Table of Contents

• Introduction

• Pick a Primary Cloud and Nail it

• Working in a Megacorp vs Startup or SMEs

• The Fear of Failure

• Company Research

  • Company Fit

  • Researching

  • We are going to search for ex-employees first

  • Now onto current employees

• Essential Reading

• Backing from the Senior Stakeholders

Welcome to the second post in the AWS at Scale series: 'Making the right career choice'.

Here’s part 1:

Introduction

Welcome to the second post in my AWS at Scale series where I’m writing to share my strategies, skills and tips on how to build your AWS career, what to focus on to stay relevant, how to make an impact, and where to focus your time & energy in a large corporate enterprise.

In my previous post, agenda item 2 highlighted the following point:

✅ Making the right career choices.

What do I mean by this? Let’s start explore…. 🤓 

If your desire is to build experience and career capital with AWS platform concepts at scale, then it’s likely you’ll be covering:

☑️ Principles and standards that apply to any cloud platform
☑️ AWS Organisations
☑️ AWS Control Tower
☑️ Secure baselines for AWS account vending
☑️ Reference & reusable VPC architecture
☑️ Reusable Terraform modules for commodity AWS resource provisioning
☑️ Building a provider / consumer cloud platform model
☑️ FinOps
☑️ Observability
☑️ DevSecOps

+ many others listed in my original post then you’ll want to start by picking a primary cloud, and then absolutely nail it.

Pick a Primary Cloud and Nail it

This should be your initial plan, not to be a Jack/Jill of all clouds but instead focusing all your attention being very, very good at one of them (ideally AWS or Azure).

Use this capability to understand other Clouds (and tech stacks), but always stick with your primary.

Here's why it works:

✅ Builds rare, credible and highly valuable skills over time.
✅ Helps develop a craftsperson mindset.
✅ Builds incredible career capital.
✅ When you're very, very good at something, you feel good.
✅ Helps to push your limits, but in a more focused way.
✅ You’re not easily ignored.

This is how that looks for me right now, in my current role.

Read more about that here:

Working in a Megacorp vs Startup or SMEs

I’ve worked in all of the above and they all have their advantages and disadvantages. In no particular order, here’s what has worked well for me:

In the megacorp:

✅ Slower pace with better demand management
✅ More investment in training
✅ Experience designing and building at scale
✅ Better career opportunities (north + east/west)
✅ More opportunities for travel
✅ Better benefits
✅ Better ethics and diversity
✅ Consistent with strategy
✅ More mature, less volatility of key strategies
✅ Seeing projects and planning through to completion and adoption

Startup/SMEs:

✅ Fast paced
✅ Equity or similar early investment opportunities
✅ An amazing environment to learn quickly due to the many roles you’ll play
✅ Leaning how to run lean, and do more with less
✅ Learning how to consistently deliver against tight timelines
✅ Closer to consumers / customers
✅ More visibility and involvement around how the business works
✅ More involvement in important decision making
✅ Seeing features go out the door to consumers quickly

Having said that, burn out is very common in the startup/SME arena 👇

Wearing many hats and spinning many plates all adds to the cognitive load of having to know and learn more than you should, this will take its toll on your overall happiness and mental health, as well relationships outside of work - these roles are great but in my experience you should set yourself a timeline for an exit.

The Fear of Failure

Ah that override switch that halts all career progression, the fear of failure.

Look, if this is something you suffer from then you need to get over it, and fast - everyone talks about how healthy taking down production can be (maybe just the once... try doing that back in the 90s when there wasn’t anyone around to power the servers back on) 😅, if you’re not failing or making mistakes then you’re doing nothing of any significance.

One time, I shut the portion of a motorway down (due to a print queue), it was a long time ago and it took me a few months to get over it - looking back though, it was one of the best experiences of my professional life, I was working on a big project and I didn’t know if I could pull it off, I did it in the end, and it felt good, as did the scars.

I’ve fucked things up countless times, and each time the personal value and growth I’ve gained from it has been unmeasurable.

The fear of failure limits opportunities:

So get after it, if you fuck things up then so what 🤷‍♂️, at least you there trying to deliver by working your ass off. Nobody remembers, everyone is too busy trying to sort their own shit out, one way or another.

Company Research

Company Fit

I’ve worked for a company where Cloud was touted as a strategic, committed direction of travel (when in reality, it wasn’t) and trust me, it’s soul destroying (you'll feel trapped like general Zods crew in the Superman 3 phantom zone), so ensure you get this bit right!

Researching

If you’re on the ‘pick a primary cloud and nail it’ journey, you’ll want to do some research on the company’s commitment to AWS/Azure as a primary cloud platform (or their cloud strategy in general).

Here’s some tips on how you can do that:

1. Head on over LinkedIn

2. Search for the company you are interviewing with.

3. When the results come back, ensure you filter on ‘people’.

4. Ensure that your 1st, 2nd and 3rd connections are selected here.

We are going to search for ex-employees first

1. In ‘all filters’, ensure that you also have ‘past company‘ selected.

2. Clear the selection under ‘current company’.

3. Add additional filters name and title (title is the one you’ll find the most useful).

4. Select a title phrase like Architect and hit ‘show results’.

5. Now you’ve got all ex-employees of that company who worked in an architectural role.

6. Review everyone who worked at the company you are interviewing with and see if there’s an pattern of tenure that would indicate whether or the company struggles to retain talented staff.

7. Try to reach out to them for an honest conversation “I see you worked at x for several years back in y, I’m interviewing there shortly and wanted to get a feel of the culture and commitment to cloud strategy (or whatever you want) - would you recommend it to someone in my position etc”

8. See what they post about and what communities they are active in

9. Repeat steps 4 - 8 but do it for title phrase AWS. Again reach out to these people using the same approach.

10. Repeat steps 4 - 8 but do it for title phrase Cloud. Again reach out to these people using the same approach.

You’ll really get back some key focused information on Cloud / AWS /Azure usage and the strategic roadmap within the company and what’s rolling down from senior management.

Now onto current employees

1. Again in all filters, remove ‘past company‘

2. Ensure that you have ‘current company‘ selected

3. Repeat steps 4 - 8 for in the section above and rather than reach out, take a note of the roles that are currently active and the tenure of each person with the role.

4. See what they post about and what communities they are active in.

Key takeaways from this method

It’s worth taking the time to do this, you’ll get unfiltered and honest feedback from people rather than combing through bitter anonymous comments on Glassdoor.

You’ll also get a full view of the board, CxO and director strategy, commitment to cloud and the overall culture of the organisation (which you can cross reference against your own values and principles so you don’t end up frustrated in the role).

Essential Reading

There’s two books that have impacted me the most in my career:

📚 The Phoenix Project. I read it years ago and I couldn’t put it down.
📚 So Good They Can’t Ignore You (more on that later)

“Bill, an IT manager at Parts Unlimited, has been tasked with taking on a project critical to the future of the business, code named Phoenix Project. But the project is massively over budget and behind schedule. The CEO demands Bill must fix the mess in ninety days or else Bill’s entire department will be outsourced. Luckily for Bill, he has an unlikely ally: an eccentric potential board member named Erik.“

There’s lots going on in The Phoenix Project, the lessons never stop coming, but one of my key take aways was Erik (the board member) and his influence on the board, and more importantly, the influence and coaching he had on Bill.

Without Erik on the board, Bill doesn’t succeed in turning ‘Parts Unlimited’ around in 90 days.

That brings me to the last bit..

Backing from the Senior Stakeholders

Maybe there is no Erik from The Phoenix Project on your board (there should be!).

Maybe you’re already in an architectural position within an organisation, you’ve discovered a number of key risks that need highlighting and you’re frustrated with the lack of support and air cover within the organisation to do what you think is right which exacerbates the fear of failure.

The time is always right, to do what’s right.

What can you do here to gain backing from the board, CxO, directors, or at the most senior level stakeholders available to you?

Identifying the Risks:

Bear in mind that your no 1 priority is securing your customers data, contracted SLA out to consumers is a close second (unless you are providing critical health services etc) and TCO.

Identify the key risks, but ensure that you present them in a format that a C-level audience can understand. If you can’t do that, ask ChatGPT to give you a few examples.

Here’s an example of how to present a risk of overly permissive lateral networking.

Any CxO would understand the potential for unauthorized access to sensitive data or resources within the cloud environment due to inadequate network segmentation or weak access controls, these risks alone could result in:

A scenario where an attacker gains access to one part of your cloud infrastructure (perhaps through a compromised user account, leaked API credentials or secrets, or a vulnerability in an unpatched service).

Without proper network segmentation and access controls, the attacker could then move laterally across your cloud network, potentially accessing other parts of your infrastructure that contain sensitive data or critical systems.

Compromised and unaudited lateral movement can then lead to data breaches, major service disruptions, encrypted ransomware attacks or even a complete compromise of the cloud environment.

This could result in significant financial losses, damage to the organization's reputation, and huge regulatory penalties if sensitive data is exposed.

You would then back this up with data, highlighting:

1. How bad is the current problem? (and how not to make it worse).

2. How is it currently being threat hunted?

3. How is it currently being monitored?

4. Who is alerted first if a threat is detected?

5. What’s the current response is if a threat is detected?

6. What are the official recommended architecture patterns to mitigate the risk (from the platform vendor)?

7. What do other organisations similar to yours do?

8. Example of any news stories where this has happended in the past.

9. A good scale of how critical this risk is to the organisation based on other dependendant projects, the future growth of the company and the pressure on technology platforms to deliver in a secure manner.

10. Which vendors offer solutions?

11. How do the solutions compare with each other?

12. What is your recommended solution based on the assessment so far?

13. Provide an example budget for remediation.

14. Provide an example budget for continued governance.

15. Provide an example set of standards & principles that need to be agreed for future alignment.

16. Identify the change mechanism for implementing the standards and principles (if they don’t exist, recommend that they do and how they can be put in place).

17. Request a decision.

To sum all that up, here’s one of Barack Obama’s best interviews (and some of the best career advice i’ve ever heard) on just getting sh*t done (GSD).

Now that the risk exists, it’s on the register and it’s been surfaced at the highest level and explained to all senior stakeholders, in the right format.

The next big question is, who going to own that risk (in the event that the response is to do nothing?)

This is where you’ll start to get traction.

Hope that helps!

📚 One last book tip… It’s the only professional growth book I ever recommend:

Thank you again for reading. If you like my content pls share across your socials and support me by tagging @leewynne

All the best, Lee