• Dave Bour

How to Interview for an IT Position at a Startup

After 12 years in IT, I have reviewed countless applications across many industries for roles on my team. This post is intended to provide insight from a hiring manager’s perspective to help job seekers understand the other side.

I was lucky to join Medly Pharmacy during a high growth phase prior to COVID-19. My opinions presented here do not reflect those of my employer but if they resonate with you, I encourage you to reach out to me or check out our job board for open roles.

How to Identify a Startup By definition, Startups are immature businesses and can be characterized by the following three traits.

  1. Operate with few resources.

  2. Environment has little or no documentation, policies, or procedures.

  3. Everyone “pitches in” to make the dream work.

Whether these appear as a pro or a con is based on your perspective. For instance, someone who prefers rigidity in their role will not like helping the marketing team package flyers while a social extrovert will love the opportunity to create new friendships and eat the pizza provided in lieu of additional compensation or overtime. These same individuals may struggle with the prospect of having no guidance or be thrilled with the autonomy this environment provides and find innovative ways to solve problems with few resources.

Key terms include:

  • Runway: The amount of money your company has left before it no longer has any money.

  • Equity: Private shares in the company.

  • Social Committee: A volunteer body that governs social activities and distributes funds for game nights and dodgeball leagues.

  • Talent Team: Recruitment Department

  • People Team: HR Department

  • Town Hall/All Hands: Company-wide meeting providing transparency at a high level.

  • IT Administrator = Individual Contributor managing IT.

  • IT Lead = IT Manager, sometimes with one direct report.

  • Head of IT = IT Director

Know the Types of IT Roles in a Startup

  1. The Neo.

You’re the savior to fix all the technology at this startup. What you’re getting into Nobody who works here has experience in IT and there is no plan. The organization has accumulated 50 services that do not work together and frequently break down. Laptops in original wrapping are given to new hires. The WiFi doesn’t work in The Flatiron District conference room. You are to figure out how to fix all of this. Indicators include

  • Hiring manager is not in IT and has no experience in IT. They’ve accepted the burden to date and recognize the need for an IT professional.

  • Duties in the job description are wide ranging and require a ‘generalist’ or ‘jack of all trades’ where she will be required to ‘wear many hats’.

  • 2–5 years experience in IT

  • 2nd round interviews will include an Engineer asking how many IP addresses are in a /24 subnet.

  • Reports into Operations side of business

  • The company is likely in the middle of an Office Relocation or Build-out of a New Space. This is often the point at which the facilities administrator loses their mind and needs to hire you.

Typical Projects

  • Standardize hardware, assume procurement efforts, and create inventory

  • Create an Onboarding Process for New Hires and Training for all

  • Setup 2FA in gSuite, Slack, etc

  • Stablize the environment (videoconference likely drops out, WiFi has dead zones, former employees still have active accounts)

  • Implement a Device Management System (BYOD, EMM, MOM, etc.) JAMF, InTune, Meraki Systems Manager.

  • Implement Single Sign-On (Okta, OneLogin)

  • Take over all the IT for the New Office

2. Neo’s Replacement It turned out that having a single person act as the Network Administrator, Security Administrator, Systems Administrator, Helpdesk Administrator, and IT Director wasn’t the best idea. Now we know and we’re back at it again with the white vans. What you’re getting into You’ll take over all of Neo’s half finished projects. You’ll be asked to verify if her solutions are correct or if it makes sense to start over. You’ll step into managing one or two people or have the authority to hire one person. Indicators include

  • Reports into Engineering side of business, no longer the Operations side of the business.

  • Optimism that one person will save them has been replaced with the harsh realism that they’ll need an IT team. Desperation from the first hire has turned into wariness and you may be asked how you would structure a team.

  • Many interview questions will be prefaced by, “The person who we originally hired for this role was trying to do X, or did X. Do you think we should do X?”

Typical Projects

  • Trying to figure out the password to many services.

  • Trying to figure out why things were setup the way they were.

  • Creating network documentation and maps

  • Replacing Single Sign-On

  • Creating an IT Roadmap

3. The first dedicated support person. Neo or Neo2_Final has done all that she can and proved her solutions to be aligned with business needs. She’s now turned to scaling them and tackling Bigger Projects and has been rewarded with approval to hire a #2. She needs you to handle the ticket queue. What you’re getting into At best, the ticket queue will be a Google Group. You will receive after hours and weekend requests by people who do not stop working. You may be asked to define KPIs and Metrics to which you wish to hold yourself. Indicators include

  • Primary duty will be “handling the day to day”.

  • 1–3 years experience in a Helpdesk role.

  • Reports directly to the IT Administrator or IT Lead or IT Manager.

Typical Projects

  • Fix the printer.

  • Setup laptops for new employees. Likely figure out how to mass deploy through imaging.

  • Further configure the Helpdesk or implement one.

  • Become point of contact for all staff concerning all IT issues.

Reading between the Job Description’s lines Information Technology is a very broad term. I’ve seen IT roles include duties in engineering (must know Python!), DevOps (experience with Terraform preferred!), and even facilities or office operations (experience organizing office relocations a plus!). At the end of the day, this speaks to the breadth of the IT skillset and, unfortunately, broad misunderstandings of this ever-changing industry. For the technically-gifted, navigating these opportunities requires confidence and surety— two important qualities that I look for in an applicant.

But first, let’s clear the air on a common misperception. The job description (JD) you’re reading is oftentimes a long-shot. Whilst creating them, two common pitfalls afflict most hiring managers. First, they’re often hiring retroactively — they’re in over their heads and needed help a long time ago. Second, properly scoping the role will elude them as their needs exceed stringent definition. This plays into the broad misunderstanding I mentioned earlier and exemplied by some of the questions we get in IT: “The hard drive died in my personal computer. It’s 10 years old and I really need data off of it, can I give it to you?” or “Can I get a landline?” or “My WiFi sometimes drops out in my office, how do I boost my WiFi?” Data reclamation, voice routing, and wireless technician are three separate skillsets; but in IT, you’re expected to master them all.

Truth be told, if you find a JD asking for a one-size-fits-most skillset, then you’ve likely ran into a manager who doesn’t know how to properly structure a team or is resource-constrained by the organization, or, the hiring manager isn’t actually in IT because you’ll be the first IT person or the previous one left abruptly. Unless you want to be the first person to storm the beach, you may wish to move on.

What I’m saying here is to refrain from attempting to check all the boxes for skills on the JD and evaluating your worth based on them. More often than not, the person writing them is uninformed regarding what an IT department does or the startup is early stage and needs generalists. This can be an indicator that you will be on the hook for a lot of non-IT requests or an avalanche of IT work that needs to be done.

How to Apply Most applications are submitted through LinkedIn, Indeed, or other third party website. I recommend confirming the role is still open on the company’s website and applying through there.

If given the opportunity, always include a cover letter. Your cover letter may be reused as you apply to other jobs, but create the template yourself — do not copy an online template. This is meant to differentiate you and if it starts off in the same manner as 50 other cover letters, it’ll most likely be ignored and you’ll forfeit a competitive advantage. Your cover letter should include why you’re qualified or interested in this organization. The research you perform will help you confirm whether or not working at this startup would fit your personality and skillset and the information will be handy later on in the interview process. I recommend putting in the work.

I do not recommend following up. They will reach out to you.

Interview Format

First Round

  • 15 minutes with a recruiter to primarily determine ability to communicate. May also validate claims on your resume.

  • Provide availability in the late morning or mid-afternoon when they’ve had lunch.

  • Recruiter likely has very little experience with IT. This isn’t the time to get technical.

  • Use a few buzzwords and be very concise. They have twenty more 15 minute interviews to do today.

  • Be respectful of their time. They can end your application here.

Second Round

  • Is often a second call or video with hiring manager and one or two other team members.

  • Will include elements of a technical interview, if not specifically that. You will be required to speak to the technical elements of the role with clarity.

  • 60–120 minutes

Third Round

  • On-site or video, 120–240 minutes.

  • Often intended to determine cultural fit and achieve clarity regarding outstanding questions from second round interviews.

  • Will meet with potential colleagues across organization and tour the office.

  • Usually yours to lose at this point, or you’re one of a few remaining candidates from which they will choose.

Do/Do Not Do Qualities of a ‘Strong Hire’

  1. A ‘do what it takes’ attitude

You don’t have to know all the answers if I am convinced you’ll put in the time and effort to find them. Most startups and nonprofits will look for individuals who are willing to put in the extra commitment required to get the company’s vision off the ground or effect change in an industry. This is more important in entry-level roles as it will compensate for a lack of industry experience. 2. Enthusiasm to solve problems with a positive attitude Let’s be honest, the startup and non-profit environment requires a positive attitude. It is almost certain that you’ll face inefficient processes, ineffective projects, and have a laundry list of improvement opportunities for years to come. If you sound excited to solve some of the problems I outline, it makes me excited to get you onboard. 3. Exhibiting a Customer-first mentality IT departments setup and support technology to increase staffs’ ability to work. Knowing who your customers are and being able to describe how you serve them is essential. 4. Knowing the technology I am much more lenient on this one for entry-level positions. If I’m looking for a senior engineer or administrator, I would expect to be able to discuss the technology under your purvue at a conversational level.

Red Flags

  1. Do not take the call on the street or in your car. If you must, I recommend acknowledging it up front.

  2. Do not act surprised when they call — instead, signal that you were expecting it.

  3. Do not take the call when other priorities will create a distraction, please schedule the call around them.

  4. Do not ask stock questions that you Googled because every other applicant is also asking them. Instead come up with 2 questions you legimately have about the organization, role, or department. This may have come out of your research for the cover letter.

  5. Do not Google answers to questions while in the interview. It’s all too obvious that a candidate is frantically googling the question.

Star Candidates/Strong Hires often do this. Ask who you will be speaking with for each interview. Research them on LinkedIn andGoogle. Prepare to ask them 2 questions that have nothing to do with the organization or role. Always save these for the last question. Example 1: On LinkedIn, I noticed you earned a degree in Artistic Design. I was wondering if you still pursue artistic endeavors in our role as COO or what keeps you engaged with it outside of work? Example 2: I read your interview in Toggle Magazine and caught your Simpsons quote. What is your favorite Simpsons episode? Example 3: I’ve never lived in another country and admire your leap to move to the US. What was it like moving to the US for school and staying? Example 4: I saw you previously worked at Adobe. I love graphic design, what is your favorite Adobe tool to touch up an image?

Reference Check Nearly all estabished organizations will perform a reference check. While it feels like a vestige of before-times, it actually yields useful information in developing a candidate once you’ve hired them. Like an AirBnB review, former colleagues may allude to potential issues without explicitly stating them. This is what I use to help identify growth opportunities for someone I hire. Always provide at least 1 managerial and 1 colleague reference. Cultivate these references in your professional career, you don’t want to get to this step and appear disorganized.

I hope this is helpful to anyone looking to break into IT at a startup. If you have any questions, concerns, or comments — please drop me a line.

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