Strategy for Startups: When and How to Make Your First IT Hire

Hello! I build IT teams and design IT Systems for startups and nonprofits. I consistently encounter the same problems, so I set out to create a series of guides to help others navigate the IT Ecosystem. You can learn more about my philosphies via my website dave-bour.com or via my weekly newsletter.

A day will come when you say “I can’t do this anymore” and you’ll be referring to setting up a constant string of new computers, making menial decisions between mice and monitors — this one costs $300 more but the screen refresh rate is higher and there’s a blue tint, is it worth it? You’ll transfer the responsibilities to an administrator or someone in HR and an engineer will help with the networking until they, too, say “I can’t do this anymore”.

The truth is that IT work will be part of the scrappy background noise for years as you focus your energy on your product or service. Recognizing when the cost no longer outweighs the benefit will be crucial to avoiding excessive technical debt down the road.

When to Hire an IT Administrator

Most of the startups I’ve worked with seem to wait until there’s roughly 50 staff before hiring a full time IT person; although those with early backing or in a highly regulated industry hire them in the first 15. Here are some of the factors to consider when deciding what is right for your business.

You Anticipate High Headcount

If you expect to grow rapidly or consistently after 4–6 months, post the role now. This gives you time to find the right candidate, evaluate them in the role, and allow them to setup some systems prior to scaling them. If you wait and hire the wrong person out of desperation or don’t hire at all, your systems will introduce inefficiences throughout the chain. Let’s look at how the hidden costs add up.

For this hypothetical, you wait to hire an IT administrator until after you have high headcount or a high number of new staff starting each week.

7 Developers, 2 Marketers, 1 HR, 2 Finance, 10 Sales, 1 Executive start before you hire an IT person.

You don’t spec the right laptop for your developers and have to replace them 6 months later. Subtract the difference as you’ll reuse them. -$7,000.

You spend 30 minutes ordering equipment and 2 hours setting it up. -$400

Each person needs an email and Slack account, and you’re not getting discounted licensing. -$200 for time and $2*23 licenses * 12 months = $-552

No one is in the right groups or channels and the developers start signing up for Dropbox, but you already have Google Drive. In 1 year from now, your IT team will spend 3 weeks planning a migration of data from Dropbox to Drive to rectify the mistake and consolidate the services. 5h/d*15d/w*150/h=-$11,250 + all Dropbox users time restructuring data and learning a new system

A developer signs up for the enterprise version with annual commitment. You stop using the service after 3 months. 9months*250/mo=-$2,250

These are common scenarios I see when I join a startup — close to $20k in preventable costs and 1/2 the time of an employee.

Your Environment is Technologically Complex

Since our gauges of complexity will differ, I’m listing some guideposts below. Each item itself may not be complex but carries implications of greater complexity within an environment.

• You have dedicated wireless access points in your office(s).
• You manage your own internet access at 2+ sites.
• You host infrastructure on-premise, at a colo, or in AWS/GCP/Azure.
• You’ve been asked to fill out a vendor assessment from a client.
• You’d like a PCI, SOX, HITRUST, or other certification.
• You’re signing multi-year agreements with vendors for voice services.

Your Industry is Regulated

Especially in healthcare. The misunderstandings of HIPAA and technology are massive. If you deal in PII, you need an IT person early as a cost of doing business measure. The technical measures that must be in place to ensure protected storage and transfer of PII become compoundingly difficult to implement as you grow. Your staff, lacking security and compliance training, will handle PII without the proper measures. You will lose it, you will be fined, and that reputation will follow you.

Great! You’ve decided its time to make your first IT hire. Onto the next step — how to do it!

When to Hire: Summary

• You’re in a highly regulated industry and have less than 20 staff.
• You’re approaching 50 staff members.
• You anticipate a high growth period or a period of consistent growth.
• Your environment is technologically complex.

How to Hire Your First IT Person

Once you’ve determined that you may need an IT person, let’s look at how to find them.

Deciding between Third Party, Freelancer, or Full Time

First, rule out alternatives to full-time by deciding if third party IT or a freelancer makes more sense for your business.

The most obvious benefit to a non-full time IT hire is that it will buy you time to confirm your growth suspicions without the commitment to a full time employee — but this comes with a premium.

The cost will vary by market and depend on the role requirements and whether they will be working remote or in-person. Let’s look at an example in New York City.

An IT Administrator with 2–3 years experience for in-person roles will be ~95k plus benefits and overhead (desk space, pizza friday headcount, equipment, etc).

An MSP at $160/h * 20h/w * 52weeks = $166.4k

An independent freelancer at $110/h * 20/h * 52weeks = $114.4k

The non-W2 options are roughly on-par or greater in cost and provide half the time of an employee. They’ll setup accounts, perform break/fix, and configure computers but you’ll lose the strategic investment in your IT infrastructure as these roles simply maintain the status quo.

Deciding on a Title, Compensation, and Writing the Job Description

Most startups can simply call this an IT Administrator. It checks all the important boxes and attracts the right skillset. If you’re attracting too many junior applicants, though, you can change it to IT Manager or Manager of IT Operations but this is generally considered an inflated title as their role lacks a managerial component.

Compensation will vary by market. In NYC, I advise $95k and set the compensation band at $85k — $105k. I’ll stretch $5k for a star. Resources to check your market rate include Payscale and Glassdoor, but your HR and Recruitment team may have insight, too.

It is no exaggeration that the time you put into the job description will pay you back many-fold. In future role openings, you’ll use 60% of it as a template, but more importantly, the thoughtfullness acts as a signalling device to potential candidates. Experienced professionals can tell if a JD was written by an IT person, an HR person, or an executive and it signals the technological competence of the organization.

Below is a sample JD that is free to use and modify as you see fit. Google Doc link here.

Job Description: IT Administrator

At Dave Bour Consulting, we place the customer first and build solutions around their needs. In their first few years of existence, our technology plans help startups navigate the challenges that can make or break their business. We work with exciting new startups across all industries through genuine partnerships that transcend the transactional nature of business. Our past success is largely attributable to this key differentiator but our future success depends on finding authentic individuals committed to our mission.

DBC has an immediate opening for an enthusiastic IT Administrator seeking to take the next step in their career. In this role, we’ll challenge you to use your experience in IT to build a technology ecosystem that helps us serve our customers, rapidly scale, and most importantly, is HIPAA compliant. You’ll be the first to assume this role and have an opportunity to institute the solutions you believe in.

Our team is small and each addition has a great impact on the company culture. For this reason, we believe a candidate possessing an entrepreneurial spirit, a can-do attitude, and who would score high on an emotional intelligence test will feel right at home. If you’re ready to roll up your sleeves and commit to Dave Bour Consulting, then we’ll commit to you!

Once you hit the ground running in the first 90 days, we expect a candidate to:

Streamline our onboarding process by standardizing hardware and software procurement and setup,

Create an inventory of all equipment,

Fix our conference room WiFi problems 🙈,

Manage our gSuite account and secure email with SPF, DKIM, and DMARC.

In this role, you will:

Take the helm as the point of contact for all IT issues and see them through to resolution.

Become the company point of contact for account provisioning and deprovisioning,

Manage a fleet of company equipment including Macs, PCs, and Chromebooks,

Create company policy handbook in partnership with our HR Team,

Create a Staff Security Training Deck and train staff in-person and remote,

Institute a BYOD policy and enforcement mechanism to secure our company data and resources,

Develop your Vendor Management skill set by placing orders and coordinating payments with our Finance Team,

Consult with our engineering team regarding the existing office network infrastructure and transition ownership to IT,

Maintain a client VPN for remote connectivity to on-site resources.

To succeed in this role, we believe a candidate possesses:

A four-year college degree with a focus in Computer Science,

Several years of direct experience in a Senior IT Support or Administration role,

Hands-on exposure with basic network topology design, configuration, and troubleshooting,

Experience in gSuite’s administration console with command line experience a nice-to-have,

Ability to research and make recommendations given a set of technical and non-technical requirements,

Conceptual understanding of A/V as it pertains to conference room AV using Google Meet,

A strong interpersonal foundation, collaborative spirit, ability to work autonomously, and a customer-first mindset.

It is inadvisable to attempt making this a catch-all role. I often see job descriptions including Salesforce/CRM management, database management, website management, and Python/Coding experience. Exposure to these skillsets is often outside the scope for your average IT Administrator.

Posting the Role

You may already have a Recruitment platform of choice — BambooHR, Google Hire, Indeed. While tech-specific boards such as Dice.com exist, they do not cater to this role nor Organizational IT in general. Dice, in particular, is for developers and engineers.

You’ll have the most success using LinkedIn, Indeed, Glassdoor. You may wish to look at angel.co which caters to the startup community.

How to Evaluate Candidates

Follow the same evaluation process as for other candidates is fine, but you may need to recruit a third party to help evaluate the technical competencies. In some cases, an engineer with experience with servers or networks is a great go-to, but managed service providers can perform interviews on an paid-hourly basis. It is not uncommon to reach out to a former colleague or friend who manages IT — these people are always willing to help.

If you’re unsure where to start, I have found success using the workflow outlined below.

15–30 min Round 1 —

• Quick personality assessment
• Ability to communicate, summarize, and express basic concepts
• Looking for technology keywords to assess competency levels
• Clarify the role for them. I prefer to be very transparent, including base compensation.

90 min Round 2 + 30m with 2 IT/Tech employees—

• In depth technical chat assessing breadth and depth of skillset in (1) Support/Break/Fix/Troubleshooting, (2) Networking, (3) Servers/SaaS, (4) Security
• Confirm alignment between your technology trajectory and their approach

30 min Round 3 with 3 colleagues —

• Assess cultural fit
• Interpersonal communication style
• Ability to operate cross-functionally

Sample Interview Questions

1. The Sales team is looking to standardize on a laptop. To make a recommendation, you identify several categories to perform an analysis. Rank the following categories in terms of importance when recommending a solution.

• Weight, Battery Life, Cost, Features/Functionality (ie: touchscreen or 4G slot or headphone jack), Specifications (RAM, HDD, Processor), Usability (ie: Trackpad known to be wonky, webcam is at the base of the screen)

2. Let’s say someone spills water on our firewall and we need to buy a new one. Regardless of what it is, walk me through the first 3–5 things you do when it arrives — starting with taking it out of the box (give them a freebie to start).

3. When you arrive on a Monday morning, you’re faced with the situation below. Please tell me the order in which you would address the problems.

• You received an email that a new hire was made over the weekend and we need a computer setup for them today.
• The CEO is unable to access email on their phone.
• Two people come up to you stating they cannot print and there is an email from someone who stayed late on Friday saying they could not print.
• One person comes up to you saying they forgot their computer at home and need to use a spare for the day.

4. What is multifactor authentication and would you recommend we use it on email? Why or why not? (They better recommend it, but don’t lead them).

5. What are 3 security recommendations you would make to any company of 100 or more employees.

6. What does SPF, DKIM, and DMARC apply to and what does each one do?

7. If you determined what we need Active Directory, would you host the domain contollers in the cloud or on-premise? What are some pros and cons to each pathway?

8. What is the built-in disk encryption called for Macs and PCs? (Filevault, Bitlocker respectively)

9. If you came into an environment without hardware inventory, what systems would you put in place to manage and inventory all the equipment?

10. Tell me about a time you disagreed on a decision with management and how did you express your perspective?

Reach out!

These three recommendations are just the tip of the iceberg when it comes to organizational technology postures. Please reach out if you’d like a consultation customized for your business.