An Engineer’s Perspective on Onboarding

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Engineer onboarding: two perspectives

Before I joined the security industry, I was an end user. Coming in with that first-hand experience equips me to talk about secure remote access from multiple perspectives: as a vendor and as a practitioner. This lets me see the technologies available and also understand the drivers and issues engineering orgs face adopting them, particularly with onboarding engineers.

I’ve been a support engineer for over 20 years, across Operations and System & Database Administration. I’ve always found something very rewarding about helping people solve problems, which rings true for most people who decide to go into Technical Support.

In this post, I’ll share my experience as an end user of the access plane tech, going into detail on the significant impact it had on my onboarding experience, along with why I decided to join the team as an employee.

Onboarding: A security pain point

In my experience, the operational overhead for security is painful — often requiring a dedicated Security team, allocating the required 3rd party key fobs for OTP, registering and activating, password management, and the list goes on. It only gets worse as your computing environments grow, and the teams get larger and more fragmented.

The security needs of new employees in particular can pose a challenge. At one company I worked for, it took a month just to get my laptop, and a full 3 months to get all the logins. Ironically I went back after several years away to find my critical accounts still in place, as were several of my ex-colleagues who had left before me.

The onboarding process has certainly improved generally with SSO in recent years, but this hasn’t necessarily trickled down to the engineer layer. The on-call routine has largely stayed the same: is everything working? Have I still got direct access to the critical servers, or have there been any firewall changes overnight that have cut me off? Are my key fobs working? Have I got access to those shared secret password vaults on the network? Etc, etc. All this equates to additional stress on engineers that can be avoided.

Introducing the Access Plane

Over time, I accepted the pains of provisioning and de-provisioning access for engineers as inevitable, until we discovered the concept of an access plane at my previous employer.

The idea behind an access plane is access consolidation. Gartner uses the term “secure access service mesh” to describe this architectural approach:

Effectively, the pain is reduced by shrinking the configuration (and attack) surface area from thousands of endpoints to just one.

Engineer onboarding: personal experience

At a previous employer, I joined a Cloud Operations team, supporting a managed service for multiple clients across the 3 main Cloud vendors, using the open source access plane called Teleport. It allowed us to SSH into everything after going through Okta SSO.

Teleport features the single sign-on access for users and administrators via an external proxy using short-lived SSL certificates. This access enables SSH, K8S, DB and Application endpoints. Handily, session activity is also recorded, so it helped our team meet our external customers’ security compliance requirements.

The access plane concept was a revelation for me at the time. By the close-of-play day 1, I had my access. After a month, when I lost my phone and frantically pinged our head of security, he set up a new URL minutes later to register another authenticator on a spare handset.

The Teleport access worked seamlessly the entire time I was on the team — every SSH connection, Dev and Prod, across Azure, AWS and GCP. Group sessions with colleagues in Sydney, Boston and myself in London. The cloud vendor VMs, not so reliable.

As an end user, this experience was painless. Now of course I might be a bit biased, but the advantages of having a session recording available to your colleagues, when you’ve pulled a remote 15-hour stint on a P1 and need to sleep, speak for themselves. And our founders OSS’d the code too, so you can run Teleport on your home lab!

The software is evolving with new features and compatibility growing over time, without being over-engineered. With the upcoming release of Teleport 8.0, we’ll have full Windows support, so you can seamlessly access your Linux devices from the cmd prompt, and hit remote Windows servers.

My experience as a user of Teleport had a significant impact on me. So, when the opportunity came up to work here, it really was a no-brainer.

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An external perspective on onboarding

My experience as a Teleport user was not unique. Recently, my colleague Ben Arent, a Developer Relations Engineer, sat down with Mario Loria, Senior SRE at Carta, to chat about how his team adopted the Access Plane concept.

One of the major themes of that conversation centered on the impact of the access plane on simplifying & securing the onboarding process.

“With Teleport, we can onboard people quickly and have assurance that they’re going to be able to access only the systems we intend them to,” says Loria, “Fast and easy onboarding is something that we need to get right. We could have built our own secure access team to do this. With Teleport, I don’t think we need to do that.”

Creating a secure onboarding process is essential for any team, and the value of a fast, simple onboarding experience as a user is significant.

Become a security engineer

The access plane technology can solve a lot of pain points for secure connectivity, authentication, authorization, audit, and visibility for both support staff and end users. This architecture works seamlessly across clouds, on-prem resources, edge, and colocated infrastructure in the post-COVID world.

That’s why I joined the Teleport team, and you can too! Check out our open roles on our careers page.

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