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Breaking into Tech with no Technical Background or Experience - Discussion with Jeremy Schifeling, Founder @BreakInto.Tech

Jeremy Schifeling, Founder of BreakInto.Tech, a startup that helps people with non-technical backgrounds land jobs in Tech, shares numerous tips on how candidates can structure their job search and improve chances of success.

BreakInto.Tech has helped candidates land jobs at well known Tech companies such as Amazon, LinkedIn, Microsoft, etc. Jeremy has a BA in Political Science & Education from Swarthmore College and MBA from Ross School of Business, Michigan University.


Check out the podcast below to listen to the complete discussion! 

Note from LED: If you have upcoming Product Management interviews (one of the most sought after functions in Tech!), don't forget to check out our Interview guide for PM interviews in Tech, our Question bank for behavioral questions, and our Question bank for Product Design questions​, to help you prep for your interviews!


Some of the areas that Jeremy touches upon in this episode include:

1. Why Jeremy started Break into Tech
2. How Jeremy realized that a technical background is not needed to work in Tech
3. Jeremy's recommendation for how to structure your job search process - Identify what role, position yourself, systematic approach to your applications, and interview prep
4. Examples of roles that are open to non-technical profiles
5. How non-technical roles tend to lie on a spectrum of super analytical (Eg: Business Analyst), to super relationships oriented (eg: Sales)
6. How to assess fit with a role - talk to people + volunteer for projects/gigs
7. Positioning yourself - focus on your LinkedIn profile and resume
8. How to optimize your LinkedIn profile - keywords and where to include them, good summary, and experience
9. Examples of how to phrase resume points differently depending on the function you are applying for
10. Don't wait for a referral when applying. You can add it to your application later
11. Resources - Google Alerts, Techmeme, Wikipedia, read 10K,, AngelList, LinkedIn , 
12. Don't hide your quirks and edges - they will help you stand out!

Thank you for listening!! 

Detailed transcript of the discussion:

[00:02:17] [LED]: Why don't you give us a very quick introduction to your company?

[00:02:22] [Jeremy]: BreakInto.Tech is sort of a culmination of what I've experienced in my own career. As someone who got his start as a kindergarten teacher, moved to nonprofit sector and worked his way into the tech world - I realize that there's not a lot of resources out there.

I want to help people follow in those footsteps, try to figure out how to break into tech, even from a non-technical background. And so I want to basically be a Sherpa to guide others on this adventure. 

[00:02:49] [LED]: What was your first job in Tech?

[00:03:04] [Jeremy]: I had an internship at Apple where it basically opened my eyes to the fact that wow, this whole world that I thought was only for coders and data scientists has all these other roles that are open to lots of different people from around the world.

But I had never been exposed to that before. And that's what sort of gave me this idea for the company.

[00:03:21] [LED]: And if you don't mind sharing, what exactly was your role during your internship?

[00:03:28] [Jeremy]: Absolutely. I was a product marketer for the iOS team there. And one of the things that really surprised me was the fact that there was even a job called product marketing. I'd heard about marketing in general, but again, tech is such an interesting and unique world. There are all these roles from product marketing, to product management, business development, to corporate development and everything in between, that folks on the outside don't know about, but they might actually be a really good fit for.

[00:03:55] [LED]: Was it a challenge for you getting a job at Apple?

[00:04:00] [Jeremy]: Here's the interesting thing - it wasn't that much of a challenge? Once I realized a couple of key things, number one, that there's not some sort of special birthright that some people have to be in the tech world and others don't. So the fact that I was a kindergarten teacher didn't mean that I could never get into that world. 

And number two, the fact that I had the sort of non-traditional background, possibly offered a different perspective or more creative perspective compared to others actually gave me a leg up, gave me a differentiation in a pool of me too candidates.

I think once I sort of switched from a deficit mode to a surplus, I started to get opportunities.

[00:04:38] [LED]: That’s a great point. Of course, you probably cannot be an engineer unless you teach yourself, but a lot of other roles are still very much open to you. And your background could actually be an advantage. 

[00:05:00] [Jeremy]: Absolutely. And here's the craziest part. I actually did some research on LinkedIn a couple of years ago and basically said, show me all the roles in the U S tech industry.

So startups, big companies, engineers non-engineers after crunching the data. It wasn't just that there were some business roles, some non-technical roles. They were actually the majority of jobs in the tech sector. Something like two thirds of jobs were outside of technology itself. And I think that says, Hey, there's a huge opportunity out there.

But it's up to folks to go explore it and to seize an opportunity for themselves.

[00:05:32] [LED]: Tell us a little bit more about where your company and how you work.

[00:05:55] [Jeremy]: Absolutely. So basically having run the business for a couple of years now I'm pretty confident in the fact that the methods are those that I've used in my own career.

And I've coached hundreds of others on really doing the work. And it has to do less with, again, learning to code or learning various sort of specific technical skills and more about figuring out where you belong in this crazy world and positioning yourself to win those jobs. And basically I encourage anyone, whether you're a kindergarten teacher or an architect or a chef, you have a passion for this space to check it out and break in today.

And then basically see, what's the right pathway for me? How can I ultimately get into the tech world if that's where my passion lies?

[00:07:00] [LED]: All right, then let's try and understand some of your methods then. So let's say I am currently a grad student, or maybe someone who's relatively early in my career and I don't have a technical background. Maybe I have an MBA or something else. How would you suggest I structure my job search process in Tech?

[00:07:24] [Jeremy]: Absolutely. Let me just start by laying out sort of the four key steps and then we can talk about each. I think the first thing is not to focus on the tech industry in general, or even on companies that you really like, focus on what you can do with those companies and specifically identify a role where you can bring your passion and your skills to bear every single day.

I think if you can sort of start with that foundation, recruiters, hiring managers, people on the inside are going to open their doors to you because you can actually provide value. You're not just a fan boy. So that's the first step. Second step is all about positioning yourself to fit into that specific role.

So for example, if you say, I could be really great as a sales person in a tech space, make sure that your LinkedIn profile, your resume, your cover letter, all of that scream sales, to someone you want to work with. 

The third step I think, is to be really be systematic about your application process.

You don't just apply sort of Willy nilly once in a while. Hope for the best instead, turn your application game into a machine and make sure that it's powered, not just by jobs, but also by referrals. We'll talk about that in a little bit. And then finally, I think when it's time for the interview stage again. Caught up in that classic tech trap of saying, I've got to learn SQL. I've got to learn to code before I can even enter. Instead focus on the really important human elements of the human interviewer at the end of the day, what do they care about? Typically it's only two things -  Can you do the job and would they want to do it with you?

[00:08:59] [LED]: You make it sound so simple! So let's go deeper into each of them. I think the first step in particular is probably very important - identifying the role. So can you give us an overview of the various roles that a person with a non-technical background can consider in tech?

[00:09:16] [Jeremy]:  The way to really think about them is to think about them on a spectrum. So if you think about different jobs as being more analytical, so working on your own crunching data, trying to come up with insights and recommendations all the way to interpersonal. Working with other people, working collaboratively, trying to influence.

And then trying to figure out sort of where you lie on that scale in terms of your personal preferences. So do you like working with data? Do you like working with people? Are you a mix? You can start to figure out which of the various tech roles fit onto that spectrum. So on the more analytical side there's roles like business analyst where you're using SQL to pull data and sort of analyze it. There are roles like this in operations where you're again, getting access to lots and lots of data, and you're crunching it to develop strategic recommendations for a company all the way to corporate development, where you're looking at financials and trying to sort of build valuation models potentially for mergers and acquisitions. So all very analytical roles. On the other side of the spectrum, the interpersonal pole, there are roles like business development often called BizDev, which is all about building partnerships.

How can you forge relationships with other companies? Similar also to sales or going out into the world, trying to influence others to purchase something from your organization. And then of course, roles like HR, where you're working very closely with teammates and potential hires for the company. 

And just some roles in the middle. These are the classic tech roles of product management, product marketing and customer success. We really have a mix. Yes, you have to be very analytical, but you also have to work cross functionally with others to get things done.

[00:11:43] [LED]: Let's say that I am trying to assess fit with any of these roles. You've given us a framework in terms of how to think about what these roles are like. How do I assess fit?

[00:12:06] [Jeremy]: So I think it's a couple of steps. The first thing you want to do is figure out what these roles actually do all day.

I think one of the biggest traps people can fall into when it comes to the tech world is because these roles aren't widely known. We all haven’t them grown up knowing about them necessarily. It's easy to glamorize them, being a product manager is like being the CEO of a company. It's going to be so sexy when you really want to do is talk to as many actual product managers who are doing this job every day and figure out what those days are.

Is it as exciting as, I'm in the corner office and I'm calling all the strategic shots, or am I in the trenches, working with the engineers, trying to solve a really tricky bug. You're trying to get through a tough resourcing sort of constraint, because if you can start to figure out what it actually feels like day to day, you can start to imagine whether you're going to feel happy in that role or not.

So that's the first piece. Once you compare that to what you actually like doing. So if you look back at your past career again, whether you were a teacher or an architect, and you can pull out some of those flow moments when you were so immersed in what you were doing that you literally lost track of time and then say, Hey, what was I doing in that moment when I was in that moment of, of flow and which of these jobs that I just outlined are going to give me the most kinds of similar moments, whether they're analytical or entrepreneurial.

[00:13:21] [LED]: Apart from talking to people, are there places where I can try and get some sort of hands-on experience?

[00:13:40] [Jeremy]: Yeah. Great question. So I think one of the more aggressive definitely time-consuming strategies is to actually just start doing some of these jobs. Let's say for instance, maybe you were a kindergarten teacher and you said, Hey, I think I could probably be pretty good at marketing. It feels similar in some ways, in terms of trying to influence other people, understand other people, but I've never done it in a professional capacity.

Well, what if you took your sort of most exciting company and said, Hey, could I do a marketing project? Even if it's just purely on my own, or even if it's purely on a volunteer basis and you might actually say, okay if I want to help an ed tech startup, for instance get their product into the hands of as many teachers and families as possible, what's a marketing plan I might put together?

Who's the audience, what are the channels I can use to reach them? What am I going to tell them, how am I going to measure my results? And as you start to do that kind of project, you start to say, Hey, this is what it actually feels like to do this role. Am I enjoying this or is it a total turnoff?

And if you realize at that point, the role is just not right for you. You've saved yourself years of pain by stimulating an experience ahead of time.

I'll just give a real example. When I was at LinkedIn, I was a product marketer, but there was a young man, right out of undergrad who was doing our sales rotational program. And it turned out that he wasn't really infatuated with it, he had a hard time to really enjoy it. Turns out, he really wanted to get into marketing.

And so he approached me and said, Hey, could I do this project for you? Could I actually lend a hand? And just like you said, even in a large company like LinkedIn, I could always use more resources, more bandwidth. So I took them on kind of as an apprentice. And he used that project to figure out whether marketing was right for him. And be a piece of his portfolio to ultimately get a marketing job.

[00:15:56] [LED]: So at the end of the first stage, you've now figured out one or two job profiles that you're interested in. What’s next?

[00:16:15] [Jeremy]: Then you can sort of move into that positioning stage. Using the laser focus that you've built in that first stage, you can now go to your LinkedIn profile and to your resume and really hammer home - I'm a marketer or a product manager or a business analyst.

As I say, in their LinkedIn headline, passionate about tech open to anything or future product manager slash product marketer slash salesperson slash business analyst.

[00:16:47] [LED]: I want to break this down a little bit because I think this is an area which, some people are naturally very good at and some people struggle with it. I myself struggled with it. So this is a learning moment for me when we talk about positioning yourself. First and foremost, what are the pieces that I need to be thinking about as far as positioning myself as concerned? Is it my LinkedIn profile and my resume? Are those the only two things, or are there some other areas?

[00:17:10] [Jeremy]: I would say your LinkedIn profile in some ways is your most important piece of the puzzle in this day and age, because you're not only going to use it to apply, you're also gonna use it to network. So when we talk about referrals in a little bit, one of the first things you're going to do is you're going to reach out to someone, either on LinkedIn or off LinkedIn, but regardless, they're going to look you up on LinkedIn.

And because it's your public resume these days, you want to make sure that it's good. Whatever function you've chosen, as opposed to that wishy-washy positioning we were just talking about.

[00:17:52] [LED]: Maybe you can take an example of one of the jobs, maybe business operations or product marketing, if that's what you're most comfortable with and how would I position myself to be well suited for one of these jobs on my LinkedIn, what should I be thinking about?

[00:18:43] [Jeremy]: Yeah. So first the first thing I would say actually is don't overthink it. I've seen a lot of people get a little too creative when it comes to LinkedIn. And what they don't realize is that there are two audiences that you're solving for. Number one is absolutely the recruiter, but number two is also the algorithm.

And by that, I mean the fact that if a recruiter goes on LinkedIn today and says, Hey, I want to find product marketers for my tech company. They're going to search product marketing manager. And so if your LinkedIn profile says, John ham looks the like Don Draper marketing abilities, blah-blah-blah all this.

But it doesn't actually include the words, “product marketing manager”, you're not going to appear on their radar. So it's important to really be very sort of specific in terms of matching the job descriptions. So if you can say, Hey, I want to do product marketing. And I found 10 job descriptions in that space that I'm really excited about and notice that they're all sort of titled the same thing.

Again, product marketing manager or business operations associate or whatever it might be. Make sure that the same phrase is in your headline, on your LinkedIn profile, because your headline actually has the most weight of any piece of copy on your entire profile. Because it's the most character limited and therefore can't be gamed.

[00:19:54] [LED]: Before you carry on, this is very important. So I want to make sure that I understand what you're saying. So one you're saying that your profile should clearly have the keywords the recruiter would be using when they're searching for potential candidates. And so what you're saying is that in order to find what those keywords are, just look at 10 or 20 odd job descriptions for that particular role, see what they're using in their job titles and use those keywords in your profile.

[00:20:22] [Jeremy]: You nailed it. Exactly.

[00:20:24] [LED]: So the next question is where do I put these keywords? And you're saying, put them in the headline of your LinkedIn profile. So what do you mean by headline? Is that the name?

[00:20:35] [Jeremy]: Yeah. Sorry about that. A little bit of inside LinkedIn jargon.

So the headline is basically that sentence that appears next to your name and picture everywhere on the site. So. Yeah. Typically LinkedIn will recommend whatever your current job title is, but like here's a danger for students. If your most recent experience on LinkedIn says, you know, a student at the university of Pennsylvania, then that becomes your headline.

Well, again, the recruiter searching for product marketing manager will never find you, even if she's looking for students, because what she wants is people with a specific focus. And so that's why it's important. You don't just focus on where you've been in the past. But you actually focus aspirationally and where you want to go, because that's where the recruiters are looking.

[00:21:21] [LED]: I see. Okay. So then what do you suggest the headline should be?

[00:21:25] [Jeremy]: Yeah, absolutely. So ideally if you're already in the space or have already sort of repositioned yourself for the space, I think the headline can be as simply the job title that you're looking for. Product marketing manager.

This is an operations manager, a business development partnership, a lead, whatever. Because that way you match those keywords if you feel comfortable doing so, you can definitely build on that by including, you know, something that might be a little bit appealing in terms of a big brand that you've worked for or including a really important skill.

So like product marketing manager with a specialty in e-commerce, for instance, that's a place that you really want to double down. But I would always start with the job title itself because that's what the recruiters are going to search for.

[00:22:10] [LED]: Oh, I see. Okay. So would you say former product marketing manager, or will you just say product marketing manager?

[00:22:19] [Jeremy]: Yeah, I would say product marketing manager. So as long as that's where you intend to be in the future.

[00:22:24] [LED]: Okay. And then would you say comma student.

[00:22:28] [Jeremy]: That's right. So if you are typically applying for companies that want to hire people straight out of school in the tech world's case, that's typically the biggest tech companies.

And that's great because that's a feather in your cap. However, this is the tricky part about the tech world startups, especially smaller ones. Aren't always in love with hiring MBAs right away, or students for that matter. And so if it might become sort of a Scarlet letter on the other hand, instead of a feather in your cap, you might, might want to actually not make that a key part of your positioning.

[LED]: [00:23:00] Very interesting. Where else do you recommend I should be including these keywords in my LinkedIn profile. 

[00:23:07] [Jeremy]: So let's talk through sort of the three key areas. So we talked to the headline, which is number one, the number two most valuable from a LinkedIn SEO perspective is your summary.

So that's sort of the couple of paragraphs of texts that you can include right below your picture and your headline on your profile. So typically you'll see someone say, Hey, I have five to 10 years of experience, blah, blah, blah. Here are my specialties. And so you want to make sure that the job titles, again are included there, ideally some skills and supporting evidence.

So what I always like to see there - Product marketing manager with expertise in these areas as demonstrated by these three career highlights. And that's because while the machine might not care about the beautiful writing, the human at the end of the machine, who is now seeing you on their LinkedIn search is going to come to your profile and they have to be impressed on a human level.

So if you can give them a really quick summary, a highlight reel, if you will, of the best things you've done in this space. That'll help them immediately say, Hey, this person belongs on my radar right away. Yep.

And then the third area is in your experience. A lot of the students that I've coached will often say, oh, Jeremy I'd feel kind of weird putting my resume bullets on my LinkedIn. Isn't that a duplicate? But the power of having all those great resume bullets that you probably spend time working on on LinkedIn is that they're actually working for you constantly.

You could have the world's greatest resume, but if it's only sitting on your hard drive and no recruiter in the world can see it, it's got no value for you. Whereas being on LinkedIn, you can be found 24*7. That's tremendous value. 

[00:24:49] [LED]: So then in positioning yourself I think we've covered everything on the LinkedIn profile. Is there anything else that you think people should be aware of?

[00:25:06] [Jeremy]: Yeah, I think the one tricky thing is that let's say in that initial stage, you just can't decide between roles.

Maybe you say, well, product management and product marketing, both sound good. And it's true that there are some similarities, right? So in that case, you know, you may actually want to start by exploring both roles simultaneously. And so the tricky piece is on LinkedIn. You can typically only choose one area of focus.

It may feel a little bit sort of a little bit mixed up if you will, to have both things listed at once. But the beauty of the resume, of course, in comparison to LinkedIn is that you can have two totally different versions. So what I encourage folks to do is not necessarily to have a different resume for every company or for every job that you apply for, because that can get totally out of hand.

But if you decide to go after two functional areas, make sure that you at least have a different resume version for each one. Because nothing looks worse than getting a resume where it says I'm interested in working in the tech space where I want to do product marketing and product management, because that just gives me a sense that you don't have clarity.

If I'm a recruiter, I want the exact right person, not the person who's only 50%.

[00:26:14] [LED]: So then coming to your resume - can you share some examples of what that customization of a resume for a specific role might look like? 

So if let's say we take a kindergarten teacher profile. Kindergarten teacher who then worked in a nonprofit. You're applying for a product marketing role. Can you share an example of a potential resume bullet point, which you'll phrase differently for the PMM versus a BM job?

[00:27:32] [Jeremy]: Sure. Yeah. So I think it's all about understanding what the outcomes are that are important in each role. Because a lot of times what I'll see with bullet points, is that it's all focused on - “here's my responsibility” and not actually what I accomplished and the tech world is so fast-moving and resource constrained that they are extremely results focused.

And if your resume doesn't match that, you're going to be in trouble. So to give you an example, when I was a kindergarten teacher, I would often talk in my resume about, you know, “I lifted student grade point averages” or “created a great classroom culture”. They were very relevant for the education space, but didn't speak to the outcomes that a product manager or product marketer cares about.

When I applied for product marketing jobs, I took the exact same stories in terms of working with students and working with families and I focused on marketing outcomes, namely influence. So for example, I talked about the fact that I created a classroom blog, not just for pedagogical reasons, but to actually drive engagement with families.

And I could point to how I had 95% of my audience engage on a weekly basis. Just by creating this sort of classroom community online, that's speaking the language of tech marketing, which is obsessed with the idea of daily active users and weekly active users. So even if it was a very different industry, I still convey that I understand the lingo.

[00:28:56] [LED]: That's a great example. If you were to take the same story and spin a product management bullet out of it, how would you do that?

[00:29:08] [Jeremy]: Yeah, absolutely. So again, if I was focusing on the idea of a blog as being a “product” I’ve developed if you will, I might talk about that.

Maybe I’d talk about really high satisfaction with the families. So for instance, I did survey the families at a couple of points in the year, and the families were really satisfied. PMs care about that. So that would be a way to talk credibly about having done something similar. 

[00:30:21] [LED]: So then the next stage was a systematic approach to your application process. What does that mean?

[00:30:48] [Jeremy]: Yeah, so it means taking a lot of, sort of the analysis paralysis out of the job search process and putting as much of it on autoplay. And what I mean by that is don't get into the habit of trying to hunt for jobs manually.

A trick - everything is alert based whether you use Indeed or LinkedIn or Glassdoor or AngelList for the startup space. All those have alert features. So on a daily basis, they'll say, here are the jobs that match your search requirements and just let that come to you. That's the first step. 

Then what I always recommend is that people make a habit of applying to a certain number of jobs each day.

And applying right away. So the jobs as they're posted, one advantage I've seen on the inside of tech companies is that a job application that's received on the very first day, is going to get a lot more attention than one that comes in on the 10th day. I think it's just human nature.

It's sort of that Christmas morning feeling of, I'm excited to see, you know, a new application if I'm the hiring manager, but after a couple of weeks, I'm totally bored of the whole thing. In general, there’s an advantage to applying earlier. 

[00:32:06] [LED]: And I guess that's where alerts can be very helpful, coz  you'll be notified as soon as the job opening is up.

[00:32:12] [Jeremy]: That's right. And on LinkedIn, you know, I think if you have a premium account, you can actually see how many people have applied already and you'll notice within a week or two, a lot of jobs have hundreds of applications, but within the first 24 hours, it's typically just a handful. 

[00:32:28] [LED]: And then if I’m applying within the first 24 hours, then does that mean that I'm simply applying on the website and sort of filling out the form and hitting submit? Or am I doing something else?

[00:32:40] [Jeremy]: Yeah, so that is what you're doing. And I know people are going to say, oh, Jeremy, like everyone knows about the internet. You know, job search is a black box. You just put these applications in and you never hear back. And I totally understand that, but I want to explain my strategy here.

Part of it is that there's an aspect of momentum and human psychology of, if you can get in that rhythm of applying quickly, getting them in the door, you're just going to feel like, Hey, I've accomplished something. I've sort of planted my flag, but the other thing is that a lot of times people say, well, I know referrals are important and we'll talk about that in a second - so I'm not going to apply until I get a referral. But what typically happens is because referrals can be tough to get, people wait around for weeks and weeks and weeks, and their referral never comes through. And now the job is filled and they just sat on the sidelines the whole time. 

And so I don't think it's either or,  like either apply online or get a referral. I think it's actually both because from what I've seen, even people who applied on the first day and been rejected right away get pulled out of the fire so to speak, if someone on the inside puts in a good word for them. And so it almost gives you two shots at a job to apply online and then get the referral also.

[00:34:11] [LED]:  What process should one follow for getting a referral? 

[00:34:32] [Jeremy]: One hangup people have is that they say, oh, I looked on LinkedIn and I don't know anyone there. Okay. I can't get a referral. And that is absolutely a trap because there are so many other ways in, so let me give you a couple of examples.

You can say, okay, maybe I don't know anyone there, but maybe I know someone or excuse me, maybe I can find someone there who went to my school. Whether it's my undergraduate university or my graduate university, be open-minded about that. Also note that LinkedIn often categorizes graduate schools separately from overall universities.

So for example, the university of Michigan and the Ross school of business are considered different entities. So it's important to search both and that's going to give you access to potentially hundreds or even thousands of people you can talk to look for people who have other shared affiliations.

Did they work at a former company where you used to work? So maybe in some cases I've seen people get referrals from people who did Teach for America. So not the same school necessarily, but the same organization, the same former employer. And they feel that sense of shared affiliation. 

And then of course, there's that really powerful and exponential piece of friends of friends. So you might not know someone who works there directly, but someone that you know, and they may know someone. And that's where LinkedIn is really powerful, it's showing you the second degree connections as they're called.

So you can really say, I might only know a thousand people, but those thousand people know a hundred thousand more people, and that gives me way more entries into this.

[00:36:10] [LED]: My other question for you is that - if I know someone, I'd be more than happy to do a referral. But if you don't know someone and let's say they went to the same school, or you were part of some organization together, how do you suggest the candidate should frame the request?

[00:37:04] [Jeremy]: So I'm going to give some controversial advice here, and this is something I've seen work in my own job search.

I think people typically have this vision of, unless this person is already a good friend, I kind of have to wine and dine them. I have to reach out and reach out again and have a million conversations. And I think that can certainly work. Like I've seen in the MBA world. People build relationships with alumni a year in advance of the need.

And then because they have that great relationship, it's a lot easier to ask for whatever.. What most people don't know is where they're going to be in a year, let alone the jobs they're applying for, let alone where they're going to need a referral. And so because you know, human nature is what it is and people often need things at the last second, I think you need a very different winning strategy.

Just go to that person and just put them in your shoes, say, Hey, you know as someone who's a fellow Teach for America alum or a fellow Habitat for Humanity volunteer, etc, just want to let you know that I was super excited to come across your profile. It seems like you've done some really cool stuff. And I'm really passionate about this particular role. Here's why I think I'd be good at it. 

And what you're doing is you're kind of saying, Hey, if you refer me, It's not like putting an application for a crazy person or you're gonna look really bad. It's actually a total slam dunk where you're going to be helping out someone from the shared tribe.

I know that sounds like a relatively short transaction or relatively quick, compared to the wine and dine approach. But I would suspect that I got somewhere between a 30 and 50% response rate, just based on going out like that and saying, “Hey, I could be really good for your organization”.

[00:40:27] [LED]: Is there anything else that you’d like to point out?

[00:40:49] [Jeremy]: Two quick points. Number one is in general, I recommend applying pretty broadly. And the reason for that is not that you necessarily want to settle for a job that you're not excited about, but what I've seen happen is at the later stages of the process, when you're either being interviewed or about to get an offer, having lots of other irons in the fire just gives you leverage and it gives you lots of options. 

Companies respond really quickly to someone who has other offers and other opportunities compared to the candidate who says, oh, I'm all in for you. And I have no other opportunities cooking right now. So just from the aspect of giving yourself leverage, I would say, apply pretty broadly.

And then the last piece is if you absolutely cannot get a referral, think about just reaching out to the hiring manager. If you have a really good case to make and could point to a piece of portfolio work, that's really astounding. Just go to them directly and again, make your case in a diplomatic and friendly way. You'd be surprised how many folks actually respond positively to that because at the end of the day, your incentives are aligned.

You want a great job where you can really kick it. And they want a person who can do a great job and kick butt for them. And if you could demonstrate that over email, you can often turn that into an interview.

[00:42:09] [LED]: What would be your advice for interview prep?

[00:42:56] [Jeremy]: I'll start off with the sort of classic trap of people who are preparing for interviews, especially in the industries that they're not familiar with like Tech - they tend to take a very prescriptive approach. They try to find all the possible interview questions on Glassdoor and from friends and just sort of cram for them as much as possible. That process inevitably fails because every company is gonna be different.

Every interview is going to be different. They're not just going to give you the same interview questions that you already prepared for. And because you have such a fragile process, that's built on the exact questions that you plan for. You're going to have sort of a crash and burn experience in the interview room, which is not fun.

So instead of that sort of inflexible approach, take a more flexible humanistic approach where you just say, okay, what does it feel like to be on the other side of the table? And even if you've never been an interviewer yourself, you can start to imagine. That if I'm going to hire someone from my team, I need someone who can do the job first and foremost, because I don't want to have to sort of, you know, pull up the slack for them or find excuses for them.

And then number two, I'm going to spend more time with this person every day. I better like them. I want to spend time with them. And so if you can nail on both of those counts there, as far as competence and warmth, there's actually some sociological work in terms of this is the way humans make judgments about all other things.

And as you can show off at, Hey, I know what I'm talking about and I'd be a great person to work with. You're going to tend to get the job more often than not versus the person who's only prepared to answer robotically, certainly a certain set of questions, but can't demonstrate the warmth or can't demonstrate the general competence.

I want to emphasize that warmth piece because I know it can seem like wishy-washy like, oh yeah, of course.

But there are things you can actually do to help with that. I think number one, this is so basic. It's just like bring positive energy into that room because one of the things that humans do very naturally and subconsciously is they mimic each other and I've actually seen people tank an interview just by bringing sort of negative energy or an anxious energy into the room because then the hiring manager starts to absorb that themselves.

And the way that you prepare for that is by having someone practice with you and just say, do you like me? Do you like me? Do you like me? And regardless of the words coming out of your mouth, if your body language and your energy are just radiating negativity, and they'd give you that feedback, you'll be way more prepared than just walking in and hoping for the best.

So even the warmth can feel kind of a little bit out there, approach it in the same way you'd approach any interview. Practice, practice, practice.

[00:48:57] [LED]: You've coached so many candidates. Do you see any common stumbling blocks or mistakes that people tend to make?

[00:49:08] [Jeremy]: I think I've mentioned a bunch of them, I’ll mention three higher level ones that I see across the tech world.

First one is you make yourself a commodity by which I mean, people tend to try to want to become the median of all applicants. So play it safe. Copy language from other resumes, use a generic cover letter template they found on the internet somewhere. And the problem with that is that at least in the tech world, as far as I've seen people who are differentiated, who are sort of luxury and premium products are the ones who get the jobs, not the average play it safe candidate.

So definitely go above and beyond, get a little bit outside your comfort zone and really pitch yourself as opposed to saying, Hey, I'm just going to play it as safe as possible.

I think people try to sort of maybe round off their quirky edges, the same, like a homogenous camp. You know, I don't want to seem too crazy or out there, but one of the things I did in my cover letter for Apple. So I talked about how, when I worked in the nonprofit sector, I was so nerdy. I was known as sort of like the tech guy for all my nonprofits, that for Halloween, I actually dressed up as Excel man. And I had this like recursive error happening on my costume. People said to me, oh, Jeremy, that's crazy. Like, what are you doing? But I remember distinctly my interviewer asking me about it and saying that would fit in perfectly with Apple's crazy culture.

So that's the first one. The second one is a lot of time with tech, for people on the outside looking in, they'll confuse research with progress. I would definitely say, like, I think it's one of these almost avoidance behaviors that humans have where we do the safe thing as opposed to the important thing. But even if it feels crazy to get out of your comfort zone and start applying for something that's totally new, just go for it.

Like rejection, as hard as it feels at the moment is actually better for you to get it now and than putting it off. So if you're thinking about breaking the tech, definitely go for it sooner rather than later. And don't get stuck in that sort of research block. 

And then the last thing - And this something I've fallen into many times over in my life is prioritizing prestige over fit, which is really easy in the tech space. Especially given that there are so many sexy brand name companies. Don't worry about the company that your mom wants you to work at, or your friend or your roommate think about the company that's actually right for you.

You know, if you know, in your heart that you belong in a really fast paced small environment, don't go for a giant company, no matter how great the logo is on the outside. Make sure that it's the right one for you, because you'll actually be more successful in the job and get more jobs based on that.


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