For many years, an extremely tight labor market made finding, recruiting, and retaining talent one of the top struggles for tech companies. For tech startups at their earliest stages, it could be nearly impossible.

Now, the economic downturn has significantly altered the environment, and thousands of highly qualified candidates are in search of new roles. In just a few months, the population of job-seekers will further expand as a wave of fresh graduates – many of whom will be taking on the first serious role of their career – enter the market. The dearth of open roles can be discouraging to any candidate, and those at the beginning of their careers may feel this even more acutely.

A bright spot in this otherwise difficult time is early-stage startups that are still in need of talent to form their core teams. For many, the best match may be between the newest startup and the newest job-seeker. Early career candidates bring a fresh enthusiasm and willingness to take risks that may become tempered later in their profession, and startup hiring managers can give relatively inexperienced candidates the opportunity to contribute and grow at levels that would take years to achieve in a more established company.

“One of the things that we’ve seen repeatedly throughout all the startups we work with is how many different things get thrown at you. And early career people have a huge appetite for that,” says Yuliya Mykhaylovska, who leads university recruiting for Greylock’s core talent team. “For candidates who are extremely hungry and willing to roll up their sleeves and work hard, joining a startup can be a life-altering opportunity.”

Moreover, today’s recent grads enter the workforce with considerably more real-world experience and startup-culture familiarity than previous generations, says Mykhaylovska. That said, evaluating recent graduates requires hiring managers to take other factors into account and adjust their interviewing, onboarding, and retention strategies. Likewise, candidates must approach the potential role with an understanding of the risks, and the possibility of major changes such as pivots in product development or go-to-market strategy, which can significantly alter the nature of one’s job function.

“That risk is worth taking if you’re excited to really accelerate your career,” says Mykhaylovska. “Absolutely consider startups, but do know it’s not for the faint of heart and it is extremely hard work and it’s also extremely competitive.”

Mykhaylovska joined me on the Greymatter podcast to discuss what she looks for in early career candidates, how founders can best structure roles for these hires, how to stand apart from other candidates, and how the Greylock Talent team finds new talent. You can listen to the conversation at the link below or wherever you get your podcasts.


Heather Mack:
Talent is an all-important focus area for startup founders, and we’ve discussed various aspects of the hiring and recruiting process on Greymatter several times. Today, we’re focusing on hiring at the earliest stages, both for the company and the candidate.

Many startups find some of their earliest employees right out of college. Given the wide range of experience and insight different people may have depending on their course of study, internships, and networking opportunities, how can founders establish a framework for evaluating such candidates? Conversely, how can people fresh out of school carefully vet a startup for their first real job?

These are questions my colleague Yuliya Mykhaylovska handles every day. As part of Greylock’s talent team, Yuliya heads recruiting at the university level for a range of positions including engineering, product, and design. She’s going to share her top recommendations for lending top talent.

Yuliya, thanks so much for being here today.

Yuliya Mykhaylovska:
Great to be here, Heather. Excited to talk about early career talent.

Awesome. Now let’s start with the basics. To understand the kind of roles a recent grad can be expected to handle in today’s startup landscape (which is all over the place) tell us about the kinds of companies that are sourcing talent this early in their career.

Well, to be honest, every kind of company is open to early career talent. Even the ones that don’t initially say they’re looking to hire somebody who has fewer years of experience, once they meet some of the candidates we introduced them to, they’re open to it.

In the past three years, I’ve seen companies from the seed stealth stage up to pre-IPO companies in our portfolio hire talent across primarily engineering, but also design and product roles. What’s been so interesting, especially after the pandemic, is seeing that candidates are coming in with far more experience, internships and coursework and projects under their belt than most founders remember having at the similar life stage. So I really do think that over the last five to 10 years, there’s been a massive acceleration and the kinds of knowledge and skills that students are coming in with, and many of them are coming in with two to three years worth of full-time experience and therefore a bit more ready to hit the ground running.

In our portfolio, there is a lot of appetite and interest in hiring early career talent and whether it’s at the early stage and a company might take on one or two students or at companies of Figma or Convoy stage where they’re going to have an actual cohort of new grads or interns. There’s a lot of interest from both parties to work together.

The other thing that’s really changed is that over the last few years, there’s a lot more information on campuses about what startup opportunities look like. In the early 2010s, a lot more people were going into traditional roles within finance and banking and consulting. Now, it’s a lot more de rigueur to go into the startup sector. So you see students who are organizing treks to the West Coast to meet with startups there, treks to the East Coast as well. You see students participating in a lot of hackathons and competitions and programs like that. And so they’re really informed on a variety of sectors. They’re coming in asking great questions and you’re just seeing a lot more fidelity and a lot more knowledge of what might be a good fit for both parties.

I think what continues to hold (and would be an interesting thing for both founders and candidates to consider) is that there continues to be more of gravitation towards consumer businesses from the student’s perspective. And I think that’s because consumer businesses are typically things that you can easily explain to mom and dad and your professors and your classmates.

Now, that being said, what people should keep in mind, again, both from the founder and candidate perspective, is that enterprise companies have a massive demand for hires. They don’t always have the biggest talent brands, but that’s something worth digging into. So from the founder’s perspective, I think it’s super important to lay out what business problem does the startup solve and really help students understand what the B2B landscape looks like so they can see what kind of impact is possible there.

And then from the candidate perspective, it is doing a little bit more research and not just gravitating towards the names you know and the companies that are on your iPhone, but rather doing the research, looking at market landscape maps of what are the different sectors than AI or cybersecurity, et cetera, because the enterprise software market has tons of opportunities for new grads. So it’s worth not just focusing on something that you already know.

What’s another advantage that a really early career person could bring to a startup when they’re really at their foundational stages, they really need to build the company? You would think maybe they need some with more experience, but what’s an extra special aspect of an early career employee?

I love that question because I think that’s one of the favorite parts of my job. It’s that I work with people who are all unique and have things to contribute. So in addition to the fact that they’re amazingly experienced, most of them at this level, they just have a lot of drive to get things done. They’re capable, a lot of them are able to juggle so many things between schoolwork and on campus jobs and internships and research. They can handle so much. And I think one of the things that we’ve seen repeatedly throughout all the startups we work with is how many different things get thrown at you. And early career people have a huge appetite for that. They don’t have the weight of other commitments to family and mortgages and things like that. Students have an appetite to learn and to grow. So that energy honestly means a lot.

And our founders comment (time and time again) how much that fresh energy just lifts that culture and helps propel it forward. Also, there’s a lot of diversity in terms of backgrounds that students are able to contribute. As campuses have gotten much more diverse, you’re seeing that reflected in the makeup of CS graduates, and companies certainly look to early career talent to help diversify their ranks.

Last but not least, what the students and recent grads can offer is actually future company leadership. We’ve seen even within our own portfolio folks that start out as early career employees at companies like Rubrik and Stripe, Asana, et cetera, who are now founders of businesses that we’ve invested in.

And so you think about that two- to three-year journey initially as what the candidate will contribute. But longer term, I think there’s a lot of entrepreneurial spirit and relationships that are formed at the early career level and lead to really great options and opportunities for folks involved. So junior talent can definitely deliver not just in terms of the experiences, but in terms of their background and ideas and energy, which that’s what so many teams run on.

“At startups, we’ve seen repeatedly how many different things get thrown at you. And early career people have a huge appetite for that.”

Yeah, that’s great. And you mentioned before that people are much more experienced than they used to be, but still, I’m curious what this really looks like. When I’ve spoken with our colleague, Holly Rose Faith, who leads executive talent recruiting at that stage, you have so much to look for in terms of a candidate’s experience and technical and interpersonal skills. So when you’re working with these really early stage people, how do you recognize what great looks like and what would translate from an internship or any early work experience into actually being a core member of a startup?

Absolutely. What I initially saw when I first started at Greylock is just fantastic resumes. So many students are coming in with a 4.0, multiple extracurriculars, TA-ing the best classes, et cetera. And I thought, “Wow, these are all people who could really make a difference.”

As I got further along in my time at Greylock, what I noticed is you really need to better understand the motivations of candidates and ask different kinds of questions to really understand what their interests are and how well defined they are. So one of the biggest challenges in recruiting early career talent is that oftentimes the candidates themselves don’t have a clear definition of what they want to be doing. Most people will say something like, “I’d love to join a fast growing company and have a great manager and grow a lot.” That doesn’t really help the candidate and that doesn’t really help me because I would argue every company that we work with fits that description.

So the thing I would encourage people to look at is, has the candidate really done their diligence on a specific sub sector of their industry? If they’re interested in FinTech, are they primarily interested in payments? Are they interested in something else in that sector? Can they name companies outside of Stripe or Chime? Right? So just probing a bit deeper of how much research you have really done. Is it a more developed perspective on where an industry can go? It definitely helps when folks have experience in the sector that our companies are looking for, and it helps them just come in with a more informed idea of where the opportunities are and really hit the ground running.

“To learn the motivations of candidates, ask different kinds of questions to really understand what their interests are and how well defined they are.”

The other thing that’s key when working with early career candidates is figuring out what they themselves accomplished versus what they were able to do as part of a team.

One of the questions I often dig into in my conversations with candidates is, “Have you been able to take a project from zero to 1 in a previous internship or group project etc.?” And if not, “What part of a project or initiative did you come in at, and where did you specifically contribute? What were the roles of your teammates?” I want to see if you are able to delineate those different things and also tie in self awareness about your strengths.

A big difference between early candidates and the more experienced candidates I work with is that the early in career ones have this tendency to generalize a lot of different strengths versus having a more acute awareness of different strengths.

The reality is, the better that a manager or future manager knows what a candidate’s strengths and weaknesses are, the better they can evaluate the fit of the role, and then the better able they are to onboard the candidate, train them, retain them, etc. So it is essential to a strong working relationship between an early career candidate and the team and manager to have that awareness going into the interview process and joining a team.

Great. And where are you finding the top candidates?

We’re finding the top candidates through a variety of ways, sourcing them, hosting events, talking to various groups and programs, having a lot of referrals come in through other students I’ve worked with over the past few years, as well as through our founders and people that they meet.

But certainly one of the biggest mechanisms and tools for sourcing these amazing students and early career graduates is through Techfair. Techfair is an annual event that we’ve hosted at Greylock for over a decade now, and it’s an opportunity for thousands of candidates to apply for a chance to meet some of our companies. So we run a process every spring and I’ll screen thousands of candidates and identify the top 15 to 20% of them across 150-plus schools in the US and Canada and set up a way for them to have conversations with the engineers and PMs and designers at a variety of fast-growing companies. What the event gives people a chance to do is to actually talk to their peers about what the day-to-day work would be like, what are the challenges, instead of talking with recruiters only and having a higher level conversation.

What I love a lot about how the event has evolved in the past few years, especially with COVID and the move to a virtual setting, is that it’s really helped us expand the diversity of students and schools we reach. And my thinking has always been we’re looking for the top students, not necessarily for the top schools. Oftentimes those things do go hand in hand, but I have to say that CS programs have grown so much in size over the last few years that you’re seeing amazing talent at liberal arts schools that you don’t traditionally think of as having CS students. I also see some great schools with competitive programming clubs and interesting group oriented project based groups, things like that.

So the talent is really coming from everywhere, but Techfair has always been one of the best ways we’re building that pipeline and following through with candidates that we meet from across the US and Canada.

And thinking about the founder’s side or the hiring manager’s, one of the most important things is how they present or sell their company, the job as the product. And sometimes that’s hard depending on how early stage the company is. So what are the key things that you advise them that they need to get across to someone who’s perhaps less experienced with evaluating a potential job and what’s another thing that they should really try to help the candidate understand about startup life?

Absolutely. I think with any job that we take on, you can only know so much before you step into it, which is why I strongly recommend that companies do an internship or short term project before they (candidates) go to the full-time stage. Certainly with people who are looking for full-time jobs, it’s not always possible, but the internships are a great segue for the first few hires because then you get to try before you buy for both sides to really agree on that. So that’s one thing I’d recommend.

In terms of other things that founders should really be looking to get across to folks when they’re evaluating opportunities to join their startup: One, what is the overall market? Where is it going? I think that highlighting to candidates that you’re not just joining a specific business, but rather you’re joining a certain sector that’s on a growth rate like artificial intelligence. You are not just learning about that within the context of one company, but you are starting to open the door to a whole spectrum of opportunities that will impact your career.

Another thing that’s been a very big topic throughout the pandemic and still is to the present day is the stability of the business. So with COVID and other things going on, there have been people who’ve gotten offers rescinded and that’s made a big impact on folks’ risk tolerance to join different businesses.

So startup founders need to be able to explain in simple terms how stable is the business, how much runway does it have, who are the investors and why did those investors matter? One of the things I often do when I’m putting our companies in context is sharing a bit more about the background of the partner who led the deal. So [for example] explaining that Asheem [Chandna] has two decades’ worth of cybersecurity experience and he’s seen the playbook multiple times. That helps students get comfortable with the idea of going to an earlier stage cybersecurity startup. So the stability of the business does not necessarily only have to cover the numbers of the business, but it can also talk about why do the stakeholders involved matter and how does that contribute to a successful and stable business, one that’s “de-risk” for the candidates to join.

I also think it’s extremely important to talk about the manager and relationship and the mentors that are going to be in that company. So ensuring that students understand that there’s that immediate team they’re joining, but also how experienced is the skip level person and the founder, et cetera. Showing people that they’re not going to be just having one key relationship within the business, but multiple people to rely upon because as confident as some early career candidates will be, at the end of the day, everyone knows they have so much more to learn. So highlighting things such as, “Hey, this manager has managed X, Y, and Z, and now look at where their former reports are at, this is a potential track for you.” That’s really helping sell candidates on the opportunity because it helps them know, Okay, even though this is an early stage business, this is not a first time manager. This is somebody who’s been able to develop people before.”

The thing that founders should also be able to have an honest conversation about is it’s not going to be a lot of hand holding. So while you have these experienced teammates that have built businesses before, you’re still at some points going to have to be a manager of one and you’re going to have to speak up, voice those questions. And I’ve seen over the last few years how our managers and companies have helped early career folks develop that confidence to ask the right questions and to throw their hand up when they’re not sure what’s going on. But these are already folks that had from the get go a bit more of that self-starter mentality and were able to get things kicked off.

So you’re not changing somebody’s DNA from being somebody who loves to be in a very structured environment to somebody who’s comfortable in that unstructured environment. Rather, you are accelerating and doubling down on that inherent inner drive to be comfortable taking risks and building things from scratch and not always needing something fully laid out in terms of a plan. And for many students, that’s a very attractive opportunity. For folks I’ve talked to who interned or worked full time at big tech companies, they hate it when things are overly delineated and too scripted. They find that it’s really putting up barriers in their career progression. So for most people, they see the opportunity of things being less defined as being a positive aspect of startup life.

But for people who have doubts, that’s an important doubt to voice for the founder because then you can have an honest conversation if that particular stage is right for you. And certainly at the seed and Series A stage, there’s going to be a lot of ambiguity. As you’re moving further along, there’s less ambiguity, but there’s also more of a specific skill set and kind of candidate companies are looking for. So typically folks have been advised to look for serious B and C companies, but what early career candidates should keep in mind is that it’s harder to get into those companies as they get to a later stage because they’re going to be a lot more specific type roles versus generalists.

“Understand that you’re not just joining a specific business, but rather you’re joining a certain sector that’s on a growth rate…you are starting to open the door to a whole spectrum of opportunities that will impact your career.”

Right. And this next question is right in that same vein. In talking about that ambiguity, which can be fun and exciting and appealing to candidates and necessary for the stage of the company, that’s great, but then when you do need to put some structure on it enough so that you can explain what someone’s role would be and as a candidate, how do you get enough clarity about a kind of ill defined role that you can understand if you could do it?

Absolutely. It’s a challenge, but it’s a fun challenge if you’re up for that challenge. One of the biggest perks of being in a startup is that you can talk to almost everybody as you’re interviewing, so you get the chance to understand what the company needs and then propose ways of how you can contribute rather than being told, “Here’s how you can contribute and here’s what you can do.”

I think taking diligent notes during those early conversations is really important because you’re trying to piece together, as a candidate, where the sectors of opportunity or even interest, curiosity, and then form things around those conversations.

I recently had an early career candidate join Scenery, one of our series A companies in the video collaboration space. And initially, the company wasn’t even looking for someone at an early stage in their career, but I had a candidate who had a great technical background as well as a very creative set of interests and a creative minor. So I introduced her to the business and they were able to carve out the role together. It took multiple conversations.

There’s certainly the technical assessment piece of the interview, and so the hiring manager’s able to get a sense of where the person’s strengths are and then build the role around that. So it’s very much a collaborative process where the more you get to know about the candidate and see their strong suits, the better you’re able to together form a theory of what the role could look like. But that’s an iterative process that’s more creative rather than prescriptive. So for both parties to really be able to have an open conversation of where is the business, where are the initial needs, but also how might those needs evolve for the company and then for the candidate to say, “I’ve done some work on the front end side, but I also would love to learn more about the product perspective. Are there things we can do three to six months down the line that would give me that experience?”

And most companies at the early stage, they’re growing so quickly that rising tide helps all boats and as long as there’s a plan that’s getting built together, there’s an opportunity to insert some of those additional aspects to the role.

One thing I would very much advise against is trying to go too broad in defining that role. I’ve seen some candidates say, “I’d love to be both a PM and a chief of staff.” While I think if you’re trying to be the jack of all trades, especially early in your career, that might cause some founders to hesitate when it comes to hiring. So it’s better to come in with a more narrowly defined set of tasks you’d want to do versus things on opposite ends of the spectrum.

The other thing that people do is they’ll talk to early career folks in their network or in our companies to figure out how they structured that role and use that as a way to bring some additional clarity. But as businesses change and our businesses at the early stages certainly change every three to six months, these roles are going to evolve as well. And so you really want to be a candidate who’s flexible with those changes and not just stuck to one specific role or title or function.

That sounds pretty fascinating though. It sounds like a fun thing to work on together. And so say a startup’s done great and they’ve secured a great candidate, are there differences in the way that you would onboard someone at this stage of their career versus someone in their late stage in the career?

Certainly with people who are early in their career, there is a bit more effort you have to put into welcoming new folks and having them feel as part of the team. For early career people, work is really the main thing in their life. And so in addition to just having a job, people are looking for community and teamwork and camaraderie. So little things like a surprise and delight experience when you extend the offer, that goes a long way. One of our companies, Tome, sent cupcakes to an early career candidate whose birthday was around the time that they signed the offer. And that really goes far in helping someone feel that it’s a friendly and pleasant environment to work in. You have to remember, these people are coming out of colleges, so they’re used to just being in person with lots of folks all the time and they’re wanting to see that joyful piece of work as they enter their jobs as well.

There’s also a very big culture of having mentors and buddy systems when people join their startup roles. At Truera, they have a program where they have onboarding cohorts. And so each cohort is meeting together for the first few months, getting to have fireside chats with the founders, meeting with engineering area leads and having a bit more of a structured experience.

One of the big changes between how school and college works versus how companies (especially startups) work is that there’s no direct supervisor or teacher-student relationships. So people are having to learn in those early years at work, how do you drive projects forward and how do you focus on the bigger picture? And there is time that needs to be spent on how do you run an effective one-on-one? How do you bring up the right problems to your manager? And that is an ongoing process versus a set two-week onboarding period.

Something that managers need to be aware of and that students, as they made that transition to full-time workers, need to actively think, “How am I now a full-time adult in the workplace versus an intern who’s going to be looking to their supervisor to guide every piece of it?” The new approach is more of thinking of your hiring manager and supervisor as a coach, so what the overall goal with the business is, but you’re going to have to work together with them to drive the projects forward.

For people who are more inclined to have a very structured experience, they could put together a 30, 60, 90 day plan. There’s a great book from HBR called The First 90 Days. It’s a classic, all about the strategies for how you make the first 90 days count and how you take in the whole organization as well as your own role and put together a plan of impact. So you could try to make a 30, 60, 90 day plan for a startup. It is a bit harder because startups move so much faster, but for folks who like having a roadmap, that’s not a bad plan.

And last but not least, I would recommend that for onboarding, whether it’s the founder or an engineer lead or a recruiter who does this, it’s really important to ensure that the candidate sets up time to meet every single team member and understand how does their role play into the larger business so that they can understand how they might be able to collaborate going forward. So playing all the puzzle pieces together to see how the cookie crumbles or how the bigger picture comes together.

And then also, this is a special population of people. Are there any extra challenges that hiring managers and founders might encounter when dealing with a candidate from this group that might not be as common when you’re dealing with a mid or senior level employee?

There are certainly challenges. One of the biggest challenges is if you don’t do enough work up front to understand someone’s motivations and true interests in taking the startup route, they might not be as strong as a fit… Because again, you’re hiring more somebody who’s curious about the business or about working at a startup versus has true conviction and that’s the right fit.

So one of the big things you keep hearing is about early career people who are job-hoppy. Again, that’s something that if you are screening for early in the process, you’re going to not end up, I think, with as strong of a job-hopping culture. But that’s all the more reason to ensure that people are truly brought into the business that they see themselves there for at least a few years versus making a decision for only the next six months to a year.
With everything going on with COVID and the economy, there’s also been a challenge around having to rescind offers. So companies in our portfolio are extremely mindful to ensure that they’re strong edge leadership and management that could help onboard and support their earlier career hires. If there are changes to that leadership, there’s not going to be the same kind of support to ensure that early career folks are thriving.

For our AI and machine learning companies in particular, a lot of the candidate population is international and they’ve studied in the US or Canada for their masters and PhD programs. So what I see from that perspective is reticence around joining an early stage business versus going to a larger company where they feel more secure and the visa process and navigating all of that.

That being said, this happens a lot. Our companies are absolutely hiring early career folks from international backgrounds. And so being able as a founder or hiring manager to talk through all the resources and support you’re able to give them will really go a long way to quelling those hesitations and helping someone develop the confidence to go early stage. As an immigrant myself, I’m especially invested in this topic and I’ve coached multiple people or I’ll coach dozens of people over the years about why not to hesitate. So I think that people shouldn’t assume that a startup doesn’t have the same ability to support an early career candidate as a Google or a Facebook might.
What we saw during COVID in more recent times is when people are impacted, whether it’s in our portfolio or people who joined other tech companies and then get their offers, and then if I built a relationship with that person, I will go the extra mile to help them find a new role.

Got it. What I’m hearing is people can justifiably have concerns about beginning their career at a startup, but generally speaking, the job security aspect can be pretty similar at a large established company. And startups, even the earliest stage ones, still come with big established networks, so there are many channels by which people can continue moving forward with their career even in challenging times.

For candidates who are extremely hungry and willing to roll up their sleeves and work hard, joining a startup can be a life-altering opportunity. You’ve seen multiple examples of people who joined our portfolio companies early, like TellApart or Coinbase, and it has put them on a trajectory that would otherwise take them 20 or 30 years to be on. So that risk is worth taking if you’re excited to really accelerate the career, absolutely consider startups, but do know it’s not for the faint of heart and it is extremely hard work and it’s also extremely competitive. A lot of people are surprised when they see how hard it is to get a startup opportunity, but the reality is that our companies are extremely selective and they are looking to make a few of the best early career hires versus hiring on bulk.

So, do know that it’s a challenging road to take, but extremely fulfilling. And that here on an almost daily basis from the early career folks working in Greylock companies, how much they’re learning, how much they love it, and they’re just getting stretched in ways and growing that they didn’t know is possible. And sometimes they’ll reach out and say, “I’m working on things that my manager was doing previously,” and they’re almost surprised by how much they can accomplish. But that’s really the beauty of joining the startup ecosystem, you get tested and the best people rise with the most challenging situations. They’re able to get even better at their craft and it’s an absolute privilege to work with some of the most incredible engineers across North America to help them join our companies. So I really hope that this episode convinces folks to believe in themselves and be open to going early stage.

Yeah. This is really fascinating. I wish I could go back in my career and work at a startup, at an early stage, but alas I’m way too old for that now. But thank you so much for taking the time to talk about this really fascinating work that you do with the early stage candidates and companies for Greylock. I know anyone who’s interested can find more information on our website under the university program section. And thank you so much for being here today.

Thank you, Heather. Take care.


Heather Mack

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