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Enterprise Solutions Architect at AWS

Hi, I'm Shola.
I architect cloud at enterprise scale.

I help some of the UK's largest organisations migrate, modernise, and cut cost on AWS - and I help people break into cloud and AI careers.

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0K+
Amazon employees
Top 120 - AWSome Legend 2025
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cloud certifications
5 AWS / 4 Azure
0K+
LinkedIn community
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1:1 into cloud and AI
Olushola Oladipupo, Enterprise Solutions Architect at AWS
London, UK
What I work on
AWS cloud architectureCloud migrationLegacy modernisationCost optimisationAI strategy on AWSCloud certificationsBreaking into cloud & AI careers
About

From agricultural economics to the cloud.

I was terrified I'd made a huge mistake. Six months into cloud computing, I felt like the dumbest person in every room. Then something shifted.

I started with an Agricultural Economics degree from the University of Ibadan, then moved to the UK for a master's at Bournemouth (Distinction, 2018), where I discovered data. NHS England hired me as an entry-level Data Analyst. By 2021 I'd hit a ceiling, so I asked a deputy director for a cloud secondment I wasn't qualified for. He said yes.

I earned four Azure certifications in a year. AWS hired me in 2022 with zero AWS certs - just Azure badges and stubborn determination. Within 18 months I was promoted, and in 2025 I won the AWSome Legend Award: top 120 of 900,000+ Amazon employees globally.

Today I design cloud architecture for migration, legacy modernisation, and cost optimisation at scale, and I help leaders shape practical AI strategy. The rest of my time goes to the people coming up behind me - through mentorship, guest lectures, and my newsletter.

Experience

The path here wasn't a straight line.

Agricultural economics to enterprise cloud - the long way round, on purpose.

  1. earlier

    BSc, Agricultural Economics

    University of Ibadan, Nigeria

    Where it starts - a long way from the cloud.

  2. 2018

    MSc, Distinction

    Bournemouth University

    Executive Dean's Scholarship. Discovered data and fell for solving problems.

  3. 2018

    Data Analyst

    NHS England

    Entry-level. Learned the craft. By 2021, I'd hit a ceiling.

  4. 2021

    Cloud secondment

    NHS England

    Asked for a six-month cloud role I wasn't qualified for. Got it. Earned 4 Azure certs in a year.

  5. 2022

    Solutions Architect

    Amazon Web Services

    Joined with zero AWS certs - all Azure. Promoted within 18 months.

  6. 2025

    AWSome Legend Award

    Amazon

    Top 120 of 900,000+ employees globally.

  7. Now

    Enterprise Solutions Architect

    Amazon Web Services

    Migration, modernisation, cost optimisation and AI strategy for the UK's largest organisations.

Speaking

On stage.

Sharing what I've learned - at AWS re:Invent, AWS Summits, and beyond.

Olushola Oladipupo on stage beside the AWS podium at AWS Summit London
Olushola Oladipupo mid-talk on stage at AWS Summit London
On stage at AWS Summit London - to a 20,000+ audience.
AWS Summit London
2026
ExCeL London
Customer Experiences at Scale with AI-powered Amazon Connect

Session BIZ202, co-presented with Gulcin Batmaz to a 20,000+ crowd.

AWS Summit London
2025
ExCeL London
Migrating and Modernising VMware Workloads to AWS

Co-presented with Sivasakthi Shanmugam, showcasing Amazon Q Developer.

AWS re:Invent
2025
Las Vegas
LinkedIn for Developers: Building Your Technical Brand

Invited speaker at re:Invent 2025.

AWS Summit Johannesburg
Aug 2024
Sandton Convention Centre
Improving Generative AI Applications with Human-in-the-Loop

My first breakout session, co-presented with Cheikh Mahaman - human feedback for FMs on Amazon Bedrock and SageMaker.

AWS Skills Centre
Seattle
Building Your Technical Brand: Own Your Story, Open Doors

Invited in-person talk at the AWS Skills Centre.

Guest lectures
Bournemouth University
Cloud careers

Recurring guest lectures for the next generation.

Certifications

9x cloud certified.

Five AWS, four Azure - earned the hard way, mostly at night. Proof that the badges follow the work, not the other way round.

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Writing

Shola's Tech Notes.

Every Tuesday I send one practical email on AWS, AI, and building a career in cloud. Read by 1,000+ engineers and tech leaders.

Each week, you get
  • Industry & AI trends, with a builder's take
  • AWS technical deep-dives and cheat sheets
  • Cloud career playbooks from lived experience
Contact

Let's build something that scales.

Speaking, mentorship, or a cloud problem worth solving - I read every message.