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In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work.
Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.
Topics we cover:
- (2:27) – Launching a lower-priced version and building expansion revenue
- (6:40) – How lead-gen shops are outpacing legacy rev ops
- (12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
- (18:15) – A surprise Salesforce breakthrough and what it means for product strategy
- (24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check
Links from the Show:
- Join the TinySeed Mailing List
- Apply for TinySeed – Applications reopen September 1, 2025
- OutboundSync
- Harris Kenny | LinkedIn
- Coaching Call Bonus
- Dynamite Jobs
- Vanta
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify
Rob Walling :
Welcome back to Season five, episode two of TinySeed Tales. Before we jump back in with Harris, I wanted to let you know that if you’re a founder who’s looking for the right amount of funding, a community of like-minded founders and a world-class network of mentors, you should apply for TinySeed. Our Fall 2025 batch applications open on September 1st and close on September 9th. Also, on September 3rd, we will be doing a live q and a with the TinySeed team, so you can ask any burning questions ahead of submitting your application. TinySeed is the world-class accelerator for B2B SaaS founders, and if you want to work with me and my team, you should head to TinySeed dot com slash apply. There, you’ll see all the details and you can sign up to get notified when the q and a is going live, as well as when applications open. That’s TinySeed dot com slash apply. And as a reminder, the episode you’re about to listen to takes place a few months after episode one. That’s the beauty of TinySeed Tales is that I follow a founder over 12 to 18 months and we record six to eight episodes. So there’s these lovely time gaps between the episodes where we can really see things unfold. So with that, let’s dive in to episode two.
Harris Kenny:
I’ve had calls with these traditional rev ops shops agencies, and they don’t go anywhere. They don’t get it. They don’t understand why. So even though on paper it seems like that would be a great fit as a HubSpot partner with 25 million in annual revenue, that should be a great account, but it’s actually this little scrappy half a million dollar a year agency that’s excited about what we’re doing, and I don’t know where it’s going to go, but momentum wise, it feels like there’s a lot of momentum happening with the types of people that we’re working with.
Rob Walling :
Welcome back to TinySeed Tales, a series where I follow a founder through the roller coaster of building their startup. I’m your host, Rob Walling, a serial entrepreneur and co-founder of TinySeed, the first startup accelerator designed for Bootstrappers. In this episode, I pick back up on my conversation with Harris Kenny, founder of Outbound Sync. Last time we learned that Harris has made the hard transition from agency owner to SaaS founder, and in just over a year has built his MRR to $10,000 a month since we last spoke. He’s been working on his positioning and has decided to do a Zoom in pivot to focus on agencies who are using outbound sync. I wanted to dig in and find out why he was making this move.
Harris Kenny:
We did roll it out, so the short version of the genesis of it or the decision was at the kickoff for our batch. Talked about it with you, made you talk to me about it outside of the elevator for a couple minutes. Talked to Andy who’s in my batch, and decided to just push out a data sync only and lower price version, and it has gone very well. It’s working kind of how exactly you would hope the agencies will. They’re now talking about it in their sales process. Some of ’em are actually starting to put it in their decks and in their contracts of like if a user wants a CRM integration, they’re going to use outbound sync and there’s additional costs, and then they close these deals and they just send me a Slack message. And so we’ve got expansion revenue now and they’re happy to do it.
I’m trying to figure out the balance of the support that they’re supposed to get because some of their clients are kind of needy and others are really easy. Some of the agencies do the onboarding on their own. Other ones, we do it and they’re requiring a lot of help from us. So I would not say that the operational side of it is figured out, but in terms of it’s growing, they’re happy. We’re signing new agencies. We just signed a first client with a very big agency that has 150 active clients, and this is just one for them, but obviously that could grow a lot. So yeah, it’s really working very well. But we do still have teams that come to us and we have to have brand and we will talk about security, and we have to also be able to stand on our own feet because those end clients are also evaluating us too, because we’re the ones that are ultimately going to connect with their CRM and outbound sync is the thing that’s showing up in their CRM data. So yeah, so there’s this balance of serving the agencies but also building our own direct thing. And I’m still figuring out, but in short, we’re making money. I’m glad we did it. We’re going to keep doing it, and there’s still a lot of figuring out to do, I think.
Rob Walling :
Do you feel like you are going to focus on serving just agencies from now on and either not market to not sell to other customer types or even turn them away? What’s your thinking there?
Harris Kenny:
Yeah, I am starting to lean that way, even just unconsciously because they understand our product so well and the problem that it solves so well, the sales process is very low friction, right? Because they get a customer and the customer says, Hey, okay, we use Salesforce, we use HubSpot. It’s really important to get this in the CRM, and they already know why. They already know why outbound sync. They’ve typically tried to do some automation on their own. They understand the value of it, and they love being able to just pass these questions off to us. And so yeah, I’m finding myself spending more time there and thinking about features for them. They have very specific features that they want that we can definitely build that I can see that would be valuable for them. I think that if a direct team comes in and they’re motivated and they’re ready to go, it’s like, of course I’m happy to work with them.
And we’ve had a couple, we had one that between our recordings that came in, I had one call with them, one call closed, they onboarded themselves. I literally haven’t heard from them in over a month, but the data’s flowing and they’re happy. But there’s definitely a lot of teams are not in that situation, and so it’s like I don’t want to chase someone down if they don’t have the internal alignment and decision-making ability to move forward. I mean, it can take a year plus of conversations because for our product to be used, there’s hundreds of other things that have fallen into place. And then with the agency, those things have all fallen into place basically.
Rob Walling :
So you have a customer type that is easier to sell to really just understands the product better, that is easier to onboard, that probably potentially has less price sensitivity, maybe passing it along to clients. They are less support. They will probably be higher annual contract value because all these things, so that feels like at your stage, early stage, that’s it. That’s CICP, right? And let’s just be honest, if you hit two, three, 4 million and you’re like, wow, I’ve just got a lot of agencies here and it’s slowing down, obviously you can kind of go back. You can undo this decision at any time. But for now to become positioned and known for being the sync engine for agencies, I think is a really interesting approach.
Harris Kenny:
I’ve thought about giving ’em a seat for free and being like, Hey, use this for your own campaigns because I know they’ll make content about it. And from a cost perspective, it’s not really that big of a deal. And I know if they get familiar with it that they would use it. I don’t know, maybe I charge ’em a low price, but I feel like if I say, Hey, here’s a free seat, they would be jazzed about it. And as they’re getting more mature, well, okay, so this is a little bit of a sidebar, but something that’s happening in this agency space is there’s this huge disruption happening where you’ve got these traditional marketing and rev ops and CRM shops, and then you have this emergence of this tool called Clay and these lead gen agencies that are really going to the real job to be done.
The reason why most people hire agencies in the first place marketing and sales agencies is they want more leads and a lot of agencies will do other things On top of that, they’ll build forms and landing pages and persona development and hundreds of thousands of dollars of extra services. And so these other agencies have come up, these cold email growth hacking clay agencies that are just going to the main thing that people want, which is like, here’s leads for your sales team from scratch. And so there’s this balancing act of the traditional ops shops and stuff are starting to encroach on this space. They’re getting listed as experts in some of these tools, but I see their LinkedIn posts and I watch their videos and it’s like they don’t get it. They’re just missing the point. And so in my head I’m like, who’s going to, as this encroachment is happening between the two who has a skillset that’s harder to learn?
You have these scrappy agencies that are doing the hardest possible thing, getting business from nothing. Then you have these, it’s hard to run a rev ops and CRM shop, but you’ve got referred leads, you’ve got this whole infrastructure, you’ve got a huge multi-billion dollar SaaS company snowplowing for you, and then they’re trying to be nimble, but then the nimble people are basically trying to learn how to do the easier things. And so I suspect that these agencies that we’re working with are going to grow and they’re going to start adding more services, much easier services, delivered paid ads, these other things. So anyway, this is a little bit of a side thing, but I’ve had calls with these traditional ops shops agencies and they don’t go anywhere. They don’t get it. They don’t understand why. So even though on paper it seems like that would be a great fit, it’s a HubSpot partner with 25 million in annual revenue. That should be a great account, but it’s actually this little scrappy half a million dollar a year agency that’s excited about what we’re doing. And I dunno where it’s going to go. But momentum wise, it feels like there’s a lot of momentum happening with the type of people that we’re working with.
Rob Walling :
There’s a shift in the market
Harris Kenny:
Happening
Rob Walling :
And this is what we see. We see this a shake up or a shift or whatever we want to call it. You’re calling out momentum in this direction in it and can see that from the outside. I’m like, I know something’s happening, I’m hearing, but I don’t understand exactly where it’s going. I hear from folks like you and Valentine, the finding mail in this space. The same thing happens with email marketing or marketing automation. It’s like every five to seven years there’s this big shakeup, and I was in on probably the last one or two times ago that was my startup. And these days it’s players like beehive and substack that are, they’re redefining it in a new way. And I remember when beehive launched, I was like, wow, I don’t know that that will work. But they figured something out. They had their lead, and there are things that are changing.
This is why it’s so hard to run a SaaS company for more than, I don’t know, 10 years. It gets the markets shift and especially a 10-year-old SaaS company is a lot of legacy code and you start moving slower and you can’t hit that momentum. So I’m bringing up product stuff, of course a product guy. But you’re seeing the market shift and you’re saying that the old agencies almost don’t understand that there’s a sales marketing, there’s an understanding, there’s a shift in the understanding of where the puck is headed, and you feel like you’re more towards the cutting edge of that.
Harris Kenny:
Yeah, that’s right. And they have relationships with the traditional vendors in the space. So they have a partnership with ZoomInfo, they have a partnership with an outreach or a SalesLoft. So they get a new customer and they say, now you’re subscribing to ZoomInfo, you’re paying them a hundred thousand whatever, plus a year. Now you’re subscribing to Outreach or SalesLoft. So it’s just there’s a lot of cost and process and legacy stuff that’s built into that. I mean, I guess we’re part of outbound sync is kind of part of this unbundling movement that’s happening. And it’s API driven and webhook driven and data portability. You still end up spending money, you just spend it in different ways, but you can do a lot more interesting things right now. But my public pricing and my public positioning, I haven’t made that change yet. It’s still kind of an if you know sort of thing. But I’m in the WhatsApp groups with these agency owners. I just got off a call with one and he’s like, Hey man, yeah, I’ve been following your stuff forever. This is how we’re doing this stuff right now. But we have this one client and I wanted to see what you’re up to lately, but he already knows me. And so I don’t need to be necessarily aggressively marketing to them explicitly as such because I’m already kind of in those watering holes.
Rob Walling :
For years. I’ve been saying build your network, not your audience. And the inbound interest that Harris is getting is a perfect case study of why this is so helpful. When we spoke with Harris in episode one, he was building out, his team was worried because he was hiring ahead of revenue. I wanted to check in to see how things were going.
Harris Kenny:
I mean, I’ve been running a fully bootstrap business for five years, and so I just have some real habits, ingrained habits built in that were built in there. But beneath that, I have taken some chances and then this was the big chance, okay, I think this is maybe the best idea I’m going to have. I don’t know what else I’m going to come up with the rest of my life. Maybe this is it, so let’s go for it. So I remember we were sitting around the table at the kickoff for our batch and each person was going to bring up ideas, things they needed help with. And my big thing that I’ve been wrestling with was like, oh, is my developer working out or not? And this is how much he’s working 15 hours a week, but it seems like he’s got these other projects.
And I remember just everyone around the table was just like, what are you talking about? He needs to be full time. What are you expecting him to get done? And 15 hours a week, it was just immediate. You don’t know what you’re talking about. Everything’s fine. Yeah, I mean there was not even, especially in a room of contrarians and independent thinkers, usually someone’s going to come up with some reason why there’s another way. But literally every single person was like, yeah, yeah, 40 hours. I was like, cool, okay, I’ve got 19 minutes left in my 20 minute, I got to think
Rob Walling :
Of something else,
Harris Kenny:
Idea session, what else? And everybody’s right. I mean the change has been massive and I like him. I like working with him and the output is just way, way better. And so we’re rocking. I mean we’re shipping stuff really fast. And then the customer success, a couple months ago when we were talking about this initially, I remember just being like, oh, I don’t know. And you were like, trust me, you will find 40 hours a week for a customer success person. Just trust me. And I was like, okay, I hear you. Okay, lemme shut down my old agency and get my feet under me. But here we are three months later and I am swamped in customer success stuff, onboarding tickets, feature requests, it’s all good. There’s no problems with the product, it’s just the natural thing that happens when you’ve got a few dozen companies using your thing.
It’s all normal stuff. And fortunately, I did start the hiring process with Dynamite Jobs about a month ago. So my new CSM did start on Monday of this week. And so he’s ramping pretty quickly and I’m amazed they found him, his experience. He had been a third hire at a SaaS company before where the first was a founder, the second was a full-time dev, and then he was the third founding CSM. It’s like the same thing here. He’s familiar with HubSpot, confident, willing to take on a challenge, excited to be do the remote thing. It was a tough hiring process, but dyna, my jobs made it easier, but it was tricky. I dunno, I wasn’t sure I’d find somebody, oh, the applicants were all over the map. I wasn’t sure. What do I really need here? So there’s this heuristic of hiring for people based on what they’ve done, not based on what they can do.
And so then I’m like, okay, but what is it of the things that people have done that I’m looking for? So like CSM experience, is it like HubSpot experience? We make this HubSpot product. Is it understanding outbound tools? Is it working at a small company? And it’s kind of all of these things. And so different applicants had different strengths across those different areas. And one amazing one came through but wanted a ton and ended up ghosting anyway. And it’s like, okay, well I got to find somebody who’s excited and sort of crazy enough to be a third hire at a company. I mean, that requires a type of person, risky. It requires a lot of trust in me. Yeah, so that was what was tricky. It was hard to find apples to apples comparison because we have these different requirements and then different ones were strong in different areas.
Rob Walling :
It’s always tough. Customer success and marketing are two unexpectedly complex things to hire for. And I don’t want to dismiss hiring a developer, hiring sales, hiring support, but it’s kind of like you need to be able to sell, you need to be reliable, get it done. You need to understand the product. And a developer we can go through, but it’s like you need to write good code. You need to not be a jerk and you need to do whatever else and show up and be reliable. Customer success, there are a lot floats into that. It’s like you’re rapport with other individuals. Do you know how to re-architect my entire onboarding and track metrics? That’s part of customer success. Now, not everybody needs to know how to do that, but others do. There’s ongoing, there’s a lot to it that other, and it’s still a new role. I mean, the first time I ever heard the term was probably, I dunno, 20 12, 20 13. So this is a decade old versus a sales person as old as time. You know what I mean? And customer support goes back, what do we think 50, 60, 70 years? Success is a newer role. And so it can be hard to hire for because there isn’t as much, not legacy, but as much foundational knowledge about it.
Harris Kenny:
Yeah, for sure. No, I agree with that. He’s working out
So far. I mean it’s been a couple of days, but yeah, he’s eager he, he’s taken on new things and I have a decent, there’s the pieces of a CSM role in place, so he’s not starting from scratch, which I think is helpful, but I’m like, Hey, here’s our onboarding. There’s a single page in our knowledge base, and then there’s this onboarding plan tool that we use. They’re not the same. They’re out of sync. So one of your first things, go through those, identify the inconsistencies, identify some room for improvement. And he started to do that. He actually has an engineering background, which is kind of interesting. He studied engineering in school and then worked for aerospace company before going into SaaS. And so in the interview process, he had said a few things like, oh, we should do a root cause analysis of what went wrong.
And I remember just thinking like, oh yeah, our product is really technical. And the thing is, our customers don’t really want to talk to us. I mean, they’ll be happy to chat, but we kind of need to be in the background. If they’re talking to us a lot, that means something is really not working. It’s not a product where it’s fun to talk to the team. It’s like sync issues and stuff. And so it’s like, okay, I need someone who’s going to be able to really drill down. And so I really, I thought that skillset was cool because I just thought it was kind of more to what we need to be able to do, just really drill down and understand why these properties aren’t mapping or whatever. Because we can’t hand wave away a problem. It’s either syncing or it’s not. And someone who can figure that out quickly is like, that’s a very valuable skill.
Rob Walling :
I love how fast Harris is iterating. He’s been exploring, integrating with Salesforce, which can be challenging to say the least. Before our conversation, he sent me this audio note.
Harris Kenny:
I have this sort of Eureka moment. I’m pretty excited about it. I know we’re not going to talk for a little while, but I wanted to share it. So context are go to market motion, working with agencies continues to be getting more and more traction, and several of these agencies are working with customers who are using Salesforce. Now, I’ve only built this HubSpot integration, but I really built it kind of painstakingly to think about how everything maps. And what I’m really excited about is that our HubSpot sync to Salesforce is working very cleanly. I just spun up a developer account in Salesforce after having a call with a series E startup. So just a ton of traction, really mature company with a lot of money, and the agency they’re working with is crushing. They’ve booked 90 meetings for them so far, and so they’re really happy with their agency, but they want to get that agency’s work in Salesforce.
And anyway, it’s working. I was surprised that it worked as well as it did. But it looks like I had been building for this because I built, I think so tightly to HubSpot that it worked. And so this is opening up a whole different set of doors for us. I think in the short term, I want to focus on the HubSpot to Salesforce path, but then there’s also room to potentially build just a standalone Salesforce integration and serve a hopefully different section of the market. Yeah, I dunno, it’s a Friday afternoon right now, almost four o’clock and unbelievably excited.
Rob Walling :
And this Eureka moment wasn’t just groundbreaking. It seemed to reignite something inside Harris.
Harris Kenny:
I haven’t had a feeling like this since kind of early days. I discovered that multiple users had already been using our product in Salesforce, which I didn’t know. Nobody had told me that or asked or anything. Not that they have to, but it just never came up. And that was part of the downside of the agency thing is that I just didn’t realize that. And so then I tested it myself. I spun up a dev account and it worked. It’s like, oh, you can go from outbound sync to HubSpot to Salesforce. And then I talked to more and more people and realized, oh, actually quite a few users are doing this. And then these new enterprise deals that are coming in are also saying, oh, we actually need, so this is the thing that more and more I’m hearing that people actually wanted, people that understood the value of the product tended to be actually in that ecosystem. Now there are also HubSpot people, but it was the Salesforce people who were kind of more into it. So that was an interesting learning. And then when I spun up the sandbox account, I actually kind of liked it. I hadn’t used Salesforce in 10 years, but I kind of liked it and it was said, no one ever. Well, so you’re the one.
Well, I liked it because for the reasons why a lot of people don’t like it. In HubSpot, it’s very intuitive and it’s user friendly, but it’s like Apple versus Android. And sometimes I want to see a big settings menu with a compact tight table where I can see everything, and it’s not nestled between these dropdowns and you got to click through to this, to this to to actually get to the toggle. So in a weird way, it was kind of like, oh, I feel like there’s a lot in front of me here. So I dunno. It was just interesting. It was a very unexpected response because in the HubSpot ecosystem, it’s very territorial of like, oh, orange, good, blue, bad, whatever. So it was like, okay, this is kind of interesting. So we talked to a company that made a toolkit product, and so basically it was a quick integration.
They’re basically themselves infrastructure as a platform, as a service. So they’re an IPA and work kind of an ipa. I was like, okay, well maybe we can work with them. And then anyway, the developer jumped into it and he was like, I’m not getting the error messages I need from these API calls. I think I can just do it on my own. I was like, honestly, man, you’ve got me here. I trust you. Whatever. Take a shot at it, work on it for a couple of weeks and let’s just see what happens. He kept doing some bug reports here or there, but in general, this was his focus for a couple weeks, and sure enough it works. We’re going to be announcing a Salesforce beta. I just posted on LinkedIn. We already to our agencies were like, Hey, I’ve got customers that want the Salesforce thing, so send me a Stripe link and let’s go. And already we’ve solved problems that you can’t do if you’re doing the HubSpot sync,
Rob Walling :
Then the Salesforce integration, you’re in beta. It took you weeks five to six weeks. Is that right?
Harris Kenny:
Yes. Which is kind of crazy to me. I think it’s because we spent a year and a half on HubSpot that when Vitali jumped in, and also what we do isn’t actually that complicated. All things considered something like a drip. It’s like there’s a lot going on with that product. I mean, we’re basically like, does this contact exist or not? If not, create it, log these emails to it. I mean, there’s more to it, but fundamentally, I think other products have a lot more problem things they have to think about. We’ll see, I might be talking to you next time and be like, Rob, I was wrong. We missed it. We forgot this thing. We hit an iceberg. I don’t think
Rob Walling :
It’ll be on your side though. I don’t think it’ll be your code. It will be. If anything, the experience that we started having and that other founders have had as they’ve tried to do this, is that Salesforce says, oh, great, you have this code now in order for anyone to deploy it, you need to go through our security audit and our this and that audit. And each one of those takes two months or something waiting on Do you have to do any of that?
Harris Kenny:
I think that, I mean, to get formally listed in the exchange, yes, but because that’s not how we’re acquiring customers, actually, it’s been a year and a half. We’re like, there’s one app in front of us in the queue before we’re going to get listed in the HubSpot marketplace. We haven’t even been in the HubSpot marketplace yet because we’re in these other,
Rob Walling :
You’re sound direct.
Harris Kenny:
So I think that we’ll be able to get away with being like, Hey, this is a beta developer version of the app. And then over time, yeah, we’ll be in the app exchange and we’ll pay the few thousand dollars. And we are starting SOC two tandem with this because the Salesforce people, they want SOC two. And so I suspect that if we do that, then it’ll make some of the security stuff easier because we will say like, Hey, here’s our trust center, and we ended up, yeah, that was a whole thought process over the last couple of weeks.
Rob Walling :
If you’re unfamiliar with SOC two, it’s all about making sure your company’s security controls and data handling practices are up to snuff. It’s like getting a seal of approval that says these folks are doing things the right way when it comes to protecting customer info. And as startups want to move upmarket and sell to bigger companies, SOC two can be a game changer, but it’s expensive and it’s a ton of work.
Harris Kenny:
Looking through the SOC two attestation, it makes sense to me these policies and controls that we should put in place. Sometimes some of that stuff just feels like a song and dance, and I’m sure that a little bit of it is. But I mean, for me, as a non-technical founder, we’ve got one developer. Some of these things are very good for me. If something happens to him for whatever reason, if we have these controls in place, I’ll be in a better position in terms of being able to business continuity or something happens to me. So it’s funny, but some say, oh, you’re too small to do it right now. But because we’re small, I look at these things and I’m like, these are actually kind of viability of the business. If we can resolve these, it actually kind of helps me sleep a little bit better at night, which is kind of funny. But yeah,
Rob Walling :
That’s the glass half full view of it. Most people hate SOC two and hate going through it, and you’re like, this, actually, you are definitely, you’re on the optimist side, which I think is really good for you as a founder.
Harris Kenny:
It’s like, oh, what happens if the one person who is putting code in production, what happens if thing happens to them? I should probably have an answer to that before it happens.
Rob Walling :
So you wrote me a note and the note said, I realized we weren’t really spending the TinySeed money yet. It had been three months, and we had effectively only spent $8,000 of the check you wrote us and revenue growth had slowed with you being bogged down in customer success stuff. So talk me through where you are with that. Have you started spending more money? Is this the hires and the full time and that kind of makes all that work?
Harris Kenny:
Yeah, definitely. There’s just old habits from how I’ve been running my business, and so I was treating that money in the bank. It wasn’t there. But something that you’ve said that kind of rings in my ears from time to time is that having more money in a business can save you years of time. And so I sort of made this decision of it was customers and prospects were coming in and they were asking for these things. They were asking for SOC two, they were asking for Salesforce, and it was like, okay, well, I probably just need to spend money to do those things. So now we’re in this spending era a little bit. And so my job now is to get it back. So it’s like, okay, we’re going to start sending the link to our trust center for our security stuff to people. And so now you need to come up with pricing for what those people who ask for that thing, what are they going to pay?
And I went to an old startups For the Rest Of Us episode, I just searched security and I’ve listened to every episode that I found where security came up in the Spotify search thing and something about five figure annual contract value stuff. We did close our first annual contract. We a company where it was like, okay, the people are willing to sign that type of contract with us even before we have the Salesforce or the SOC two. So that gave me a really big boost of confidence because I’d never sold an annual contract of anything in my life of my own companies. And so it was like, okay, we’re solving a problem enough that they’re willing to write that check. How much more would they be willing to pay if we could solve these problems even better? So we decided to go. I went with Vanta, which is kind of like the category creator in the GRC compliance software space, because I just kind of want to get it done the first time, send it to people, and they’ll be like, cool, you pass review and not have to go back and forth and maintain a bunch of stuff and a Google Drive and things like that.
So yeah, so that was the decision of consciously, let’s spend this money, let’s get these deals in rework pricing and try to be a little bit more confident in the sales cycle instead of before being like, well, it’s supposed to be 500, but you could pay a hundred and it’s month to month, but you can actually cancel yesterday. It’s just like, come on, dude, this is cool. You built something cool. Sell it. And I think part of it’s going to give me the confidence to do some of that.
Rob Walling :
Harris’s bold moves are paying off an outbound sink is gaining momentum, but as he navigates this entrepreneurial roller coaster, every decision carries weight. Will his growing confidence be the key to unlocking even greater success? Buckle up for next week’s episode where we’ll follow up on his SOC two compliance journey. Find out how he’s scaling outbound campaigns without losing the personal touch, and talk about a potential positioning pivot that could catapult outbound sink into a whole new league. Don’t miss out on the twists and turns of Harris’s journey next time on TinySeed Tales. Hope you enjoyed this episode. If you’ve ever wondered what it’s really like inside TinySeed and want to hear a raw candid coaching conversation between Harris and I, we put together something special for you at TinySeed dot com slash bonus. You should check it out. I’ve never released anything like this before. I hope you enjoy it. It’s at TinySeed dot com slash bonus.
Welcome back to Season five, episode two of TinySeed Tales. Before we jump back in with Harris, I wanted to let you know that if you’re a founder who’s looking for the right amount of funding, a community of like-minded founders and a world-class network of mentors, you should apply for TinySeed. Our Fall 2025 batch applications open on September 1st and close on September 9th. Also, on September 3rd, we will be doing a live q and a with the TinySeed team, so you can ask any burning questions ahead of submitting your application. TinySeed is the world-class accelerator for B2B SaaS founders, and if you want to work with me and my team, you should head to TinySeed dot com slash apply. There, you’ll see all the details and you can sign up to get notified when the q and a is going live, as well as when applications open. That’s TinySeed dot com slash apply. And as a reminder, the episode you’re about to listen to takes place a few months after episode one. That’s the beauty of TinySeed Tales is that I follow a founder over 12 to 18 months and we record six to eight episodes. So there’s these lovely time gaps between the episodes where we can really see things unfold. So with that, let’s dive in to episode two.
Harris Kenny:
I’ve had calls with these traditional rev ops shops agencies, and they don’t go anywhere. They don’t get it. They don’t understand why. So even though on paper it seems like that would be a great fit as a HubSpot partner with 25 million in annual revenue, that should be a great account, but it’s actually this little scrappy half a million dollar a year agency that’s excited about what we’re doing, and I don’t know where it’s going to go, but momentum wise, it feels like there’s a lot of momentum happening with the types of people that we’re working with.
Rob Walling :
Welcome back to TinySeed Tales, a series where I follow a founder through the roller coaster of building their startup. I’m your host, Rob Walling, a serial entrepreneur and co-founder of TinySeed, the first startup accelerator designed for Bootstrappers. In this episode, I pick back up on my conversation with Harris Kenny, founder of Outbound Sync. Last time we learned that Harris has made the hard transition from agency owner to SaaS founder, and in just over a year has built his MRR to $10,000 a month since we last spoke. He’s been working on his positioning and has decided to do a Zoom in pivot to focus on agencies who are using outbound sync. I wanted to dig in and find out why he was making this move.
Harris Kenny:
We did roll it out, so the short version of the genesis of it or the decision was at the kickoff for our batch. Talked about it with you, made you talk to me about it outside of the elevator for a couple minutes. Talked to Andy who’s in my batch, and decided to just push out a data sync only and lower price version, and it has gone very well. It’s working kind of how exactly you would hope the agencies will. They’re now talking about it in their sales process. Some of ’em are actually starting to put it in their decks and in their contracts of like if a user wants a CRM integration, they’re going to use outbound sync and there’s additional costs, and then they close these deals and they just send me a Slack message. And so we’ve got expansion revenue now and they’re happy to do it.
I’m trying to figure out the balance of the support that they’re supposed to get because some of their clients are kind of needy and others are really easy. Some of the agencies do the onboarding on their own. Other ones, we do it and they’re requiring a lot of help from us. So I would not say that the operational side of it is figured out, but in terms of it’s growing, they’re happy. We’re signing new agencies. We just signed a first client with a very big agency that has 150 active clients, and this is just one for them, but obviously that could grow a lot. So yeah, it’s really working very well. But we do still have teams that come to us and we have to have brand and we will talk about security, and we have to also be able to stand on our own feet because those end clients are also evaluating us too, because we’re the ones that are ultimately going to connect with their CRM and outbound sync is the thing that’s showing up in their CRM data. So yeah, so there’s this balance of serving the agencies but also building our own direct thing. And I’m still figuring out, but in short, we’re making money. I’m glad we did it. We’re going to keep doing it, and there’s still a lot of figuring out to do, I think.
Rob Walling :
Do you feel like you are going to focus on serving just agencies from now on and either not market to not sell to other customer types or even turn them away? What’s your thinking there?
Harris Kenny:
Yeah, I am starting to lean that way, even just unconsciously because they understand our product so well and the problem that it solves so well, the sales process is very low friction, right? Because they get a customer and the customer says, Hey, okay, we use Salesforce, we use HubSpot. It’s really important to get this in the CRM, and they already know why. They already know why outbound sync. They’ve typically tried to do some automation on their own. They understand the value of it, and they love being able to just pass these questions off to us. And so yeah, I’m finding myself spending more time there and thinking about features for them. They have very specific features that they want that we can definitely build that I can see that would be valuable for them. I think that if a direct team comes in and they’re motivated and they’re ready to go, it’s like, of course I’m happy to work with them.
And we’ve had a couple, we had one that between our recordings that came in, I had one call with them, one call closed, they onboarded themselves. I literally haven’t heard from them in over a month, but the data’s flowing and they’re happy. But there’s definitely a lot of teams are not in that situation, and so it’s like I don’t want to chase someone down if they don’t have the internal alignment and decision-making ability to move forward. I mean, it can take a year plus of conversations because for our product to be used, there’s hundreds of other things that have fallen into place. And then with the agency, those things have all fallen into place basically.
Rob Walling :
So you have a customer type that is easier to sell to really just understands the product better, that is easier to onboard, that probably potentially has less price sensitivity, maybe passing it along to clients. They are less support. They will probably be higher annual contract value because all these things, so that feels like at your stage, early stage, that’s it. That’s CICP, right? And let’s just be honest, if you hit two, three, 4 million and you’re like, wow, I’ve just got a lot of agencies here and it’s slowing down, obviously you can kind of go back. You can undo this decision at any time. But for now to become positioned and known for being the sync engine for agencies, I think is a really interesting approach.
Harris Kenny:
I’ve thought about giving ’em a seat for free and being like, Hey, use this for your own campaigns because I know they’ll make content about it. And from a cost perspective, it’s not really that big of a deal. And I know if they get familiar with it that they would use it. I don’t know, maybe I charge ’em a low price, but I feel like if I say, Hey, here’s a free seat, they would be jazzed about it. And as they’re getting more mature, well, okay, so this is a little bit of a sidebar, but something that’s happening in this agency space is there’s this huge disruption happening where you’ve got these traditional marketing and rev ops and CRM shops, and then you have this emergence of this tool called Clay and these lead gen agencies that are really going to the real job to be done.
The reason why most people hire agencies in the first place marketing and sales agencies is they want more leads and a lot of agencies will do other things On top of that, they’ll build forms and landing pages and persona development and hundreds of thousands of dollars of extra services. And so these other agencies have come up, these cold email growth hacking clay agencies that are just going to the main thing that people want, which is like, here’s leads for your sales team from scratch. And so there’s this balancing act of the traditional ops shops and stuff are starting to encroach on this space. They’re getting listed as experts in some of these tools, but I see their LinkedIn posts and I watch their videos and it’s like they don’t get it. They’re just missing the point. And so in my head I’m like, who’s going to, as this encroachment is happening between the two who has a skillset that’s harder to learn?
You have these scrappy agencies that are doing the hardest possible thing, getting business from nothing. Then you have these, it’s hard to run a rev ops and CRM shop, but you’ve got referred leads, you’ve got this whole infrastructure, you’ve got a huge multi-billion dollar SaaS company snowplowing for you, and then they’re trying to be nimble, but then the nimble people are basically trying to learn how to do the easier things. And so I suspect that these agencies that we’re working with are going to grow and they’re going to start adding more services, much easier services, delivered paid ads, these other things. So anyway, this is a little bit of a side thing, but I’ve had calls with these traditional ops shops agencies and they don’t go anywhere. They don’t get it. They don’t understand why. So even though on paper it seems like that would be a great fit, it’s a HubSpot partner with 25 million in annual revenue. That should be a great account, but it’s actually this little scrappy half a million dollar a year agency that’s excited about what we’re doing. And I dunno where it’s going to go. But momentum wise, it feels like there’s a lot of momentum happening with the type of people that we’re working with.
Rob Walling :
There’s a shift in the market
Harris Kenny:
Happening
Rob Walling :
And this is what we see. We see this a shake up or a shift or whatever we want to call it. You’re calling out momentum in this direction in it and can see that from the outside. I’m like, I know something’s happening, I’m hearing, but I don’t understand exactly where it’s going. I hear from folks like you and Valentine, the finding mail in this space. The same thing happens with email marketing or marketing automation. It’s like every five to seven years there’s this big shakeup, and I was in on probably the last one or two times ago that was my startup. And these days it’s players like beehive and substack that are, they’re redefining it in a new way. And I remember when beehive launched, I was like, wow, I don’t know that that will work. But they figured something out. They had their lead, and there are things that are changing.
This is why it’s so hard to run a SaaS company for more than, I don’t know, 10 years. It gets the markets shift and especially a 10-year-old SaaS company is a lot of legacy code and you start moving slower and you can’t hit that momentum. So I’m bringing up product stuff, of course a product guy. But you’re seeing the market shift and you’re saying that the old agencies almost don’t understand that there’s a sales marketing, there’s an understanding, there’s a shift in the understanding of where the puck is headed, and you feel like you’re more towards the cutting edge of that.
Harris Kenny:
Yeah, that’s right. And they have relationships with the traditional vendors in the space. So they have a partnership with ZoomInfo, they have a partnership with an outreach or a SalesLoft. So they get a new customer and they say, now you’re subscribing to ZoomInfo, you’re paying them a hundred thousand whatever, plus a year. Now you’re subscribing to Outreach or SalesLoft. So it’s just there’s a lot of cost and process and legacy stuff that’s built into that. I mean, I guess we’re part of outbound sync is kind of part of this unbundling movement that’s happening. And it’s API driven and webhook driven and data portability. You still end up spending money, you just spend it in different ways, but you can do a lot more interesting things right now. But my public pricing and my public positioning, I haven’t made that change yet. It’s still kind of an if you know sort of thing. But I’m in the WhatsApp groups with these agency owners. I just got off a call with one and he’s like, Hey man, yeah, I’ve been following your stuff forever. This is how we’re doing this stuff right now. But we have this one client and I wanted to see what you’re up to lately, but he already knows me. And so I don’t need to be necessarily aggressively marketing to them explicitly as such because I’m already kind of in those watering holes.
Rob Walling :
For years. I’ve been saying build your network, not your audience. And the inbound interest that Harris is getting is a perfect case study of why this is so helpful. When we spoke with Harris in episode one, he was building out, his team was worried because he was hiring ahead of revenue. I wanted to check in to see how things were going.
Harris Kenny:
I mean, I’ve been running a fully bootstrap business for five years, and so I just have some real habits, ingrained habits built in that were built in there. But beneath that, I have taken some chances and then this was the big chance, okay, I think this is maybe the best idea I’m going to have. I don’t know what else I’m going to come up with the rest of my life. Maybe this is it, so let’s go for it. So I remember we were sitting around the table at the kickoff for our batch and each person was going to bring up ideas, things they needed help with. And my big thing that I’ve been wrestling with was like, oh, is my developer working out or not? And this is how much he’s working 15 hours a week, but it seems like he’s got these other projects.
And I remember just everyone around the table was just like, what are you talking about? He needs to be full time. What are you expecting him to get done? And 15 hours a week, it was just immediate. You don’t know what you’re talking about. Everything’s fine. Yeah, I mean there was not even, especially in a room of contrarians and independent thinkers, usually someone’s going to come up with some reason why there’s another way. But literally every single person was like, yeah, yeah, 40 hours. I was like, cool, okay, I’ve got 19 minutes left in my 20 minute, I got to think
Rob Walling :
Of something else,
Harris Kenny:
Idea session, what else? And everybody’s right. I mean the change has been massive and I like him. I like working with him and the output is just way, way better. And so we’re rocking. I mean we’re shipping stuff really fast. And then the customer success, a couple months ago when we were talking about this initially, I remember just being like, oh, I don’t know. And you were like, trust me, you will find 40 hours a week for a customer success person. Just trust me. And I was like, okay, I hear you. Okay, lemme shut down my old agency and get my feet under me. But here we are three months later and I am swamped in customer success stuff, onboarding tickets, feature requests, it’s all good. There’s no problems with the product, it’s just the natural thing that happens when you’ve got a few dozen companies using your thing.
It’s all normal stuff. And fortunately, I did start the hiring process with Dynamite Jobs about a month ago. So my new CSM did start on Monday of this week. And so he’s ramping pretty quickly and I’m amazed they found him, his experience. He had been a third hire at a SaaS company before where the first was a founder, the second was a full-time dev, and then he was the third founding CSM. It’s like the same thing here. He’s familiar with HubSpot, confident, willing to take on a challenge, excited to be do the remote thing. It was a tough hiring process, but dyna, my jobs made it easier, but it was tricky. I dunno, I wasn’t sure I’d find somebody, oh, the applicants were all over the map. I wasn’t sure. What do I really need here? So there’s this heuristic of hiring for people based on what they’ve done, not based on what they can do.
And so then I’m like, okay, but what is it of the things that people have done that I’m looking for? So like CSM experience, is it like HubSpot experience? We make this HubSpot product. Is it understanding outbound tools? Is it working at a small company? And it’s kind of all of these things. And so different applicants had different strengths across those different areas. And one amazing one came through but wanted a ton and ended up ghosting anyway. And it’s like, okay, well I got to find somebody who’s excited and sort of crazy enough to be a third hire at a company. I mean, that requires a type of person, risky. It requires a lot of trust in me. Yeah, so that was what was tricky. It was hard to find apples to apples comparison because we have these different requirements and then different ones were strong in different areas.
Rob Walling :
It’s always tough. Customer success and marketing are two unexpectedly complex things to hire for. And I don’t want to dismiss hiring a developer, hiring sales, hiring support, but it’s kind of like you need to be able to sell, you need to be reliable, get it done. You need to understand the product. And a developer we can go through, but it’s like you need to write good code. You need to not be a jerk and you need to do whatever else and show up and be reliable. Customer success, there are a lot floats into that. It’s like you’re rapport with other individuals. Do you know how to re-architect my entire onboarding and track metrics? That’s part of customer success. Now, not everybody needs to know how to do that, but others do. There’s ongoing, there’s a lot to it that other, and it’s still a new role. I mean, the first time I ever heard the term was probably, I dunno, 20 12, 20 13. So this is a decade old versus a sales person as old as time. You know what I mean? And customer support goes back, what do we think 50, 60, 70 years? Success is a newer role. And so it can be hard to hire for because there isn’t as much, not legacy, but as much foundational knowledge about it.
Harris Kenny:
Yeah, for sure. No, I agree with that. He’s working out
So far. I mean it’s been a couple of days, but yeah, he’s eager he, he’s taken on new things and I have a decent, there’s the pieces of a CSM role in place, so he’s not starting from scratch, which I think is helpful, but I’m like, Hey, here’s our onboarding. There’s a single page in our knowledge base, and then there’s this onboarding plan tool that we use. They’re not the same. They’re out of sync. So one of your first things, go through those, identify the inconsistencies, identify some room for improvement. And he started to do that. He actually has an engineering background, which is kind of interesting. He studied engineering in school and then worked for aerospace company before going into SaaS. And so in the interview process, he had said a few things like, oh, we should do a root cause analysis of what went wrong.
And I remember just thinking like, oh yeah, our product is really technical. And the thing is, our customers don’t really want to talk to us. I mean, they’ll be happy to chat, but we kind of need to be in the background. If they’re talking to us a lot, that means something is really not working. It’s not a product where it’s fun to talk to the team. It’s like sync issues and stuff. And so it’s like, okay, I need someone who’s going to be able to really drill down. And so I really, I thought that skillset was cool because I just thought it was kind of more to what we need to be able to do, just really drill down and understand why these properties aren’t mapping or whatever. Because we can’t hand wave away a problem. It’s either syncing or it’s not. And someone who can figure that out quickly is like, that’s a very valuable skill.
Rob Walling :
I love how fast Harris is iterating. He’s been exploring, integrating with Salesforce, which can be challenging to say the least. Before our conversation, he sent me this audio note.
Harris Kenny:
I have this sort of Eureka moment. I’m pretty excited about it. I know we’re not going to talk for a little while, but I wanted to share it. So context are go to market motion, working with agencies continues to be getting more and more traction, and several of these agencies are working with customers who are using Salesforce. Now, I’ve only built this HubSpot integration, but I really built it kind of painstakingly to think about how everything maps. And what I’m really excited about is that our HubSpot sync to Salesforce is working very cleanly. I just spun up a developer account in Salesforce after having a call with a series E startup. So just a ton of traction, really mature company with a lot of money, and the agency they’re working with is crushing. They’ve booked 90 meetings for them so far, and so they’re really happy with their agency, but they want to get that agency’s work in Salesforce.
And anyway, it’s working. I was surprised that it worked as well as it did. But it looks like I had been building for this because I built, I think so tightly to HubSpot that it worked. And so this is opening up a whole different set of doors for us. I think in the short term, I want to focus on the HubSpot to Salesforce path, but then there’s also room to potentially build just a standalone Salesforce integration and serve a hopefully different section of the market. Yeah, I dunno, it’s a Friday afternoon right now, almost four o’clock and unbelievably excited.
Rob Walling :
And this Eureka moment wasn’t just groundbreaking. It seemed to reignite something inside Harris.
Harris Kenny:
I haven’t had a feeling like this since kind of early days. I discovered that multiple users had already been using our product in Salesforce, which I didn’t know. Nobody had told me that or asked or anything. Not that they have to, but it just never came up. And that was part of the downside of the agency thing is that I just didn’t realize that. And so then I tested it myself. I spun up a dev account and it worked. It’s like, oh, you can go from outbound sync to HubSpot to Salesforce. And then I talked to more and more people and realized, oh, actually quite a few users are doing this. And then these new enterprise deals that are coming in are also saying, oh, we actually need, so this is the thing that more and more I’m hearing that people actually wanted, people that understood the value of the product tended to be actually in that ecosystem. Now there are also HubSpot people, but it was the Salesforce people who were kind of more into it. So that was an interesting learning. And then when I spun up the sandbox account, I actually kind of liked it. I hadn’t used Salesforce in 10 years, but I kind of liked it and it was said, no one ever. Well, so you’re the one.
Well, I liked it because for the reasons why a lot of people don’t like it. In HubSpot, it’s very intuitive and it’s user friendly, but it’s like Apple versus Android. And sometimes I want to see a big settings menu with a compact tight table where I can see everything, and it’s not nestled between these dropdowns and you got to click through to this, to this to to actually get to the toggle. So in a weird way, it was kind of like, oh, I feel like there’s a lot in front of me here. So I dunno. It was just interesting. It was a very unexpected response because in the HubSpot ecosystem, it’s very territorial of like, oh, orange, good, blue, bad, whatever. So it was like, okay, this is kind of interesting. So we talked to a company that made a toolkit product, and so basically it was a quick integration.
They’re basically themselves infrastructure as a platform, as a service. So they’re an IPA and work kind of an ipa. I was like, okay, well maybe we can work with them. And then anyway, the developer jumped into it and he was like, I’m not getting the error messages I need from these API calls. I think I can just do it on my own. I was like, honestly, man, you’ve got me here. I trust you. Whatever. Take a shot at it, work on it for a couple of weeks and let’s just see what happens. He kept doing some bug reports here or there, but in general, this was his focus for a couple weeks, and sure enough it works. We’re going to be announcing a Salesforce beta. I just posted on LinkedIn. We already to our agencies were like, Hey, I’ve got customers that want the Salesforce thing, so send me a Stripe link and let’s go. And already we’ve solved problems that you can’t do if you’re doing the HubSpot sync,
Rob Walling :
Then the Salesforce integration, you’re in beta. It took you weeks five to six weeks. Is that right?
Harris Kenny:
Yes. Which is kind of crazy to me. I think it’s because we spent a year and a half on HubSpot that when Vitali jumped in, and also what we do isn’t actually that complicated. All things considered something like a drip. It’s like there’s a lot going on with that product. I mean, we’re basically like, does this contact exist or not? If not, create it, log these emails to it. I mean, there’s more to it, but fundamentally, I think other products have a lot more problem things they have to think about. We’ll see, I might be talking to you next time and be like, Rob, I was wrong. We missed it. We forgot this thing. We hit an iceberg. I don’t think
Rob Walling :
It’ll be on your side though. I don’t think it’ll be your code. It will be. If anything, the experience that we started having and that other founders have had as they’ve tried to do this, is that Salesforce says, oh, great, you have this code now in order for anyone to deploy it, you need to go through our security audit and our this and that audit. And each one of those takes two months or something waiting on Do you have to do any of that?
Harris Kenny:
I think that, I mean, to get formally listed in the exchange, yes, but because that’s not how we’re acquiring customers, actually, it’s been a year and a half. We’re like, there’s one app in front of us in the queue before we’re going to get listed in the HubSpot marketplace. We haven’t even been in the HubSpot marketplace yet because we’re in these other,
Rob Walling :
You’re sound direct.
Harris Kenny:
So I think that we’ll be able to get away with being like, Hey, this is a beta developer version of the app. And then over time, yeah, we’ll be in the app exchange and we’ll pay the few thousand dollars. And we are starting SOC two tandem with this because the Salesforce people, they want SOC two. And so I suspect that if we do that, then it’ll make some of the security stuff easier because we will say like, Hey, here’s our trust center, and we ended up, yeah, that was a whole thought process over the last couple of weeks.
Rob Walling :
If you’re unfamiliar with SOC two, it’s all about making sure your company’s security controls and data handling practices are up to snuff. It’s like getting a seal of approval that says these folks are doing things the right way when it comes to protecting customer info. And as startups want to move upmarket and sell to bigger companies, SOC two can be a game changer, but it’s expensive and it’s a ton of work.
Harris Kenny:
Looking through the SOC two attestation, it makes sense to me these policies and controls that we should put in place. Sometimes some of that stuff just feels like a song and dance, and I’m sure that a little bit of it is. But I mean, for me, as a non-technical founder, we’ve got one developer. Some of these things are very good for me. If something happens to him for whatever reason, if we have these controls in place, I’ll be in a better position in terms of being able to business continuity or something happens to me. So it’s funny, but some say, oh, you’re too small to do it right now. But because we’re small, I look at these things and I’m like, these are actually kind of viability of the business. If we can resolve these, it actually kind of helps me sleep a little bit better at night, which is kind of funny. But yeah,
Rob Walling :
That’s the glass half full view of it. Most people hate SOC two and hate going through it, and you’re like, this, actually, you are definitely, you’re on the optimist side, which I think is really good for you as a founder.
Harris Kenny:
It’s like, oh, what happens if the one person who is putting code in production, what happens if thing happens to them? I should probably have an answer to that before it happens.
Rob Walling :
So you wrote me a note and the note said, I realized we weren’t really spending the TinySeed money yet. It had been three months, and we had effectively only spent $8,000 of the check you wrote us and revenue growth had slowed with you being bogged down in customer success stuff. So talk me through where you are with that. Have you started spending more money? Is this the hires and the full time and that kind of makes all that work?
Harris Kenny:
Yeah, definitely. There’s just old habits from how I’ve been running my business, and so I was treating that money in the bank. It wasn’t there. But something that you’ve said that kind of rings in my ears from time to time is that having more money in a business can save you years of time. And so I sort of made this decision of it was customers and prospects were coming in and they were asking for these things. They were asking for SOC two, they were asking for Salesforce, and it was like, okay, well, I probably just need to spend money to do those things. So now we’re in this spending era a little bit. And so my job now is to get it back. So it’s like, okay, we’re going to start sending the link to our trust center for our security stuff to people. And so now you need to come up with pricing for what those people who ask for that thing, what are they going to pay?
And I went to an old startups For the Rest Of Us episode, I just searched security and I’ve listened to every episode that I found where security came up in the Spotify search thing and something about five figure annual contract value stuff. We did close our first annual contract. We a company where it was like, okay, the people are willing to sign that type of contract with us even before we have the Salesforce or the SOC two. So that gave me a really big boost of confidence because I’d never sold an annual contract of anything in my life of my own companies. And so it was like, okay, we’re solving a problem enough that they’re willing to write that check. How much more would they be willing to pay if we could solve these problems even better? So we decided to go. I went with Vanta, which is kind of like the category creator in the GRC compliance software space, because I just kind of want to get it done the first time, send it to people, and they’ll be like, cool, you pass review and not have to go back and forth and maintain a bunch of stuff and a Google Drive and things like that.
So yeah, so that was the decision of consciously, let’s spend this money, let’s get these deals in rework pricing and try to be a little bit more confident in the sales cycle instead of before being like, well, it’s supposed to be 500, but you could pay a hundred and it’s month to month, but you can actually cancel yesterday. It’s just like, come on, dude, this is cool. You built something cool. Sell it. And I think part of it’s going to give me the confidence to do some of that.
Rob Walling :
Harris’s bold moves are paying off an outbound sink is gaining momentum, but as he navigates this entrepreneurial roller coaster, every decision carries weight. Will his growing confidence be the key to unlocking even greater success? Buckle up for next week’s episode where we’ll follow up on his SOC two compliance journey. Find out how he’s scaling outbound campaigns without losing the personal touch, and talk about a potential positioning pivot that could catapult outbound sink into a whole new league. Don’t miss out on the twists and turns of Harris’s journey next time on TinySeed Tales. Hope you enjoyed this episode. If you’ve ever wondered what it’s really like inside TinySeed and want to hear a raw candid coaching conversation between Harris and I, we put together something special for you at TinySeed dot com slash bonus. You should check it out. I’ve never released anything like this before. I hope you enjoy it. It’s at TinySeed dot com slash bonus.
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