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Ask a Recruiter: Hiring Your First Management Layer Mina Benothman

If you’re a company about to embark on the transition from Series Seed to Series A, building out your first management layer correctly is crucial. To help founders make that transition as smooth as possible, I spoke with two recruiting experts in our community, Marissa Iteld and Dena McHenry. Read on to learn more about how to think through your hiring process, to save your org time, energy, and possibly even some money.

About Our Experts

Embedded in the startup ecosystem for nearly two decades, Marissa has helped numerous technology companies build and scale their teams. Marissa is Partner at Guild Talent, a boutique executive search firm that focuses on supporting venture-funded technology companies, where she focuses on critical leadership hiring, working directly with executive teams and founders at startups nationwide.

Dena McHenry was a contract recruiter for 20+ years building out engineering teams at companies such as Snowflake, Bleacher Report, Quizlet and many others. She now runs Dena McHenry Search, a contingency firm specializing in engineering, product and design searches.

Key Roles to Prioritize

There’s no right or wrong answer to this question; it really depends on your company. For example, cos that sell to consumers or have a primarily bottom-up GTM strategy should hire engineering and product leaders who understand excellent user experiences and features that drive adoption. Cos that sell to the enterprise or have a primarily top-down GTM strategy should focus on engineering and sales leaders with experience building and working with buyer personas.

Though there’s no one-size-fits-all answer, when deciding what your org’s first key roles should be, the most important consideration is the experience (or lack of experience) that the founding team brings to the table.

If you’re a founder with a technical or marketing background, you can handle the technical or marketing work yourself (for the most part), so address the gaps that need filling first. As Dena points out, as your company scales, IC engineers are going to look for who your CTO is and what the engineering culture is like. A non-technical founder trying to ramp up engineering is going to reach a breaking point so finding a technical leader first, makes for a better long-term hiring strategy.

Building an Employer Brand

The current market is competitive, for both talent and employers. But as a stealth or pre-GA company, how do you make sure you attract exceptional candidates? The reality is that proactively building a strong brand presence doesn’t happen until around after Seed, when there are enough people on the team to want to make that change.

But that’s not to say there aren’t steps you can take to make your company stand out to candidates. Your first 4-6 employees could build their personal presence online and participate in existing communities to signal what the culture and pulse of the company is like. The founding team should produce thought-leadership through blog posts. You don’t need a fully fleshed out messaging framework but have a 3-5 sentence elevator pitch ready for your internal team and external stakeholders who’d be willing to spread the word for you.

Marissa and Dena both highlight that they key here is selling an opportunity, a future.

It’s not about where your company is at right now, it’s about where it’s going. There are plenty of people out there who prefer and enjoy working with early-stage startups, so just focus on pitching to them.

Job Descriptions

Before you even write the job description, you have to know what you’re looking for; if you don’t know what you’re looking for, you shouldn’t be hiring. Spend some time looking at existing roles at companies similar to yours. It doesn’t need to be complicated.

Dena finds that the less formal the job description is, the more traction it gets. She recommends writing it as if you just pulled up a chair for a chat at their desk. Imagine they already work for you and just write down what you’d want them to do and how you’d want them to perform. Marissa adds that candidates are more likely to notice your JD when you personalize it to your company’s “voice.”

Sourcing Candidates

As a Seed stage company, you probably don’t have the purchasing power to be spearfishing experienced veterans at well-known companies. The best and cheapest way to find hidden talent is to ask your network and have people you trust advertise the role for you.

Even before shelter-in-place, but more so now that most companies have embraced remote work, Dena urges employers to stay open minded, whether that means being agnostic on the programming language or the location of the talent pool. Companies that invest in those hidden pockets, reap the benefits.

Shortening the Time to Hire

Paradoxically, the more time you spend thinking through and preparing for the above, the quicker you’ll be able to make the hire. But Marissa emphasizes that hiring is going to take time. Period. Sometimes you don’t realize exactly what it is you need until you’ve already spent time interviewing people and that’s alright. Making it a priority and understanding the ROI of doing it correctly, means not only will your time not be wasted, it’ll also help streamline the process.

Dena warns that trying to find a candidate that checks all the boxes is only going to slow the whole process down. You can compete all you want with the Googles and the Apples out there for all-star candidates but it’s only going to hurt your business. You’re not going to find the perfect someone so it’s ok to take a calculated risk. Also avoid falling into the analysis paralysis trap. Don’t pass on the best candidate just because they happened to be the first person you interviewed.

In-house Recruiters vs. Agencies

There isn’t an exact timing (that isn’t to say there isn’t bad timing) to transitioning away from founder-led hiring but how much time you have and how much hiring you need to do should drive that decision. Marissa finds that founders don’t normally have the bandwidth to work on more than 1-2 roles, so when 2-3 roles are open at the same time would be good time to get additional support. Dena suggests when your company scales to more than 15 (though your CTOs and CMOs will continue to build out their respective orgs, at some point they’ll have to delegate some steps in the process,) is when you should definitely bring in someone dedicated to hiring.

Keep in mind that filling entry level roles yourself isn’t difficult but having a recruiter take care of it can save you from having not-so-great fits that require time getting up to speed.

Whether an in-house/contracted recruiter or contingency recruitment agency fits the bill boils down to the number of open reqs that need filling and the types/levels of roles you’re looking for. Agencies are great for 1 to a handful of specific roles at a management level. And say you have a technical background, agencies would also be great for filling the gaps in your network that aren’t very strong.

If you have over 7-8 reqs, particularly for IC roles, you should consider having an in-house or retained recruiter who can focus solely on full cycle recruiting and building a recruiting brand specific to your company. If you decide to go with an agency, make sure the assigned recruiter meets and gets to know your company really well since they’ll be tasked with functioning as an in-house recruiter.

Onboarding for Success, Especially while Remote

Unfortunately, there’s no silver bullet to the million dollar question that we all suddenly find ourselves facing (literally, the companies that can afford to, are paying top $ to HR people to figure it out.) But rest assured, from Dena’s experience, startups actually have it easier than larger companies.

Regardless of whether remote work is a temporary or permanent state, Marissa’s advice is that new employees of all levels and seniority should be made comfortable, as soon as possible. The first couple of days should be only meetings with others in the company. Make sure they sit with a manager, to get the lay of the land, and at least 1 person from each function, to understand how they’ll be working together and who to go to when they need help.

Have additional questions? Need a recruiter? Reach out to Marissa and Dena on LinkedIn, and make sure to check out our other hiring-related content in the Heavybit Library.