I wish I’d met Eleanor Meegoda, founder of JobStep, when I was at Apple Retail, trying to plot my next move and unsure how to figure out my next step (and questioning whether there was one). I met Eleanor by chance in June 2020. She’d come across a future of work article I’d written and reached out on LinkedIn.

Little did I know that connecting with her would be a ray of light in the bleak week following the killing of George Floyd. Eleanor started the call by sharing her mission: giving jobseekers the tools and resources they need to win the job hunt game and level up through it.

Her mission resonated with me as an Apple retail alum. Apple taught me how to listen, connect, drive results and lead but it also made me doubt my abilities and the opportunities available to me as a retail worker. I remember googling how to get out of retail and feeling discouraged by the lack of available solutions. JobStep is a solution that serves candidates by working with them 1:1 through their job search journey to build confidence and help you level up.

Inspired by our call, I introed Eleanor to a good friend who I thought might benefit from joining their pilot program. A good friend who has all the potential in the world but was a little stuck in that self doubt trap. Six months and multiple job interviews later, that good friend landed a manager level job and salary at a quickly growing startup.

I caught up with Eleanor in April 2021 to see how JobStep is doing. Interview below. If you’re looking for your next opportunity, JobStep might be able to help you.

Key takeaways

The best way to overcome imposter syndrome is to just get started: “[Before community art project] “I had never built anything quite like this. I had always wanted to push myself to do this. And I thought it was a really great metaphor of kind of empowering people who don't think of themselves as engineers or math people or builders or artists to kind of get together...I think that initiative is what I think gave me the confidence to go after kind of business development and or product roles and, and, kind of get over some of my imposter syndrome. ”
JobStep’s goal is to help candidates play and win the job seeking game while creating an amazing experience: “Search engines are just tracking clicks and their business model is to maximize clicks. Their business model is actually to send you as many jobs as you might click on not necessarily to send you the best job that is actually a good fit for you. What we do is reverse engineer the system, figure out how to play the game effectively. And then we play the game for job seekers. So you can concentrate on taking care of your family and learning new skills. We know oftentimes job seekers don't get to do enough actual interview prep, reflection and practicing. We give you back your time so that when you get an interview, you're ready for it. You can ACE it and hopefully get a job.”
Eleanor understands the treasure chest of transferable skills and potential many job seekers with less traditional backgrounds have: “In these jobs, you're often working in fast changing environments. You're learning new technology. You have to have great customer service. You have to be able to think on your feet. For people who've never done retail or hospitality restaurant work, I think they totally underestimate how much on your feet thinking you have to do.”
One of the best ways to show you’re ready for a higher level opportunity is by being fearless and trying new things: “Take a SQL course or take a Zendesk course, or take a Salesforce course to show that you are not afraid of learning new technology, because I think that's a big bias against people coming from outside of tech.”
If you’re interviewing, lean into what you’re running towards, not what you’re running away from: The best thing you can do is just take some time to reflect on what you are good atTry to figure out okay, as hard as it is, because you spend so many hours in that terrible job, you are yourself an amazing human. List the things that you are proud of. Even if it wasn’t perfect because some team member or your boss undercut you or whatever, you did some amazing things. The best thing you can do in a job search is to go in confident because it helps you see yourself in new roles. And then when you get an interview, you want to show that confident side, not the angry, tired, emotionally strained side.
Everyone gets a lot of nos, do not let the nos discourage you: “One number that I like to share is in a good economy in 10 applications, you get one interview. That's the average. In a bad economy, 25 applications to get one interview, at least that's what it was. For most of COVID, we typically get one interview for every seven to 15 applications that we send out. So if you’re not hearing back, remind yourself that you probably just need to play the numbers game a bit more. Apply to 50 similar types of jobs before you decide you need to tweak your approach.”
JobStep is here to help: “We want to make sure that candidates get a great experience because that's what makes us different. And that's the way we think the jobs search should be. For the investment of time and money, you should get a seamless but also empowering experience.”

JobStep guarantees 5 interviews in 6 weeks.

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Interview with Eleanor Meegoda, Co-founder and CEO at JobStep

Eleanor’s Career Journey from Princeton to nonprofits to VC to tech

I was lucky enough to have gotten in and graduated from Princeton. I studied African development and so I thought that I was going to work in international development. I studied politics and governance and I thought it was really cool to think about the world from a non Western perspective.

I landed on a couple social entrepreneurship courses my senior year, having worked in the nonprofit space and being a little frustrated about the power structures. Even if the org, the organizers and employees and staff were so committed to the work, nonprofits were often building services and products that their fuders wanted and not what their end users and beneficiaries wanted.

So that's what led me into entrepreneurship. I took these courses and fell in love! Since then, I have worked at the intersection or kind of jumped between non-profit social impact and for-profit tech for most of my career.

Bringing people in Detroit together through inclusive problem solving

I spent some time in Detroit and worked in venture capital for a couple of years. I was struck there by how segregated that city is. That’s what led me to my first, I guess, entrepreneurial personal and entrepreneurial endeavor. I started with a friend and an initiative to build, try to build the largest Rube Goldberg machine in the world. We didn't succeed.

What is a Rube Goldberg Machine?

You remember home alone, home alone movies?

Ya, they’re my favorite Christmas movies of all time. I own them on VHS, DVD and iTunes. Please continue.

Ever since watching those movies as a kid, I've always wanted to build those machines. I had never built anything like this before. I had always wanted to push myself to do this. And I thought it was a really great metaphor of kind of empowering people who don't think of themselves as engineers or math people or builders or artists to kind of get together.

I'd heard of other cities doing these connected Rube Goldberg machine projects. So a friend of mine and I said, Detroit has a diversity segregation problem. Let's see if we can bring different communities together. Let's use this metaphor of building these Rube Goldberg machines together and see what happens. Detroit has an amazing art scene. I would say it is actually one of the more few integrated spaces in the city. That was a great launching pad and, and that was kinda my first foray into business development in to reaching out to total strangers in sales and marketing and figuring out the hustle.

And it was amazing. We had people of neighborhoods from all across Detroit--elementary school students, we got college students, high school students, artists, a group of Lyft drivers participated. They sent a bunch of their driver communities to build a Rube Goldberg machine. The startup community came out. So we had, I think a hundred different people building rebuilder machines. I think we had like 17 or 18 specific sets. Of course it wasn't the largest because none of the first graders could get their machines to work. And somebody let their two year olds kind of get under the little blockade we'd had to protect the machine. We had this locally famous Rube Goldberg machine maker, ready for this great ending that would set off a balloon, but then we all got to the end and some three-year-old was holding the balloon, so...

Oh my gosh, stop. That's so funny.

Yeah. So anyway, so that was, that was, I guess my first foray into entrepreneurship.

What a source of inspiration, using that event to work on the segregation problem in the city.

I appreciate that. And that was really the vision and the goal. Of course, it's a tiny, tiny project in a giant city.

Ripples send out ripples. Like that's a huge, a hundred people. That's huge. I mean, wow. Really cool.

It was really fun. I think that initiative is what I think gave me the confidence to go after kind of business development and or product roles and, and, kind of get over some of my imposter syndrome.

Discovering a passion for building products for end users who need a helping hand instead of businesses

From there I said, where do I go next? What, what is the startup that I want to work for? I landed back at a nonprofit, in their for-profit arm, building financial solutions for low and middle income New Yorkers. The organization had been providing long term financial advising. I was part of a team that was trying to build out these technology tools to kind of operationalize some of that advice and nudges to help people pay their bills on time.

My friends told me that I've been thinking about the job world since before that, but I think that’s where I started really thinking about it. The story that I remember is being frustrated. There are these amazing people! Cooks, chefs, customer service workers. So many people who reach a cap at what they can make--salary-wise--and they don't know where else they can go. And so they go for financial advising services, which are so important and financial literacy is not where it should be in this country, but the financial advisors are trying to kind of make do, and like move limited money around and saying, okay, cut down on your Starbucks consumption or cut down on fancy dinners, or, you know, take the bus instead of taking it over or all these things, which you know, are good practices.

But I think there's another solution, right? It's not just making it easier to access loans. It's also, how can we increase your wealth. How can we get you more income in the first place so that if you wanted to have Starbucks or send your kid to like a fancy daycare, or like, get them the new backpack, you don't have to choose between Friday night dinner and something else. That's when I started thinking about the job search:how does a typical everyday person figure out their career?

At the time I was, I think 25 or 26, and I was like, I'm struggling. And I am lucky enough to have gone to Princeton. I have a great network. I'm an extrovert. I can, I meet people. They give me advice. I'm struggling to figure out where I go next in my career. If you are working one or two jobs and you have a kid and you've come from a community where everyone is doing like the same three jobs, how do you figure this out? So I knew I wanted to work in that space. I was looking around for data-driven companies in that space and I found Jobcase, moved to Boston, both for personal reasons also, because that was the company I wanted to work for.

I joined their their marketing team as a data analyst and then moved into product. And that's where I learned about just kind of how messed up the job search industry is for almost everyone who goes into this industry. Well-meaning people want to change the world, they want to help people get jobs, but it’s hard to do because the industry is so siloed.

The job to be done at JobStep: helping candidates win the game by leveling up with a new job

Search engines are just tracking clicks and their business model is to maximize the number of times job seekers click on jobs. Their business model is actually to send you as many jobs as you might click on not necessarily to send you the best job that is actually a good fit for you. And then you have integrations with applicant tracking systems that are taking these resumes, and then hopefully they get you hired, but they have a subscription business model. So their business model is not focused on quality. They just care that employers continue to hire and continue to pay them. And then you might have other kinds of intermediary steps. And then the person who is making the decisions about how much to spend on advertising these jobs is not, is almost never the hiring manager who is deciding on the candidate pool and what kind of person they want to hire.

It's like a terrible game of telephone. In the start, we're not going to solve that entire telephone problem. But what we want to do is say, okay, this bad telephone problem, the person, the people that are hurting the most are the job seekers, because this telephone problem, while it's all of these kind of different parts of the employer, at least the employers are paying, they have more choice, and they're using all these, these pieces of software, but it's set up the game so that they're getting a higher volume of candidates. Each of those candidates is a person who is waiting to hear whether they're going to get a job.

That's whymy co-founder and I started JobStep. We said “Hey, there's a system that is poorly built for everyone, and it's particularly bad for job seekers.” What we do is reverse engineer the system, figure out how to play the game effectively. And then we play the game for job seekers. So you can concentrate on taking care of your family and learning new skills. We know oftentimes job seekers don't get to do enough actual interview prep, reflection and practicing. We give you back your time so that when you get an interview, you're ready for it. You can ACE it and hopefully get a job.

Ideal candidates for JobStep are people looking to make the leap from retail/hospitality jobs into customer support, success or data analysis

When we started, when we landed on this product, this like our job step guaranteed interviews product. In June, we were looking at the market, the industry and the economy and seeing that hospitality and retail were not going to look the same after COVID. In these jobs, you're often working in fast changing environments. You're learning new technology. You have to have great customer service. You have to be able to think on your feet. For someone who's for people who've never done retail or hospitality restaurant work, I think they totally underestimate how much on your feet thinking you have to do. So we said, okay, well, what are, are there jobs that are growing that and where might these core critical skills fit.

That’s where we landed on customer support and entry-level customer success, because those two careers, those two jobs have grown exponentially. There’s a 5x-10x increase year on year when you compare the last five years in terms of the growth of customer success jobs. Employers are increasingly hiring them because of the rise of SaaS technology companies. With that kind of exponential growth, that’s is no small pipeline.

That's so interesting.I remember joining IDoneThis this six years ago. I was their first customer success hire, and there were only a handful of customer success jobs on We Work Remotely at the time. Lincoln Murphy was still very early into blogging about customer success. Now I look at LinkedIn and I see maybe 10% of my former Apple network with customer success titles. It's really exciting to see that as a bridge to move forward. Although it seems like a lot of people are still maybe doubting their ability to make that jump. I got a message from a former coworker earlier this week who wanted an intro to someone I know for an open customer success opportunity. They needed help playing the game. I introed but also immediately thought of JobStep.

One of the things that we've learned in the last year is that you can absolutely get in the interview for a customer success job if you’re coming from a retail or hospitality or other non-tech industry. Many of our clients not only get the interview, but then obviously get the second round interview, the final round interview, and the offer. Part of the work to getting a job is being qualified--which many career transitioners are. Another part of the work is being very clear and articulate about the skills and experiences that make you qualified so that you reassure this employer, most of whom have not worked in retail or hospitality or whatever job you've come from and really translate that.

Through our guaranteed interviews program, we have expanded beyond customer support customer success. We also help people looking for their first software engineering job. If you're a bootcamp grad, we help get you into solutions engineering or that first software engineering job. We help data analysts. There's a lot of data analysts who kind of get stuck at the 50-60K level who absolutely have the capacity to move into a 70K-90K job, especially if they have a SQL or Excel background. That’s a big opportunity. We are actively thinking about other tech roles. For people who have always kind of wanted to break into tech, we are, we're constantly kind of opening that up.

Then there is one piece that I learned from talking to you and other hiring managers. We haven't gotten this perfectly right, but we have started to kind of layer in additional resources and skills and course as one way to show that you are very tech savvy and you're going to be a valuable addition to this team. Take a SQL course or take a Zendesk course, or take a Salesforce course to show that you are not afraid of learning new technology, because I think that's a big bias. If you are kind of technically savvy the other piece is also just understanding business operations. If you come from different types of companies, you may not have always known what the bigger picture was and how you solve the bigger picture. That is something that we really hone in on with our interview. Prep is when you were talking about your stories really dry, when you're picking the stories that you're talking about, when you're talking about the obstacles that you solved, and then the results you had, do your best to tie it back to the business outcome. Not just like what I learned, or like, I was happy that day, or I learned a new skill, or I helped this one particular customer. It is also talking to talk about the revenue brought in or the cost savings, or how much faster you were able to do this over time. Or your team was able to do this over time to show, not only that you have the customer service skills, but as a potential customer success person, you can start to do that translation of what your customers need from the business perspective. That was a big learning. It's something that we realized we needed to incorporate. It's been fun and it's been validating to see that we can help people get the job.

Why do people come to JobStep for help and what advice do you share with them?

There’s a couple of different types of job seekers. There are the job seekers who are currently working, whether it's part-time or full-time, and they don't love their job options. Oftentimes they hate their job, but because they hate their job and working, and often working so many hours, or even if they're not working long hours emotionally, there's a toll, or maybe there's a little bit of a procrastination element. A lot of them are very reasonably overwhelmed, especially this year with everything that's going on.. Those folks see all the reasons why they aren't qualified for a job or not sure what they need to do with their resume or how they articulate their skills and they get overwhelmed. And so I think for those folks, we’re kind of a kickstarter.

Then there's a whole other group of folks who didn't realize, you know, they just think send your application and go. For those folks, there's a lucky few for whom it works, but it doesn’t work for most people. Instead, you apply, and if you haven't thought about where you go next, you were likely just going to get jobs at your level or lower or not ever hear back because you haven't played this game of optimizing for the job board and the ATS and the recruiter which are all different, different types of optimizations that you need to do on your resume and your application.

For those folks, we get a lot of folks who have been searching for three to six months and then say, okay, I wanna try JobStep because I need to try something new.

What would I say to those job seekers who are procrastinating, who are in a toxic work situation, that's emotionally draining? The best thing you can do is just take some time to reflect on what you are good at, right? Try to figure out okay, as hard as it is, because you spend so many hours in that terrible job, you are yourself an amazing human. List the things that you are proud of. Even if it wasn’t perfect because some team member or your boss undercut you or whatever, you did some amazing things. The best thing you can do in a job search is to go in confident because it helps you see yourself in new roles. And then when you get an interview, you want to show that confident side, not the angry, tired, emotionally strained side.

For the job seekers who have been searching endlessly, and then not hearing back or not hearing back as much, I would say the job search is not an indication of how qualified or how good you are, right? Because there's so much noise from all these different levels. If you can get feedback from people, if you have a network of people who are in the types of job that you want, get their thoughts on what's missing. Also remember, okay, here's what I am good at. Here's what I can do. And, you know, there are many people who are overconfident and apply to jobs that they are not yet a fit for. Maybe in five years, but not today. I would say don't lose hope because you're not going back. One number that I like to share is in a good economy in 10 applications, you get one interview. That's the average. In a bad economy, 25 applications to get one interview, at least that's what it was. For most of COVID, we typically get one interview for every seven to 15 applications that we send out.

One of the things I've been so blown away by with JobStep is your level of commitment to every job seeker.You know your users so well, and you've been so committed to helping them find their next step, however long that takes. How do you scale that level of service?

One of the best pieces of advice having been at early stage startups before, and then also having a really great network of early stage founders, is to do things that don't scale so that you do understand your users. I do that both because it's good business, but also like the problem we're solving, the reason no one else has solved it is because they're solving it from the employer side. Most products in this space, the employer is paying and the job seeker is a by-product.. Those products are like, yeah, we have to be nice enough to the job seekers to get them to click or to get them to sign up or just get them to show up. But we don't really care. It's not that they don't care, but from a business perspective, their interests are not fully aligned. For us, a big differentiator is that we are a job seeker not just ally but champion.

At JobStep, we want to make sure that candidates get a great experience because that's what makes us different. And because we think that’s what the jobs search should be. For the investment of time and money, you should get a seamless but also empowering experience.