Job Search: Not-Entirely-Human Resources

This week on Trailblazers, we look at the evolution of the job search in the internet era.
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Not so long ago, we were all applying for jobs in person. The internet, and companies like Monster and CareerBuilder, changed all that.

Technology is now changing it all over again, with artificial intelligence and machine learning taking some of the unconscious biases and manual labor out of the job hunt process on the other side.

This week on Trailblazers, we look at the evolution of the job search in the internet era.

In this episode

● An early dot com success story. (0:00)

● It all started with a “help wanted” ad. (2:42)

● Going from job search to finding jobs using search. (5:12)

● Fax machines portend a technological future for job hunting. (8:26)

● “If you aren’t one or two, you’re toast”: online job search during Web 1.0. (11:29)

● Tech comes to the recruiters’ rescue. (19:14)

● Tackling bias in the job search with AI. (21:01)

● People will always be needed to recruit other people. (26:24)

“Where the industry is facing this obstacle of there is not enough supply out there to meet the demand, and so recruiters arereally having to go and move from this post and pray mentality, into how do I leverage technology to help me do the work for me?”

— Irina Novoselsky, CEO of CareerBuilder

Guest List

  • Mark Lobosco is Vice President of Talent Solutions at LinkedIn.
  • Jeff Taylor is the founder of the online jobs site
  • Somen Mondal is a co-founder of, a company which uses artificial intelligence and machine learning to help companies optimize their high-volume hiring.
  • Richard Johnson is the founder of, one of the first niche job posting websites, which was eventually bought by Monster.
  • Irina Novoselsky is the CEO of CareerBuilder.

Walter Isaacson: It’s a sunny day in May, 1998, and Richard Johnson is on the train on the way home to the suburbs from his job in New York City. By all accounts, he should be a happy man. His company,, which he’d founded two years earlier, is an early dot-com success story. It’s one of the first companies to put help wanted listings on this fascinating new technology people can’t stop talking about.

Walter Isaacson: The internet. Hotjobs is growing fast. They’re the fifth leading company in the internet jobs space, but that’s a problem. In the early land grab days of the net, fifth best might as well be last place. Other competitors like and Career Mosaic are in first and second place and are quickly pulling away from the pack. If Isaac son doesn’t do something to improve its position soon, it’ll be left in the dust.

Walter Isaacson: Sitting there on the train, Johnson is despondent. Should he give up? Should he just close his company? Tell all his employees to go home? Or should he bet it all on a Super Bowl ad? The idea makes no financial sense, but he can’t shake the thought. And that’s why just a few months later, Johnson finds himself mortgaging his own home in order to take the biggest gamble of his life, a $4 million wager that would decide the future of his company. What he couldn’t know at the time, however, was that his plans would be quickly turned upside down. The Super Bowl ad he’d spent so much money on would never air, but it would end up having an impact that he could never have imagined. I’m Walter Isaacson, and you’re listening to Trailblazers, an original podcast from Dell Technologies.

Speaker 2: When you’re searching for work, you’re fishing for a job.

Speaker 3: The company just up and started firing people.

Speaker 4: Where did you find out about this job?

Speaker 5: Oh, from newspapers and local libraries.

Speaker 6: Why did you choose this job?

Speaker 5: I need a steady job with the chance to go places.

Speaker 2: Every person has the ambition someday to land the big job.

Speaker 5: Maybe I’d like to work for them.

Walter Isaacson: Job searching has come a long way since the days when hopefuls banged out their resumes on typewriters and pounded the pavements, dropping off paper copies at reception desks and hoping for a call back. And until the early 1990s, if you were an employer wanting to list an open position, you had to take out a help wanted ad in a newspaper classified section or pin your listing to a bulletin board in an employment center. The technology revolution changed all that as it did so many other industries. But beyond the obvious improvement of being able to search job listings on websites and submit resumes electronically, there are deeper changes afoot.

Walter Isaacson: Data is changing the way employers search for and assess candidates, and the advent of artificial intelligence and machine learning is starting to have an impact on not just how we hire, but who we hire. By the time the internet arrived in the mass consciousness, job searching hadn’t changed much in decades. The process of listing a job was laborious and inefficient. Recruiters called the process post and pray.

Mark Lobosco: If you look back to the way companies and organizations have historically hired, you know, way back in the day it was a help wanted sign in a window and then that moved to maybe a job listing in a newspaper and eventually wound up being a job posting on a job board.

Walter Isaacson: Mark Lobosco is vice president of talent solutions at LinkedIn.

Mark Lobosco: Now, that was an effective way to get lots of people to apply but not necessarily the right people. And so you’ve got a high volume of applicants but maybe not always the highest quality. There was an alternative way to hire from any organizations, and that was to engage a professional staffing firm who were very effective at maintaining a network of professionals that could be a better fit for the role based upon unique skills that they kept with their own personal network. One of the challenges with that, though, is it often was lower volume of hires that you would engage a staffing firm for and it was a higher cost. And so organizations in the post and pray world, you know, had one option of posting a job to a job board or engaged a professional staffing firm.

Walter Isaacson: For many companies, neither alternative was palatable. But the era of post and pray was about to change.

Jeff Taylor: I got into the business of help wanted advertising in 1989, and what I did was I placed help wanted ads in newspapers across the country.

Walter Isaacson: Jeff Taylor is the founder of, one of the Internet’s first and most well-known job search boards.

Jeff Taylor: So you had The Boston Globe and the San Jose Mercury News, Chicago Tribune, Wall Street Journal, all had big help wanted sections, big display ads that companies placed their open job positions in. That was how people applied for jobs. You went to the address in the ad, you sent your resume to that address. And it sounds crazy now, but that was the way it was done and everybody did it this way.

Walter Isaacson: Taylor eventually became a headhunter, helping big tech firms recruit skilled talent. But he had a problem — the want ads were a slow and laborious way to sift for highly qualified programmers, and he wasn’t getting the results the clients wanted. Something had to change.

Jeff Taylor: One of my customers, after the recession of ’89 and ’90, basically said, “The newspaper help wanted section is not getting the kind of people that we want, and I’m going to fire you unless you can come up with a new idea.”

Walter Isaacson: The Web was about to break through, but it hadn’t become the all-pervading source of information that it is today. Still, Taylor saw that it had limitless potential with a reach that would one day go beyond the newspaper’s back pages. And the idea for his website came, as many great ideas do, in a dream.

Jeff Taylor: I don’t have a life. I was dreaming about work, and I had a dream that I built a bulletin board called the Monster board. I usually can’t remember my dream, so I have a pad next to my bed. And I wrote down the Monster board in the dark, and I thought I wouldn’t be able to read my writing. So I got up and went to a coffee shop and I wrote most of the interface and I drew, badly, the first Monster Trumpasaurus in that breakfast session that was about four hours. I basically created the interface for Monster. And so my address was, and the name of my company was The Monster Board. It was just a bridge from being a bulletin board.

Jeff Taylor: And that was the precursor to things called job boards. What’s amazing about that early process is job board stuck, and Monster was the first job board on the world wide web. I wanted the name to pop, and I wanted to have a mascot or a character to go with it. Trumpet was to trumpet the success of the job seekers, and the -asaurus was I had little kids and I was reading dinosaur books to my kids. And so I decided that I wanted to trumpet the success in a way like big, like a dinosaur.

Walter Isaacson: Taylor had no way of knowing that Trumpasaurus would eventually you have a much different implication. But meanwhile, just down the road from where Taylor was dreaming up his monster in Massachusetts, another entrepreneur named Richard Johnson was drawing up plans to create his own job board called Similar to Jeff Taylor, Richard Johnson got his start as a recruiter. And although the landscape was vastly different in the 1980s at the beginning of his career, he could already foresee the huge impact technology was starting to have on almost every industry.

Richard Johnson: So in 1987, really, for me, the first breakthrough was the fax machine. You’d go out in Fifth Avenue in New York City, and you’d see thousands and almost more bike messengers than you would see cars. And then within a year, all the bike messengers were gone. So, you know, that’s just how impactful just one change in technology can be.

Walter Isaacson: Johnson’s company, RBL Agency, worked with companies in the technology space, so it was only natural that they dove headfirst into the internet when it began to hit mass consciousness.

Richard Johnson: We sort of led the way. Because we are such a technology-oriented recruiting firm, we did away with hard copies of records, and we put a computer in front of each of our recruiters’ desks. We did that way early, you know, maybe ’91. And by ’93, we were the first company to ever advertise an email address in the New York Times classified. So if you’re trying to find job seekers who are in technology and you’re the only one with an email address, it just helped our company explode. I already had a glimpse as to what technology could do. And then in 1995, we were the first company to ever advertise a website in the classified section of the New York Times.

Walter Isaacson: Hotjobs began as a software solution that Johnson’s firm used in-house to help its own recruiters. Johnson then toyed with the idea of turning the Hotjobs software into a full-fledged, web-based job board. His first task was to suss out the competition. And when he looked closely at the other sites out there, he realized that despite their web presence, they still had one foot firmly planted in the pre-internet era.

Richard Johnson: In the beginning, when you looked at Monster or Career Mosaic, who was the number one job board at the time, at the bottom of their ads, it said, “To apply for this job, fax or mail your resume.” I was like, “Oh my gosh. We already have a fully interactive job board for our recruiters,” and that’s where came.

Walter Isaacson: Hotjobs made it easy to search for jobs and to apply for them without having to involve a fax machine or a photocopier. Companies paid to list jobs, and applicants could easily search and apply for free. But despite being internet pioneers, both and Hotjobs struggled in those early days when it wasn’t clear that the internet was on the verge of dominating so many industries. Jeff Taylor.

Jeff Taylor: It was a very challenging thing. My first salesperson would just cry in my office and say, “I spent an hour talking about the internet. And they said, “Thank you very much for teaching me about the internet,” and never got to actually sell the product.”

Walter Isaacson: For Hotjobs’ Richard Johnson, the problem was being a small fish in an ocean full of much larger players.

Richard Johnson: We were the 270th most recognized brand on the internet. Monster and Career Mosaic had these huge advertising budgets, and they were growing faster than we were. Back then, I don’t know if you remember the 1.0 mantras, but one of them was, “Of you aren’t one or two, you’re toast.” And, you know, if you weren’t Yahoo or AltaVista or Excite on the search engines, you were toast. And even Excite and AltaVista were toast. Then, there was Ask Jeeves, which became Ask. And so, you know, there was this whole war for the search engines. There was that same war going on for the job boards, and I was five or six.

Walter Isaacson: Amazingly, both entrepreneurs had the same idea at the same time, and that was to bet it all on a commercial to air during the Super Bowl. The same game, in fact. Super Bowl 33, on January 31st, 1999.

Richard Johnson: I mortgaged my house and my business and everything I had, and my partner mortgaged his house and all our receivables. We borrowed $4 million that we intended to spend in 30 seconds on the Super Bowl. Gambled it all.

Walter Isaacson: Jeff Taylor.

Jeff Taylor: One of the magical moments was the thought of maybe could I advertise on the Super Bowl. I had spent about $4 million, I think, in 1998 on marketing. And in the first few days of January, February, of 1999, I spent $4 million in one and a half minutes on the Super Bowl. And so I spent my entire advertising budget in just one breath almost from the year before, and I put an ad on the Super Bowl, and that was crazy town.

Walter Isaacson: Being the wacky early days of the first dot-com era, neither company was content with just an ordinary run of the mill commercial. This was the Super Bowl, after all, their one expensive chance to stick in people’s memories. For Hotjobs, That’s where the problem and the opportunity came in. Richard Johnson.

Richard Johnson: We had this ad of a elephant in a cage eating hay and a zookeeper in the cage sort of sweeping up, and they both had their backs next to each other. They were sort of backing towards each other. All of a sudden, the camera zooms on the elephant grabbing some hay in his mouth and sitting down. And from the expression on his eye, you could see that he sat on something. The camera panned back. A broom drops from the rear of the elephant, and this tagline is, “Stuck in the wrong job? Go to”

Walter Isaacson: Despite their reputation as a risque network, Fox, which was airing the Super Bowl that year, rejected the ad for being tasteless. With money spent and a house mortgaged, Johnson turned to the press in desperation.

Richard Johnson: I called Sally Beatty at The Wall Street Journal. You know, I thought the story was that Fox reject our ad. What she heard was the smallest company in the history of the Super Bowl is running an ad. So she ran a whole above the cover, above the fold story in her business section, market section. And from that point on, we got over 800 written stories about us. We got over 135 video or news station stories on us. Every major network, Good Morning America, the Today Show, they all covered it. We were actually covered more during the two weeks before the Super Bowl than the two teams playing the Super Bowl. And in those two weeks, we went from being the 270th most recognized brand on the internet to the sixth most recognized brand on the internet, so it was like $50 million of publicity. The next year, 17 dot-coms ran Super Bowl ads.

Walter Isaacson: While Hotjobs’ original ad, the one that got them so much attention, never even ran,’s commercial is still cited as one of the most memorable Super Bowl ads in history, despite having a tepid reception at the time. Filmed in moody black and white, it features short interview snippets with children who claim to have very adult ambitions for what they want to do when they grow up. “I want to claw my way up to middle management,” one says. Not everyone got the joke. Jeff Taylor.

Jeff Taylor: I happened to put an ironic commercial on the Super Bowl, and so I think I confused a lot of the population. I went to a gas station the next morning, and I bought USA Today. And they have this ad-o-meter poll that they do where they rate all the ads from the Super Bowl. I was the fourth worst rated ad in the Super Bowl that year, but I put a iconic ad in the Super Bowl. When I grow up, I want to file all day. I want to have a brown nose. Yes or no, sir, or anything for a raise, sir. When I grow up, I want to be forced into early retirement. That commercial with kids sharing these thoughts — it was a black and white commercial — slowly caught on and became of the most popular commercials of that year and, I think, even to this day, one of the most popular Super Bowl commercials.

Walter Isaacson: Their ads put both Hotjobs and Monster on the map. And despite being competitors, their fates would soon intermingle. Hotjobs was sold to Yahoo in 2002. And eight years later, it would be acquired by its rival, Hotjobs didn’t last long as a brand after the acquisition, and its listings and user accounts were folded into the larger company. But Monster is still going strong, even as it’s fended off challenges from new competitors like LinkedIn, which was founded in 2003 and functions as a social network for business, not strictly as just a jobs board. LinkedIn vice president, Mark Lobosco.

Mark Lobosco: One of the great use cases for LinkedIn is certainly helping our members connect with a job. And because the interesting parts of the LinkedIn network, we believe we’ve created a more human way to be able to look for a job, being able to leverage your connections, to be able to know more about an organization and who may be working there, LinkedIn be able to provide unique insights to a job seeker of why one company may be a better fit than another.

Walter Isaacson: Another job search pioneer from the early dot-com era was CareerBuilder. Along with and Hotjobs, CareerBuilder helped blaze the trails in how we search for jobs. And now with a new CEO at the helm, it’s taking its mandate a step further.

Irina Novoselsky: Employers are facing a really big problem …

Walter Isaacson: Irina Novoselsky is the CEO of CareerBuilder.

Irina Novoselsky: … where the industry is facing this obstacle of there is not enough supply out there to meet the demand. And so recruiters are really having to go and move from this post and pray mentality into how do I leverage technology to help me do the work for me?

Walter Isaacson: CareerBuilder’s focus these days is on using cutting edge technology to help solve those problem. One of the tools in their kit is artificial intelligence using machine learning to remove much of the manual labor involved in going through endless piles of resumes to find the one right fit.

Irina Novoselsky: We have AI that can make recruiters lives so much easier by our tech and our AI doing the matching for them. And so we’re really pushing into more of this quality game to say, “What you want is not thousands. What you want is the right number.” What we built really on our platform really focuses on that. There’s the third party research that actually came out a little while ago where it says that using our software, you need half the amount of applications to find the right hire, right? So we’re making recruiters 50% more productive. The way we’re doing that is based on that AI matching.

Walter Isaacson: But beyond making recruiters’ lives easier, Novoselsky sees that artificial intelligence technology has a higher calling with the ability to inject diversity into the workplace by overriding unconscious bias.

Irina Novoselsky: There’s a lot of bias inherent in the words we use and the tonality that we use, and so we have this AI wizard that basically highlights the words in your resume or the words in your job description from an employer’s perspective and gives you suggestions that how do you make it tone neutral? How do you make it diversity open and it’s not using words that are common for one gender, for one ethnic diversity or racially in any way bias?

Walter Isaacson: In the 1970s, it was still common for applicants to list their race and their weight on their resumes, and diversity was far from being the sought after goal. It is today. Getting a top job in corporate America was sadly, for anyone not white and male, a distant dream. But that’s all changing, and CareerBuilder isn’t the only tech company looking to combat a lack of diversity in the workforce.

Somen Mondal: Bias is a real big problem in the recruiting industry because, up until now, it’s been really an area that is hard to measure, and it’s hard to really act.

Walter Isaacson: Somen Mondal is the co-founder of, an AI-powered recruiting software company.

Somen Mondal: So, for example, if you ask a big company, “I mean, how are your recruiters picking people?” Well, it’s kind of a black box. They actually don’t know, you know, which recruiters are selecting which people. Is it representative of the people that you’re attracting? Are you hiring the same number of men and women based on the people that you’re attracting? Figuring out that data is actually very difficult.

Somen Mondal: So, you know, a lot of times in the world of recruiting, we’re building technology that’s just automating mundane tasks. You know, theoretically, if you had a lot of people to do certain tasks, you could do them. But figuring out are you introducing a bias, are you hiring certain demographics versus another, that’s actually a problem that really, you know, humans can’t spend a ton of time and just figure out. We’re now at a point where we do have the technology to figure out that data and to report on it and to make sure that we can improve.

Walter Isaacson: The idea for Ideal came out of Mondal’s own experience in hiring. The first company he’d founded created software to manage safety compliance in the energy industry. The company grew to a point where he spent a good deal of his time hiring salespeople.

Somen Mondal: For us, hiring two salespeople a week, that was a huge deal. You know, we were making the classic mistakes. We were hiring people because they played sports. We assumed that they would be good at being salespeople. We hired people that went to our universities, because we thought, “Oh, they would be a great fit because they went to a great school.” We did two things wrong. We were highly inaccurate. We got to a point we were hiring two people knowing that one would be let go, and we were making decisions full of bias.

Walter Isaacson: Bias in hiring can be difficult to spot even for the well intentioned. Almost always, it’s some sort of personal or cultural blind spot. Identifying them, not to mention combating them, is difficult no matter how well intentioned one is.

Somen Mondal: There are two types of biases. About 70% of bias comes from age, name and sex. So, for example, my name’s Somen. I’m less likely to get an interview than my business partner, Sean. Those are the real negative biases. But then there are other types of biases that people don’t always realize. For example, picking people that went to your university or college. A lot of times, companies will say, “You know, I love hiring people from MIT or Harvard. They’re the best schools, and they’re going to make the best employees.” Well, how do we know if that’s true?

Walter Isaacson: Ideal’s software strips out the data point in job applications where bias is most pervasive — age, name and sex — and will also abstract the name of the school you attended or the company where you worked, so that the human recruiter can make a fairer assessment of your experience instead of rejecting you out of hand for working for a firm they’ve never heard of. LinkedIn’s software takes a similar approach. Mark Lobosco.

Mark Lobosco: We recently launched, you know, an assessments program where our members can take a test to be able to assess whether they have a skill in Python or Java. And then based upon that, they can add that to their profile. That would then show up in a recruiter search to be able to find a candidate that maybe just didn’t go to a four-year school but has the skills, the hard skills, to be able to do the job. That’s one example of something we’re doing to help improve people from non-traditional backgrounds to be able to get roles, not just those that have gone to, you know, four-year institutions.

Walter Isaacson: And while AI can raise a scary spector, Ideal’s Somen Mondal sees it not as a way to remove humans from the recruiting process, but to make their lives easier and help them make better, fairer decisions.

Somen Mondal: I’m the first person to say that we need humans in the hiring process. Computers can’t do everything. The problem that we’re facing and that we’re trying to solve is that many of our customers ignore about 80% of the candidates that they receive. That’s a whole other problem. They’re not even getting to the right candidates because they have too much volume, because, you know, the job boards and LinkedIn have made it so easy to apply to a job that there’s a lot of noise and it’s hard to kind of take the signal out of that noise.

Walter Isaacson: Tech firms like Ideal and LinkedIn aren’t alone in seeing a technological solution to the very human problem of bias in hiring. Earlier this year, the California legislature passed a bill that urges the government to explore ways to use technology to reduce bias and discrimination in hiring, specifically calling out artificial intelligence and algorithm-based solutions. And while it’s becoming apparent in recent years that tech can’t solve all of our very human problems, if pointed in the right direction, it could be a start.

Walter Isaacson: Online job boards started as a way to help the unemployed get hired. But in the future, it could be a step to a more inclusive workplace for all. I’m Walter Isaacson, and you’ve been listening to Trailblazers, an original podcast from Dell technologies. If you’d like to find out more about any of the guests on today’s show, please visit our website at We’ll be taking a break for the holidays, but we’ll be back in the new year with brand new episodes of this show. Until then, thanks for listening.