In my career, I’ve worked for small and large companies where I was the first IT hire (twice in fact!) and part of a large team. Also, I’ve been lucky enough to work alongside a number of Greylock’s portfolio companies, of all stages, to help them figure out the right strategy to bring in IT. Below are a few of my key takeaways and lessons learned.

“Having IT people you can trust and rely on allows the rest of the team to focus on the job at hand — be it development, or sales or anything. IT is key to improving execution and increasing people’s capacity. Think of it as a multiplier effect. Every investment in IT services and technologies should be delivering greater output across product, sales, marketing, and the whole company.” — Joseph Ansanelli, CEO and Co-founder of Gladly

“When Should I Make My First IT Hire?”

When a founder is looking to build out an IT function at the company, there are many factors to consider including company size, number of offices, hiring momentum, and product roadmap. Knowing when the right time to hand off IT responsibilities is the biggest challenge, but once companies are ready to bring on IT help, they should be ready for the downstream dividends it will provide — more time to focus on priorities, preparing the team to scale, removing roadblocks for signing up customers or providing an amazing on-boarding experience for new employees. 
Depending on the stage of company, IT priorities will be different. The best approach to IT is long term — IT is not a quick fix or a band-aid, but should be able to support the company as it scales. A company’s needs will change and IT should always be one step ahead to ensure that the lights are running, devices are security and security protocols are in place.

Early Days (AKA Founders + A Few Engineers)

The company has just secured a round of funding in the bank, the team is a small group of engineers, and the founder is cooking breakfast once a week for the entire company. (This was called “Waffle Wednesdays” when I was at Lookout!). The team is focused on finding the minimum viable product, recruiting candidates to help build the product, and landing their first customers. 
IT is a big afterthought, but those pesky IT issues still crop up, and guess who fixes them? That’s right, everyone. At this stage, everyone in the company is deputized as an IT person. There will be moments where engineers will spend a good chunk of their time rebooting the wireless router (again) because the Wifi is too slow.
In this stage, founders should start thinking about finding the right IT partner that can help grow an IT function that can provide specific services, such as basic network management and help desk. An IT partner is someone who can help prioritize tasks and start thinking about services needed as the company begins to gain traction (like moving out of the founder’s basement and into a new office!), not just fix IT bugs. 
As a company grows, the last thing on a founder’s mind is IT and that’s the way it should be. This is why finding the right IT partner who can strategically think ahead about IT needs is imperative, so the team can focus on other priorities.

“Startups want to build product and grow quickly. While at the earliest stages of a company IT responsibilities are often democratized across the team. Communications, security concerns, remote workers, and other aspects of IT can slow down productivity rather than enable it. That single IT hire can allow for the founders and engineers to go back to being product obsessed and shipping code, as they should be.” — Ben Johnson, Co-founder of Obsidian Security

Mo’ Money, Mo’ (IT) Problems

Another round of funding! A new team to onboard! New office space! Things have gone well and the company is ready for IT help. 
At this stage, it’s important to invest in the right IT partner who can build and set strong foundational IT based on the company’s current and future needs, whether the company decides to bring on someone in-house or from third party. A company needs infrastructure and protocols that are fast, secure and scalable. Internet connections, firewalls, WiFi, and video conferencing need to be done right. Believe it or not, IT impacts productivity, boosts employee moral, and even helps close new candidates (who doesn’t want the option to choose Mac or PC?), which is why IT needs to be done correctly from the start. Here are a few tips and tricks I’ve learned throughout my career that will set you up for success:

  • Fast internet. Get the fastest internet access, especially fiber circuit if possible. This has the biggest impact on your overall network performance.
  • Backup internet circuit. Believe me, this pays for itself if and when your primary internet goes down. Nothing worse than telling everyone to go find their own WiFi to work.
  • Cloud based firewall. Make sure it supports internet fail over. There are many options that are not “enterprise”, which require an engineer to command line setup the configuration. Bonus points: allow for secure IPSec tunnels to your cloud compute environment (your engineering team will love you for it!).
  • Video conferencing and phones. Conference room must have wired connections. This is a no brainer. WiFi will not cut it. Get a good switch and ensure each of your conference rooms has a wired line.
  • 24 port PoE. Get a managed PoE (power over ethernet) switch to connect the stuff mentioned above. Why managed? As you grow you’ll likely introduce fancy stuff like VLANs. It’s the right investment.
“Technology is one of the main ways to increase employee productivity. With advancements in data management and automation, there are a plethora of workplace tools and software services to manage everything from security and networking to communications and email. IT is key to strategically choosing and deploying services that will support a company’s current and future needs. By bringing in the right IT team and workplace tools, employees can be more productive and focus on priorities, instead of worrying about the WiFi.” — Jay Srinivisan, Co-founder of Spoke

Holy Moly! We’re A Real Company

The company is beginning to hold weekly “All Hands” events, engineering teams need quick access to their cloud compute, and the network is starting to get overwhelmed. The company’s customer roster keeps growing and, oh yeah, that dang router still needs to be reset!
This is where things will either continue to work, or start breaking. If the company has thought through their IT strategy, built the right foundational IT, and brought on the right partner, business will go on as usual. 
When the company reaches a mature stage, here are a few things IT leaders should be focused on:

  • Cyber security. Every startup’s cyber security strategy should start with its employees. As a scaling startup, at times, IT policies aren’t fully established at startups and executives trust employees to do what’s right, have the latest update on their devices, and not click on the wrong email or attachment. It’s important to educate and train employees right in the beginning during on boarding and ensure they are continuously informed of the latest security attacks and updates. I’ve implemented monthly newsletters and company wide emails, both of which have been effective.
  • IT Policy. For startups, customers are the number one priority and IT should never not be the roadblock to customer sales. This is why companies need to take care of IT policies beforehand. For example, the larger the customer, the more security protocols need to be in place. At times, customers will ask companies to fill out a security survey to ensure their company’s PII data is safe using your service before they sign anything. This is big and messy, and should be dealt with prior to on boarding a customer which means having an IT policy in place.
  • Mobile Device Management. IT should be actively managing your fleet of laptops to ensure they are patched, encrypted, and have an Nextgen endpoint agent. This also includes being able to automate the build process for new laptops.
  • Cloud-based Identity Management service. This addresses security concerns by reducing management of all the username/passwords the team stores in a Google doc and provides 2FA (two factor auth). It also benefits the growing team — IT is now able to provision specific apps with a click of a button, giving them more time to deliver a great on-boarding experience (i.e. Okta).

Lastly, IT should always be optimizing all services that drives company culture. This could mean a well oiled weekly “All Hands”, ensuring your communication tools — group chat, email, wiki — are managed and utilized properly, and setting up AV for fun internal events. Building company culture takes a village, which includes the IT team. 
You can reach out if you have any questions! I’m at mbernal [at] greylock dot com, and if you’re an IT professional, come join ITKit, a community where we talk about the latest tools and best gadgets for the workplace.