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Crafting the Future of Marketing: A Conversation with Autumne Peth

Head of Marketing at Sailes

In this episode of Wytpod, Harshit Gupta the Director of Business Alliances at Wytlabs speaks with Autumne Peth, the Head of Marketing at Sailes. Autumne shares her career journey from Sailes, revealing her passion for blending creativity with analytics. She discusses key milestones, including overcoming significant challenges and learning from both successes and mistakes. Autumne emphasizes the importance of authenticity and personalization in marketing, particularly how Sailes’ AI enhances human interactions rather than replacing them. She also addresses the balance between automation and the human touch, the role of community marketing, and the future of AI in sales and marketing. Autumne’s insights on customer feedback and agile strategy underscore the company’s commitment to staying responsive and effective in a rapidly evolving industry.

Sailes is a pioneering AI platform that enhances sales efficiency through authentic, personalized automation.

Autumne Peth
Head of Marketing at Sailes

Hello, everyone. Welcome to another episode of Wytpod. My name is Harshit Gupta, and I’m the Director of Business Alliances at Wytlabs. We are a digital agency specializing in SaaS and e-commerce SEO. I’ve got Autumne Peth with me today. She’s the Head of Marketing at Sailes, an authentic AI for basic sales on Autopilot. So big welcome to you, Autumne. So happy to have you with me today.

So happy to be here and good morning to you. It’s exciting. An exciting way to start my day.

Brilliant. Now, Autumne, can you please start with your journey in the field of marketing and what really led to your current role as head of marketing at Sailes?

I started my career in Sailes, actually. And while I enjoyed it and did fairly well, it just wasn’t my passion. And so ultimately, went into working at a really small agency and just have built my career over there, really found my passion in marketing. I love the creative side of marketing as well as the analytics. I’ve worked at a few different organizations, reaching in size from 8 people to 15,000 people. What led me to Sailes was my deep belief in the product and that I would be a customer of the sales platform, and I wanted to be a part of what they were building.

All right. And what are some of the key milestones in your career that really shaped your approach to marketing?

Yeah, I think I touched on that a little bit. That transition from sales to marketing for me was really critical. I made a decision to get my master’s degree and that was the path I wanted to take. Luckily, there was a small agency in Columbia, Maryland, called WayBetter Marketing, founded by two owners, and they were willing to take a chance on me, someone who had very little marketing experience, but they saw an opportunity, and they really taught me the ropes. I learned a little bit about everything. I think that was such a changing moment for me because I grew a love of writing emails, learning marketing, automation, campaign development, and the analytics side of things. I even learned a lot about making mistakes in marketing. I made a really big mistake on one of our big clients, and it’s one of those things that have always stuck with me. But they were just such a great organization, very great to learn from. And that really set me up for marketing leadership roles. And from there, I went into a few different leadership roles where I was able to build teams. I would say I was able to build a scale team at a few different organizations.

Those have been such key milestones for me, learning from each of those scaling experiences, whether it was building from a startup, building a new line of business, or going through different M&A activities. There’s always something to be learned. I would say most recently, a key milestone was working at RxBenefit, having one of the larger teams that I’ve ever been able to lead, but also working for a tremendous leader there who I feel helped to grow me so much in just three years. She is an incredible marketer and really creative, and I felt her skill sets really balanced mine and helped me to grow in areas that I was really defideficient.

Okay. What are some of the core values or messages that you aim to communicate through Sailes as marketing efforts?

Yeah, that’s one of the things I love about Sailes is that they are very differentiated in the market with their messaging. Really, it’s around three things. It’s authenticity, the digital labor, and being personality-driven. And so authenticity, it’s that AI that is really authentic. I think we see tons of AI companies popping up today. Are they trustworthy? Are they authentic? Are they credible? And that’s one thing that Sailes really has. They’ve been in the space for quite a long time since 2018. It’s really not a one-size-fits-all product. It’s focused on how AI enables us to be more human, to be more authentically ourselves. And it’s not about replacing that human element, which I think is really a great message and helps to differentiate us. The second one is digital labor. So Sailes bots, of course, deliver leads. I think that’s table stakes at this point in the space. But we take it even further with that fully autonomous delivery, the entire process from sourcing the data, enriching the data, creating the campaigns, and executing that digital labor every step along the way to offload some of those manual tasks from Sailes teams so they can focus on being more authentic and being more human.

And then I think the third part is that it’s personality-driven. It is unique to each person. And so I think we see a lot of bots on the market that are a singular bot that applies to every single salesperson. But sale bots are unique to each person. I actually launched my own sales bot last week for the first time, and it was really interesting to see how it will learn my personality and my way of speaking over time. And so the way my sales bot speaks is very different from what any other sales bot speaks. That is so unique and really interesting in the AI space, and it’s one of my favorite messages and stories we have to tell.

That’s amazing. What role does personalization play in Sailes’ approach to basically AI-driven prospecting? And how do you ensure that your campaign basically remains engaging?

Yeah. So obviously, your personalization is key to any campaign in prospecting and marketing. And so we do have all the personalization abilities, the different custom tags. But I think that’s where Sailes goes one step further with that personality-driven AI, in that it is truly not only personalized to the prospect and pulling in their information but it’s also personalized to the user. I’ve never used a marketing product or a sales product that personalizes it to me as the user and my style. And so I think that is where AI can take personalization even further than we ever imagined.

No, I agree. Any specific challenges that you have faced, specifically in your marketing, in this niche space of yours, and how did you overcome them?

Yeah, There’s always skepticism around change in technology. We’ve seen this play out several times. I think back to Y2K, and the whole world was in a frenzy around what was going to happen when the clock changed on New Year’s Eve. More recently, I think we’ve seen a lot of skepticism around self-driving cars and electric cars. So there’s always that fear of the unknown, that fear of change in technology. But what I think ultimately happens is that we need to communicate the value of technology and how it actually enables us to live better lives. There’s also that element we talked about before where there are new competitors and players in the space popping up. It feels daily to me. I’m sure it’s not daily, but they all have varying credibility and product efficacy. It’s really important for us to differentiate ourselves as more well-established. We’ve been in the space since 2018, really before the AI frenzy even started, and ensuring that we can lean on our proof points. We have great case studies. We’re not somebody who has only been in the space for two years. I think overcoming that skepticism, and establishing credibility is really important in a space that is ever evolving, really on a daily basis.

Got you. If you talk about the winning channels for you when it comes to your demand and lead altogether, what are those?

I recently joined the organization in 2024, and this year has been really tough. We’re in an election year in the United States. Media is very expensive. There’s also a lot of competing for people’s attention. And so figuring out what channels are going to be most effective for us and playing in those channels. And so we’ve had to get really agile in making tests, making quick decisions. That is one wonderful thing about working for a startup or a smaller organization is you have the autonomy to make very quick decisions when things aren’t working. One challenge, though, is it’s taking us a lot of touches. It takes a lot of touches in this space to reach the conversion. Last week, I was doing an analysis of some recent conversions, and for a few of the leads, it’s taking 40 to 60 impressions before they’re actually converting on the site. I know when you think about that cost per impression, that adds up over time, and that’s over a 45-day period and 3 to five website visits that they’re having each. It’s over three different platforms that we’re running ads. So it’s ensuring that we’re in the right places, that we’re diversified enough, that we’re hitting them that 50 times and keeping them coming back until they’re ready to make that decision.

Also ensuring that we have great educational content that’s high quality that makes them want to come back and eventually convert.

All right. And what channels have been fruitful for you to achieve these results? Is it your SEO is working well for the value or you’re leveraging more of the paid channels well?

When I started the organization, it was much heavier on paid channels as a proportion of total effort, I would say, we have done a really great job of starting to balance organic and paid. I think that’s more of a long-term strategy, ensuring that we are not only focused on the paid channels. That is a requirement as you’re building your brand, making sure that we are continually looking at those every week, which ones are making the most sense for us and bringing the most opportunity for us. If they’re not, let’s re-allocate some funds to a different channel, but also balance our time with building content, building organic channels, and really focusing on SEO. I think as we become more and more mature, ensuring organic is a healthy portion of our traffic is going to be incredibly important.

Yeah, for sure. Okay. And what matrix or KPIs do you prioritize when you’re existing? Basically, the success of your own marketing campaigns?

At our stage, we are really focused on getting our product and message in front of as many sales and marketing leaders as possible. Obviously, I’m constantly looking at demo requests. But as I mentioned before, organic growth is a % of our total traffic. Also, what do website conversions look like? How much of our traffic are we actually converting to leads? How many touches is it taking for us to get to a single conversion? What’s our cost per lead spend and how does that differ across channels? Those are all things that are really important for us. And understanding that we are using our marketing dollars in the right place to get maximum ROI. I think a lot of time marketers just go straight to paid channels. Let’s put as much money behind paid channels as we can and drive leads. But I think it’s really important that we’re balancing that and looking at not only where we’re putting our marketing spend as a KPI, but also our marketing time as a KPI because time is a resource just like our financial dollars.

Yeah, and how’s the churn rate at Sailes, and any specific strategies that you have in place to basically just have better customer retention?

Yeah, we have really strong customer retention. We recently hired a head of Client Success, and she has been really great in driving that. She’s been a really great partner to both sales and marketing in the organization. Really dedicated. We are a customer-first organization, very focused on our customers. And so when we look at our churn numbers, I feel really confident our customers are experiencing positive ROI. They’re getting really high-quality leads. And so we don’t experience aggressive churn. We don’t have very high churn because once someone’s here and they’ve built a platform out, it is highly tailored to their ICP. It is highly tailored to their value prop. And so they are now starting to see those leads come in regularly. There’s very strong ROI, not only from the digital labor but also from the leads that they’re getting into the pipeline.

All right. I would love to know, how you balance the need for automation as well as the human touch within your organization, specifically for your marketing operations.

Yeah. So human-AI collaboration is core to the Sailes message from a marketing standpoint and product standpoint. It’s also core to our philosophy as a company. We are a very people-first company, and I leverage AI and automation a lot in what we’re doing from a marketing standpoint, more so on the front end and ideation. We want to make sure that what we’re putting out is authentic. That’s the core of our brand. But using it to help with those idea starters, those initial outlines, and what types of topics are trending. I do see the future of us using it more for analytics around messaging, what messaging is performing better, and what content is performing better. But for today, It’s more of those early-stage discussions, and then we’re using our internal thought leadership to take it over the finish line.

I’m glad you mentioned thought leadership. How much do you prioritize that for your company? Who are the key speakers from the company and what events do you participate in, Would love to understand that process a bit.

I am a major advocate for thought leadership. I think it is one of the biggest things a company can lean on because your people and their expertise are really at the core of what the company does. One wonderful thing about Sailes is we were founded by a deeply experienced, very successful sales leader, Nick Smith, he built the product because he was a salesperson and he recognized this was a problem salespeople were facing, and he just wanted to solve it for himself. And so he is a wonderful thought leader. He has a deep expertise in the space. He’s been in the shoes of our customers and knows the problems they face. We also have very deep experience in our head of success and our head of sales teams, as well as our engineering teams. So more and more machine learning and our engineering experts, really understand the space deeply. Those are the people I lean on to better understand what we’re doing in the space and what our customers are facing. I would love to see us dive a little more deeply into thought leadership in the next few months. I think they have a lot to say, and they’re very compelling in some of their messaging.

All right. I believe that another brilliant strategy that most of them underrate is community marketing. I would love to know your opinion about it. If you are leveraging it, how do you do it?

I have leveraged community marketing in the past. I agree. I think it’s a great path, especially for thought leadership, creating and curating your own communities, but also getting involved in the communities that exist. I’m seeing a lot of activity in Reddit, and I’m seeing a lot of marketers really leaning into that. I also see a lot of signals that Reddit is leaning and investing more into its advertising platform. So I’ll be really interested to follow that in the upcoming months. That’s an area where it’s a very organic community, and it’s user-driven. Last week, I read an article, I believe it was in Forbes about social becoming the new search. And I think that’s what we’re seeing a lot with the LinkedIn community groups, the Reddit community. And we have done a little bit of testing around that. I think there’s an opportunity for us, but at ARC’s benefit, they actually had developed some really strong communities. And I think, especially where it’s a very niche market or a lot of expertise is needed in that space. There’s a lot of need for thought leaders who are willing to be vocal. I think sometimes people are hesitant to share their voices, but each person has a lot to say.

And if you’ve been in the space for a long time, Sharing your knowledge, sharing your information, and being a conversation starter is such a great way to build just your space and your industry. There are a few sales and marketing people I follow on LinkedIn, and I learn more from them in just following the communities they’ve built than I did in college or post-grad work.

I agree. How do you see the role of AI evolving in Sailes over the next five years?

I think at this point in Saile, we’ve mastered content development or content ideation in AI. I think that was the first phase. I think where we’re going to start to see marketers leaning more, and really sales teams leaning more into AI is predictive analytics, looking to do more modeling with AI, some of those elements. We also think around messaging, seeing what’s resonated in the space. Instead of going and doing messaging testing, which could be very costly, leaning on AI to do some of that initial testing messaging against each other, leveraging an AI model, and then going to market with which one, I would love to see an AI platform that can really help to leverage some of that, and I’d love to test it. Those are really some of the areas that I have found quite interesting. I think SearchGPT is going to really shake things up for everyone. Google has really had a stronghold on search. That has been what everyone has leaned on. I think SearchGPT has an opportunity to really disrupt the way we’ve done things. There was a lot of fear around AI when it first came out, and I think marketers quickly realized this is a beneficial tool for us.

I think SearchGPT is going to be the next thing that you are going to have to learn to maintain relevancy in this space.

No, I agree. The good thing is that now people have started to take things seriously as well because they see that there has been a massive shift in the way people search, more and more leveraging Gen AI as well. Generative engine optimization, that’s the new thing, basically. I’m sure a lot of marketing agencies, brands, and everyone learns about it. Although it’s early days, but still tons of tests running and just to figure out what factors are responsible for giving you that level of exposure, give you that visibility on AI-driven search engines altogether.

Completely agree. It’ll definitely be a game-changer. We’ll have to see how it plays out.

Yeah, I think that’s the biggest shift that’s happening. How do you plan to adopt Sailes’ marketing strategy to stay ahead of industry changes and basically continue driving more growth to the company?

Yeah, I’m in a very great position in that we have a lot of autonomy in our organization. There’s a lot of trust. I think Nick has done a great job of hiring leaders that he can trust. So we have the ability to be very agile and scrappy. That means we can revisit our strategy every couple of weeks, every month if we have to. And so what I plan to continue to do is look at what’s working and what’s not and adapt to the competition in the space, adapt to how things are shifting the demands of our audience. What I really lean heavily on is what are we hearing from our customers and what are we hearing from our prospects. That’s really what’s going to guide where we go. We’ve got to be customer-led because that is who really feeds us. That’s who we’re here to serve. That is how I plan to continue to adapt, is really staying close to that customer, hearing what they need, hearing what they’re looking for, and making sure we’re meeting them in the spaces where they are.

Okay. And since autumne, you mentioned that hearing your customer is something which is vital for you. What does it look like? What checkpoints do you have within your site, within your platform, so that there’s a good feedback loop all together for you and you’re taking action on two things that your customers want?

So we have a very high-touch customer success model. Each customer gets a dedicated customer success manager. We get a lot of feedback from that team. So they’re passing along everything they’re hearing from customers directly to the sales and marketing teams, to our product teams, so that we can all react very quickly on behalf of our customers. We’re also doing other things, G2 reviews, MPS scores, and collecting those more analytical quantitative touchpoints. But it’s really about having a customer council, hearing from our customers, listening to phone conversations so that I’m hearing directly from them. What are the types of things they’re looking for? What are their pain points or what are their pain points that they perceive to have? And so how can our product continue to meet that for them?

Alright, Autumne. We’re coming to an end now, and I would love to have a quick rapid-fire with you. Are you ready for that?

Okay, yeah, I think so.

What’s your last-gen AI prompt

Oh, my last Gen AI prompt was probably a Lemonade recipe because my daughter is having a lemonade bar at her upcoming birthday party. So I think I said Taylor Swift. What are some Taylor Swift-themed Lemonades?

Okay.

Not marketing related.

This is actually a crazy video that I think ASAP Rocky launched. It’s called Taylor Swift. I think That’s the most bizarre video I’ve ever seen, basically.

We’ll have to look at it because we’re gearing up for a big Taylor Swift event.

It has got nothing to do with Taylor Swift. The name of the song is Taylor Swift. Yeah. All right. If you have an unlimited budget for one campaign, what would you do with it?

I would find an amazing spokesperson and do a really interesting video push to some of our top targets, or have them maybe visit some of our top targets in their office and do a pop-up event for them.

That’s amazing. What’s the most unexpected lesson that you have learned from a field campaign?

The most unexpected lesson was I forgot to reset the space when I was testing a campaign, so I set the triggers to all be one minute apart. My entire list received a six-month campaign in 30 minutes, and the response rate was way beyond any campaign we’d ever had because everyone responded that they had received so many messages. We were actually able to get more opportunities out of that campaign than we’ve ever had, which was pretty exciting and unexpected.

It’s amazing. What’s the most bizarre marketing campaign that you have never seen work relatively?

Most bizarre that I’ve ever seen work. Referring back to my last Arks Benefits, Kiera Hagen, an organization she worked at, had mailed trees in these glass capsules. It was something about growth and growing with you. The trees all broke in the mail processing. And so everyone had received these trees that had crumbled. Again, great response rate because everyone called to say that their trees were broken. But I thought that was a really neat thing to do send something that could be planted. You don’t think about when you receive something in the mail, a living thing, or something that can be grown. I thought that was a really neat and interesting take.

All right. Now, going to our very last question. If you could use only one social media for the rest of your life, and this is for your personal use, nothing that’s related, which would it be?

No questions asked, TikTok. I absolutely love TikTok, and I think we are going to see it continue to grow. I think we’re seeing the demographic shift on it, and we’re seeing a lot more B2B activity, and I’m excited to see where that heads.

All right. Thank you so much, Autumne. We really enjoyed this conversation. Thank you for taking the time out for this and sharing your experience with us today. Really appreciate it.

It was great talking to you and a great way to start my day.

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