Writing
How AI will change tech sales
For the past decade, enterprise software sales has been one of the best careers around for ambitious people. A strong account executive can clear seven figures in a great year, with no formal education required.
I don't think AI ends that soon, but I do think it makes the career a lot less durable. I've spent nearly a decade in tech sales, including at Cloudflare and Supabase. By 2025, AI had become good enough to automate much of the research, call prep, outbound drafting and CRM work reps used to do manually.
Here's how I expect the job to keep changing.
Short term (2026–2028): good sellers get better
AI can already do much of the prep and admin work that used to take up a large part of an AE's day. Research before a first call takes minutes now.
Good sellers get that time back for the parts of the job that actually close deals: figuring out who has real power in an account, building champions, negotiating and earning trust.
For the next couple of years, the best reps who use AI well may become even more valuable.
Medium term (2028–2032): companies need fewer sellers
Once it's clear how much more each AE can cover with AI, companies will likely need fewer of them.
You could argue that cheaper selling means more startups and more sales jobs, and there will be more startups. But companies founded now are built lean from day one, and many will sell largely through self-serve distribution. They won't hire sales teams the way software companies did in 2015.
The cuts will probably hit SMB and mid-market roles first, which is a problem because that's where people traditionally learn to sell.
Sales management will shrink too. Fewer reps means fewer managers, and AI is already becoming useful for forecasting, pipeline review and call analysis.
The top enterprise seller will still do very well. There just won't be as many ways to become one, and moving into management won't be the same fallback it is today.
Long term (2032 and beyond): humans handle the hard decisions
Over time, many standard tech purchases may not involve a salesperson at all.
Buyers will have their own AI researching vendors, comparing products, benchmarking prices and handling more of the purchasing process.
People will still matter for big, messy deals with real risk and several executives who all have to agree.
I expect the AE role to increasingly look more like an adviser than a traditional seller: part commercial strategist, part negotiator, part relationship manager.
That work will still pay well. There will probably just be fewer of those roles.
What I'd do about it
Don't leave tech sales, and don't resist using AI. At the same time, I wouldn't assume your $250K+ tech sales job is as secure as it used to be. Sales organizations will look very different in 10 years.
So:
- Save as much of your best years as you can. Don't let your lifestyle grow as fast as your compensation.
- Be careful about employer stock concentration. Your income and career are already tied to the company; your portfolio doesn't have to be too.
- Use the time AI saves you to build portable skills. Running complex deals, earning executive trust and negotiating well will travel with you to your next company.
- Stay in touch with customers and colleagues inside and outside your company. They're usually where your next job comes from.
The next few years could be unusually good for elite tech sellers.
I'd treat that as a window to take advantage of, not a new normal to build your life around.
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