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S3 Ep03 Leadership Lessons: Kyle Racki on Managing Growth, Layoffs and Company Culture image

S3 Ep03 Leadership Lessons: Kyle Racki on Managing Growth, Layoffs and Company Culture

S3 E3 · Dial it in
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In this episode of Dial It In, Trygve Olsen and Dave Meyer have a conversation with Kyle Racki, the CEO and co-founder of Proposify. They explore various themes including the importance of the fourth quarter for business optimization, Proposify’s integrated CRM features, and the benefits of machine learning for proposal management. Kyle reveals Proposify’s journey from idea to a leading SaaS company, emphasizing the value of exceptional customer support and the introduction of Proposify Automations. The episode also covers challenges like technical debt and layoffs, alongside insights on predictive AI, automation in business operations, and maintaining brand consistency. The conversation underlines the importance of a hands-on approach and a collaborative culture in driving the company’s innovative strategies.
State of Proposals

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Proposify
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Dial It In Podcast is where we gathered our favorite people together to share their advice on how to drive revenue, through storytelling and without the boring sales jargon. Our primary focus is marketing and sales for manufacturing and B2B service businesses, but we’ll cover topics across the entire spectrum of business. This isn’t a deep, naval-gazing show… we like to have lively chats that are fun, and full of useful insights. Brought to you by BizzyWeb.

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Website: dialitinpodcast.com
BizzyWeb site: bizzyweb.com
Connect with Dave Meyer
Connect with Trygve Olsen

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Transcript

Introduction to Dial It In Podcast

00:00:08
Speaker
Welcome to Dial It In, a podcast where we talk to fascinating people about marketing, sales, process improvements, and tricks that they use to grow their businesses. Join me, Dave Meyer, and Trigby Olson of PhysiWeb as we bring you interviews on how the best in their fields are dialing it in for their organizations. Let's ring up another episode.
00:00:30
Speaker
Well, I'm in much, but Dave, are you like being held against your will and some wooden cabin in the North

Seasonal Settings and Urgency in Business

00:00:36
Speaker
woods? or sure I sure am at our recording. It's the last weekend in September and it's boats out weekend. So I'm up in the cabin and it's the saddest weekend of the year. Yeah. Are the colors changing? Is everybody getting ready? Yeah. Yeah. Just a little bit. Although it's a weird one with all of the weather. And so it's going to be 81 this weekend. It's very different than normal.
00:01:00
Speaker
Well, you know, we experienced season in our business too. And one of the things that we've grown accustomed to is that once the fourth quarter hits, everybody starts to panic and realizes they have to get really good about selling and marketing. Absolutely. And they have to do it right now. So I'm excited for our our guests today. But before we get to that, we do need to to read our sponsorship. Do you have your copy ready?
00:01:23
Speaker
I sure do. I think we're ready.

Sponsorship Ad: Globex Corporation

00:01:25
Speaker
All right. Well, listeners, today's episode is brought to you by the Globex Corporation. You know, the company that's always one step ahead of world domination. Oh, i I'm sorry. I mean world innovation. That's right. And who could forget their charismatic CEO, Hank Scorpio, the man who redefined hostile takeover and made flamethrowers a casual Friday accessory.
00:01:47
Speaker
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00:02:13
Speaker
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00:02:41
Speaker
So we over clubbed on guests, one of the more major tools that we use at PizziWeb. We actually cajoled the CEO to finally come on the podcast.

Introducing Kyle Raki

00:02:50
Speaker
So our guest today is Kyle Raki from Proposify. He's the CEO and co-founder with a background in design and entrepreneurship. He's known for his focused on innovation and strong company culture.
00:03:05
Speaker
Kyle has led his team through key transformations, keeping them ahead in the SaaS industry, passionate about continuous growth. He shares his insights on leadership and entrepreneurship as a speaker and an author, and sends me cold outreach on LinkedIn when I asked for it. Hey, I don't know who wrote that bio, but i it makes me sound really good. So thank you. thank you for coming Well, we have robots for that basically. So.
00:03:30
Speaker
they Thanks

State of Proposals Report

00:03:31
Speaker
for coming on the show. I think one of the things that I, I've been a long time fan of Proposify and it's been a game changer for me, but I want to, before we get to that, I want to talk about one of the, the important things that Proposify does, which I think is a, it's a differentiator. So what is the state of proposals report? So, you know, I, this was, we kind of stole this from.
00:03:55
Speaker
now every B2B SaaS company out there, but ah particularly social media companies that used to do this a lot where every year they'd publish like their state of social media and they would share all the benchmarks and trends. And ah we kind of looked at it and said, you know, proposals are kind of a black box, right? Like nobody really knows what their competitors are sending. Everybody's using like Word and PowerPoint and these types of tools. So it's typically very hard to get access to this type of data. Like what do people actually include in their proposals?
00:04:23
Speaker
And we thought, well, why don't we just analyze our own database and share those things with people, you know, share it as a lead magnet, share it with customers. um And this year we did it a little different differently. We used to just have a human go and analyze the data. There's only so much that they can manually look at. This year we we built some machine learning models and started to feed the data to machine learning and be able to analyze text and group related terms together and that kind of thing. So this year it's a little bit different.
00:04:53
Speaker
ah where we go to We're able to go that one layer deeper in terms of analyzing ah proposal content. What were some results of the that you found that were interesting? Yeah, I mean, there's there's a few things. um I think just in terms of being able to group related industries together and being able to sort of slice the data in terms of, okay, these companies are really similar to each other.
00:05:18
Speaker
um you you know view by by deal size, by industry, by location. like So really being able to profile the types of companies and the types of content that they're creating was

Proposify Software Platform

00:05:30
Speaker
was helpful. So if you look at if you go to Stata Proposals, you can just access it for free. You don't need to sign up to anything.
00:05:36
Speaker
you can see like how how does close rate breakdown by certain segments, for example, or by deal size. One of the interesting things was like even just being able to see who's actually including videos in their proposals. We found that it was only 20% across the board of companies that actually use videos in their proposals, and you would think marketing would be number one. It was actually towards the end. It was one of the you know the the lowest Um, amounts of companies are using videos and their proposals. Wow. Cause that's something that I do on a regular basis. Just ah all the time. Cause the tool is is so dynamic. So let's back up a step for those of you who aren't massive fanboys, like I am. What, what is Proposify and what does it do? So Proposify is a software platform that essentially helps teams be able to send out
00:06:26
Speaker
professional on-brand proposals more quickly and easily and gather metrics and information on how their buyers are interacting with their with their documents. And in particular, we really focus on helping growing teams that need to get more control and consistency with their documents. Cause we see a lot of, a lot of times when a business is scaling, sales reps are kind of just winging it and putting out whatever's out there, copying and pasting from old emails. So a lot of leaders need to get more control and visibility into what's actually going out in front of buyers.
00:06:56
Speaker
I think one of the things that we love most about Proposify is the fact that it integrates seamlessly with our ah CRM of choice HubSpot. And so you can set up specific, what do we call them? Hooks for for lack of a better term, right? Where it pulls in the data from your contact records. So you can actually spin up a proposal.
00:07:19
Speaker
put it in the right template and it'll fill out all of the details if you've done a good job as a salesperson and put it all into a recognizable doc. And the other thing that Proposify does that is super important is the ability to collect signatures that are legally binding.
00:07:36
Speaker
So how did, how did all of that stuff work together or how did you come up with the idea to really build

Origin of Proposify

00:07:42
Speaker
this? Because it's, it seems obvious now, but I think back when Proposify was started, it was not necessarily a no brainer to set it up the way you guys, you know, I think maybe we all get one idea in our life that we go, wow, why doesn't this exist? Why is nobody doing that? Um, so I've used up my idea for my whole life now and it was Proposify.
00:08:05
Speaker
ah I was like 22, I think. I was ah like a young designer working in an agency and they had me putting out proposals, or one in particular for this big contract we were going after, and so they wanted me to pretty up the the proposal. I think I either did it in Quark Express or InDesign.
00:08:22
Speaker
But I was just getting fed all these Word documents from account managers. And half an ago, we we didn't have like Dropbox at the time. that's um I think we might all be in the same age group. There was no Dropbox back then. So you know I was going to like find CDs on and like a wall where we saved all of our case study files.
00:08:41
Speaker
So I was just thinking, man, this is really stupid. Like, why don't we have a tool to make this easier? And I think a Basecamp had just come out around that time. So basically it was just like, there should be Basecamp for proposals. And that was just a thought that I just sat on for a little while. And then one day I was just kind of like wire framing it up in my basement and thought like, yeah that'd be a cool little sass app. like Like an InDesign meets whatever CRM.
00:09:04
Speaker
But then I just sat on it for years. I started my first business, which was an agency business and it really wasn't until 2014 that we actually got going and found product market fit and all that kind of stuff. So now we just celebrated our 10 year anniversary this summer. ah We've been in business for 10 years and yeah, like I said, this is ah this is the once in a lifetime idea that you just go like, wow, this this thing needs to exist.
00:09:30
Speaker
I think one of the things that I really like about Proposify is really not a thing to do with the software. I mean, the software is great, and there's a lot of identifying features that I think make it better than the competition. um People, if you're you're interested, you talk to

Proposify Customer Service Approach

00:09:46
Speaker
me about that offline. But one of the things that as I got used to and becoming proficient in using it, one of the things that I found is the people who were helping me get up and running were ah oddly really nice and frank in talking with them. And they would say, they wouldn't give me the standard customer service answers where they would repeat my question. And then now they'd say, well, you know they would very kindly explain to me what I did wrong and then how I would do it better. And I found that extremely helpful. And I got really good at the software as a result of that, because people would actually just say, here's what you did wrong. Here's what you needed better.
00:10:27
Speaker
was that a Was that a cultural choice to treat customers that way? Cause I think that's a massive difference that I really don't see in any other company that I work. I would say it was a really early choice to over-index on customer service. So I remember when we were just like we had a product, but it was very early stage and we didn't have a lot of customers. like I would be up till midnight and helping customers, jumping on calls and that kind of thing. um It was really just coming from a place of insecurity. I thought like there's no way this business is ever going to work, so I need to really just
00:11:00
Speaker
uh, try extra hard to make sure people are, are successful. So I always really just wanted to offer the best support, uh, the kind of support I would want. And then once we were able to hire reps, like I was able to just kind of like, they were able to see what I was doing where I was like using animated gifts to joke around with customers and that kind of thing. You know, we weren't using a lot of pre-canned replies.
00:11:24
Speaker
And I was just lucky enough that we hired good people in the early days. Mel Gunn was, I think, number three support person who who we hired. And Chanel was our director of customer success. So, you know, getting those people early who kind of like are like, yeah, this is the kind of support I want to offer to you. And then they just took it and 10xed it. Like, I haven't really done support for years, almost a decade at this point, but that whole department just kind of runs on its own without me. So I would say that they've kind of taken the the early stuff that I started and just made it a lot better. That's amazing. One of the things that I'm always constantly and in awe of is anybody who runs a company like yours or any software platform. I think you, there's a tendency to be constantly inundated with customers who have a bad case of the Abbott's. Well, this is great. supposed but
00:12:22
Speaker
Yeah. Or, or, or the cancer just by the way, that was a really smart reference to the Hank, the Hank Scorpio episode that you referenced earlier. Thank you. Thank you. Appreciate that.
00:12:34
Speaker
um Not everybody gets my deep Albert Brooks 35 year animated humor. That's why you and I are buddies kind of I Have a whole mess of questions, but that's top of mind. That's one of the things that I always struggle with How do you how do you guys work with that as you're continually trying to improve your process? Well, I mean, I have to be really kind of frank and honest here and say that I think while we were an early innovator with our product, um we we really kind of lagged behind the competition in a lot of ways when it came to
00:13:08
Speaker
evolving the product the last like five, six years. Some of that was just internal company BS, if you will. um But I think we're so we're in a place now where we're starting to hit our yeah our stride. So I would say that probably what really helped for a long time has been the quality of the customer support.
00:13:29
Speaker
That's one of those areas where I'm able to look at our competition and say like, yeah, no I don't think anybody can offer the same level of support that we do. But that can be a little bit of a crutch sometimes too, right? Where they're going like, we know the product hasn't changed. It hasn't really, we haven't added a lot of new stuff. We haven't fixed certain longstanding issues. So the support team got really good at, you know, bubble gum and duct tape to like make things work.
00:13:52
Speaker
um And that's something that I've been a lot closer to the product in the last couple of years, and we're starting to make real headway with it, where we're now able to actually capture customer feedback and do something about it. um I'll share in a little bit kind of what that that new big feature that we're launching is, but I think Being able to listen to customers and be able to do something about it is is a really it's it's a key part of it. We weren't able to do that for a long time. We could listen and empathize and come up with a hacky workaround, but now we're able to actually make moves with the product. Got it.
00:14:28
Speaker
So what what is the big the next big thing? At the time of this recording, so it might be out by the time this this airs, but this would be the first podcast that I've

New Automation Feature in Proposify

00:14:36
Speaker
announced this on. We're launching a new features called Proposify automations. And essentially what it is, is everybody has a different way that they want their workflow to be set up within Proposify. So they might say like, Hey, when this thing happens over here, I want to notify these people in Slack and update this part of my CRM and do all this kind of stuff.
00:14:55
Speaker
Essentially, it's like if you've if you've used tools like Zapier to kind of create if this, then that type of automations, you can do it all in Proposify now without Zapier. So you can create automations within Proposify and you can also create automations that speak to third-party applications. There's a library of, I think, 100 plus different connectors. So tools that we didn't integrate with before,
00:15:19
Speaker
um Stuff like Microsoft Dynamics, Slack, Teams, Dropbox, all of these tools are now able to build custom connectors with. but like france Yeah, I love it. And I would imagine that that's not just a slice in time kind of addition, that's UI that has to be built and an entire integration or interaction set so that people can build those automations.
00:15:46
Speaker
How do you go about setting us setting up a massive addition like this to a company? Like you have tens of thousands of customers. How do how do you roll that out without crashing everything? Well, we didn't roll it out yet. So we we still have plenty of opportunity to crash it to the ground, but I don't think we will.
00:16:07
Speaker
Um, well, I think part of it comes down to choosing the right technology partner. So we're actually using behind the scenes, um, and I pass solutions. So for, you know, I don't i know how technical we want to go in this discussion, but essentially an integration platform as a service is helping power this behind the scenes.
00:16:25
Speaker
So the nice thing there is that we needed to develop our own robust API and all the endpoints that we feed in through this I pass. And then the I pass solution is the thing that powers all of these integrations with the hundreds of third party partners. yeah So for for people who aren't technical, really what Kyle's talking about is he's talking about kind of a universal translator is he's plugging into the universal translator and then the universal translators job. It is to figure out how to plug into everything else.
00:16:54
Speaker
So that in that way, Proposify as a company doesn't have to create one-to-one integration with everybody else. They just have to connect. and Absolutely. And so the workflow builders where you get the, we put the power in the user's hands to set up things how they want it to. They don't just have to rely on how.
00:17:11
Speaker
our integration works with HubSpot, for example. So like Scott, my sales leader just, you know, had a call with him and showed it to him. And he was like, I would love it if we could, you know, set a timer that basically says, Hey, if somebody hasn't viewed my proposal in seven days, send me a Slack notification. I was like, yeah, you could do that with the automation builder. Wow.
00:17:33
Speaker
Cause that, that is one of the features for those people who are, you know, trying to get better at selling and marketing. One of the neat things about having a tool like this is it can actually tell you what people have looked at. If they've looked at it, how long they've looked at it and whether or not they've kept an open. And one of the things that I learned was sort of interesting is, is.
00:17:55
Speaker
85% of the time people skip over all the finely crafted messaging that you were days on and just get to the price because you can actually see that be, but then. The neat thing is that actually helps you with your selling because if you understand that they're buying just on one thing, then, okay, then that's, that's what you end up talking.
00:18:15
Speaker
Also, it's good to know that if they've looked at it for like three days, it's because they left it open and went home for the weekend. but It's not because you're year really pithy and you're writing or anything like that. we're We're fixing that in our version three product. We're actually working on the metrics for Proposify 3

Enhancing Metrics in Proposify 3

00:18:32
Speaker
right now. And that is one of the problems we're looking to fix is like knowing if the user's not active or they've like just left their computer open. Don't count that as an actual view time.
00:18:43
Speaker
Can you talk a little bit more about that? Cause with, with all of the different privacy standards internationally, you know, we're in the United States, you're in Canada. ah What we've found is something simple and basic as to be able to understand what is like a site visit.
00:19:00
Speaker
That's an interpretive statistic and because a whole lot of different companies will give you a whole lot of different answers for that. So, yeah, did you, did you have conversations in your next iteration of Proposify on how do we make this, how do we have this clarity around these, these KPIs that we're offering? Yeah, there's a lot of improvements we want to make with our V3 product around, well, a number of things, why hence why we're making a new version of it. But one of them is with analytics and views and that kind of thing. And but and I think the approach we're going to take is basically just getting viewers to opt in and identify who they are so that it's a permission-based choice on the viewer of the proposal. um A lot of tools like i know like DealHub or DocSend, I've been sent DocSend. um
00:19:46
Speaker
documents before where they basically say like, you know, Trigg sending me the document. Hey, he wants to know who you are. Um, and you just put in your name or email address. And if we can do it that way, then we're basically getting people to like offer permission to say like, okay, yeah, you can identify who I am. The great thing about that approach that we're looking at is that you can then get individual analytics. So you can actually, you know, all, all three of you here in the room, I can see like how you.
00:20:14
Speaker
interacted with the document differently from each other, as opposed to just saying the client viewed it, the client looked at it 10 times. it's you Nicole looked at it on Tuesday for 10 minutes, and then you know Dave looked at it in a different time. And then that way, if you forward the document to someone else and they identify themselves, now I can get people who weren't even stakeholders who might have buying authority or some kind of an influence in your deal to be able to know that they're looking at your proposal.
00:20:40
Speaker
I would save so much time and frustration. Oh, I can't wait. So we're, i' we're, we're a little fan getting, grilling out on the details. I think are yeah let's, let's maybe roll out to, you know, you talked a little bit earlier, Kyle, Kyle about, Hey, we were sort of stagnant. How did you identify that? Hey, we needed to make changes. And then how did you start to talk to us about the process of self-identifying like, Hey, that we're, we can do better.
00:21:08
Speaker
Well, you know, in the early days of ah of a startup of a software company, you can move really quickly. And I think your your size and your speed and even just the urgency of going like, well, we've got, you know, six months of runway before we're dead, so we need to move quickly.
00:21:22
Speaker
as As time goes on and as we've raised outside capital and and scaled up the team, well, there's a few things at play. So I think one is technical debt. the The moving fast in the early days, you build up a big backlog of technical debt, which for anyone listening who's not you know a developer is a lot like bank debt, you know credit card debt. you kind of If you don't pay and pay it off, it builds up and up and up and it becomes unmanageable. And it can be really hard to move quickly when you've got this huge you know years history of technical debt that hasn't been repaid. um And I think that was one big factor that we we hadn't paid that back and we had built up a lot of it. The other one I think is a little bit more cultural, which is you know you raise money, you you go great, okay, we can grow the team, we can do so much more things with more people.
00:22:13
Speaker
Um, and I think what ends up happening or what ended up happening in my case, but I know I'm not alone is you start to remove as the CEO yourself from the day to day, you start to have more layers of people beneath you who are doing the work and you don't have as much input into that work.
00:22:29
Speaker
And if you're not really good at, you know, aligning people around a vision and sort of like pushing on urgency, ah people just tend to move in different directions, row in different directions, and sometimes just work on things that aren't that important. Plus with the engineering team, having had that, all that legacy we were dealing with, we were more just like keeping the lights on than actually pushing things forward. So it took a couple of years and I mean, in in our case, um,
00:22:57
Speaker
We ended up in 2022 laying off a pretty big portion of the team. And especially where we've kind of had this like pseudo downturn in the economy, everything got harder. Growth got harder. um You know, you access to capital got harder. So we really had to kind of go back to basics and say like, let's let's run this like a scrappy bootstrap business again.
00:23:20
Speaker
And I got way closer to the details and started working more closely with the team on product and marketing in particular. And I think it's starting to pay off. It's starting to show, but it definitely was you know a years long process of getting there.
00:23:36
Speaker
I want to talk about the layout because I think that especially with you personally makes you a unicorn because I saw what you did and I saw how you dealt with it. And I haven't seen anybody else do it the same way you did. So you have unfortunately had to lay off a bunch of people. And then what did you do in response? Um, I posted about it on LinkedIn and, um,
00:24:02
Speaker
I just explained it. you know I didn't think that was me being a unicorn. I just thought that you know the news gets out anyway. so if you i And I don't even want to say control the narrative. I just want to say, I want to be the one to put it out there and to say, look, we laid off a quarter of our team. Here's why. I fucked up for these reasons. We're losing some great people. We want to try to help them find a soft landing.
00:24:31
Speaker
And that's it. I didn't think that was me being a unicorn, but you know I have seen one of our competitors who I won't name, I landed on one of their Glassdoor reviews. And you know they've got all these reviews of people saying like they're doing quiet layoffs. they They're just like kind of pushing people out the door quietly so they don't have to deal with the the bad PR that comes from a layoff. And I was like, man, I'm glad we didn't do that.
00:24:55
Speaker
Well, it does make you a unicorn because you did take, um you did take ownership of where the company was, which is never happens in business. their Empathy part there too is huge in that.
00:25:11
Speaker
yeah you You announced, and it wasn't to control a narrative, it was to tell the story and what what was happening. And then the biggest part of that was teeing it up and saying, hey, these are great people. We can't have them with us, at least now, but here's, we'd we'd love to help them land. and you are yeah ultimately difference You were actively trying to find people you just laid off. You were actively trying to help them find you. Yeah, there were some great people that we let go. And I was actually really lucky just recently, ah Steve, one of our designers, she was part of that layoffs, um ah came back as ah as a contractor because he's building up his own freelance practice now. So just getting to like work with him again has been has been great. but
00:25:53
Speaker
Yeah, it was it was hard at that time especially because it was still like January 2022 was before like there was this big downturn in SaaS. And I think a year later it would have just been like, yeah, obviously everybody's laying it people off. But at the time it was like, man, you guys must really suck. That was at least my perception of it was like, everybody was still you know living living large off 2021 and all the VC money that got thrown around. So there really wasn't at the time any layoffs happening in SaaS.
00:26:21
Speaker
Yeah. And that's, that's just when people tell me again, again, I hate to beat a dead horse, but when people talk to me about, you know, why do I use that as opposed to anything else? It's because the people are genuinely better. It's things like that, that I noticed and I, I was an evangelist of the product. It's because of the people and the choices that they make.
00:26:41
Speaker
Yeah, the software is cool, but you can get the, you can get similar software or other other places. I, I arguably yours is better, but so anyway, back to the point you're coming out with version three, uh, soon, which is really exciting. Are you, are you making innovation now more part of the company culture? Are you going to continually try and evolve?
00:27:01
Speaker
yeah I mean, short answer, yes. i the The hard part of any kind of software rewrite is that you're basically starting over from scratch again. And we began that process two years ago. We basically said, okay, there's so much technical debt built up. We're using kind of like old JavaScript libraries and just built in this huge monolithic architecture that you can't can't do anything with it. You've got to start over.
00:27:27
Speaker
I was very lucky to get a great VP engineering who's um now our CTO, Mark Lacombe, about a year ago. And he was able to take what we were doing and make it and you know take it to a whole other level ah in terms of both just like speed of delivery and making really good architectural choices that will help it scale in the long term.
00:27:47
Speaker
Um, but you know, we're still in the bit of a limbo because we've got a very basic V3 product that does simple things, but doesn't do a lot. So getting to feature parody is kind of the, the number one priority right now is we need to at least offer the features we have today in version two and they have to be better than what we've got, but the basics have to be there.
00:28:10
Speaker
in order to get people to use it and and and adopt it. And at the same time, we need to be thinking years ahead and going like, what are new features? new What are new products? How do we leverage AI in a really smart way that isn't just a check the box AI feature? um We've got to be thinking about that stuff now so that we can get there when we've got enough feature parity for people to really use V3 and get value out of it.

Future Role of AI in Proposify

00:28:36
Speaker
ah You brought up the magic word that everybody seems to be talking about AI. um As you're looking at even just the future of proposals and how Proposify works, do you see like a year down the road that things would be significantly different. I mean, some of, some of the AI tools are like, obviously you can do a grammar checker against everything that you put together. Might be able to use, you know, for coding for sure. You can build a lot of things using AI.
00:29:07
Speaker
Are there levels of interaction or connection that you think the upcoming AI advancements might help do, or yeah kind of what what might that crystal ball a year invent a year and ahead? So AI is a very big part of our product vision, and I think of it in kind of three stages.
00:29:25
Speaker
When I said check the box AI feature, you know, there's always that temptation that I think everybody had a year ago or especially two years ago when chat GPT was just coming out was like, we need a, you know, AI button in our app that just like writes the proposal for you. Um, I kind of resisted that a because it wasn't our top priority. We had to fix like usability issues within our product before we could worry about throwing AI buttons in there.
00:29:51
Speaker
um But the other piece is it really doesn't fit our value prop because the reason people use Proposify and tools like ours is to actually get control and consistency in their proposals. As soon as you've got AI in there creating things, you lose the control that you wanted to have with your standardized templates and content library and all that kind of stuff.
00:30:10
Speaker
So the three stages that I think of AI and how it's gonna make our users more successful and become real value ads and instead of um you know box checking features is first of all, onboarding. So the most difficult part of using Proposify or really any proposal software is you just gotta get all your content into the system.
00:30:34
Speaker
And that's what takes the most time building out your template. And we've solved that and others have solved it with like template gallery ah where you can, you know, edit fit, like pick something that looks good and edit it to your own brand. But I think that AI will be very useful when it comes to saying like, here's my website. Well, all all that hold all we I'm going to, I'm going to interject there because, and I'll say the thing that you want, which is you had that and then other people cut.
00:30:59
Speaker
Yeah, that was actually our, ah the template gallery was our, like, it was the the catalyst for us finding product market fit because until then. people would look at it and go, yeah, this looks great, but man, I'm not rebuilding my whole, you know, proposal in your system. And so as soon as we offered a template gallery that had nice looking templates that were already baked that were industry specific that people could just like use and customize, that was like overnight pretty much we were starting to really grow. um So that's kind of table stakes now, but we still get a lot of, you know, there's still a lot of friction with that, right? Cause people need to learn a new tool. They need to learn an editor.
00:31:37
Speaker
And this is where I think AI can really be a value add is if you can just point your website or your PDF of what you're doing today and say like, here's what I've got. Can you just make it better? And then it just builds the whole template for you and you have to do minimal customization. Then more people are going to stick around and get the other benefits that you get on the other side of it with like e-signatures and metrics and that kind of thing.
00:32:02
Speaker
of the things that we learned as, as, just as, ah as, as giggles on the podcast when chat c GPT came out, we actually had the chat GPT robot on as a guest. And we, we asked somebody, we asked it all sorts of questions. And then we had somebody who had a deep baritone voice who, you know, we had a Darth Vader off with Dave and hit with his deep baritone voice. And What we learned is that yeah the the ah content creation, and I still would argue that it's not as good as something that some empathy and thought can really provide. So just having that to have it doesn't make you more effective. And that's where the things like the state of the proposals come in is the people who are really winning are trying to tailor the proposals based on the individual need and not just spraying and praying for a sale.
00:32:52
Speaker
Absolutely. Right. Yeah. We had three stages of AI. So the first one- That's where like regenerative is just, it makes, it will make the most different, but the the other ones that I think are a little bit more maybe advanced and down the road are what I'm calling preventative AI. That's not a real term. That's just a term I made up. But essentially if people want, so people put things in in place right now, like but especially bigger companies with like approval workflows.
00:33:18
Speaker
So they'll say like, I don't trust my reps to send the right thing. So I want to make sure there's barriers in place to make sure that we get notified and somebody in management gets to look at a proposal before it goes out the door. And I think that's a great use case for AI. If you can train the AI model and say, these are the things to look for, this is how to make sure that it's on brand, that they're not stretching the logo, that they're not using the wrong font.
00:33:42
Speaker
that the case studies are up to date, whatever it happens to be. There's no typos. It's not using the wrong client name. If you can train the AI and basically say, like let that give a first pass and even like allow it to auto-correct things, then you can save managers a whole lot of time and sort of free reps from being able to like put all these hurdles in place for them to be able to send out contracts. And I think the third area that it gets really interesting is around predictive AI. So that would be like, if if our system is housing all this data, especially around views and clicks and that kind of thing, what are the things that AI can generate that can actually help you identify risks to your deal closing and look at what other companies in your space are doing in real time to ensure that those deals close?
00:34:30
Speaker
That is a lot more fuzzier and far out, and I don't know exactly what those things are. But I think if you can leverage the data to be able to create predictive insights, then that can be a value add for customers.

Kyle Raki's Journey and Insights

00:34:41
Speaker
Now that you're on the cusp of ah coming out with, with, uh, version three of Proposify, you've gone through layoffs, you're still standing. What do you, what do you wish you didn't know now that you didn't know that? What do I wish I didn't know where I did?
00:34:59
Speaker
You didn't know, and which, what do you, what do you wish you didn't know now that you didn't know that? So what lessons are you taking from your journey? I think so. It's a Bob Seeger quote. You got it. Yeah, I'm trying to, I'm trying to be. No, I just, I wanted to make sure that I wasn't, it wasn't a double negative or something like that. Um.
00:35:19
Speaker
you know Everybody's talking, I say everybody, everybody in the in the the small bubble of tech startup ecosystem ah for the last few weeks has been talking about founder mode. I don't know if you guys have heard of this. so um Ben Chesky from Airbnb, the CEO of Airbnb was on a podcast I think about a year ago and he spoke about how when COVID hit and obviously it changed everything as far as rentals, um how he was he had to jump back into the into the weeds, so to speak. And he found that his company wasn't going the direction he wanted it to. And there's this great podcast people should check out of him talking about this process. And Paul Graham, who's sort of like one of the OG venture capitalists, wrote about this in an essay called, and he called it founder mode. So he talked about like manager mode versus founder mode. And I don't know if it's anything brand new, but I do think that there's this
00:36:12
Speaker
um mentality that I spoke about where you know you you get advice around the way you should run a company, which is like the CEO shouldn't be involved too much and they should just have this executive team that they delegate everything to. And that mentality I see is shifting a lot now. And especially with that like being labeled founder mode and having like Ben Chesky talking about it, I think it's giving founders a lot of permission, if you will, to go back to running the details and being involved in product development and in marketing. And we're sort of moving away from this mode of like feeling like everything happened needs to happen through layers of people and you just hire smart people and you let them figure it out. And that I have seen firsthand doesn't work.
00:36:56
Speaker
You can hire smart people, but there's something missing if the if the DNA of the company is based on what the founder did in the early days and you remove that, the company does not go in the right direction. I feel that. And there's a lot of stuff that happens, especially over the past five years, right? So over, over COVID and all the things that have happened that you know A lot of businesses, especially in the founder space seem to be succumbing to professional management.
00:37:27
Speaker
And that loses a lot of the culture and a lot of the reason that many of the best people that those companies have joined in the first place, right?

Maintaining Company Culture

00:37:38
Speaker
So injecting culture, I think everyone that we've ever talked to at Proposify, it's clear that the culture is strong and that, you know, everybody wants to help the client succeed. And that's like the biggest, you know, standard bear for the company.
00:37:56
Speaker
as you're looking back and making new decisions based on on what you know, you know, back to the Bob Seger quote that Trigby just brought up. um Yeah, as we're going against the wind, what do we need to do to kind of keep that compass for your company then?
00:38:17
Speaker
I see what you did there with Bob Seeger and I appreciate i appreciate that. well it back You know, it's not to say that you don't need a team. And I think there's there's a real balance that's needed here because I think a lot of first-time founders or or less less experienced entrepreneurs find that they become the bottleneck in their business because they they don't know how to grow through people.
00:38:37
Speaker
And a lot of it is that they are they need to make every decision. Everything has to go through them. um They don't know how to actually hire really good people and train them and empower them and coach them. they just sort of like They hire a lot of doers who just sort of bubble everything up through the CEO. And that doesn't scale, right? You're never going to grow a business beyond maybe a million or two.
00:38:59
Speaker
operating that way. But then I think the pendulum went too far in the other direction where it was like the CEO should be completely removed and have EAs manage it all and the executive team does it all. And I think I'm starting to find the right balance in a way that's actually working and it keeps me really motivated and and engaged because I certainly have a team. I don't do everything.
00:39:21
Speaker
But I'm a lot closer to the details and I'm involved a lot in the execution of what's going on. And I think that once you get over that initial shock and hurdle that people have, like if you join a company as an employee and you're used to the CEO just being this kind of name over here that everybody knows of, but they never really get involved in the details, you're kind of like, oh, why are they get why are they DMing me about stuff? And why do they want to hop on a meeting and talk about things?
00:39:47
Speaker
There's that initial fear that people have, but then once they get used to it, they're sort of like, you're just part of the team again. And yeah, you always have a certain amount of more like cloud and more, you know, they're they're more willing to defer. But I think if you can get the culture right where people feel free to disagree and share their point of view, even if you're the CEO, but they're also open and to feedback and ideas from the CEO and everything is imbued as like, oh, I'm being micromanaged.
00:40:14
Speaker
Um, that's how I think the balance gets there. And that's where I think we're at now. Excellent. It it kind of feels like maybe you're the coach and not the athlete anymore. Right. So you're, you're telling people, okay, well here, here's where we need to go. Or I see this and you know, this, this doesn't match our company values or our culture. So you're providing the guardrails, you're providing the advice.
00:40:39
Speaker
instead of literally doing it for people or micromanaging saying, you know you there was there was a typo on page 32 of this proposal. so yeah I think to take that analogy, I would probably put myself on the football team because I have my own deliverables and I'm at certain points required to run the ball up the field. um But I'm doing it with the team and I've got a great fullback and a great kicker and a great, you know, the the rest of the people need to be in place. And the other thing too is that founders need to stick to doing what they really do well.
00:41:13
Speaker
And that takes self-awareness to know what you're good at and what you're not. some Of course, some CEOs might say, I'm great at marketing and they're terrible at marketing. But I think if you really know yourself well, you can go, okay, I'm actually really good at these things. I'm terrible at finance. I don't know i don't know how to code, so I'm not a good head of engineering. I'm terrible head of customer support because Mel Gunn will tell me,
00:41:36
Speaker
you know Apparently I used to be rude to customers or that kind of thing. so like i better i've got us you know I've got a sales leader, I've got a CS leader. So you've got people who can compliment you. And then on the teams that I'm running, I've got people who are experts in paid media or experts in design. And so it's just everybody needs to be good at what they do.
00:41:57
Speaker
bring a lot to the table, make it really collaborative, but but I'm playing the role of, hey, we're on the team, we're doing this together. And, you you know, I literally just had this morning a product manager go like, Hey, can you, I'm really busy right now. Can you just make me a Google form for like customer feedback? And I was like, sure, here you go. So we're actually doing this stuff together now.
00:42:18
Speaker
Well, that's amazing. And that speaks to as ah as a CEO and as a person that they're comfortable enough to ask you that kind of thing. I hope so. I like to think that's very cool.

Connecting with Proposify and Kyle Raki

00:42:31
Speaker
So, we're going to have the ah link to the state of proposals in our show notes, but Kyle, if people want to learn more about Proposify in the demo, where do they go and how do they? Sure. So, Proposify.com is the website. If you want to sign up for a trial or request a demo, you can do that there. um And if you want to follow me on LinkedIn, I'm probably most active there. So you just look up Kyle Racky. That's my weird name and you can, you can follow me there.
00:43:02
Speaker
Thanks for joining us. Uh, it's always a joy to talk to you and it's always a joy to see what's, what's coming next. Thanks for having me. scott My pleasure. Dial it in as produced by Nicole Fairclough and Andy. whatow I'm Trigby. That was Dave. Thank you for joining us and we will try and do better the next time.