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Why it’s so hard to get that early-stage startup offer (and how to be the one who gets one)Featured

I wanted that [email protected] email address.

Sounds silly, right? But to me, that simple email spoke volumes about who I was to a startup and what my contribution could be to its growth.

My email dreams (and my career goals!) came true in 2020 when I joined Series A-funded Spot as their first Head of Talent & People as Employee #9. I’ve since been that first hire in a few other early-stage companies, too. I’ve also hired that first Marketer, first Engineer, first Product Manager, and first Sales Rep at many others.

If you’re craving that high-impact, early-stage contribution like I did, there’s absolutely a path for you to get it. It takes focus, patience, and a strategic approach to think like a Founder so you can figure out how to meet their needs.

There are unique challenges the cofounders face when hiring the first in an org. And those unique challenges shape the way they think about and conduct hiring for you, the candidate.

So, why exactly is it so hard to make that first hire in a startup?

Founders make their earliest hires to fill gaps. They hire when they don’t have experience in an area and either:

1. They don’t have the bandwidth to keep fumbling with it themselves. Or

2. It’s a strategic piece of their business and they know they need someone who can set them up for success.

The first hire steps in, essentially, to take over an entire function, like marketing or sales. Depending on the level of the person, this hire will have significant autonomy over a massive, critical part of the business.

And because the people who are the decision-makers don’t have experience in these areas, they only have their own perceptions and the advice of their advisors to guide them in figuring out who they actually need in the role.

That usually means they want to see multiple candidates (even when the perfect fit is right in front of them.) As they meet more people, their expectations change. The role requirements and responsibilities often change along the way too. And that’s never easy for candidates to contend with.

Founders are all-risk when it comes to their big idea, but far more risk-averse when it comes to building their teams. Particularly when it comes to longer processes, doubt can start to creep in around a particular area of a candidate’s style or experience, and that doubt grows over time.

This is evidenced by the sheer number of candidates I see and job search clients I work with who get to final stages in the interview process, only to get passed on for feedback that was surfaced early in the process. This sometimes happens at bigger companies. It happens about three times as often at startups. The founding teams uncover flags early on that they think they can live with, but the doubts start to grow as they reach a point where they have to actually make a decision.

VCs don’t make hiring that early team easier, either.

Have you heard of 10x hires?

It’s a concept that first popped up in 1968 in a paper published by the ACM. The original idea was that there were Software Engineers on a team who could work 10x faster and carry the load of 10 “average” Engineers, thus skyrocketing the team’s productivity and leading the business to ultimate success.

This definition has morphed over the years, from a measurement of lines of code written, to story points, to a broader impact on the product and problem-solving capabilities. And 10x isn’t just for Engineers anymore, it’s for everyone on the team. VCs (at least old school ones) love this concept, and they encourage their Founders to hold fast until they find their 10x’ers.

What does that mean in practice? Ridiculous job descriptions that include the jobs of 2 or 3 or 5 people and some serious bias. Because how exactly do you measure 10x productivity in candidates in an interview process? You can’t. And so Founders lean on their intuition to spot these “purple squirrels” (as we used to call them in my agency recruiting days.)

The “Everyone is a founder” also makes hiring a first “Head of” all the more challenging. It often means they’re looking as much for personality signals as they are for skills and experience. “Work ethic”, “drive”, “self-motivated”, and “passion” (or lack thereof) have frequented many of the feedback scorecards I’ve reviewed over the years for these early stage roles.

And perhaps the biggest, most challenging factor for Founders hiring their 1st team member is simply that they’ve never done it before.

One of the things all teams gain as they grow is structure. Structure breeds consistency. Without structure, a lot more bias creeps into the process. Despite endless research that evidence-based hiring (asking the same questions consistently, relying on behavioral interview questions instead of situational, and leveraging blind feedback) produces more successful, less biased hires, Founders struggle to implement those processes (or at least to do so effectively.)

I’m grateful that there’s been a big push in the past 2 years to hire a Recruiter earlier in a company’s growth. As someone who’s been an in-house recruiter in these early stages, my primary responsibility was to build this structure fast and to fight bias. It was not uncommon to hear feedback like “vibes with the team” and frequently witness what I call “the beer problem”.

(Startups have phased out this “Would I want to get a beer with this person?” question from hiring, but the mentality persists.)

With all these challenges, how is anyone supposed to actually land the offer?

But people do. And you can too :)

I certainly don’t mean to be a neigh-sayer when it comes to startups. I truly love them. But it does take a bit of strategy to address the unique needs of the Founders filling their roles. And honestly, it’ll be great practice for stepping into those challenges, because I promise they don’t stop once your offer is signed.

Here are strategies that have worked for my job search clients to navigate these challenging processes and ultimately get the job:

1. Speak to their motivations.

Remember why the Founders are hiring for this role in the first place. How is it crucial to their company’s growth? How does this role complement or supplement their expertise? Pro tip: Speak in interviews as if it’s your product/startup. Use we/our for every step after that initial introductory call.

2. Read the context clues.

The Founders will tell you what’s important to them in their pitches, their questions, and their feedback. Listen carefully, and lean into those areas they care most about. If they’re hiring a 1st Marketer, and all their plans seem centered on content marketing, don’t do your final panel presentation on your ads strategy experience. (Yes, even if ads strategy is what you think will be most effective in the role.)

3. Ask where previous candidates have fallen short.

When given this information, don’t try to sell them on why you’re different. Instead, seed stories that depict that difference throughout the process.

4. Act more like a consultant than a candidate in the interview process.

Build trust by solving their problems along the way. Ask lots of questions. Be generous with your ideas. And tie those ideas back to real-world scenarios you’ve seen, including enough detail to make them feel relevant.

5. Bring them down to earth.

Anyone who’s worked with a Founder will know, that they often have lofty ideas. Use examples to show what’s really possible in a role and what needs more people/time/investment to happen. You can blow smoke in the process, but then you’ll ultimately be the person who has to deliver. Plus, by not promising the moon, you build more trust.

6. Invest in building the connection.

Stay in touch frequently. Always take the opportunities they offer to meet investors and other people around the team. Be patient when they want you to meet “just one more person.” They’re going to hire someone. Don’t make that decision for them!

Startups can be so worthwhile for you if you’re motivated by big challenges, moving fast, and having a direct impact. Invest in shifting your perspective to a co-founder’s view and you’ll find yourself with offers to show for it in no time.

Good luck, and happy job hunting!

amazing tips. thanks for sharing the history as well - never heard of 10x before
Thanks @amygong. I think this Business Insider article on busting the myth is a a pretty good read: https://www.businessinsider.com/1x-engineer-open-source-project-10x-engineer-myth-2020-5
Great article. As an entrepreneur transitioning to work for a company, this confirms my approach from a point of truly listening to and iterating on what they want.
Listening (not hearing. Listening!) will get you very far in your job search.
Thanks for sharing! I recently got told by the CEO in an interview for an early stage startup lead role (have done this twice before) that I didn't have the right skillset, which knocked my confidence a bit. In the interview I felt she was asking me super irrelevant questions, and despite the fact that I tailored my answers and skills to the ones she specified in the JD, told me my experience wasn't right. Months later and I see she's still hiring for that person, and it exactly matches my skills and resume, and I really really liked the company. I can only conclude that it was a bullet dodged, as I can't believe she asked questions so irrelevant to the job spec, not allowing me to speak about anything relevant, so then concluded I wasn't the right fit.
I've worked on a few of those roles in my career. The CEO has a vision in their head of a person who doesn't exist...You did dodge a bullet! I know I wrote out a laundry list of flaws in early stage leaders, but there are some great ones out there :) I hope you find your fit!
A lot pf people say they can’t find the candidates. However, in my experience in startup so many people don’t know how to interview. They’re unfocused and fail to ask the right questions to get the right answers. Don’t take it personally it’s quite common because they are learning how to be leaders.
Really enjoyed this. I just started a new role, and even though it’s not at a startup, I think these are really insightful pieces of advice that I can apply to my situation regardless.
Absolutely. Those 6 tips are just important when you're *in* the role too!
Love this! Thanks so much for sharing, it’s super interesting and helpful
This is such a great list! As a founder, #4 especially stands out. We've found the most success hiring people who have actively made suggestions and asked deep cut questions during the interview. It's super important that you hire proactive people in this early stage since every person matters to the success of the organization
I think that also helps you find people who challenge you! As you grow, that diversity of perspective is so so important!
Great insights... I've been the first marketing hire at multiple startups. In each case, how I got the job was starting as a consultant (to your point #4, not just acting as, but actually being one). You, like the founder, have to have an entrepreneurial mindset, show that you are a thought leader not an order taker. Talk with the founder, identify the biggest pain points, and then put together a proposal that has a ramp plan to being hired full time if you both feel that it is a fit :)