How Roger Lear Built 2 Job Boards That Still Dominate After 20 Years

Introduction:

If you're building a job board or thinking about launching one, there’s no better teacher than Roger Lear. In this in-depth interview, Roger sits down with Martyn Redstone to share how he built two thriving platforms — OrlandoJobs.com and GreatInsuranceJobs.com — that have stood the test of time in a rapidly evolving industry.

Watch the Full Interview:

5 Actionable Takeaways for Job Board Builders:

1. Choose Your Angle: Niche or Regional — But Know the Landscape

Roger explains the pros and cons of going local (OrlandoJobs) vs. niche (Insurance). The key is solving a real hiring problem with a tailored solution.

2. Strategic Partnerships Are Game-Changers

He leveraged relationships with associations like SHRM and National Underwriter to build authority and win recurring traffic and revenue.

3. Traffic Beats Tech — Every Time

Forget building from scratch. Today’s job board success depends more on your ability to drive real, qualified traffic than your tech stack.

4. Be Human — Not Just Digital

Showing up in person at conferences and local events made all the difference. Relationships build trust, which builds business.

5. The Future? Influencers + AI + Networks

Roger’s launching the Insurance Talent Network — and believes the next wave of job board success lies in influencer-driven content and smart AI-backed targeting.

Full Transcript:

Martyn Redstone (00:01)

If you've ever wondered how to build a job board that actually lasts, Roger Lear is your guy. He's been in the game for 25 years, from launching greatinsurancejobs.com to transforming orlandojobs.com into a regional powerhouse. In this episode, he's pulling back the curtain on the real strategies that work and what to avoid if you're just getting started. Let's dive in.

Martyn Redstone (00:25)

Roger, thank you very much for joining me today.

Roger Lear (00:28)

Glad to be here, man. It's awesome.

Martyn Redstone (00:30)

Great to have you, great to have you. let's jump into it. Roger, you've built a portfolio of some really successful job boards, Orlandojobs.com, greatinsurancejobs.com. When I was looking at it, it's a really fascinating duality. And I was wondering, what's the biggest difference between conquering a city from a specialist perspective compared to conquering an industry from an insurance perspective?

And what can job board owners learn from that contrast?

Roger Lear (01:00)

Okay.

Yeah, you know, that's a great observation. know, Orlando jobs dot com just turned 20 years old somehow, some way. I don't know how that happened. But the the the thing about Orlando jobs dot com, it gave it since we're based in Orlando, it gave us an opportunity to get out into the community and get super involved with the local

Martyn Redstone (01:16)

Thank

Roger Lear (01:34)

HR chapters, all the different community partners that like jobs partnership and central Florida employment council and things like that and build amazing ties with these organizations that all directed traffic and jobs and potential clients back to Orlando jobs, knowing that, you know, we were very authentic and, and also the opportunity to,

go see our clients physically, you know, in a lot of cases over the years, especially, you know, especially before, you know, everything changed and everything, you know, is a a teams meeting now, right, or something like that. but, you know, back then it was, you know, nobody was doing stuff like that. And and it was good. Now, the insurance industry and great insurance shops, ironically, turns 25 years old next year.

Martyn Redstone (02:18)

it.

Roger Lear (02:34)

And it's hard to believe that, you know, that as well. But the biggest challenge as a job board owner there is getting not the business necessarily, but getting the traffic because of the spend of these companies of having all of our clients like travelers and AIG and things like that. They have jobs all over the place. And, you know, we have to be

Martyn Redstone (02:40)

Yeah.

Yeah.

Roger Lear (03:04)

Uh, in so many different cities and things like that. So the way we've been, uh, uh, combating that is over the years. And we're the only job board that doesn't in the insurance industry and even our competitors like indeed and blah, blah. But, uh, they never go to these specialized conferences and we go to about seven or eight of them a year. And when you go and use your clients, see you at these conferences and know that, Hey, you're not going to get.

85 resumes for a claims adjuster, you're going to get probably 10 and you're probably going to be able to hire one or two of them, you know, and and but they're going to know that the connection came from all the things that we do with the partnerships and associations and stuff like that. The biggest, you know, to your question, that's, know, there are two there. They really are different businesses. And in a way, we all do the same thing except

In Orlando, it's given us a we can see we can see the connections. You know, we do we do local events. We do. We just did Hired Orlando where we ran out the entire Kia Center. And that's where the Orlando Magic played basketball and stuff like that. And had about 90 employers there. We had over three thousand job seekers show up. We had.

Martyn Redstone (04:23)

Yeah.

Roger Lear (04:30)

community partners, free headshots, resume reviews, all the things for an unbelievable community day. And then all of sudden all the press shows, you know, and they're doing stories about the job, because the job world now is back in the news because it's not as, it's a little bit softer market over here, right? And they were amazed how many jobs we had at this site, right? And that kind of stuff. But in the insurance industry,

You know, we can't do that. That's a that's a you can't have that centralized thing. So we do we do virtual job fairs, but there are nowhere nearly as successful as a local really first class first class stuff. So, yeah, that's that's kind of what it is. I you know, the insurance industry is an industry a lot of people don't know anything about. And it's an amazing industry with tons and tons and tons of jobs and stability and stuff like that.

Martyn Redstone (05:01)

my

Roger Lear (05:29)

Orlando, we're all over the place. We have the greenhouse jobs where they can't hire enough people. Disney, Universal, everyone thinks about that, but all the companies that support our tourism market here, all are looking for people, but those jobs are a little bit lower paying. Then we have our technology people, we have our engineering, have our, it's just healthcare big time, all that other stuff.

Martyn Redstone (05:52)

Yeah.

Yes,

nice and such an incredible contrast when you think about it, know, locally able to kind of have those those real in-person human kind of relationships, whereas, you know, kind of a nationally wide or even globally wide niche, you know, is very much around a different type of relationship and a a different knowledge level as well, ultimately. So I absolutely get that. So let's let's go back in time a bit.

So as you said, 25 years for great insurance jobs and 20 years for jobs in Orlando. What was your background before that? What inspired you to enter the job board space? What was that moment that made you think this is a good idea?

Roger Lear (06:44)

You know, and I would tell anybody, I think this, moment that I had is the same moment that's taking place now with AI, but I graduated from Florida State here in Florida, but I knew that I needed something else to do with my life. So I started an insurance executive search firm called Lear and Search. And that was in 1991.

Martyn Redstone (07:06)

Okay.

Roger Lear (07:13)

when I started that, didn't know, I didn't know the difference between a claims adjuster and an underwriter or anything. mean, I've met somebody that said, hey, do this and you'll make a lot of money. And I'm like, okay. And it turns out that it wasn't that easy, but I still, I still, the Art Association stills work in today too, which is still blows my mind. the, the, but I really got to learn about,

Martyn Redstone (07:24)

Yeah.

Amazing.

Roger Lear (07:43)

the insurance business, just like everything in business, one of the things, the keys to anybody that wants to be in business is you gotta find people that are smarter than you, and you also have to be involved in associations and things like that, and go to meetings and learn, because if you don't, you're dead in the water. And I was fortunate enough to meet a gentleman named Jay Rollins who,

One day came to me and said, Hey, you know, this internet thing is coming on. This was like 1995. And he goes, it's going to probably replace you. You know, just kind of like job boards have been dead for years and you know, AI is going to replace the world, you know, all that stuff. Right. So I said, Hmm, that sounds interesting. So he goes, yeah, you have to register domain names. And back then it was like ridiculous amount of money and register domain name. And it really was, it just, changed from.

Martyn Redstone (08:21)

Yeah.

Roger Lear (08:39)

I don't know if you remember this, they went from IP addresses to domain names, right? Overnight, basically. then, so anyway, so I go, good. Well, I'll start an insurance job for it then. And so I go, I'll do insurance jobs. And he goes, you can't. And I go, why? And he goes, because I already have that one. then I'll do this one. I already got actuary.com. already got, and I'm like, all right.

Martyn Redstone (08:42)

Yeah. Yeah.

Roger Lear (09:02)

He has all the good ones, right? And so that's how I came up with great insurance jobs. I said, that sounds pretty cool. So I registered that and you know, back then it was.

you know, now you can register domain name for like 10 bucks or 20 bucks or whatever. Back then it was $800. You know, it wasn't it wasn't cheap at all or anything. So you had to be real careful, especially, you know, whatever. But the key back then, though, the thing that that is so interesting to me when I look back at that is when you build a job board from scratch, there were no J boards back then. You know, there were no magics. There were no job, you know, whatever.

Martyn Redstone (09:42)

Mm-hmm.

Roger Lear (09:47)

You built it from scratch and you had a higher team of people and the team that we hired loved them to death but it probably cost a quarter million dollars to build the first reiteration of great insurance jobs and They had they had You know project managers graphic designers database administrators, and I mean everybody and nobody

these white boy, my God, I don't know. I don't know how I invested in that, to be honest, because it, you know, I was running my recruiting firm using the revenues from that to pay that. I took one of my recruiters made him kind of the operations guy over that. So I could, you know, continuously fund this thing. And then, and then we went live and we were very fortunate because we were able to sign a

partnership with the National Underwriter, which at the time was the premier insurance magazine. I mean, this is like this is the New York Times of of the insurance industry and and we signed a partnership and they really helped us escalate our credibility once the market got going right and job postings and stuff like that.

So that was a really cool journey and lots of learning points, lots of ups and downs, but it did establish us years ago and we're still in that same spot as the, if you're looking for a job in insurance, there's probably some pretty good ones over here. that's that's that. So yeah.

Martyn Redstone (11:39)

Amazing.

That's

amazing. That's amazing. So you mentioned, you know, a couple of kind of bumps in the road there. What were some of those early challenges that you faced? You know, how did you navigate through them?

Roger Lear (11:51)

Yeah, it's it is the biggest challenge and, you know, is technology and having your own, you know, once we had the boards done, we had our own team then technology wise and with all the changes, just like what's going on today, you just can't move fast enough with your own team. You can't do it and you can't afford to. The business model doesn't, it doesn't allow for

Martyn Redstone (12:11)

Yeah.

Roger Lear (12:18)

hundreds of thousands of dollars in technology spend that just doesn't. You know, at the end of the day, the job board, got to be able to post jobs. Candidates have to be able to apply and they've got to be able to do that on a, on a phone and very quickly. And, you know, to do that with your own technology. So that was, that was a major, major up and down the server management.

You know, everything's in the cloud now, but remember server farms, you know, well, same still there. There's still server farms, but you know, if your thing went down, it was down, you know, I mean, I mean, you know, our uptime was probably, I don't even know, maybe 90%. It was horrible. And, then, you know, then people, you know, with all the privacy stuff, once that got going, that was never a really big thing, but

Martyn Redstone (12:49)

Yeah. Yeah.

Roger Lear (13:15)

You could break into any of these websites without even thinking boys about it. So we had a couple of challenges there, but at the, you know, it was a, it was a really cool process. So, and, you know, if I didn't, if I didn't have my recruiting firm working as well, I never would have been able to support both those things, and feel decent, like things were going to move forward, but.

Within about a year, year and a half, that thing was self-sufficient. And we didn't have a huge staff or anything, but we started, we did hire our first employee, salesperson and so forth, and they were able to go out and they're literally educating companies on what this means, you know, and so we were able to, you know, make some pretty good alliances there.

Martyn Redstone (13:50)

Okay.

Interesting, interesting. Did you find that that was starting to compete with the search firm? Did you feel like there was a bit of competition between the job board and the search firm? No.

Roger Lear (14:20)

No,

no, no. And no one ever knew there was there was any correlation between the two anyway. and and I always thought that was an issue. But that's where that's we'll talk about that later. But there's a that's I think a big, big opportunity for job board owners is understanding that, you know, need talent and they

Martyn Redstone (14:43)

Yeah.

Roger Lear (14:48)

would love to get it through a job board by just posting a job and getting a candidate and having the, you know, somebody else do all the interviews and just them show up one day, right? Without them doing anything. That's exactly what a client wants, but that's not reality. The reality is, is they need a lot of resources, but to be able to, to find the right people and, get them hired, onboarded, all that other stuff, but, and it could require other resources for sure.

Martyn Redstone (15:18)

Yeah, no, I get that. I get that totally. So you've obviously got the experience of both the insurance niche and also the regional kind of focus on Orlando jobs. If somebody was starting a job board today,

What factors should they consider when deciding whether to go kind of deep from a niche perspective or whether to go wide from a regional perspective? What are those factors that a startup should consider to make that decision?

Roger Lear (15:53)

Yeah, I think anyone that's starting a job board today, first of all, has to understand that the math that they do in their heads, hey, I'm going to get 100 postings at $300 apiece every single week. And this is, this is how I want to make one. It doesn't work that way, you know? And I say that initially because when you're deciding on what you should do a job board in, you have to take into consideration.

A things. The number one thing for us and anything is what is the challenges within the market that you're putting your job board in? You know, and and for instance, I'm just for the insurance industry. We know that 40 % of the insurance professionals are retiring in the next three years, right? And that's a

That's a real stat theoretically, whatever that means. And when you, when you are looking at your either niche or your city or whatever it is, that could be a potential opportunity. And then you research and find out who's might be serving that opportunity and then figure out what competitive advantage that you might have by building a job board to be able to.

be a solution based type of company. I do believe the days of the job board person that wants to start a job board and just fill it up with crap backfill jobs and try to get clicks and do some social media posts. I think you'll never make a lot of money doing that. But those days I think are over for a lot of people potentially. And again, I'm just speaking

candidly, if you're serious about making a business, job board owner has to understand their market, has to understand the challenges within that market and then have the internal staff to be able to go and talk to your clients because they're the ones that paying the bills and figure out how they can fit in.

And then when you get the, especially if you're starting a job board, how are you going to get traffic to that job board is, is just, uh, you know, it's, there's a lot there and, um, uh, most job boards that are starting will just buy traffic, um, and so forth. And a lot of that traffic doesn't get hired and, um, it takes a while to get your natural traffic going. But I think, uh, for a job board owner, if you're

decide to do a niche city or niche sector of any marketplace, I think there's a huge advantage now with so many other ways to drive traffic to a job board that if you understand that and can get your clients some decent hires, know, it doesn't happen overnight, but when it does and you customer service them, it'll be a, it'll be a

It'll be a good match for you. It's tough.

Martyn Redstone (19:23)

No, that's great. That's absolutely great. And one of the things that you've consistently mentioned about driving, you know, either regional or sector specific niches is, is around strategic partnerships, building partnerships with, you know, magazines, underwriters, but also regionally with, you know, HR forums and associations. So it seems like that's quite a

sensible route to take in order to grow a job board. What advice would you give to job board owners who are looking to forge those partnerships? What are the potential pitfalls that you should avoid when trying to create those partnerships?

Roger Lear (20:05)

Yeah, I think the biggest pitfall for most is they're not involved themselves, right? You can join any of the associations that you want to partner with and get to know the players within that partnership. You know, this world is about people and it's about knowing people and it's about people liking you and you liking them. And I can't even stress enough that if you want to be successful in any business, it doesn't matter job board or anything.

You better get out there and meet as many people as you can. And hopefully lot of people that are a lot smarter than you, because they, if they like you, they're going to take you under their wing and help you achieve a lot of the goals. But with the associations, I forged a, an amazing opportunity with our local shurm chapter called go shurm. has 800 HR members, right? And.

I formed this about 15 years ago and it's still active today. And I went to them and I said to him, I cause all associations have one thing in common. They all need revenue and they have something in most associations called non dues revenue and things that they don't get from conferences or, know, and so forth. And I went to them and I said, Hey,

this is what I'm going to do. And you're to have to trust me on this because we don't have any traffic to our site yet. This is what I'm going to do for you. But we we said we'll give all the GoSherm members a opportunity to go on OrlandoJobs.com and they get a free post all your jobs, anything that you want to do with the site, resumes, blah, blah, blah for 45 days for free.

And then if they want to stay on, they'll get discounted rates on whatever products are and we had a price sheet and all this other stuff. And back then it was more about job postings and job packs and things like that. And then what we did was we whatever they got, they got the discount. And then we took whatever the total was and gave him 10 percent of that deal back to go.

And on a monthly basis, we literally got up to where we were giving them a significant amount of money every single month. And it really, it really, it really worked out well. In return, we were able to be a sponsor at all their monthly meetings and be involved in a lot of their community events and things like that.

Martyn Redstone (22:58)

Yeah.

Roger Lear (22:58)

The Gosher and partnerships over the years have been very instrumental in the core fabric of Orlando jobs and getting known and stuff like that. But every association that we do, and we have quite a few in the insurance industry, we have others in Orlando as well. I don't do any other revenue share models with anybody. I haven't had to because like the CLM, the Claims Litigation Management, amazing organization.

amazing and they needed jobs, claims jobs for their website just as a resource. we asked them, they said, hey, we'll feed these over to you. They built out their own technology over there. And now we're able to not only provide those jobs for them and they're excited about that, but for us, we're saying, hey, your jobs also get posted to the CLF.

you know, website, you know, get a claims job and it has all the top claims professionals of the country. So I mean, it's just those are the things and job board owners, they, you know, it, it floors me. It absolutely floors me that a lot of, well, the successful ones get it. There were so many startups fail because they just don't work the business. It doesn't happen through emails and, and,

Martyn Redstone (24:06)

Thank you.

Roger Lear (24:26)

spamming town acquisition managers, offering free posts. know, it doesn't, none of that stuff works. If you're going to, if you're really going to build, build something and it's not going to happen overnight. You gotta, you gotta, you gotta, you know, that my, my thing to a job board owner would be, you know, really take a look at how you're going to be competitive, but how you're going to also make a difference and give back, give back to whatever community that you're going to be in. So.

That's what I would say.

Martyn Redstone (24:58)

Yeah, that's fantastic. Fantastic piece of advice there to give back as well, think is super important, really, really important. So, you you've had an incredible career so far in this space, you know, 20, 25 years of running job boards. But looking forward, looking into the future, you know, hopefully kind of into the crystal balls and the tea leaves.

Where do you think the biggest challenges and opportunities are going to be over the next five years for job boards? You know, we've already mentioned, you know, some of the changing winds and the changing ways that we're seeing in the world. What do you think? What's going to happen in the next five years?

Roger Lear (25:36)

Well, I think a few things. Number one, know, AI is gonna play a role in a lot of things, but it's still not gonna play, know, the AI never had childhood drama, you know? So if you really, if people really understand what that means, they're going to know.

that the job business of connecting employers and job seekers is an emotional human interaction. And yeah, there's some certain jobs that can be done without a human ever touching it. And I get that, but clients, humans still want to be human and they still want to have interactions and things like that. I don't think anything like that has changed. I think the opportunity for a job board owner today.

is off the charts awesome. Because in my opinion, and this is what we're doing, I'm getting ready to release two huge networks. And these networks, one's called the Insurance Talent Network, and it's going to be all of our, I've been buying up some sites and things like that, but it's great insurance jobs, claims jobs, underwriting jobs.

go down the list and then insurance sales jobs. And then Florida, have Miami jobs, Tampa Bay jobs, Jacksonville jobs, Orlando jobs, Tallahassee jobs, all this other stuff. the big challenge in our industry right now is this backfill nightmare that's going on. And companies buying and selling candidates and email addresses and resumes, not giving a damn about

an internet, a hire, not carrying one iota. And, that has to go away. in my opinion, and the way that goes away is you have natural traffic to your job boards and you build, you build your, you build your own network and you have your own, direct connection when, and when a candidate comes in where they can't

quick apply to 80 positions in five seconds, you our friends at Indeed, you know, they're just crazy over there, right? And in a way, what I mean by that is talk to any employer. They have to use them because they're still, you know, they're not doing backfill jobs. They just have fake jobs and not abusing Indeed people. what I mean by that is anybody can access that site, but they're not.

buying jobs and doing all other stuff. When you apply to a job, you still have a decent chance to get noticed. The challenge is they mask emails, they mask resumes, they mask all this stuff. Now they even make you sign in before you can even do anything. And for employers, if they want to contact anybody, they have to basically talk to Jesus first, you know, to make that happen. And that's not how the business works.

Business for talent acquisition is they want real quality traffic knowing that they're going to get a lot of crap. Nobody's going to get rid of the crap. But if you make the process very simple direct into their applicant tracking systems things like that. The thing about the job boards though that gets me more excited is now we have a way to be so competitive to get traffic to these sites.

And with our networks, we're doing something completely different and to drive traffic because we're hiring influencers all over the place that are going to be part of our influencer team to help drive our message in a fun way, right? And then we're also going to do our own, you know, a completely different, you'll see, you'll start seeing it come out because

Martyn Redstone (29:42)

Mm.

Roger Lear (29:55)

We're announcing the insurance down network at rims, which is in Chicago in a couple of weeks and very, very excited about it. But, we've had, we've been testing a lot of this stuff here and it's, it's, I, I'm just, I'm just really excited. the other thing for job board owners too, is with AI being able to really do a deep dive into a marketing campaign to drive traffic and how to do that. And also.

Martyn Redstone (30:01)

Yeah.

Roger Lear (30:25)

Maybe not make the creatives. I mean some can I mean well they all can some of them just look I still think a great graphic designer is is worth their weight and gold and and so forth, but I even even there You're watching chat come up with these unbelievable graphics, right? I mean, it's just crazy but all of that stuff and the being able to analyze your analytics like no other right

of being able to figure out, hey, what's working, what's not with one click now, instead of having to take forever to analyze it. That's a huge opportunity. And I believe we're at the flip phone stage of that. That's why I think there's a huge opportunity for job boards. The new search engines are going to be the chats, chibits and the gemini's and everything else. You want to be cited in those things. So you have to.

make sure your site is structured properly so it has the information that chat would love to know and stuff like that. Because it is capturing a tremendous amount of search traffic, right? And so forth. I think we're at that, I think we're right at the beginning of that opportunity. So I look forward to seeing, I look forward to seeing what's gonna happen, man.

I'm very, very, very positive about it. Very positive.

Martyn Redstone (31:53)

And me too.

No, I'm excited to see what the future looks like as well and I think it's absolutely excellent. So the last question I tend to ask people is, if you were going to start a job board today and with all of the experience that you've gathered over the last 20-25 years, what are the three things that you would do differently?

Roger Lear (32:23)

Well, the first thing is I would have a much better, in the early days, a much better CRM to manage the whole process. So we know where people are calling, what the messaging is and all that other stuff. Thankfully, in today's world, you've got a lot of that stuff.

but it's still with all the bells and all the whistles, it still takes a while to get it set up the proper way and so forth. we're very big fans of HubSpot and their CRM and all the AI capabilities within that. So a good CRM too, I would say you have to understand the problem that you're solving and understand that there is no such thing as

beginning a job board and having traffic and employers come and start posting jobs. And if I were to start a job board again today, I think I'd jump out a window. I don't know how I would do it. Except I would tell anybody that it's starting a job board today is get with a mentor.

that has started job boards in the last 10 years or so whenever and just absolutely ask them every question under the sun. Most people want to give away everything because they know everyone knows that's successful in anything is they can tell you all day long. If you really want to do it, you can do it. A lot of people choose to, you know, everyone's looking for the easy button. There is not in my opinion, the job board. Maybe there is. I don't know. I haven't found it yet.

And was one other thing. Let's see. The third thing is, is, is you gotta, you know, for, for, for me, the thing that changed us was hiring better people instead of trying to go, we just didn't have a lot of money. and we, we really put these, these,

Martyn Redstone (34:43)

Mm.

Roger Lear (34:48)

way we sold our business and sold the packages and things like that, we made it more commission heavy than salary heavy. And we were unable to attract the best. And when we switched it the other way around, it really changed the direction of great insurance jobs. No question about that. And as a matter of fact, I've got, I've had some of the top top people in the industry start here.

They've gone other places, but they've started here, made a bark, and then we couldn't afford them anymore. So that's what I would tell you.

Martyn Redstone (35:28)

Brilliant, no absolutely brilliant. So three absolutely fantastic things to think about. I really love that last one, really really love that last one as well. Roger, thank you so much for giving up your time to impart the absolute wisdom that you've accumulated over what is a fantastically long and successful career in the job board space and you looking forward to many more years in the future but for now.

Roger, thank you so much for your time.

Roger Lear (35:58)

Yeah, excellent conversation. Thank you, man.