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SaaS Marketing: Strategies for the Present and Future Success | VWO ConvEx 2023

Join Charlie Windschill for a deep dive into SaaS marketing's future, blending growth tactics and retention strategies for lasting success.


Charlie is the director of Growth Marketing at Ortto. Charlie's role focuses on driving sustainable new business growth with a retention-first mindset. Her day-to-day activities involve defining the ideal customer profile (ICP), building messaging frameworks, and hiring a team that can make a difference. Emphasizing experimentation as both a mindset and a mechanism, Charlie highlights the importance of understanding metrics and insights for effective experimentation.

Ortto's approach includes a hierarchy of metrics, from North Star metrics to program-level metrics, and weekly team meetings to review progress. The company's content strategy underwent an overhaul, focusing on thought leadership, SEO-driven content, and product marketing. This strategy significantly improved the quality of trial users and overall engagement. The session highlights Ortto's growth strategies including segmentation, automation, and a strong focus on SEO, both content and technical aspects.

Key Takeaways

  • Amid economic challenges, Ortto's growth strategy emphasizes new business development while maintaining a strong focus on customer retention.
  • Ortto adopts a dual approach to experimentation, combining mindset and technical mechanisms, and uses a structured hierarchy of metrics for decision-making.
  • Ortto revamped its content strategy to better align with its ICP, focusing on thought leadership, SEO, and product marketing, leading to improved engagement and trial quality.


[00:00:00] Divyansh Shukla: Hello, everyone. Welcome to ConvEx ’23. VWO’s annual virtual summit for growth and experimentation professionals. 

[00:00:14] My name is Divyansh and I’m a marketing manager at VWO. Thousands of brands across the globe use VWO as their experimentation platform to run websites, apps, and products. 

[00:00:26] I’m excited to have Charlie Windschill with me here today, who is the Director of Growth Marketing at Ortto.

[00:00:32] Hey, Charlie, excited to speak with you. 

[00:00:35] Charlie Windschill: Yeah. Thanks for having me. Happy to be here. 

[00:00:38] Divyansh Shukla: And as we kickstart the conversation, Charlie, I want to understand how your journey has shaped up at Ortto. Can you give me a glimpse of your day at your role at Ortto? 

[00:00:48] Charlie Windschill: Sure, certainly. I think a great place to start is a bit of context that will be relevant for my role and for our conversation.

[00:00:57] Before I joined Ortto, we were actually known as Autopilot. And we rebranded to Ortto in March of 2022. And that was actually a complete product rebuild. So Ortto is a marketing automation platform and our co-founders built it to take everything that people loved about Autopilot, our visual journey builder, and they added a customer data platform, and analytics, and a few other marketing automation tools to address the evolving needs of that customer base. They’ve been with us since 2015 or so. 

[00:01:33] So, fast forward to when I joined in November of last year, the business was just really starting to think about its next phase of growth. So we’d launched this new product. We were working on helping Autopilot customers migrate over. And that body of work was really wrapping up.

[00:01:51] And so I was brought in with the remit of growing the brand, growing under this new product from the ground up. The second bit of context is along the same time frame, when we were all starting to face a bit of that economic uncertainty. If you cast your mind back, it was really starting to pick up. And then the banks collapsed.

[00:02:14] So I came in with this remit of building up our growth strategy. But at the same time, the business was really turning an eye to retention. So that had a fundamental impact on my role and how it shaped up. We needed to drive new business growth, but with this retention-first mindset.

[00:02:33] Broadly to answer your question, my role has been to come in and drive sustainable, highly renewable, new business with this startup and really identify our go to market fit so we can scale in the process. 

[00:02:49] Now, to look at the day to day, and what that actually looks like in practice. The first few months were beginning to define our ideal customer profile.

[00:02:58] So we worked really hard on that. We built a full messaging framework around that ICP. And then in parallel also hiring out the team. So a lot of first order of business work. Since then my day to day ranges quite a lot actually. So the last quarter or two have been laying foundations across core channels and excited to dig into some of the details within each of those.

[00:03:25] But yeah, that’s a bit of my journey and what the day to day looks like. 

[00:03:31] Divyansh Shukla: And this definitely gave me a broader storyline of growth marketing at Ortto. With that Charlie, I’d also like to understand what is your perspective on experimentation? How do you set it up at Ortto? 

[00:03:45] And as a follow up to that question, I’d also want to understand how does experimentation translate into your content strategy?

[00:03:52] Charlie Windschill: Yeah, yeah, absolutely. I love the idea of experimentation. And what I’ve brought in is that experimentation is both a mindset and a mechanism. And I think it’s important to preserve both of those elements.

[00:04:11] What I mean by that is from a mindset standpoint, I think we can all agree and we’ve all probably experienced a moment where we’ve known that like fear of failure really stifles growth and creativity and that’s so, so, so crucial at these early stages. 

[00:04:26] But I think folks are probably more interested in some of the technical mechanisms of experimentation. So when I talk about everything we do as a test, what it means for us is that you need to approach everything that you do, knowing exactly what metrics you’re trying to move, or what insight you’re seeking.

[00:04:46] To actually set that up and make it actionable, at Ortto, we have a approach to our data and to our goal setting that uses a hierarchy of metrics. So we have a North Star metric or two. We have two in our marketing department. These are aligned with the business with the board approved goals. And that’s our North Star across the board.

[00:05:11] And then the next layer in our hierarchy are our leading indicator metrics. The things that drive the trends, if you will. And then we actually add a third layer and these are more like program level or campaign level metrics. These are the things that are much more tactical, allow us to optimize in the day to day.

[00:05:31] But having this hierarchy of metrics allows us to adopt everything is an experiment. And we’re always aware of what we’re trying to do, what metric we’re trying to move. So with those frameworks in mind, we’re lucky that Ortto has actually got pretty, decent analytics capabilities within it.

[00:05:52] So we set up a bunch of reports and dashboards that allow us to keep track of all those metrics. We do look at some native platforms reporting as well, of course. But we’ve got all of that created. And then we also do weekly team meetings where we’ll come in, we’ll review our metrics, we’ll review what we’re noticing and observing in our functional areas and then talk about right based on everything that we’re seeing. What do we want to do next? What’s the biggest opportunity area or potential like red flag area that we need to tackle together? So we’ve got this consistent, always on experimentation, flowing through all the different parts of our program. 

[00:06:36] Divyansh Shukla: That’s really exciting to know, Charlie. And with that, I want to understand, how do PLG principles transpire at Ortto and what role does marketing pay in a PLG inspired company.

[00:06:51] Charlie Windschill: I think PLG at a company like ours is really interesting because we are first and foremost, a product company. And so our product is our primary driver for new business growth. A 14 day free trial is actually our core offer in the business. And so as a company, what that means is marketing is, first and foremost, focused on demand generation. And that’s as opposed to lead generation.

[00:07:22] And I think the distinction is really important for companies like ours. Because what we’re trying to do is take that spirit of product led growth and really have it transcend everything we do. And what I mean when I say that is product led growth is about getting folks to the product faster, removing as much friction as possible so it can really sell itself.

[00:07:44] So we take that idea and we apply it to everything. So we want to build brand awareness and brand equity. We do so through great content that adds value to people’s lives. And we try to remove as much friction as possible, getting folks to that content. I also love to ask the question, are we giving more than we’re getting out of this interaction?

[00:08:06] If the answer is yes. We’re doing it right. 

[00:08:08] And then of course you have a moment where you need to capture that demand but we’re really focused on high intent demand capture. Lead generation is just going to be any engagement we have, how can we create friction to capture that lead, pass it on to sales, etc.

[00:08:24] Nothing wrong with that approach, but it’s not the approach that we take. I know it can be tricky and sticky for some. But we’ve really embraced demand gen at Ortto. I think one of the keys to success on that front, and for product led companies who are trying to adopt these principles, is we’ve actually completely done away with the idea of MQLs.

[00:08:46] So that alleviates all the lead gen pressure. And also it helps us to be able to do things like gating content very sparingly and very strategically, growing our database with as low friction as possible and coupling that with great lifecycle programs so we can provide ongoing value.

[00:09:10] As I’m thinking about it, I’m thinking back to your other question about like experimentation and content. And I think this all is relevant as well. So I’d love to tell you more about that as well. 

[00:09:24] Divyansh Shukla: Definitely. I’d love to know more about it. And especially as a content marketer, I appreciate the fact that the focus falls back on the value of the content rather than the other objectives of the business.

[00:09:38] And, it’d be great if you can elaborate more on that. 

[00:09:42] Charlie Windschill: Yeah, I think you’re going to love this then because that’s exactly right. And when I joined, what I found is that our content maybe didn’t have that strong sense of direction yet. And value wasn’t the shining light that guided everything that we did.

[00:09:59] And so we had a lot of traditional SEO driven content. Our content strategist calls a lot of it stealth sales, which I just love as a term, but it was that stuff that on surface level, it looked like it was going to provide like useful strategic or tactical advice. But if you looked a little bit closer, it was more like product marketing materials.

[00:10:22] Seeing this organic growth was like good, but maybe lacked really strong alignment with our ideal customer profile in terms of who we were bringing in. And also there was a bit of like brand misalignment, that value element we were just talking about. So we actually overhauled our content strategy and we set out some really clear buckets of content to add more distinction.

[00:10:47] We had a thought leadership bucket which was the emerging bucket and it really features subject matter experts talking about timely topics, hard hitting stuff, having opinions. Then we’ve got the SEO driven content. Again, coming back to that high intent demand capture element. And then product marketing. And intentionally separating those to do what they’re meant to do.

[00:11:14] And we’ve rolled this out. We found that thought leadership, that bucket was the most lacking. So we doubled down there. And the metric we were trying to move, thinking about that hierarchy of metrics that we have was actually the percentage of new trials who were high ICP fit. So not changing the volume, but changing that quality question within the volume of trials.

[00:11:40] And we rolled everything out with the hierarchy of metrics so we could look at leading indicators, using things like engagement metrics, time on page, pages visited sessions, that kind of thing. And what we found was that our ‘new strategy content’, if you will, had actually doubled the time on page our old strategy content did.

[00:12:02] And some of the other SEO technical work that we were putting in parallel, we saw a cumulative impact 40% lift in organic search traffic for this new content. And also the percentage coming back to that guiding metric. The percentage of our trials that were high fit went from 31% up to 51%.

[00:12:28] So nailed it across the board, feeling really great about it. But like experimentation is so layered at our startup that like this gets me excited, but probably what gets me more excited is that content is really the backbone for everything else, right? Life cycle programs that we wanted to launch, the dependency was great content to drop in somebody’s inbox. We now have that. Paid social same thing. Like it’s layered in all of our paid social programs. So then with that content, validated, we’ve been able to turn on these other channels and then begin optimizing and experimenting within them on everything from content themes and add formats to the hyper tactical things like subject lines and email designs.

[00:13:16] So we’ve got these like layers of experimentation and it’s all born out of content and it all, just to tie back in, aligns with our perspective on being a product led organization. And as a marketing team, tying in that spirit of product led growth across every moment of potential value. 

[00:13:38] Divyansh Shukla: It’s crazy to learn how well connected is the entire strategy at Ortto.

[00:13:43] And I personally love the distintctions and the division into objectives and particular task that are coming out of them. As a next question, Charlie, I’d love to understand, as your product is fundamentally selling to marketeers, what are the fundamental changes do you see unfolding in this industry, especially in context to SaaS?

[00:14:11] And I’d want to understand how’s the experimentation going to evolve with these trends? 

[00:14:18] Charlie Windschill: I feel like we’re in a time of such insane pace of innovation. There are so many different topics we could touch on. I have three main ones (trends) that are probably the most glaring for me and for the other marketers that I get to talk to day in day out. So, i’ll go into details on them.

[00:14:42] But the three I think would be, one that just like the complexity of the customer journey and how multi threaded it is. The second is, I think, evolutions and how we are thinking about and using data. And then a third is just this mass product and content saturation. 

[00:15:04] So let me touch a little bit more. I’ll try and answer your question as well about the layer that has come into play with experimentation. 

[00:15:14] But firstly, talking about, the customer journey being so complex and multi threaded. I think we all can understand how fragmented the experience is for a brand when in terms of trying to understand customers and how they’re engaging with you. You’ve got your light funnel and dark funnel, if you will, you hear people talking about. And we feel this impact as a marketing team on my end where we’ve talked a bit about like the top of funnel demands with building brand and providing value. But we also look after the whole of the product. So taking that demand converting it engaging it and then turning trials into paid customers. We own that whole funnel. And we have to because one we’re a small team And to the customer journey is so multi threaded.

[00:16:07] You don’t really know where they’re at at any given point. You might have some sense from your data, but it’s likely incomplete. And so I think that combined with the impact of the big correction we’re seeing in the market, and how that’s impacting marketing budgets and consumer confidence with SaaS purchases.

[00:16:28] It’s a tough time for marketers and we’re going to have to really upskill ourselves on a wide range of channels, a wide range of tactics for understanding the customer journey. And at a minimum just knowing how your part fits into the sum of the whole. So that everything that you do everything that you launch can contribute to this idea of creating a consistent and holistic brand experience for the end user with that super fragmented multi threaded experience.

[00:16:58] And then the really practical thing is just being judicious with your investments with considering how complex it can be. So I think that’s one that I’m exploring more and more and speaking to people more and more about how you tackle such a complex meaty topic.

[00:17:16] But a couple other ones that layer into that. Data is at the heart of what I just talked about, but also there are further evolutions and how we’re thinking about data. I think come back to a bit of the bad behavior of marketers in previous years. So I think we saw an inch and took a mile sort of thing when it comes to access to user data access to customer data.

[00:17:44] And consumers have let us know that they are not about it anymore. And we see that in the form of things like really stringent data regulations a lot of enforcement of those. They’ve influenced the product led buying trends, right? Like marketers have seen that buyers are no longer interested in having marketing materials thrown in their face all the time They want to jump in self discover. And they also jump in on the dark funnel.

[00:18:11] So working with their peers social groups, communities, that kind of thing. So for marketers, what I think that means is one, we need to focus on zero party data collection. It’s super, super important right now. And then two would be maximizing all of the first party data that you have from across all the tools in your stack.

[00:18:36] And both of those things need to be coupled with prioritizing having a more reciprocal relationship with buyers. So I think we need to rebuild a bit of trust with consumers. So that factors into experimentation in a lot of ways. Like collecting zero party data.

[00:19:00] How can you design tests to balance that give and get. So you get more zero party data and you give things away. How can you use complete first party data to guide testing decisions and call the results of tests? So I think there’s an interesting element there with data. And I’ll come back to content because we both love it so much.

[00:19:23] I do like content and product saturation, and I wonder what you have seen as a content person yourself. I just think that with Generative AI just blowing up as we’ve seen and then like mass adoption of social media platforms like TikTok, of course, but even LinkedIn. I just read something recently about their algorithm update was like driven in part by 42% increase in content shared from 2021 to 2023. So there’s just a explosion of content out there. And it’s at the tail end of a decade of just massive tech boom.

[00:20:04] So we’ve got so much content, so many products. So much saturation. And what I’ve been speaking with marketers about my peers, my team, we’re having this conversation internally is how do you stand out in a sea of sameness? And I think it’s going to be the teams that are incredibly human centric, like what does Charlie need and how can I help her get it?

[00:20:34] And how can I create content that has a unique perspective that AI just can’t replicate? Because You haven’t done the grind of my job. And then like orchestrating product experiences. Again, I’ll come back to eliminating friction. I’ve heard of this like idea of a reverse trial. 

[00:20:53] And another I think interesting one will be like either tech will massively consolidate because of all this product saturation and/or there’ll be extreme niches carved out. So I would say marketers start to think about where you can carve out niches if you’re in a really saturated space. 

[00:21:15] Divyansh Shukla: Definitely. And Charlie, I personally think that it is going to be more about value versus volume.

[00:21:22] There’s so much clutter out there. How do you deliver that valuable piece of content to your target audience is going to be a really important piece of advice going forward. And with that, I’d also want to understand as a marketer, what channels do you leverage for growth? Can you share a few channels that you have been personally bullish on along with the reasoning? 

[00:21:48] Charlie Windschill: Yeah, absolutely. I guess the first thing I would say is that my answer would probably change if you asked me at a different point in my like career depending on which companies I work with and their maturity. But right now my perspective is that like the core channels I’m starting out with, again considering we’re trying to establish go to market fit.

[00:22:08] We’ve got this interesting legacy history. My core channels are firstly organic search. It’s just the most scalable way to drive growth. It’s most universally engaged with channel and it’s the long game. So every day that you put off focusing on organic search, you’re just delaying that exponential growth.

[00:22:31] So that’s my first and foremost. And then I love paid LinkedIn. I think it’s such an amazing platform. The targeting options are so tight. The intent alignment is so perfect for what I’ve been trying to do. So I see paid social LinkedIn in particular being really important. Other, I think core channels I would say must haves, email.

[00:23:02] So, I think it’s really unlikely that your very first engagement with somebody, they’re going to become a super fan or a power user. If that happens, brilliant, good on you. But I think it’s unlikely. So, really, what you need are well orchestrated lifecycle programs, and email just refuses to die.

[00:23:21] If anything, it’s stronger than ever. So I think that’s really important to have layered in. And being a product led company, if I think about like my product as a channel, it’s all of the different ways in which I can leverage the product, as a channel in itself. 

[00:23:39] So templates, we create templates that ties in with our organic play. We’ve got our free trial and freemium as a mechanism for growth. So I think product as a larger category. So those would probably be the core channels. Now, paid search, people would probably right away be like, where’s paid search? I do think for a lot of folks it is a core channel. However, because it’s less controllable, and it has so much more hands on attention required, I would just be thoughtful about when I turn it on. 

[00:24:16] And then my next layer of relevant channels that I think once I’m comfortable with my core channels, how do I layer and layer and layer? I would potentially look at things like affiliates or third party promotions, like where’s my audience already engaging and can I meet them there? And similarly with events, though, usually events, higher investment, spikier levels of engagement. So yeah, I think that those are some of the channels I think about for growth and how I prioritize them.

[00:24:48] Divyansh Shukla: It’s funny because my next question [is] a controversial one. I really wanted to settle the debate between a paid search and the organic growth. So how do you balance both? Is there a specific ratio or a specific mix that you recommend? And as an extension, Also want to understand how do you optimize both for growth?

[00:25:15] Charlie Windschill: You’re not gonna like my answer, which is that I think you need both. And I can’t give you a specific mix. I think that you need both most of the time and the question should really be, how can I make both of them work together considering the resources I have available? The answer is always optimizing your resources.

[00:25:37] And the reason I can’t give you a specific mix is it just varies so drastically depending on everything from your product, which stage of growth you’re in, the category of maturity. Even organizations I’ve worked with in the past where we were expanding internationally, the mix looked completely different region to region.

[00:25:58] So I don’t think that you can set a hard and fast rule. However, if you do take this approach, which I do of like, how can I make the most of having them work together with the resources I have available?

[00:26:12] I think you should ask, a two pronged question. First is, how can I make these channels work together harmoniously to optimize them for growth? And then how can I optimize within each of them for growth? 

[00:26:25] So you have this one-two punch impact. If we take like coming back to my knit about paid search versus organic search, we just take that as a super simple case study, if you will. You might look at paid search keywords that you can bid on now immediately that are aspirational to your SEO program.

[00:26:48] Like you want to rank for them. You’re not there yet. Can you pay for those rankings until your SEO catches up because it is a long game. Or i’ve seen this work sometimes not always, but can you blitz a set of keywords. So really refined group, use dual content learn faster if you can fit for that particular niche of content.

[00:27:13] So again, it’s how can I make them work together? And then within each of them, the typical layers of test and optimize across the relevant surface areas of each. 

[00:27:25] Divyansh Shukla: The original question. I personally agree that there’s no specific mix, but it’s a solution for a specific problem that the business is facing.

[00:27:35] And it’s always about experimenting between paid and organic to find out what works best for the brand. 

[00:27:44] Coming on to my next question, Charlie, I’d really want to understand few intuitive growth strategies that have worked well for you at Ortto. Can you share them? 

[00:27:52] Charlie Windschill: Yeah, certainly.

[00:27:53] I think the first thing, that has been really important to us at this stage has been segmentation. So how the work that we put into really understanding and defining our ideal customer profile has allowed us to then segment our database for high and low fit potential customers and existing customers, and then optimize everything that we do to those groups.

[00:28:25] So for the high fit, we’ve got all of our content optimized towards them, our messaging, our targeting across channels. So that’s fundamental is your segmentation strategy. And so we’ve launched with it. And I think the cool thing is that once you start segmenting you begin learning and then you further segment.

[00:28:43] So it’s like an additive, like constantly adding value. And it does tie into probably the second, growth strategy, if you will. Now I’ll just call myself out that we’re a marketing automation platform. So of course, I’m going to say automation and life cycle programs, but very genuinely like at Ortto and every other organization I’ve worked at automation is so critical.

[00:29:10] So having our customer journey mapped out and automations built across all of the funnel. And I know I’ve said funnel isn’t linear, but like best you can do to move people through to the appropriate touch points, and that’s just so fundamental. And I think we’ve put a lot of time and effort into mapping that journey and building the appropriate automations for each stage.

[00:29:37] And then we’ve talked a ton about SEO. Talked about the content side. There has been a lot of technical work as well. I think you cannot forget about the technical side of SEO. That combined with the content, it’s hard to tease apart the results, but combined are the results that we’ve noted already the 40% growth in organic search and in this short period of time has been pretty incredible and has taken a lot of focus on SEO. 

[00:30:05] Divyansh Shukla: Great to learn, Charlie. And as we wrap up the session, I want to understand if there are any recommendations for great reads, the books that you have read and personally recommend to marketeers or viewers that are watching us today.

[00:30:23] Can you share a few recommendations? 

[00:30:24] Charlie Windschill: Sure. You can probably see I’ve got this is one of three bookcases, I love. But let me think. So some of my favorite content sources for regular consumption. One, I actually love the Huberman Lab podcast. So he’s a professor of neurobiology at Stanford.

[00:30:45] He talks a lot about human performance and optimization, both physical but also mental performance. And he has a lot of content related to productivity and goal setting. And the neuroscience behind it. And I find it extremely valuable for managing a small resource constrained team.

[00:31:05] So I would say that’s one. And then another great resource, [The] Demand Curve. So I love everything that they do. They deliver really great newsletters. I’m also right now taking a course on brand building for growth. Very topical to my environment. But yeah they do great work as well. And yeah, I guess in terms of books, let’s see.

[00:31:35] Atomic Habits, I’ve come back to re-read that one recently. So it might be like a recency bias. But it’s a great one to come back to time and again. 

[00:31:47] Divyansh Shukla: Really great reads, and I’ll personally refer to few of them going forward.

[00:31:52] Thank you for an amazing session, Charlie. It was an insightful conversation. And we got a glimpse of how marketing works at Ortto. And, I’m sure personally attendees are going to take back a lot of sincere insights from this conversation. Thank you again. And, hopefully I’ll see you soon. 

[00:32:12] Charlie Windschill: Yes. Great. Thank you so much.


Charlie Windschill

Charlie Windschill

Director of Growth Marketing, Ortto

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