[SaaS Series] Creating Happier Workplaces Through AI With Taylor Halliday

Taylor Halliday is the Co-founder and CEO of Ravenna, an AI-powered helpdesk software company that simplifies IT support and internal operations for organizations. Under his leadership, Ravenna raised $15 million in funding from Madrona Venture Group and Khosla Ventures, gaining recognition for its innovative Slack-native platform that streamlines support for IT, HR, and revenue operations teams. Before founding Ravenna, Tylor served as Director of AI Engineering and New Products at Zapier and also completed a fellowship at Y Combinator, experiences that brought both technical depth and startup expertise to the company. 

Here’s a glimpse of what you’ll learn:

• [4:01] Why Taylor Halliday believes AI is transforming internal support through Slack integration
• [7:04] Two major ways Ravenna automates workplace operations
• [11:18] How Ravenna delivers precise answers with the data you choose
• [13:56] Why IT is the launchpad for next-gen help desk innovation
• [16:00] Ravenna’s secret to expanding beyond IT into new teams
• [17:42] Inside story of landing Ravenna’s very first customer
• [21:59] Crucial customer feedback that shaped Ravenna’s analytics
• [27:42] Lessons learned at Y Combinator: focus, humility, and defining your customer
• [34:36] How Taylor’s time at Zapier shaped Ravenna’s internal automation vision
• [44:54] How life changes and family support drive founder decisions

In this episode…

Internal operations often struggle to keep pace with modern technology. Companies are buried in employee requests, scattered knowledge bases, and clunky help desk systems. What if AI could bring clarity and automation to that chaos — transforming Slack and other team platforms into true hubs of support?

Taylor Halliday has helped shape the future of workplace operations by drawing on experience at Zapier, along with a fellowship at Y Combinator. He brings a blend of technical expertise and startup leadership to solving the challenges of modern internal support. Known for a customer-led approach to product development, Taylor focuses on intuitive design, automation, and data-driven decision-making that enable organizations to scale more effectively. His work highlights how the right mix of AI and human insight can transform team efficiency and build stronger, more resilient companies.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Taylor Halliday, Co-founder and CEO of Ravenna, to discuss how Ravenna is reinventing internal support, co-founder dynamics, the role of customer feedback, and key decisions behind growth and fundraising. Taylor also shares stories on winning early customers and why trust and speed are vital in client relationships.

Resources mentioned in this episode:

• Taylor Halliday on LinkedIn
• Ravenna
• Y Combinator
• Kevin Coleman on LinkedIn

Special Mentions:

• John Waldman on LinkedIn
• Gavin Zuchlinski on LinkedIn
• Acuity Scheduling

Related episodes:

• “Automation Solutions with Wade Foster Founder of Zapier” on Inspired Insider Podcast
• “[Venture Capital Series] Triaging Growth Challenges in Startups With Brett Browman” on Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on Inspired Insider Podcast
• “[SaaS Series] Tips To Thrive in the SaaS Space With Sujan Patel” on Inspired Insider Podcast

Quotable moments:

• “Whatever the customers say is the golden path.”
• “Ravenna becomes the front door to your internal operations.”
• “None of us are as smart as we think we are — especially when building products.”
• “Slack gives us years of request data to jumpstart AI automation.”
• “Speed is the only advantage startups have over incumbents — use it.”

Action steps:

1. Automate internal requests through Slack: Integrate an AI help desk like Ravenna directly into team chat tools. This meets users where they already work, making support faster and more intuitive.
2. Segment support into knowledge vs. action: Separate questions that require simple answers from those that trigger workflows. This distinction helps optimize AI support and eliminate unnecessary human involvement.
3. Invest in internal analytics: Make it easy for IT and HR teams to prove their value with built-in reporting and insights. This transparency helps secure the budget and improve performance evaluations.
4. Start with IT for internal tooling rollout: IT teams are typically gatekeepers and well-positioned to vet and deploy support tools. Starting with them provides a smoother expansion path to other departments.
5. Prioritize user feedback over assumptions: Use customer interviews and behavior data to guide product features. Continuous feedback loops create tools that solve real pain points and accelerate adoption.

Episode Transcript

Intro 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz 00:22

Dr. Jeremy Weisz here Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Taylor Halliday of Ravenna. You can check them out at Ravenna.ai. And Taylor, before I formally introduce you, I always like to point out other episodes of the podcast people should check out, since this is part of the Top Software Series. We had the Co-founder of Zapier who Taylor knows well, Wade Foster, and just amazing what they’ve done and how they’ve grown throughout the years. So you can check this episode. I had Brett Browman who is the Growth Operating Partner at Khosla Ventures, who also invested in Ravenna. And I know Taylor knows Brett too. That’s also a great episode on just growth and growth in SaaS companies. 

Some of the other ones. The Co-founder of Pipedrive when I had him on, they were, I think 10,000 customers. Now I think they have over 100,000 customers. So but it’s always a rocky journey, Taylor as you know. So even now it looks easy or whatever. From the outside it was definitely there were a lot of ups and downs. It’s interesting to hear that. And then I, the Founder of Mailshake on. Check out more at InspiredInsider.com. 

This episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships. We do that in a few ways. One. We’re an easy button for a company to launch and run a podcast. We do the strategy, accountability, and the full execution and production. We actually get people on podcasts so they can, you know, have their authority on various shows across the internet. And then number three is we are an easy button for a company’s corporate gifting. So we make gifting and staying top of mind to your clients, partners and prospects. 

Simple and easy and actually affordable. So you send us the addresses. We do everything else and actually send a campaign of 3 to 4 gifts a year for 3 to 4 years. So, Taylor, we kind of call ourselves the magic elves that run in the background to make it stress free and possible for companies to build amazing relationships. You know, for me, the number one thing in my life is relationships, and I’m always looking at ways how I can give to my best relationships. 

I personally have found no better way over the past decade to profile the people and the companies I most admire, and also send them sweet treats in the mail. So if you’ve thought about doing any of those things, go to Rise25.com or email us at [email protected]. I am super excited to introduce Taylor Halliday, Co-founder of Ravenna with Kevin Coleman. Before Ravenna, Taylor was a Director of AI and new products at Zapier. 

I think Kevin describes you as a technical genius, from what I’ve heard on the internet, and Kevin previously actually worked for Amazon Web Services. And they also completed a fellowship at Y Combinator. And Ravenna raised $15 million from companies like Madrona Venture Group and Khosla Ventures. And Ravenna is an AI solution that provides smarter support and happier employees through an AI enabled help desk. So basically, what they do is they provide internal support that starts in Slack and resolves with AI and intelligent workflows. So Taylor, thanks for joining me.

Taylor Halliday 03:43

Hey, Jeremy, thanks for having me on.

Dr. Jeremy Weisz 03:45

That’s Kevin’s words, not mine. So I’m just saying.

Taylor Halliday 03:48

Flattery is a game now. Yeah. I appreciate that.

Dr. Jeremy Weisz 03:52

So just tell people about Ravenna and what you do. And when you’re doing that, I’m going to pull up your website so we can share that too.

Taylor Halliday 04:01

Cool. I mean, you did a pretty good tee up on the basis of it. You can think about it as like the IT help desk, the HR help desk, like pretty much operations roles at large companies, you know, at a certain size have the need to have some software to support their colleagues, their internal employees. And as I just mentioned, you did too. The most prevalent form of that typically is like the IT help desk and HR help desk, what have you.

And so at Ravenna, we’ve decided that basically a lot of the incumbents in this space weren’t making the best use of what we call it like modern AI technology. And on top of that too, if you look at a lot of the incumbents in the space, I would just, I don’t know, go on a limb to say that the software experience is called lackluster. And so we really want to come in here and provide an absolutely just unmatched experience, both from a product design UX and also from an automation angle. So we go ahead and partner with IT groups predominantly. Although we have, we are working with some HR teams and revenue ops teams. 

And we’ll go through there and be the software that really is kind of the front door, if you will, for their operations at large at the company. So if you, you know, work at a company and have an IT help desk or an HR help desk, you can imagine that Ravenna effectively is a software that you’ll interface with when you reach out for assistance, for help and and I realise it. That could be something like a software access request in the realm of HR that could be, you know, a benefits question and revenue officers that have a myriad of a lot of questions around enablement for a lot of sales teams. And so and I’m just actually kind of, you know, really looking at our site, one of the kind of big things I think that we really focus on, and this is purely just like from a lot of customer interviews before we even wrote any code. Was that feedback from a lot of it? 

HR call operations professionals said that a lot of the existing solutions just did not integrate well with where people work, and where people work effectively. Is a team chat based application. And so slack is the one that we’re just, you know, doubling down on super hard. The idea is that, like I said before, we want to create an incredible experience for, you know, the employees of the organization with the software. And we have a very, very keen belief that the best experience here is just natively integrated with the team chat integration like none other. And so it’s Ravenna.

Dr. Jeremy Weisz 06:25

Yeah. And what’s interesting is you kind of what I like about the site and what you do is you kind of look at user behavior and you don’t want to go around what user behavior is. Right. You’re like, they’re already in slack. They’re already sending messages.

They’re already answering questions. How do we basically organize it? Right. And so you can see here it’s like turning slack chaos into clarity. So what are some. I don’t know. Use cases. Right. We’re looking at obviously they can turn these slack messages into tickets. I know, like SOPs. What are some things you have seen use cases for Ravenna?

Taylor Halliday 07:04

Sure. And actually, before I touch on that, I want to just kind of double down on something that you kind of subtly, you know, just kind of talked over for a second. But one of the fun things about working in this company and being so tied in to slack. From a person who, you know, spends a lot of time thinking about how you automate things? You know, I’m a Zapier person.

We just talked about that. It’d be a popular call right now, I always say automation. It’s effectively, in my opinion, kind of what really the value prop AI really is at the end of the day. But a lot of times if you’re starting, let’s say, an AI company, you’re, you know, faced with a cold start problem, right? Like you have this great solution, you have some great tech, an algorithm, what have you. 

And then when I say cold start in the sense of like often, more often than not. A lot of times, you know, these companies are faced with like, I just need more data, more instances to actually kind of refine do evals, what have you on the different things that we’re trying to go ahead and fine tune one of like the just fun things about basically this market is and then we get dropped into people slacks and we’ll have more often than not, you know, years of just requests, interactions. We know based upon being plugged into what people are asking, how they’ve asked for it. We know about the lingo of the company, the funny acronyms, all that type of stuff. And so call it. 

You mentioned the data of slack. I just wanted to double tap on that because it really is such a powerful thing to actually just be able to kind of start with effectively. So anyways, to answer your question, what do you automate here? Like what are we doing here? So when we talk about automating for the operations roles you can, this is a big generalization. 

And this changes per customer. You can think about basically the types of automations are kind of split in two like bifurcate roughly. So if you were to look at let’s say an average IT help desk channel inside of slack. Sometimes they’re called a help desk or an HR help desk, what do you have? The nature of the questions can be kind of roughly divided into like one group is like this. 

Hey, I have a question. And the answer to that question is just written somewhere. Okay. Classically it might be written down in a knowledge base. KB more interestingly it could be in slack, it could be in past tickets. There’s a lot of different things that you could go ahead and draw on to actually try to figure out from an automation standpoint, this person’s asking a question. There is knowledge somewhere in this organization. And so it’s our job at Ravenna to go ahead, find all the relevant pieces, rank them appropriately, and figure out what is the best way to answer this question based upon preexisting knowledge. 

And so that’s half of, I’d say, the stuff that we automate in these channels. The other half of it has to do more of, I’d say, interesting things like actions. Okay. And so this is kind of a funny, contrived example rather than like, you know, the I don’t know the policy for taking time off. You know, I want to take time off now or sorry in a week now or whatever. Right. I guess what I’m trying to, you know, illustrate here is that, like, there’s a difference between asking a question where the answer for that is just something that’s written down versus something that needs to be taken an action upon. 

And so the other half of the stuff that we do here is we help act upon basically those requests. And so what that does is it relieves the need for a human to either kind of look in their knowledge base and find that that question to that answer, or b go into the system of record or what have you, and other things that they just don’t have the employees don’t have access to due to a myriad of either security licensing or whatever concerns Ravenna can I can sit there and just take a lot of folks out of the equation for a lot of these kind of like, you know, rote questions that just don’t need human involvement.

Dr. Jeremy Weisz 10:32

Talk about. And I think you it looks like you integrate, obviously it starts in slack, but you can pull in your I can analyze people, connect other applications they used to.

Taylor Halliday 10:44

Absolutely. That’s a cross section right there. We do much more than that. But absolutely it’s it’s everything we do here is frankly customer led. And so we have to connect to quite a few systems at this point. It’s all just based upon customer feedback. Confluence isn’t listed there. A handful of others aren’t either, but Google Drive, what have you.

Dr. Jeremy Weisz 11:05

So basically, if someone asks a question and it’s, they just connect their Google Drive or their notion into there, and then it kind of just draws from all of the collective knowledge of those places to answer it.

Taylor Halliday 11:18

Sort of. So there’s an approach here that I think is worth calling out in how we kind of think about this. And it’s a little different than I think a lot of popularized enterprise search products. So if you’ve ever heard of a product called glean and there’s a, there’s a bunch of them like glean, but glean is very much like a horizontal enterprise search. The value proposition there roughly is like, hey, you give us everything we got and we’re going to suck through all that type of stuff and we’re going to, you know, present it back to the entire company.

It’s a very peanut butter spread approach where, like, we’re just going to grab everything that’s ever been written and like, give it to all the employees, and then we’re going to create a better experience there. And I’m sure they have a better pitch than what I just gave. But regardless, the way we think about it honestly is I said before, like, we have three folks predominantly we work with, we do work with some other groups, but like it HR, revenue ops inside our product, we go ahead and basically create a UX where, yes, we integrate with these things, but we’ve just gotten a lot of feedback around like, look, the problem about these enterprise wide search stuff is they’re they’re pulling up stuff that, yeah, it might have a keyword that overlaps or something like that, but it’s not really relevant. There’s so much stuff out there and like the universe of company documentation and data. And so what I’m trying to say is that we go kind of the extra mile to, from a user experience standpoint, to let you be really precise about what data it is you want inside that realm of your IT help desk or your HR help desk, right? 

And furthermore, we just really, really try extremely hard to make sure that we are never answering a question that you don’t explicitly like to give us data for, right? So if you ask us who the 40 niners are and you didn’t tell us who the 40 niners were, despite the fact these models absolutely know who the 40 Niners are or what city they came from, we won’t answer it. So anyway, it’s just a subtle yet like I think very, very important distinction because it has actually been pretty much kind of like the yes on a lot of different purchases being like we have had enterprise wide things. It’s been good or okay, but it hasn’t been able to kind of really get down into the nitty gritty of the details that we get asked for these help desks in a way that we, you know, basically think that we win here effectively is just making it really explicit about the data that comes into play, that the data that’s allowed inside of these channels.

Dr. Jeremy Weisz 13:32

Taylor, I want to learn more about the niche. Obviously, anyone who uses slack and wants to have a better, you know, support their employees and make it easier, faster, more intelligent can use this. But talk about why IT is a big component. I know you help HR and revenue ops. Why focus on IT as a niche?

Taylor Halliday 13:56

Good question. And you know, part of it is I’ll just say there are several reasons here. And so classically, if you were to look up like what is this help desk market? Okay. And even when I first started looking at it, it wasn’t super clear to me kind of what the larger market here was. It’s a long standing market. It’s called ITSM okay. Giveaway. It’s half the acronym. So this software has not just been around recently. 

It’s been very much a thing since, you know, basically, you know, I don’t know since air operations groups have pretty much decided that they need software to make their lives easier. Okay. And so it has typically been the entry point for a lot of these types of purchases and sales. I think there are a few reasons why. One is that this is basically software that can span across operations groups more often than not, especially if you call it in the enterprise to mid-market to upper mid-market. It is kind of the gatekeeper for a lot of those types of software purchases. Okay. And so, you know, had it come to be exactly. There might have been a little bit more, hey, someone’s smart. The buyers can be. 

It might as well put them in the acronym. That’s part of it. And then the other part as well I would say that, you know, it especially is very, very close typically to the team chat applications and the control mechanisms there. You know, it’s the folks who allow and who really take pride in making sure that they’re, you know, writing or letting the right applications inside there. And then just furthermore, they also just have a myriad of requests and questions that come across their desk, which are highly automatable, frankly speaking. So perhaps that’s the most important one. But there’s a bit of kind of retro reasons and there’s a bit of just kind of current current affairs.

Dr. Jeremy Weisz: 15:38

No, that makes sense. I mean, it seems like it, even across lots of industries are the decision makers, gatekeepers, and everything flows through them. And if you can make their job easier, better for the organization, then you can, you know, essentially, you know, kind of go across different markets. And in the end, too.

Taylor Halliday 16:00

There’s another I will say one more thing too, is that, you know, one of the one of the things that’s exciting about this, this, this market, which I always kind of hoped would become true, and it really is proven to become true as we’ve, you know, gone to market more. It’s not just the IT help desk. I’ve already said HR revenue ops. Right. But what’s been happening is we’ll go through and start working with a team.

It predominantly, but it can kind of start anywhere and we just get inbound like, wait a minute. I put in an IT help desk request, I work and name it Marketing ops, right? We have an operations desk. Like, where did the software come from? There’s a lot of visibility that you get just by being in someone’s slack, which is great from an expansion standpoint. 

Then it goes back to your IT question about the glide path of expansion going from it. Who’s already blessed the software to a marketing group or two different HR groups? That’s very easy. It’s much easier. I would just say glide path rather than like we started with revenue ops. They just kind of okayed it in there and then it goes to it. Then you’re going to go through a lot more different reviews and what have you. So again, there’s just kind of some, I don’t know.

Dr. Jeremy Weisz 17:03

Like frictionless I guess.

Taylor Halliday 17:05

Yeah, that’s a good way of thinking about it. But that’s definitely a component of why we also, to be clear too, we’re always looking just for a front door in the organization. We have a strong belief, like I said, that once you get in there, you can show great value and efficiency and it’s going faster. It’s going to expand. But the better glide path is typically to start with it.