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CEO @ Unbounce | Former CEO @ Pipedrive & Constant Contact | Advisor | Investor | Board Member
Many businesses aspire to move upmarket to enterprise, but long deal cycles and demanding customers can make it a tricky place to play.
If your small business deals aren’t fueling your growth, don’t underestimate the mid-market. Mid-market companies (typically 50-250 employees) can offer a sweet spot for scaling your business.
In this episode of Closing Time, we sit down with Steve Oriola, CEO of Unbounce, a landing page builder that recently acquired Insightly CRM. Both companies are key players in the SMB and mid-market space.
Steve shares his insights on how to best sell to mid-sized businesses, effective strategies for sales reps handling these deals (vs. SMB and Enterprise), and an exciting preview of what the future holds for both Insightly and Unbounce products.
In the fast-paced world of MarTech, when the right companies join forces, the results can be transformative. Unbounce’s recent acquisition of Insightly is one such move that’s creating buzz in the industry. Steve Oriola, CEO of Unbounce, brings over 23 years of experience in SaaS and MarTech, having worked with well-known companies like Constant Contact and Pipedrive. With this acquisition, Steve is now at the helm of two influential brands in the industry.
Steve’s extensive background in the CRM market informed his decision to bring these two brands together. “What was really appealing was the combination of the two brands and the two platforms,” Steve said, highlighting the unique opportunity to integrate Unbounce’s MarTech expertise with Insightly’s comprehensive CRM.
Steve says that Insightly stands out for its robust CRM capabilities, particularly in sales, marketing, and customer service, while Unbounce is renowned for its advanced landing page solutions with experimentation and optimization features. Steve saw this as a chance to capitalize on the industry’s shift towards more integrated, all-in-one solutions. “We feel like we can help accelerate that and support that,” Steve emphasized, referring to the growing need to break down silos between sales and marketing.
Under Steve’s leadership, Unbounce is poised to lead the charge in creating a unified platform that empowers businesses to streamline their operations and achieve greater success in the MarTech space.
Through this acquisition, Unbounce is not just expanding its global reach but also tapping into powerful synergies between the two brands. Steve explains that this partnership is more than just a business deal—it’s about blending strengths to offer something truly compelling for mid-market companies navigating the complex MarTech landscape.
What exactly are those synergies? According to Steve, both companies share a focus on the mid-market segment, making this a natural fit. While Unbounce operates on a more global scale (with offices in Berlin and Vancouver), Insightly has been preparing its product to cater to a worldwide audience, especially in Europe. Steve noted that these overlaps have allowed the brands to learn from each other and create a stronger, unified front. “We’re a global company now, and we have a global solution that we’re going to market with,” Steve explained, highlighting the enhanced global reach they now possess.
Another key synergy lies in the alignment of company values. Both Unbounce and Insightly have cultures that, while not identical, are closely aligned. This cultural compatibility has made the integration process smoother. Steve emphasized the importance of shared values in driving the success of the acquisition, saying, “At the values level, which is really important, that’s really sort of lubricated the whole deal and the integration.” He also pointed out that both companies are working at high velocity while planning, decision-making, and execution, which has further eased the transition.
Steve believes these synergies—shared market focus, global reach, and cultural alignment—will provide a strong advantage as the combined company moves forward. It’s an exciting time for both Unbounce and Insightly as they come together to create a powerful, globally competitive solution.
If a “middle child” of B2B selling existed, it would be the mid-market. Steve firmly believes that the mid-market is the sweet spot for growth, especially for companies like Unbounce and Insightly. Both organizations have a strong focus on the mid-market, and now, as a combined entity, they are fully committed to serving this segment.
One of the key reasons Steve finds the mid-market so appealing is the balance between the user and the buyer. In small businesses, the buyer and the user are often the same person, which simplifies the sales process but limits growth opportunities. In enterprise environments, however, the buyer and user are typically separate, leading to longer sales cycles and a disconnect between the purchasing decision and user satisfaction.
The mid-market, according to Steve, strikes the perfect balance. Here, the buyer and the user may be different, but they are still closely aligned, making it easier to satisfy both parties. This alignment leads to stronger customer loyalty, lower churn rates, and more opportunities to expand within an account. “Our mid-market customers are loyal, they’re happy, and we can find more ways to add value,” Steve explains. He emphasizes that this loyalty and the potential for expansion make the mid-market an attractive and sustainable focus for growth.
Additionally, the buying process in the mid-market tends to be more straightforward than in enterprise settings. While there are buying committees, they are typically smaller and more manageable, leading to shorter and more predictable sales cycles. Steve appreciates the predictability and efficiency that comes with mid-market sales, as it allows Unbounce to deliver value more effectively and build stronger, long-term relationships with their customers.
In Steve’s view, the mid-market may be the “middle child” of the business world, but it’s one with a lot of potential and plenty of opportunities for companies that know how to navigate it.
Navigating the mid-market as a B2B seller requires a nuanced approach that balances understanding industry-specific needs with delivering tailored solutions. Unlike selling to small businesses or enterprises, mid-market customers demand a deeper level of engagement and expertise.
According to Steve, mid-market buyers are discerning and more focused on finding solutions that truly fit their specific needs. Unlike small businesses, where the sales process is often quicker and less involved, mid-market buyers expect a deeper understanding of their industry and unique challenges.
Steve emphasizes the importance of tailoring your sales pitch to reflect a strong grasp of the customer’s industry. “Even if your product is a horizontal solution, you need to articulate your understanding of their business,” he advises. For salespeople, this means not just selling a product, but demonstrating how that product aligns with the customer’s vertical or industry-specific needs. It’s crucial to be prepared to speak the language of the industries you’re targeting, whether it’s three or ten.
When selling to mid-market customers, the sales process can be more time-intensive and detailed than with small businesses. Steve points out that the increased lifetime value of mid-market customers justifies spending more time on each sale. “The range of things you’ll be talking about is greater,” Steve notes, including considerations beyond just the product itself, like regulatory compliance (e.g., SOC 2), or specific buying criteria tied to the industry’s unique processes and challenges.
Steve also highlights that selling to the mid-market may require a broader set of resources. Depending on the complexity of the sale, you might need to involve technical account managers, in-house legal counsel, or other experts to address the various aspects of the deal. This approach is especially important in industries with strict regulatory requirements or complex buying processes.
Overall, adapting your sales approach to the mid-market involves a deeper level of engagement, a focus on industry-specific needs, and the flexibility to bring in additional expertise when needed. It’s about understanding that mid-market sales are not just about the product—they’re about fitting into a broader set of criteria that matter to these buyers.
With the merger of Unbounce and Insightly, customers of both companies can look forward to an integrated, powerful solution. Steve shared that while the full integration won’t happen overnight, significant advancements are on the horizon. Customers can expect a gradual but accelerating rollout of new features that blend the strengths of both brands.
One of the most exciting developments is the increased application of artificial intelligence and machine learning within the Insightly CRM platform—areas where Unbounce has already made significant strides. Steve explained that Unbounce’s expertise in AI, which has already transformed its landing page solutions into an advanced experimentation platform, will soon extend to Insightly CRM—this means customers can anticipate more intelligent, data-driven features to enhance their CRM experience.
Additionally, there will be a substantial investment in the marketing automation platform, leveraging Unbounce’s deep understanding of the marketing buyer and their needs. Steve emphasized that this will lead to a more comprehensive platform, with CRM becoming a key entry point for businesses using the combined solution.
Despite the integration, Unbounce will continue to support its independent landing page solutions—a core part of its business. However, the overall vision is clear: a more unified, AI-enhanced platform that offers a seamless experience across CRM and marketing automation, benefiting customers of both Unbounce and Insightly.
As Steve shared, both teams are energized about the future, eager to bring these innovations to life and deliver even greater value to their customers.
New! Keyboard shortcuts … Drive keyboard shortcuts have been updated to give you first-letters navigation What’s the secret to selling to mid-market businesses and why should you focus on this category? Let’s talk about it in this episode of Closing Time. Thanks for tuning into Closing time the show for Go to Market Leaders. I’m Val Riley from the marketing team at Insightly CRM. And today I’m joined by Steve Oriola,. CEO of Unbounce, a landing page builder company that recently acquired Insightly CRM. So, yes, Steve is my new boss. Steve, welcome to the show. Thanks for having me. Well, let’s get you introduced to that closing time audience. You’re the CEO over two brands in the MarTech space right now, but that category isn’t new to you. No, it’s not. I’ve been in the MarTech category for SaaS for about 23 years. So, yeah, a fair bit of time. You know, it began with my joining. Constant Contact, you know, very early. I think I was the 25th employee or something like that and was there for ten years. I’ve also been at Pipedrive, which a lot of folks may know. So, yeah, I’ve got I’ve got a fair bit of experience and a pretty wide range. So you’re familiar with the CRM space and how competitive it is. Last count I saw, there are more than 1700. CRMs on the market. So what was appealing about jumping back into that space, Steve? Sure. What was really appealing was the combination of the two brands and the two platforms. Less than excitement to jump into a very competitive space. Insightly is a pretty comprehensive CRM, and that was important to me as we, me and our investors, made that decision and Insightly focuses on the sales use case from a go to market perspective. The product they’ve built covers marketing and services as well and Unbounce, we know the marketer, right? That’s our buyer and we understand those use cases and we’ve built a very, very robust landing page solution that includes experimentation and optimization capabilities. So it’s a pretty powerful tool. And we also, under our tent have an attribution solution. So we looked at the marketing automation platform that Insightly has and we got very excited and the industry certainly has moved to more comprehensive solutions in CRM, some would call them all in one and as well, I think everyone’s realizing that from a technology perspective you can’t treat sales and marketing as silos because, you know, healthy, modern companies that are that are progressing are breaking down those silos and we feel like we can help accelerate that and support that. So that’s the strategic synergy that jumped out at me several months ago when we started this journey. And that’s what we’re excited about. Yeah, let’s let’s dig a little deeper there because I think there is significant overlap in just in the verticals, in the mid-market focus, geographically. How do you see those synergies becoming an advantage? Sure. Unbounce as well has been focused on the mid-market as Insightly is, Unbounce operates a bit more globally than Insightly, yet Insightly has prepared to operate globally at the product level, probably more than Unbounce. Brands are learning from each other in that regard. We have an office in Europe. We’re capable of going to market in Europe. Insightly is a localized solution for most of Europe, so those overlaps, as we looked more deeply, were pretty synergistic, to be honest. We’re a global company now and we’re one company and we have a global solution that we’re going to market with. I think another interesting point,. Steve, is how both companies really had an alignment on values out of the gate. How do you see that as an advantage moving forward? Yeah, the cultures felt pretty similar and not identical. You know, they never are. But the the integration is is not that painful because at the values level, which is really important. That’s really sort of lubricated the the whole deal and the integration. And, you know, we’re very focused on, on velocity of planning, decision making and execution, and everyone’s aligning to that pretty easily. I will say. I can validate that from the inside. We are we are very focused on velocity. So it’s an exciting time,. I think, to be at the company. So both of these organizations were previously selling to the mid-market and as a combined organization, we are the mid-market. So let’s talk a little bit about that category and what you feel maybe makes it a sweet spot. The way I think about it is, you know,. I got a lot of experience in mid-market and small business and some experience with Enterprise. And for me, it’s it’s about the user and the buyer. And, you know, small business go to market and cracking that knot is not easy. The part that’s a little simpler is that the the buyer and the user are almost always the same person. And as you go up market, those, those tend to start to separate. I would say they’ve probably start at the mid-market 50-100 people, you know, the buying decision and the user can be different. You get to enterprise and they’re very different. And and the, you know, the requirements for the purchase don’t always accommodate the user. And I’ve just found myself very uncomfortable at that level where you’re selling to someone in the criteria to get the deal done aren’t really the criteria to keep the user happy. Now, that’s certainly changed over the last 10 to 15 years where, and especially is new generations of workers come into, you know, big corporate environments. They just have certain expectations that IT kind of needs to meet. But there’s still that separation. And that’s the big difference for me is it’s appealing to go to the mid-market for a company like ours because, you know, you end up in a situation where there’s more opportunity to expand that account, there’s more things to sell to them and they’re stickier. They stay around longer, they’re more loyal. You know, small businesses tend to be, you know, a bit transient, you know, to put it mildly. And and small businesses fail at some rate. I think the failure rate for small business in the U.S. is somewhere around 2% a month. So your churn rate sort of starts there. That’s zero. And it’s just different when you’re in the mid-market. So we find that appealing. We’re excited about our mid-market customers. They’re loyal, they’re happy, and we can find more ways to add value. One thing I especially like about the mid-market is kind of echoing what you were saying about the buying processes, the buying committees. They’re there, but they tend to be more reasonable in size and a sales cycle tends to be more reasonable versus the enterprise as well. Yeah, the and that’s true as well. I’m not averse to, you know, enterprise selling an enterprise focus. You just have to build your business around the economics of a sales cycle that can be six months, can be two years. And, and you have to have a certain type of sales team and compensation plans. And it’s just a different business. It’s not better or worse. It’s just different. So you have to design for it. We’re really focused on the mid-market. So the mid-market is the middle child, right? But there’s there’s a lot to be said for that middle child. There’s a lot of opportunity there. Yep. Yep. That’s right. So let’s talk to a salesperson because that’s the typical type of person that listens to Closing Time. What advice would you have for a salesperson that’s selling to the mid-market? They’re discerning buyers and they do have buying committees. It’s not as complex as enterprise, and they more than small business, they’re looking for the solution for them. Right? And they’re very focused on understanding their vertical, their industry, their business. So if you’re not a vertical solution, you at least need to, you know, articulate or build messaging and build your pitch as a salesperson to really clarify that understanding of their business. It does benefit you as a salesperson to be working in maybe several lanes, maybe not one. Certainly one is ideal, but if your company isn’t vertical, if it’s horizontal, you can be a horizontal solution and still accommodate certain industries. You need marketing support to do it. No doubt. So make sure you have that. But learn the industries and it might be three, it might be five, might be eight or ten. I wouldn’t recommend more than that as a certainly as a salesperson, but understand the industries you’re selling into so that you can speak in their language and, and that that really is almost a requirement to the mid-market. So in thinking about the conversation that a salesperson has with a small business buyer and an enterprise buyer, how is the conversation different when you’re talking to a mid-market buyer? Sure. Small business is going to be just because of the economics of it for your company in going to market for small businesses, you’re going to have you know, it’s going to be lighter touch, it’s going to be less time, less involvement. And, you know, you might be on the clock. You know, you might be directed as a salesperson in an environment like that, to not spend more than 15 minutes or more than a half hour. You might be trying to talk to 20 or 30 people a day. When you get to the mid-market, the economics change, right? The lifetime value that you’re selling, that is the opportunity there is greater. So you can invest more in the sales process, You can spend more time. The range of things that you’ll be talking about are greater. There are buying criteria that have nothing to do with the product and the product experience. It might be SOC 2 compliance. So they may be, you know, very sensitive to regulatory issues, especially depending on the industry they’re in. So you need to understand that. You also need to understand, you know, their their process. They’re all going to have a different process around buying. And so there’s all these buying criteria that are way beyond product and you need to understand that, you know, depending on the business and what sort of profitability targets they have, you might build a small team, you know, for that sales process at the mid-market, certainly at Enterprise, you’re going to have you’re going to have to have a range of people with a range of expertise supporting you in that sales cycle. But even at mid-market, you know, you may need technical account help, you may need you know, your in-house counsel, you know, to weigh in on contracts. There’s just a broader range of things to consider and to deal with. And, you know, we see that because we both brands have been serving both small business and mid-market. And it’s just a very different set of activities. Great stuff, Steve. So starting today, these two companies are one, what can customers of Unbounce expect and what can customers of Insightly expect with this merger? You can expect a broad integrated solution, not tomorrow, but certainly not a year from now. And it will happen in increments and it will accelerate as we do this. You know, you can expect to see more artificial intelligence and machine learning application to the CRM. That is sort of the bailiwick of of the Unbounce brand. We have a we have a large team that does that and and that has that’s how the landing page solution has become much more than a landing page solution. It’s really become an experimentation platform. And that’s through, you know, good application of a machine learning. We as well on the on Unbounce brand were early to generative A.I. and we were honestly attempting generative A.I., not attempting, we built some generative AI solutions before chatGPT came on the scene and blew up and all of that. So you can expect to see that in the CRM, you know, fairly soon and you can expect to see a bigger investment in the marketing automation platform because, you know, the Unbounce folks understand that buyer, understand those use cases very, very well. So you’ll see the platform become, you know, more comprehensive. The combined org Unbounce will still be in the independent landing page space. That’s a very healthy business for us, but you’ll see a much more combined solution with CRM being the entry point for that business. So that’s what you’ll see. Well, I can tell you from the inside that folks on both brands are really excited about the future. Steve, thank you so much for joining us on Closing Time. Great. Thanks for having me. And thanks to all of you for tuning in to Closing Time. Remember, you want to like this video, subscribe to the channel and hit that button for notifications so you don’t miss an episode. We will see you next week.
