that that would be interesting commentary to see if that comes out from the new CEO.

00:50:30] What do you see as the most important milestones for Upland's strategic reset over the next 12-24 months? Are there specific things that you would be watching out for to gauge how well the company is performing or to determine if it is moving in the right direction, particularly in terms of KPIs or operating metrics?

SM [00:51:19]: For me, it would be what is the thought leadership coming out of Upland from the executive and what is the strategy? Is it clearly defined? Can you follow it along? Are the products releasing features in line with that strategy? Are they talking about, "Hey, we're focused on knowledge and this is what knowledge looks like moving forward? Are there feature releases? Are there customer testimonials and customer case studies that are easily discoverable on the website and things like that." You can see that the products are innovating and aligned with where the market is going.

DK [00:52:13]: We need to look for a clear strategy that translates into these product releases and broader performance indicators showing an uplift in an ideal world. Is there anything else important to highlight about Upland? Is there something underappreciated or misunderstood about the company?

SM [00:52:54]: No, I don't think so.

DK [00:53:01]: Thank you for all your great input over the last hour. I really appreciate all of the time and help today. Thank you to our clients for listening and reading Third Bridge's Interview on Upland today.

SM [00:53:15]: Thanks.

Transcription ends at 00:53:19 of the recorded material