– + Learn

How to Automate Your Job Search And Focus on Strategy, with Danny Leonard

by

Share

Listen On:

If you’re spending an hour or more customizing a resume and cover letter for each job you apply to, you’re wasting time, says Find Your Dream Job guest Danny Leonard. Danny specializes in helping folks cut the grunt work and focus on the tasks that result in interviews and job offers. Begin by knowing what job you want and why. Make a list of companies you want to work at, and then pursue conversations with them. Danny suggests using LinkedIn to make connections at your targeted companies. Use your time wisely and nail down a job search strategy that gets results.

About Our Guest:

Danny Leonard is the co-founder of Ramped. 

Resources in This Episode:

Transcript

Find Your Dream Job, Episode 488:

How to Automate Your Job Search And Focus on Strategy, with Danny Leonard

Airdate: February 12, 2025

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

Every Wednesday, I talk to a different expert about the tools you need to get the work you want.

Your time is your most valuable asset.

And too many job seekers waste time on repetitive tasks.

It’s not only boring to do this.

It also makes it harder to do the strategic work that can help you find your next job faster.

Danny Leonard is here to talk about how to automate your job search and focus on strategy.

He’s the co-founder of Ramped.

It’s a mission-driven technology company that’s revolutionizing the job search.

Danny joins us from Los Angeles, California.

Well, let’s talk about automation in your job search, Danny. Why is it important to find ways, using software and other tools, to do routine tasks when you look for work?

Danny Leonard:

The high-level or overarching theme that we are seeing today is the job market has changed significantly since 1970 or even 1990, or even 10-15 years ago. A lot of things, the tools that people are using, have improved but at the same time, the job search has remained largely the same, and I’ll go into what I mean by that.

The tools are obvious. The tools like ChatGPT or using these large job search aggregators to find open roles, that’s obviously improved. The way the job search functions, though, has remained pretty much the same.

You are submitting a packet of job search assets like a resume and a cover letter, and ultimately, speaking with a bunch of people in your network and recruiters and hiring managers. That’s kind of the exact same but the way that you go about it has changed and a lot of this, let’s call it constant friction between those two things, the tools and the way the job search works, has created this surplus of activities for job seekers now, while they’re figuring out how to navigate the current landscape of the job search while using tools that are vastly improved and optimized and automated, but the job search and the way that you speak to people and the way that you have to communicate with individuals and the players within the search remains really human.

What people are doing today is they’re at this, “I feel lost. I feel disheartened,” by the amount of effort that it’s taking them to find a job and a lot of that is economic factor-based, but there’s so many opportunities for them to just scrap all of that, I’ll call it grunt work, and focus on the things that actually matter, again, the way that the job search has always functioned, being human and communicating with people.

Mac Prichard:

Okay, well, let’s talk about grunt work, Danny. When you’re thinking about grunt work, what comes to mind? Give us two or three examples.

Danny Leonard:

Yeah, absolutely. So, today, you are almost forced by the large swaths of language, either on LinkedIn or with recruiters or hiring managers, to customize a resume for every single job that you apply to, or customize a cover letter for every single job that you apply to, and our data, and we have hundreds of thousands of job seekers on our platform, Ramped, shows us that nearly 77% of cover letters go unread and you are likely to find a job after your 206th application.

Mac Prichard:

Danny, why would somebody send 206 applications if they’re going to focus on the “human side” of the job search? Do you think that’s a good strategy, to blanket the internet with applications?

Danny Leonard:

No, I don’t. Frankly, I think folks should be really specific with their job search. However, I think it’s almost common knowledge that the job search is a numbers game and you have to get your resume out there, and all of these job search aggregators, Indeed, LinkedIn, Monster Career Builder, they’re all telling you, “One Click Auto Apply to hundreds of jobs at the same time using no effort.”

Mac Prichard:

Say more about that, Danny. Why don’t you agree that that’s a good strategy, using auto-apply and sending out lots of applications with seemingly no effort? Why don’t you think that works?

Danny Leonard:

I actually think that that part of the job search is the part that can be automated and it’s almost table stakes. What I think you should be doing as a job seeker is a mindset shift. The way you should think about your job search is how, let’s call it, a wealth manager would think about a portfolio of investments. You have to be really diversified across a bunch of different factors. The job search is much simpler, I think, obviously than managing money.

One part of your job search should be this spray-and-pray game, and that’s the portion that can be automated almost entirely.

Mac Prichard:

Let me pause there, Danny. If you don’t think sending out large numbers of applications works, why would you recommend investing time in spray-and-pray?

Danny Leonard:

You may get hits from that effort, or that strategy. That part should be effortless. You may get interviews from that. Again, we have evidence to show that that strategy, as part of a basket of strategies within your job search, will yield some results. For that reason, I would still recommend doing it, but not spending all that much time on it.

Mac Prichard:

Alright, so that’s one task you could automate. How much time would you recommend investing in using automation tools and sending out applications in large numbers?

Danny Leonard:

If you’re thinking about your job search from 0-100 and assigning the amount of time that you should be spending on it, it’s somewhere in the 5-10% range. The rest of your job search should be on strategically oriented tasks.

Mac Prichard:

I want to dig into those strategic tasks in a moment. Let’s talk more about “grunt work.” One thing that you can automate is spending 5-10% of your time sending out applications using easy, quick-apply.

What are other tasks, Danny, that you recommend automating, examples of grunt work?

Danny Leonard:

Building resumes that you plan to submit to any company, I would deem today as grunt work. The yield that you get from customizing a resume in today’s age, is very low. The yield that you also get from customizing a cover letter is even lower, especially since around 75-77% of cover letters just go unread. Those are two really big buckets that you can just easily automate away.

Mac Prichard:

How do you do that, Danny? How do you automate the creation of a resume or a cover letter that’s going to be persuasive when you do send it out?

Danny Leonard:

Yeah, absolutely, so if you would like, you could come up with your own prompt on ChatGPT. I think this is a little complex because of the tools that are out there, but again, there are a number of prompts or ways you can get to input the job description, input the responsibilities, and then spit me out a beautifully created resume on ChatGPT or a similar AI platform.

Mac Prichard:

Any pitfalls that you’ve seen in helping people use those tools that listeners should be aware of so that they avoid any rookie mistakes when customizing their cover letters or resumes using ChatGPT?

Danny Leonard:

Yeah, I think that what I would avoid on ChatGPT is ultimately solved with our platform, but I will say, you will need to proofread every single resume and every single cover letter because ChatGPT is only as good as the prompt that you give it. So if you really want to be locked in, you’ll still have to tweak and edit, and I think that defeats the point of my ultimate recommendation, which is to automate that part away.

Mac Prichard:

Well, let’s take a break. When we return, I want to talk a little bit more about grunt work that you can automate, that you recommend, and steps for doing that.

Then, I really want to dig into the strategic choices that I know you encourage job seekers to make and how they can spend their time on that.

Stay with us.

When we return, Danny Leonard will continue to share his advice on how to automate your job search and focus on strategy.

We’re back in the Mac’s List studio. I’m talking with Danny Leonard.

He’s the co-founder of Ramped.

It’s a mission-driven technology company that’s revolutionizing the job search.

Danny joins us from Los Angeles, California.

Now, Danny, before the break, we were talking about how to automate your job search and focus on strategy, and you shared some tips for us about how to use ChatGPT to create customized resumes and cover letters and also encouraged listeners to not spend more than 5-10% of your time on easy, click-apply applications.

You’ve got three steps that you encourage people to take when focusing on strategy in a job search.

Before we walk through those, I’m curious, Danny, you talk to candidates all the time in your work at Ramped. What stops people from following a job search strategy and doing the strategic work?

Danny Leonard:

The thing we hear most often, and since our company started in early 2020, we’ve met with hundreds of thousands of job seekers, the thing that we hear most often is, “I am applying to hundreds of jobs and I am spending 30-60 minutes on my cover letter, on my resume, for each job that I apply to.”

And that is simply too much time to spend on those assets that aren’t yielding the amount of lift that they need for that amount of time. I think people get bogged down spending time on those elements of the job search when they really should be thinking about their job search holistically and from a strategic standpoint.

Mac Prichard:

Danny, when you follow, in your experience, when you have a strategy for your job search, do you find that people are applying for fewer jobs, but the right jobs?

Danny Leonard:

Yeah, I do think that is usually the case. I think that folks find when they follow a specific strategy that they are, at least in their heads, applying to less. You know, the automation part will probably boost those numbers up but they’re not, again, not spending so much time on it, but the jobs that they actually care about, they are taking the time and energy and effort to connect with the right people at the companies they want to work at and it ends up being a lot less companies that they’re actually applying to.

Mac Prichard:

Well, let’s talk about the 3 steps that you recommend candidates follow when creating a job search strategy. The first one is you’ve got to know the exact job that you want, and why is this important, Danny?

Danny Leonard:

Well, it’s back into the mindset of a job seeker. When you’re starting a job search, you’re probably feeling a lot of different things. You’re feeling, maybe, disheartened if you were just let go, or there was a change in your career. You’re possibly feeling excited about what’s new, but we hear a lot of pain in today’s market, which is significantly tougher than it was 5-6 years ago, and that pain often leads to some sort of desperation. I don’t mean this in such a down or negative way, but that’s what we feel and hear so often.

“I’ll take any job,” and I recommend that folks take just a beat and think about what their life would be like in 6 months or a year if they found a job that they’re really interested in, rather than taking any job, anywhere, and the reason that step one is figuring out what you want is because that will eliminate all of this extra noise from your job search.

I’ll give you an example. If I said to you, Mac, “I’m a new job seeker. I was recently let go from my company; they had lay-offs because of the economy. Look, I was a salesperson last time, but I’m interested in sales. I’m also interested in operations. I’m interested in maybe customer service, and I could maybe do a little bit of marketing.” I don’t want to put words in your mouth, but I believe that you would say back, “Well, I don’t know what to do with this candidate. They’re kind of all over the place. They don’t know what they want.”

It’s really important to focus in on the one, maybe two, things that you are really interested in and go really hard at those.

Mac Prichard:

In your experience, Danny, what stops candidates from doing that work, from figuring out that answer and coming up with the one or possibly two jobs that they really want?

Danny Leonard:

I mean, look, it’s really, really tough. The job search is tough and it bogs people down on an emotional level and you get so much rejection, you’re probably not used to the rejection that you’re going to get and have to get, and when anybody, if you ask 10 people on the streets today, “How was your last job search?” I’m positive 9 or 10 of them would be like, “It sucked.”

It’s just this mental block or mental hurdle people have to get through to become focused. I think it’s taking the…whether that’s giving yourself space, whether that’s a week for you or two weeks, or whatever it is given your financial circumstances, just take some time and really evaluate where you’re at in your life and what you want next and then focus in on really what you want.

Mac Prichard:

What have you seen work best when you’ve talked to candidates who have taken that time to do that self-evaluation and set those goals? Are there any tips you might have for listeners about how to do that effectively, especially in the relatively short period of a couple of weeks?

Danny Leonard:

Yeah, the time-bound is less important, it’s really like, if you have a financial consideration that you have to meet that’s time-bound, oftentimes it is under 30 days, but I think the one thing that people need to feel is a confidence about the path that they go on.

They just have to talk to enough people in their sphere, trusted experts, mentors, family members, friends, and kind of validate these points of what they want to do next to build up some of that confidence. I think that circle, or your own personal board of directors, or whatever you want to call it, generally reinforces some of that, “Yeah, you’re right, you should be doing this. Just go after what you want next.”

I think that builds up confidence to hit the ground running.

Mac Prichard:

Step one: figure out the job that you want and do the work to answer that question.

The second of your three strategies that you recommend candidates focus on after automating their job search is to identify where you want to work. Danny, why is it important to know where you want to go?

Danny Leonard:

Now that you have the what, and I hope, a little bit of the why, the next part is where, and that should be easier. The reason I say that it’s easier is because there’s going to be a bunch of companies that are exciting to you but don’t necessarily have the open roles. Those could be on your later-stage hit list of companies that you look at.

What this does is allow you to focus in on what’s available at this specific time, given your specific job search parameters, so the where becomes an easier or natural step two.

It’s less of an existential question and more of a practical question.

Mac Prichard:

What’s your best advice for building that list of target employers, Danny, and how many companies or organizations should be on the list? 25? 100? What do you recommend?

Danny Leonard:

Yeah, good question, I think 100 is a stretch. Anywhere from 50-100 is great and the where, honestly, the job board that I like best today is Google Jobs.

I think that they do a great job of aggregating the most amount of jobs into a simple enough platform to understand, and you can apply filters based on where you want to work, the type of work that you want to do, and if you want to be part-time, remote, full-time, et cetera.

Mac Prichard:

The third and final tip that you recommend people follow when creating a job search strategy is to connect with people in your field, especially the employers where you want to work. Why is this important, Danny? Why do you need to do this?

Danny Leonard:

Yep, so it goes back to the portion of our conversation at the very beginning, where the job search hasn’t changed all that much even though it’s changed a ton. It’s this back-and-forth of friction, but the job search is still going to be about talking to people. Until you have an AI-based persona that can talk to an AI-based recruiter, you’re still going to have to talk to people, and honestly, sell yourself to them at some level at the company.

Once you have that targeted list of 50 to 100 jobs that you want to apply for and companies that you want to work at, I would make a list right next to that company name, and the job that you want to apply to, of the first way you will connect with that company. Ideally, it would be a first-degree connection; obviously, not everyone has first-degree connections to a company, and then a second-degree connection and then a third-degree connection.

For all its faults, I do give credit to LinkedIn a lot for making it really easy to find those connections in a company, so I would use LinkedIn heavily here, to at least do the connection part, and connect to anyone at that company. You never know who’s going to open a door for you. It could be someone in a totally different portion of the company who knows somebody in the division that you want to work at, but just have a conversation or try to have a conversation, and get connected into that company through networking.

By the way, this is not a magic bullet. You’re still going to get rejected or not hear back. Set your expectations as such.

Mac Prichard:

Well, it’s been a great conversation, Danny. Now, tell us, what’s next for you?

Danny Leonard:

We’re still building Ramped. You can find us at rampedcareers.com. Our mission is to fix the job search. It has been painful for so long, there’s so much friction in it, and there’s so much excess that can just be stripped out. That’s my focus right now. We’ve got a great team, I have great co-founders, and we’re excited for what’s next.

Mac Prichard:

I know listeners can learn more about you and Ramped by visiting the Ramped website, and that URL is rampedcareers.com, and you also invite listeners to connect with you on LinkedIn. When you do reach out to Danny, please mention that you heard him on Find Your Dream Job.

Now, Danny, given all of the great advice that you’ve shared today, what’s the one thing you want a listener to remember about how to automate your job search and focus on strategy?

Danny Leonard:

The one thing I want people to remember is to make sure that 80, even 90% of your focus goes into the strategic activities that will yield the highest results. Scrap the grunt work, scrap those cover letters that you have to build or spend 30-60 minutes on per job, scrap those resumes that you have to spend 30-60 minutes on per job, and really think holistically and strategically about your search, and then hit go and have great conversations with people at companies where you want to work.

Mac Prichard:

Next week, our guest will be Jess Guzik.

She’s a career and executive coach.

Jess helps women build confidence, communicate powerfully, and get leadership jobs.

She also hosts the terrific podcast, The Art of Speaking Up.

Confidence matters, especially when you talk with a hiring manager.

You don’t want doubts about your skills and abilities to prevent you from showing your best self.

Join us next Wednesday when Jess Guzik and I talk about how not to let imposter syndrome derail your next job interview.

Until next time, thanks for letting us help you find your dream job.

This show is produced by Mac’s List.

Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media.

Our sound engineer and editor is Matt Fiorillo. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week.