Given developers’ focus on hacking pretty much every aspect of modern life, it was only a matter of time before some of them turned their professional eye toward the complicated topic of the job hunt and employee hiring. Can software change how we connect (and eventually work for) desirable companies? Carlos Miceli thinks so; the startup maven, currently based in Estonia, is interested in seeing how to best bring companies and international startups together, all while closing the skills gap. The job hunt, in other words, is evolving. Miceli is joined by Steve Dean, co-founder of JobSuitors, which takes a dating-app approach to matching potential talent with companies. They sat down to talk the job hunt, mentorship, and how apps could potentially solve some thorny conundrums related to hiring. (This conversation has been edited for clarity and content.)

The Problems With Hiring

Carlos Miceli: “The way companies search for talent is very inefficient and slow. Most people think it's a skills gap when it's really a communication gap. “First you have that assumption, that you know how to communicate what you need. Then you have the assumption [that] you are communicating through right channels. You also have the assumption that the right people want to do that job, as well as the assumption that the right people are available. The chain of recruitment can break down in so many moments; that's why it's so inefficient. However, some companies like Google, Yahoo, and Amazon can get away with it; most companies don't have that luxury. Companies think they are hiring to solve a problem and they think they are hiring expertise—but what they really want is to hire potential.” Steve Dean: “I see plenty of recruiting companies fumble around with paper resumes. They are still in this age where they use paper to determine compatibility. They are making hundreds of people do these paper assessments; it's a huge waste of human energy.” Carlos Miceli: “The truth is that colleges and universities don't train for the job market. Let's get more coders and pay better—that's not what the gap is all about. Sending in a resume is not how looking for a job is done; you get it by knowing the right people and communicating your credentials the right way. I used to think it's a logistics gap. [But] when it comes to the gap between companies and talent, companies don't know how to say what they want and people don't know what to say about themselves. There are better ways for people to communicate their potential.” Steve Dean: “I think that we are seeing two separate trends taking off at the same time. Hiring analytics—via internally through testing and tracking systems—allows companies to perform greater analytics on people you’re hiring. Previously, you just looked at a resume and had just a few data points. Now we have the ability to do psychometric testing and analyze their networks to see who people are connected to.”

How Candidates Can Expand Their Job Hunt Networks

Carlos Miceli: “If you want to expand your network, the first thing you want to do is define a criteria and know what kind of people to meet, movement to join, or event to attend. You want to reach out over email or meet in-person, or see who you know who works at those companies. Every time you meet someone, you ask that person, ‘Who else should [I] meet?’ “If you are looking for a job, the first thing you have to accept is that you don't know what you are looking for. You want to tune up serendipity: you want to travel and go to new events. Start tweeting and emailing people and expose yourself to as many new things as possible. "The biggest problem is not tactical; most people don’t know what they want. It is important to have some process, to have some criteria for that exploration. You want to read more books and take courses, and do everything to expand. A new idea is a new way to see the world. If everything you are looking for in life is behind someone, you need to understand how you provide value to that person. If you know what your values are, if you have the self awareness of what you want and how you are good, and how you help people, this is how [you] become better.”

How to Find a Mentor

Carlos Miceli: “I had my first mentor after I emailed him after following his blog. I said to him, ‘I want to help you on what you are working on.’ I worked with him for free for three months. His name is Josh Kaufman of The Personal MBA. The best jobs are created through suggestion. “To work with people you like and respect, you need to understand their problems. It comes down to empathy. Empathy is the root of good communication. If you just send resumes, you don't get to communicate with each other. People are under-trained in how to frame themselves, and how people frame those things matters deeply. It's statistically hard to not get a job if you put yourself out there consistently. The best way to do this is to understand the value you can bring to companies.”

Letting People Know About Your Opportunity Search

Carlos Miceli: “I stepped away from my startup in November. I made a list of 70 people [who] are either close allies, friends, and mentors and I emailed them saying: 'Hey, I am thinking of transitioning, can we get on a call?' I had 50 calls lined up in a month and I did all those calls. I asked: 'What are you working on, what do you think I should be paying attention to, what is relevant, and what do you think of my decision?' I was opening up to new angles and perspectives. “This gave me a bombardment of new thoughts. I had a somewhat high level of understanding of what I was interested in doing. After that, I emailed the document as a summary called ‘The Carlos State of Affairs.’ People are really open to helping, especially if they are investing in me because they think I am going somewhere.”

What the Job Hunt Will Look Like in 10-20 Years

Steve Dean: “Most investments in analytics will pay off to make consistently good hires. People in tech want to be around people they like. So if you have one really good engineer leave, it can affect the rest of the team. For instance, the analytics can be: What are the personality types on your current team and what is the person you need to hire to balance out the team? Or perhaps, the recruiting company may want to make sure the person they are hiring doesn't have the plan to move within 6 months of working there. “The vetting process can take them months, so it is useful if you can find that out ahead of time if they are a lasting fit. Using algorithms, the interview process goes down from taking months or weeks to just hours or minutes. We have access to new technology in the last five to 10 years that was never possible before. Then there's a separate trend, which isn't so much a tech one, but a shift in how people work—the shift to the freelance economy. By 2050 or 2020, half of all workers will be freelancers. You can hire an entire remote team and not have to worry about the employee benefits. You can hire people remotely for temporary work via oDesk and Elance (which are examples of companies capitalizing on the shift to freelance labor). “My focus is on that first major trend, with companies who want to have an in-house workforce and rely on finding the people who will best complement their team and who can make a lasting impact as full-time employees. Companies want to find people who are connected fundamentally to their mission and are motivated by more than cash.”

How the Job Hunt Will Resemble Online Dating

Steve Dean: “My entire background revolves around online dating and match-making… My initial market is all talent that can excel at startups and can be hired by a startup: engineers, product managers, marketers, and salespeople. As we grow and bring on larger companies, we can expand our focus to include other types of job seekers.”

Job Hunt: Learn How to Negotiate

Steve Dean: “Make strategic introductions and manage expectations across all these relationships. One of the fun things, which I've built onto my site, centers on how to negotiate. What are the important variables in the decision process? [My site] shows a priority ranked list; sometimes it will say, you are not a good fit with this company because they don't offer as much vacation time as you require. Both sides always see the same information about the fit. Issues such as vacation are easy to negotiate.”