MUST KNOW Differences Between Start Ups & Large Companies - Ft. Rebecca Oppenheim

Hey, everyone, this is Self Made Millennial. I'm Madeline Mann. In today's video, you're going to learn what the heck you're getting yourself into when you pursue a startup versus big company opportunities. You'll learn the major differences as well as how to market yourself to each opportunity. The bottom line is if you're approaching these companies the same way in your resume and the way you interview and answer questions, then you're setting yourself up for failure, my friend. I brought in an expert for today's Rebecca Oppenheim, who is an executive recruiter and the co founder of Next Op Search, a national recruiting agency that donates career coaching services to a survivor of domestic violence for every candidate hired. That's pretty freaking cool. Let's jump in. Hey, Rebecca. Welcome to Self Made Millennials. So great to have you.

Thanks for having me. Hi.

Yeah, so I'm so excited because today we're talking about the difference between pursuing opportunities at a startup versus a large company. And you have placed so many people at lots of different companies. You've also been an incredible career coach to people pursuing a lot of different paths. And so I'm really excited to dig into the nuances and some of the perceptions of different size companies. So I just kind of want to just like, tee it up with getting your thoughts on what are some of the key things for someone to know when they're deciding which path to choose? Like, what is the true difference between an opportunity at a startup versus at a larger company?

Sure. I mean, this is a question that I get all the time. So I would say that the three biggest differences that always come to mind are the scope of your role, the culture, and then the risk between the two. So I would say the role really, it's much different in a startup because you are wearing multiple hats. You. It's constantly changing. You're versatile. You might not have a lot of team members. You might be doing nine things in your job. Your job description might not have fully described all the things that will be expected of you when you join a large company. You're usually more of an expert in one vertical, so, you know, much more experienced in depth. You are not going to be doing billing and budgeting if you're a marketing analyst, but that might be something you're doing if you're at a startup. So kind of that duality is number one. Culture is usually, it can be very different startups and early stage companies are still figuring out their culture or it's extremely defined because a lot of times progressive Companies are focusing on their culture and so that foundation can be set from the beginning, but it is changing. And as you grow from a company of 10 people to 150 people, it's not going to be exactly the same. And then with larger companies it's much more established. Right. You've got formal policies and procedures that are put into place. They've existed for a long time. You're already way past that. 150 employee points.

Yeah, I feel like there's so many pros and cons and it's very difficult to decide. And have you noticed that anyone kind of pursues one path but is a bit misguided? Like their expectations don't really match what they thought a startup was going to be? Or any kind of misconceptions about larger companies?

Oh, definitely. I would say hours, number one. I think sometimes people think that if you work for a startup, you'll have flexible hours or maybe you'll get to work remote and. And that's sometimes. It's the opposite, honestly. Sometimes the hardest working people are at startups. There's no one else that you can pass the buck to. So if an emergency client call comes in at two in the morning or an email, you sometimes have to answer to it. I would also say career progression, especially for people earlier in their careers and even later, actually, if you're really looking to get to the C suite and or executive level, people will sometimes assume that if you're going to join a company that's high growth, that it's a great way to quickly grow your career because as people are added to the team, you'll be promoted. It's not always the case. A lot of times companies do bring in outside experts as they need them. It's something that you always want to talk about and have discussions about with whatever size company you are with.

But with smaller companies you're the first person in that career path, whereas if you're with a larger company, you're not the first person. So you can talk about the career progression and what people have done before you. So that's definitely a myth. And then I would say the third one is salary. I think a lot of people assume that if you join a startup you'll be paid less. And that isn't really the case. It's just different. Budgets can be tight, but that just means kind of the compensation can be structured differently in the sense that equity might be involved. And just on that note, I would like to point out that if you are getting paid less than market Value cash wise. And you do get a piece of equity as part of your compensation. This is a mistake that I see a lot of people making earlier in their careers is you need to get a lawyer to help you look at the contract and negotiate your compensation.

Yeah, I've definitely heard a lot of people who are excited about equity, but really it's kind of a world that a lot of us are not very familiar with. Like what is a number of shares at one company does not mean the same thing as the number of shares another company and the context around it is tough, but that's in schedules and their cliffs.

And what happens when your company does rounds of funding. And there are just a lot of nuances that unless you're a lawyer or you took classes on this, you're not even really expected to know.

Right, right. But it is a very cool compensation. I mean, that's how, you know, you look at the first hundred or so employees of Google and they're doing very well for themselves. They got a sweet chunk of equity.

Right. Well, that's one of the things that I mentioned at the beginning. The biggest differences between the two is risk. Right. That's probably one of the biggest things people say, I don't, I can't take on the risk. I'm gonna go to a Fortune 100 company, I can't go to a startup, I don't know if they'll be here in three years. And that's actually a misconception because although communication is really strong, usually in startups you're a small team, everyone's talking to each other. You know, if you're short on money usually, or if you're not gonna make it in the next six months.

That'S not always the case, obviously in much larger organizations. But the risk is that that communication isn't there. You're not necessarily going to get an inkling if there's going to be a RIF or a company wide layoff or restructuring. And there really is risk in both. It's just different.

Yeah, I know a lot of people who are just a complete blindside layoff.

And so it's not stability necessarily though.

Right, right. And so as people are kind of weighing their options and either deciding to after one opportunity or the other, or even both in some cases. What are some of the ways that we can market ourselves either to a startup or to a large company so that they will see our value?

If you are marketing yourself towards a startup, you want to make sure that you stress certain things. For example, your agility you know, your ability to take on a wide array of skills, to work in an ambiguous environment. Like you said, it's constantly changing. So do you, do you have ways to prove that in your past you've been able to pivot or take on new responsibilities or implement things really fast and how did that affect the company? On the other hand, if you are marketing yourselves to kind of a larger organization, then you really want to show that you are an expert in that specific domain. So, you know, what can you talk about specifically? Just kind of take away all the distracting information to keep them focused on what that job, what that team is. If you're going to be in digital marketing, focus on digital marketing. Right. They don't need to know that you did nine other jobs at your last company. That will distract them.

Yes. I love that. Yeah. People always think that their resume has to be the truth of exactly everything that is, but really it's more of a curated reading experience.

You have to filter.

Exactly. Exactly. And so when you're applying, does it also matter? Like certain types of companies you should include a cover letter and certain you shouldn't. Or certain ones you should apply to the online portal and other ones you should contact the recruiter directly. Like, is there any kind of, I guess, general rules about that stuff?

Yeah, I mean that one's really case by case. It's so difficult. I would say smaller organizations, startups. Angellist is a great resource for finding those jobs and applying it will probably go to their ATS. I always suggest networking with actual hiring managers. LinkedIn is a really great tool for that to start relationships, ask about the culture, ask about how they like working there. Do they have a background that's similar to yours? How did they make the transition? Start a conversation first.

In order to do that and then like I said, you know, kind of pinpoint the certain skills that you think those organizations will be looking for. Right. You always want to think about how you're coming off to the other person.

Absolutely. And I think, I think across the board that is the number one way to get hired. Right. So I work in the startup world and a hiring manager will get a resume and, and it will have someone who has worked at only large companies in their career and hiring manager generally is like, you know, I don't think they would fit in here. I don't think they'll understand the startup culture. And I know the same thing happens reverse. Right. For large companies looking at people who have just startup career path. And so how do we bridge the gap? You Know, if I'm someone who works at startups and I want to work at a large company, how do I then convey my value so. So that they see that I can also work in that different environment?

Definitely. And this is something that I run into almost daily because we have companies coming to us from early stage, even pre seed looking for heads of sales and such like that all the way up to Fortune 100 banks. So I think the best way to make sure that you are being considered for the role is to address those concerns head on. So if you are applying to a startup and you don't have any startup experience, you want to address the concern that they're worried that if you've only worked in a corporate atmosphere, you don't necessarily understand what it takes to be scrappy or not have resources or quickly make decisions. There's not a lot of kind of policies and procedures put into place. So you want to make sure that the experience that you're highlighting in your background shows that you can quickly pivot that you that maybe you managed X amount of sales by yourself. Right. Like maybe you don't have direct reports that have been helping you or whatever it might be that just show that you don't need hand holding, you can just hit the ground running. Startups need people who can hit the ground running. Now, vice versa, if we flip it right. So you are applying to a large enterprise corporation, but you've only worked in startups. Their worry is that you're not going to be okay with sometimes how long it takes for decisions to get made or how slowly. Sometimes you can implement new initiatives working on large global teams where communication can take a little bit of time. So you want to make sure that you can show your experience following all of those guidelines that you are accustomed to larger teams. So maybe you worked with an offshore team or something like that even when you were at the startup. Maybe. Maybe everything that's outsourced can kind of be explained in your resume as if it was internal. Because when you go to a large company, that stuff is internal. Yeah.

And so when you say address it head on, does that also mean like have an objective statement that says, you know, I'm making a transition and here's why? Or does that mean in the interview when they say tell me about yourself, you include how you are an unusual candidate or how do you like address it? Truly, is it just in the bullets or.

Sure. So it depends how you're applying. If you're just applying with your resume, then it should be in your Resume. I'm not a huge fan of COVID letters because I worry that they don't get read. So if you do have information that is pertinent to your application in your cover letter, find a way to put it in your resume as well. Just in case no one gets your cover letter. So those really should be in your bullet points of your resume if you're applying that way. If you're having an informational meeting, coffee meeting, something like that, you just want to address the concern. Like I know I've only had a background in startups, but I'm really interested in making the move to a large corporation. I know I'd be great at it because XYZ be very forthcoming with that information. In case no one asks you that question, they still might reject you for the lack of information they're getting, if that makes sense.

Yes. And that's actually even a sales tactic that I've heard is that if you are as a salesperson, if you're the first person to say the objection that you think that they're thinking, then that shows a level of empathy and also self awareness. Such as if they reject you for a certain reason, the worst thing that can happen is that you haven't had the chance to defend yourself against that reason. And so you are bringing it forward and being able to say exactly why you're a great fit and it's necessary.

In every career transition. Right. So if you're going from marketing to sales, you're going to obviously need to address it. Going from startups to corporations and vice versa really should be looked at as a career transition because the opposite types of sized companies are weary of someone who's only had experience on one side. So you need to address it. Don't just leave it up to chance.

Got it, Got it. Okay, very cool. So this has been super helpful, Rebecca and I want to make sure that everyone who loved this video knows where the heck to find you.

Yeah, I'm most easily found on LinkedIn.

Okay, perfect. So we will link your LinkedIn profile in the description. Thank you so much for being on today.

Thank you for having me. I hope this helps people really decide. It's a case by case basis and you're allowed to change multiple times in your career. It doesn't have to be the biggest decision. I think people sometimes get caught up, so hopefully this helps people. Amazing.

Well, thanks so much and Wi Fi high five.