HubSpot's Enterprise Evolution: What Leaders Miss in CRM Decisions | Lauren Ryan

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From Trade Show Floors to HubSpot: Lauren's Origin Story

Brendon Dennewill: I'm joined by Lauren Ryan, Senior Corporate Solutions Engineer and CRM competitive expert at HubSpot. Prior to joining HubSpot, Lauren was the founder of Coastal Consulting, where she quickly became known for her expertise in integrating HubSpot and Salesforce for optimal performance. At HubSpot, she helps organizations tackle complex CRM challenges with confidence. She brings a unique perspective on how teams can successfully leverage enterprise-grade tools while scaling with clarity and alignment. Lauren, welcome to the podcast.

Lauren Ryan: Hey, thanks for having me.

Brendon Dennewill: I'm going to dive right in, Lauren, because we've known each other for a few years from when you were a partner, and it's so awesome to see you using all your incredible experience and expertise now at HubSpot. You've described your mission in some cases as demystifying the HubSpot-Salesforce integration, which is kind of how we got to know you in this ecosystem. What inspired that mission, and how did it matter so much for the teams trying to figure it out?

Lauren Ryan: I started my career in trade show management. My role on the marketing team was figuring out what shows we went to, getting our sales team aligned and on site, doing the lead generation leading up to it and the follow-up afterwards. We had integrated HubSpot and Salesforce, and that was around 2015, maybe 2014. So it was very early in HubSpot becoming more of a CRM-focused platform. I found there was a huge disconnect between sales and marketing. My role was really to advocate for sales at trade shows while also achieving marketing's goals, and I found intense misalignment between the two.

I traced that back throughout the years to a systems misalignment. If we're not communicating well with our systems, we can't communicate well as an organization. Throughout my career, from logistics marketing to startup marketing to financial services marketing, I saw a pretty consistent trend: HubSpot and Salesforce being the system of record for marketing and sales. I had this theory that if I could make those tools work well together, I could make the teams work well together. I saw that to be true in the organizations where I implemented the tools and helped teams use them.

In addition to my regular job, I started freelancing around 2016, right after I got my master's, to really start building my skillset outside of just my regular company. I wanted exposure to more and more companies to test this theory, and I consistently saw it ring true. Whenever your systems are connected and your teams are on the same page technologically, it reflects in the results of the business.

I came to HubSpot because I truly believe HubSpot improves people's quality of life. Having a better tool and a better experience at work gives you a better life. I feel kind of evangelical when I talk about HubSpot sometimes. I started my career as a marketer, but I got into the technology space because I wanted it to connect well with Salesforce. I've used both for over a decade, figured out so much on the front lines of how it works, and saw there wasn't really documentation in that space. So I narrowed in on creating that documentation, being the teacher I wished I had when I started using this integration. Once I felt like I had accomplished that mission and helped over 60 companies over four years, this opportunity opened up at HubSpot, and I decided to move from partner to in-house.

Brendon Dennewill: Very cool. We're so happy to have you at HubSpot. I think you're essentially extending on all the experience you have and creating potentially even more value than you were already creating on the partner side.

Lauren Ryan: I hope so.

Why Technology Alone Can't Fix Misaligned Teams

Brendon Dennewill: You talked about the importance of alignment between the systems that marketing and sales use. In our experience, when companies come to us, they're typically expecting a technology implementation solution. What they're often not expecting, even for larger implementations at companies with 500 or 1,000-plus employees, is that in order to implement the CRM successfully, we have to go back to the alignment of their people, their processes, and their data. Would you agree that even if the technology is aligned, if the people and processes aren't, it's really hard for that to be successful?

Lauren Ryan: For sure. Revenue operations as a specialty was formed because the more people did CRM implementations, the more apparent it became that your CRM was your business strategy. In order to properly implement your technology, you had to have a cohesive strategy. The people who became your implementers became the ones most in touch with how your business actually operated, because there's the executive declaration of what we're going to do, and there's the real-life lived experience of what your end users are actually doing. There are all the pieces in between: who owns where the data is coming from, who's administrating, who's actually using this, what message is actually ending up in the customer's inbox.

All of that was very disconnected before CRMs were implemented in companies that either had no CRM or had a homegrown CRM forced to fit around broken processes. Implementers became consultants of your organization in order to get your technology rolled out. Where people fail at implementations is when they decide to forego the people development piece: the interviewing, the research, the end-user acceptance testing. When they say, "We just need to turn on the tool and start using it." While you can do that, it misses what's actually going to drive adoption, which is understanding what your customers need and what your people need, then tying that together towards your business goals.

Brendon Dennewill: Right. We often talk about how implementing a CRM isn't just about the technology; one of the hidden, and potentially biggest, values of an easy-to-use CRM today is employee experience. I give the analogy of the Sunday barbecue when people are catching up with friends and start talking about what friction they're experiencing at work. It's often the tools they've been given. And of course, when people's lives are made easier by technology, adoption is far more likely, and adoption is what leads to a successful use of technology.

Lauren Ryan: Yeah, one of our sales leaders has a great story. HubSpot's adoption rate is about 30% higher than the industry average, which hovers around 50%. We sit more in the high eighties when people are actually using HubSpot. One of our sales leaders used to lead sales at LinkedIn, where they used an enterprise-grade competitor. She had a candidate she loved for a sales leadership role and called with an offer. The candidate asked about the tech stack, and when she shared it, he essentially declined. She asked why, and he said he doesn't work at companies that don't use HubSpot.

That was her first introduction to HubSpot. He told her that as a leading sales rep, his toolkit was the biggest way he won, and he sells best when he sells with HubSpot. That led her on a journey that eventually brought her to HubSpot, because she did her research, found it to be true, and became a genuine believer. She now speaks about how if you want your team to grow, you need to give them the tools to do that.

Brendon Dennewill: I love that story. A highly valuable salesperson actually making a career decision based on the tools they'd be using. Salespeople want to maximize what they're able to earn, and they know that if the tools create friction in how many customers they can help, that's a real problem.

Bringing Operator Experience to the Enterprise CRM Space

Brendon Dennewill: You touched on how your expertise led you to your role at HubSpot today. Looking back over the last few years, how relevant is that expertise in your role, and what doors has it opened for you in terms of increasing the value you bring to complex CRM decisions?

Lauren Ryan: I have an entrepreneurial background, and I joke with my boss that I'm kind of an entrepreneur here at HubSpot, figuring out how I can best leverage my skills for the benefit of the company. At the base level, my job is to help demonstrate HubSpot to new potential customers and show how HubSpot can meet their business case. I'm also aligning on competitive deals in the enterprise CRM space, bringing my lived experience to the conversation. I can say, "I implemented Salesforce and HubSpot for years across a variety of industries. Here's what I've experienced and here's how people enjoy either one."

My favorite observation, which I see play out in the community and in customer references, is this: people who are very proud to be Salesforce customers are proud of what they've built on Salesforce. They're proud of the white-labeled app, the complexity of their Apex code, the sophistication of their flows. People who are excited in the HubSpot community are excited about the time it saves them, the results they've driven for their business, the end-user experience, the adoption rate.

I'm certified in both tools deeply and extensively experienced in both. When I decided to sell my agency and choose between going to work at HubSpot or Salesforce, I chose HubSpot because I'm very aligned with the results-focused mission. I've built really cool things in Salesforce and I'm proud of that. But when it comes to the results and the technology I want to put into businesses, I'm very aligned with HubSpot because I've always presented myself as a people-first leader, and I think HubSpot is a people-first platform.

I drive value in my role through three things: one, being an operator in my previous life; two, being deeply certified and experienced hands-on in both tools; and three, doing a lot of internal enablement on the integration, upping our materials, and helping our customer success team understand more about that integration. I've taken the content creation I used to do externally and am doing it internally now.

Brendon Dennewill: Your roots in marketing are serving you well as HubSpot grows as a platform. There needs to be internal education about what's possible, and the perspective you bring is really quite incredible.

A Cautionary Tale: When a Tech Buying Decision Goes Wrong

Brendon Dennewill: Let's go back in time a little. Do you have a personal story of a tech buying decision that didn't turn out exactly as you expected, and what you learned from it?

Lauren Ryan: Not to name names, but when I worked in financial services, it was before HubSpot became SOC 2 compliant, which we are now. There are droves of banks and credit unions coming to HubSpot today, which I love. But back then, I worked at a credit union and had to implement an enterprise solution to integrate with Financial Services Cloud. It wasn't a decision I made happily, because I knew the power of HubSpot and where I wanted to be aligned in the market, but it was one I had to make from a compliance perspective. I'm sure plenty of people in high-compliance industries can relate.

I really regretted that decision, because we went with Salesforce Marketing Cloud, which in its own right is a very powerful tool. It took me about eight months to implement it, integrate it with our tools, and deploy an email. The email wasn't mobile-responsive out of the box, so we had to bring in a developer to do AMPscript and HTML. I had to learn how to write SQL just to build segments to send an email to begin with. And we still had to integrate with Salesforce separately, since Marketing Cloud is still built on ExactTarget.

All of that, for someone who already had six years of marketing automation experience and a lot of Salesforce experience. I ended up leaving the company because of the software we chose, because I had to build a skillset that was different from the one I came in with just to use the tool. We never really got to use my actual marketing capabilities, because I was too busy trying to figure out the technology.

That's really what I'm trying to help people avoid now: being able to focus on what you're actually good at. Focus on sales, not your CRM configuration. Focus on marketing, not figuring out your marketing tool. Focus on strategic administration, like growing your team and implementing new ideas, rather than editing formulas all day. It's not just one tool versus another; it's the opportunity cost. We had Marketing Cloud implemented and we were able to do some things with it, but it took so long that the question becomes: was it worth it? And I've always answered no.

As a separate example, I changed project management software a lot as an agency owner, and I regretted almost every switch a few months in. It was always challenging to find one that could track agency tasks by project and also track time and billable hours. I never really found one that worked well for that.

Brendon Dennewill: You're choosing between something easier to use but not quite as robust, or something more complex that creates its own friction. I want to zoom out a bit. You mentioned strategic administration, and with everything happening with AI right now, business leaders are often solving for the wrong thing. We get caught up on needing the technology, thinking it will solve all our problems. But we know that's not the case, and it goes back to having your people and processes aligned. What advice do you have for people who have made a technology decision, or are in the process of making one, where they might not be thinking strategically enough?

Thinking Like a CEO: A Strategic Framework for Software Decisions

Lauren Ryan: I think it's important to get everyone who could be impacted in the room. Often in the HubSpot buying process, you start with a marketer or a VP of Sales who's really interested in change, but doesn't run that idea up high enough.

A credit union is a good example right now. HubSpot can be used not only for marketing your credit union, but your tellers can also log into HubSpot and leverage it on top of your core banking and FinCER systems. When a member walks in to make a deposit, a teller can see that this person is highly ranked for a home loan. Now they can start a conversation about that, generate an internal referral, put more money in the teller's pocket, create more leads for the loan servicing team, and deliver a better experience for the member, because you've enabled your team with the right data.

I talk to financial services teams that are still having their frontline staff log into their core banking system as their only insight into their members. There's so much more available today. Let's say a loan servicing team comes to us to talk about managing deal processes in HubSpot. We should actually be talking to your CEO or chief experience officer, because you can put loan servicing, marketing, and frontline customer service all into HubSpot, not replacing your core financial services tools, but surfacing and aggregating that data where you can actually act on it in a meaningful way.

Something that's been the most fun part of my job is seeing those dots connect for customers: "We can create this amazing experience and beat out the competition by simply surfacing the data we already have."

When you're evaluating new software, I think you can really grow by challenging yourself to think from a strategic leadership position. If I were the CEO, what decision would I want to make? If you're a marketing analyst thinking about a new HubSpot feature that could save significant time, zoom out. Think about what would sell your boss on the idea, what would make HubSpot more valuable for her boss, and for her lateral colleagues. Think about the impact it can make for the whole company.

When we only think about what we need to send marketing emails or automated sales sequences, we end up with a fragmented tech stack with data siloed in different places. When you actually look at how your organization benefits from software, you end up with a full customer platform rather than a series of bolted-together solutions, because HubSpot allows all your data to live in one place, all your teams to work from one tool, and it connects your organization at a strategic level.

Brendon Dennewill: A lot of that, I think, comes from leaders in more traditional industries who grew up with siloed tools. Thirty years ago, that was your only option: this tool for marketing, this playbook for sales, this system for customer service. And I'm guessing the metric of lifetime value probably wasn't even used much back then. We started moving from providing marketing automation to cross-functional solutions to full HubSpot implementations covering marketing, sales, and customer service, and then integrating all of it. Business is no longer just cross-functional; it operates in a matrix. And AI is only going to make that more real. It enables us to incorporate intelligence into all the technology we use in that matrix fashion, where a teller at a credit union can now impact what the CEO is doing to grow the lifetime value of a member. The future is incredibly exciting from that perspective.

HubSpot, AI, and the Shift Toward Running on Data

Lauren Ryan: Something I've seen in the market over the years: Salesforce has long been seen as the safe decision. What I've seen in recent years is that it's no longer the safe decision. Buying that software, implementing it poorly, and not having a team to manage it well actually puts you at risk. I have seen a lot of people who were in charge of Salesforce and the success metrics Salesforce was responsible for generating no longer be with their companies.

People say, "I don't want to be the person who chose the wrong tool." What I've seen throughout my experience is that I've seen people get promoted, grow, and companies get acquired because of the success they've proven through using HubSpot. And when we think about strategic growth, you're actually seen as an innovator when you bring on HubSpot, because we're leading in AI application. We're not advertising that we're laying off half our workforce because of AI. We're talking about how AI is accelerating our growth, and that's largely because of the way we're applying AI internally and for our customers.

If you look at the efficiencies AI can generate organizationally, it can exponentially increase what your team is able to do with the time they have, rather than asking how many people you can get rid of. The goal of AI is to help you grow so you don't need to get rid of people; you just need your people to be able to do more without burning themselves out. That's really how AI is peppered throughout HubSpot. If you click "Create Property" in HubSpot now, it asks for a prompt. It's removing friction at every point in the process.

I love how HubSpot has applied AI compared to some other enterprise tools, where you have to configure the bots and build the AI logic yourself. HubSpot has identified those key points where it adds value, removed the friction, and built it for you. It's ready to use on day one, and it's just so cool to see how it's been evolving.

Brendon Dennewill: So Lauren, with all of this data flowing through fully integrated tools, what separates companies that just have data from those that actually run on data?

Lauren Ryan: A few years ago, when the conversation about first-party data started to heat up around Google's ad changes, we talked about how first-party data was going to become, behind your people, the most valuable resource any company had. Now that we're in this AI era, that's even more true, because AI is only as strong as the context it has. Our data at HubSpot is unified in one place, which is a big reason our AI is so powerful.

The difference between running on data versus just having data is this: if you're leveraging data in your everyday activities and it's actively pushing you forward, that is very different from having a monthly report of what happened. If I'm spending hours generating a report to send to my CMO at the end of the month, that's one thing. But if I'm actually using data to iterate the process as it goes, generate new ideas based on what we've seen working, and get directional insights rather than just reports, it really changes the culture of the organization. You become proactive. If you wait until the end of the month to review historical reports and then adjust for the following month, you're way behind someone who's adapting daily, or better yet, leveraging technology to do that for them.

When you hop into HubSpot now and open up a contact, you can use Breeze AI and just say, "Tell me about this contact," and it summarizes the entire history of your relationship in seconds. That's running on data. Instead of knowing you need to look at a specific property or open a related object to get information, it's all surfaced for you right away. You can use it to advance your conversation instead of spending time hunting for it.

I was talking recently to a company that does field sales: they walk in and sell into retailers who sell on their behalf. Before meeting with a retailer on site, they need to know the sell-in amount, the sell-through in the past year, and the full customer history. Before HubSpot, they were opening two different tools for sell-in and sell-through data, then their database for customer info, then their sent inbox to check recent communications. When I showed them that HubSpot surfaces all of that, including sent emails and sell-through percentage, in a single screen when you open the contact record, it was a jaw-dropping moment for their team.

Companies that understand how surfacing data and bringing it to the right people at the right time completely changes how they work, operate, and perform. Those are the ones running on data rather than just having it.

Brendon Dennewill: As you were saying that, I realized how tightly connected it is to what we talked about earlier: giving people the tools they need to do their job. If you're going to give them the tools, why not give them the data inside those tools? One of the huge value propositions HubSpot offers is having everything unified in one easy-to-use platform that is increasingly more powerful because of the AI they're building into it.

HubSpot Is an Enterprise Platform. Here's Why That Matters.

Lauren Ryan: Something I've been working on and talk about almost daily now is this: HubSpot being easy to use does not mean it's not an enterprise platform. The perception in the marketplace is that HubSpot started as a marketing platform. Sure it did. Apple started in a garage. There's a starting point for everyone. When we talk about HubSpot today, being easy to use doesn't mean it's simple.

You can do really complex things with HubSpot and run enterprise organizations with thousands of employees on it. The permissions, visibility controls, custom page configuration, and reporting capabilities are remarkable. I've been on a personal mission to overcome the narrative that HubSpot isn't an enterprise-level CRM, because it absolutely is. And that's someone with a lot of Salesforce experience saying it.

I'm blown away by what you can do in HubSpot and how quickly, compared to what it takes in Salesforce. That doesn't mean you don't need someone to administer HubSpot. It just means that person is going to accomplish so much more in the same amount of time than they would using Salesforce, Dynamics, or a more legacy CRM, because HubSpot has removed friction for both the end user and the admin. Just because it's easy doesn't mean it's not enterprise.

Brendon Dennewill: Which comes back to what we talked about earlier: total opportunity cost. Someone is buying a shiny new CRM, but they're only looking at the upfront price. They're not thinking about what it costs to maintain and optimize that CRM over time, or the real value of it. All these types of investments should be seen as capital investments, and a capital investment needs to continuously work harder for you as its capabilities improve, as your processes change, as you grow.

Lauren Ryan: Yes, and something people consistently leave out of the total cost of ownership equation is the license conversation. A license to Sales Hub is not the same as a platform license in Salesforce. A Sales Hub seat gives you access to the HubSpot CRM, a meetings link, document tracking, sequenced email scheduling, deal pipeline management, forecasting, and reporting dashboards. That's not what you get with a Salesforce platform license. You get access to the CRM.

So when sales conversations come down to comparing seat pricing side by side, we're missing the forest for the trees. One Sales Hub seat is not equal to one seat in another platform. It's equal to your CRM, your meeting scheduler, your calling tool, your forecasting tool, all in one. And beyond that, there's the implementation, the ongoing costs, and the training. If you've built so much customization on a platform that it no longer looks like the out-of-the-box version, it becomes very challenging to maintain your training and enablement internally.

With HubSpot, the enablement you receive from your agency on day one continues to live on. The free resources in HubSpot Academy are there for your entire team. You don't need ongoing development resources unless you're maintaining a complex API integration, and for that you can use a partner team rather than building it in-house.

The TCO is not just the upfront license cost or the implementation fee. It's the ongoing headcount, the supplemental licenses needed to get all the features you require, and it's a much bigger conversation than we usually have. What can we replace? What can we consolidate? How can we pare down and streamline? HubSpot admins are given so much more time to be creative, to optimize, and to grow the business, because they're not bogged down with arduous point-and-click administrative tasks.

Leading Through Uncertainty: A People-First Decision Framework

Brendon Dennewill: As we're heading into the end of 2025, 2026 is setting up to be a real roller coaster for so many businesses. You can choose to see that as an exciting ride or be afraid of it. But a lot of business leadership teams are facing real uncertainty and will be making tough decisions as they head into the new year. What is a principle or a mantra you lean into during tough times or when facing hard decisions?

Lauren Ryan: I think it goes back to the golden rule: treat people the way you want to be treated. All business decisions come back to people and how they'll be impacted, whether we're growing, declining, doing layoffs, or hiring. As we go into this strategic planning period, it's really important to think about how decisions will impact your workforce, because at the end of the day, the most valuable thing you have are the people who work for you.

Think about how hiring will impact them. Think about how not hiring will impact them. Think about the technologies you're bringing on. What is the cost of no change a year from now, and what is the cost of change a year from now? Zoom past the short-term pain that might come from migrating a tool, hiring a new team, or changing job descriptions, and think about what you're gaining or losing in a year by those decisions. Think about the overall morale of your company and your position in the market relative to others.

Thinking about it a year from now and thinking about how it impacts people, positively or negatively. I've always tried to be people-first in my decisions. It's a legacy my grandfather started, and I try to carry it on. I always look for that impact a year from now when it comes to the people around me.

Brendon Dennewill: That's really good advice. It reminds me of a high-level takeaway from the recent Inbound conference: to be innovative, you also have to be very good at change, because you cannot innovate without it. The question you're posing is: where do we want to be a year from now, what needs to change to get there, and how do we help our people navigate that change together?

Lauren Ryan: Things are going to change with or without you. So you should get on board with it. In today's world, being change-resistant doesn't stop the change; it just determines whether that change happens for the better or the worse. What do you want your part of that to be?

Brendon Dennewill: Absolutely. And I think for us at Denamico, and for a lot of folks in the HubSpot partner ecosystem, that's one thing we all share in common: we all want to lead the change, be part of the change, and make it happen together.

What's Next: The Future of Enterprise at HubSpot

Brendon Dennewill: Lauren, to wrap up, what are you most excited about as we close out 2025 and head into 2026?

Lauren Ryan: My son's first birthday is next month, so I'm really excited about that. I'm also really excited about the future of enterprise at HubSpot. I've been working on the HubSpot pre-sales team and have seen HubSpot grow from having to code your own landing pages to where we are today, and I'm constantly blown away by the growth of this platform. I've built my career on it. I'm excited to expose more and more upmarket customers to HubSpot because there's so much happening here that's genuinely exciting. And I'm grateful to be positioned in the market to talk about it all the time and get paid for it. It feels like a dream.

Brendon Dennewill: That's very cool. For folks listening, when you talk about enterprise and the upmarket from a HubSpot perspective, what does that mean in terms of company size?

Lauren Ryan: I don't know if I can share the exact specifics of HubSpot's definition, but I'd say probably a thousand or more users in your instance. When your frontline GTM team across sales, marketing, and service consists of a thousand or more people, that's the target audience I'm really looking at. We're bringing on customers with 1,500-plus users. When people say HubSpot isn't enterprise, I don't know how you can say that with that kind of background. But people just don't know. There are a lot of really large businesses running on HubSpot now, and I'm excited to keep increasing that number, because I genuinely think our economy and our workforce need it right now.

Brendon Dennewill: Really well said. Depending on where people are coming from, enterprise means different things. We often refer to it as the mid-market, which is up to around 2,000 employees or users, and HubSpot is a perfect fit in that space. But to your point, it will increasingly extend beyond that.

Lauren, thanks again so much for joining me today. It was so cool to catch up.

Lauren Ryan: Thanks for having me. Loved it.

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