📦The Great Job Roll-Up: What Amazon's CEO Sees in the Future of Work

Amazon CEO Andy Jassy sent a memo to employees this week that grabbed my attention. He mentioned two things that I think add clarity to illuminate where our working lives are heading.

“Getting more done with scrappier teams” and “becoming conversant in AI."

Let's unpack what he means, and I’ll run through how I’m applying this thinking to my situation.

Getting Scrappy

Jassy gives us a good view of what it means to be scrappy: "When I first started at Amazon in 1997 as an Assistant Product Manager, I worked on leaner teams that got a lot done quickly and where I could have a substantial impact. We didn't have tools resembling anything like Generative AI, but we had broad remits, high ambition."

For me, he's describing:

• Fewer people on each team

• Broader responsibilities per person

• Faster execution with less bureaucracy

• High ambition despite resource constraints

He's talking about the practical reality of doing more with less simply because they had to. The 20-person project team with specialized roles is becoming extinct—I see this already in my line of work. I used to work on massive teams deploying SAP to corporations—hundreds of people performing specialised roles. I haven’t seen a project like this in years, and AI will only push this trend further.

Getting Conversant in AI

But scrappy teams are only half the equation. The other half is what Jassy means by becoming 'conversant in AI' - because that enables the kind of people you need on these teams.

AI allows individuals to absorb functions that used to require separate people.

Take my work as an example. I no longer code every single nut and bolt of a solution. Instead, I guide a skilled AI model to adhere to development best practices and client requests. I then use another for strategy and documentation. So what does that make me? Am I still a developer, data engineer, or data analyst?

And it’s here where I believe that "conversant in AI" skill comes in—the knowing of how AI can perform functions that used to require separate people. The marketing person who can now also do data analysis, copywriting, and campaign optimization. The sales rep who handles lead generation, proposal creation, and basic contract work. The operations manager who does financial modelling, process automation, and strategic planning.

The specialist versions of me are “rolling up” into a single generalist. AI isn’t replacing me—it’s amplifying my ability to handle tasks that once required a whole team.

The question becomes: which version of my role am I preparing for? The narrow specialist version that's disappearing, or the broad generalist version that's emerging?

Getting Prepared

1. Thinking in functions, not job titles: Instead of the "I'm the email marketing person," I’m now expected to be the "I handle customer acquisition” person. The broader the remit, the more valuable I become on a small team.

2. Build my AI toolkit: Identify AI tools that can help me “roll up” jobs in the function.

• Cursor or Windsurf with MCPs for Code Editing and development

• Claude for strategic direction and technical documentation

• Dalle for image generation (a lifesaver as I am a terrible graphic designer)

With these tools, I am now a developer, analyst, business architect, API specialist, technical writer, and graphic designer in one - I honestly don’t know what to call myself.

3. Develop "Broad Remits" thinking: To pursue this further, I ask myself: What adjacent skills could I develop that would make me more useful on a five-person team?

Subject matter knowledge, delivery strategies, user testing.

If you're in marketing, it might be: Can you also handle basic analytics? If you're in sales, can you create your own products to sell? If you're in operations, can you interpret financial data?

4. Embrace Resource Constraints: Scrappy teams get better results because they can't rely on unlimited resources. If you’re like me, you suffer from decision overwhelm—there is so much to read, so much to learn, and so much to do. I find that when I start culling things, I operate on a higher level.

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The Real Message

I think Jassy's memo paints a picture of the future we can learn from. It's about where work is heading everywhere, not just at Amazon: smaller teams, broader responsibilities, and AI as the force multiplier that makes it all possible.

For me, this happened before the emergence of AI due to sheer cost savings. Now, AI makes this business strategy available to any company.

Teams are getting smaller, which means I need to be more capable. If I have more skills, I am more valuable to a potential employer - simple equation.

Now to work out my job title - the only thing I’m sure of is that it’s certainly not “graphic designer.”