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A Taste To Start

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It is not the strongest or the most intelligent that will survive, those those that can best manage change.

Charles Darwin

On The Menu

Market Tasting
The Cellar — Alternative assets, ranked by momentum

Asset Price / Index Since Last Issue
Gold
per oz
$4,177 -3.9%
Real estate
REIT index — VNQ
$97.26 -0.8%
Classic cars
Hagerty Market Index
flat mkt. mixed
Handbags
Resale — Birkin / Chanel
1.4x retail avg. softening
Gemstones
Ruby / Emerald / Sapphire
$34.9B mkt. +30–40% 2Y
Sports memorabilia
Cards, game-worn, collectibles
$70B mkt. +18.2% CAGR
Bitcoin
USD spot
$83,448 +9.9%
Oil
WTI crude / bbl
$90.10 -12.1%
Watches
WatchCharts index
38,580 -0.2% mo.
Data sourced twice monthly. For informational purposes only — not financial advice.

Tastemaker’s Note
The floor the salesman worked on is dead because the consumer moved online and never came back. What's replacing it is experiential retail, service tenants, and mixed-use conversions and is quietly becoming one of the more interesting plays in commercial real estate right now. Bitcoin is up nearly 10% this issue, gold is pulling back as rate pressure eases, and oil is finally cooling after two months of geopolitical noise. Watches slipped -0.2% in September, but the 1-year picture at +8.7% tells the more honest story — the secondary market for Rolex, Patek Philippe, and Audemars Piguet doesn't care who's on the floor. It never needed a salesman in the first place.

Letter From The Tastemaker

The traditional sales funnel was built around a fairly simple premise: get the prospect in front of a salesperson, give the salesperson enough information to persuade them, and move them toward a purchase.

The internet disrupted that model and today, AI is compressing it.

In March, Gartner reported that:
→ 67% of B2B buyers prefer a buying experience without a sales representative.
→ 45% said they had used AI during a recent purchase.
→ 73% of buyers avoid suppliers who send irrelevant outreach.

According to G2's 2026 research, 51% of B2B software buyers now start their research with an AI chatbot more often than Google and 71% use AI chatbots somewhere in their software research process.

Think about what that means for a second.

The buyer can ask the machine:

What should I buy?
Who are the best companies?
How much should this cost?
What are the alternatives?
What questions should I ask?
Compare these three vendors.

And receive an answer before a salesperson ever gets their name.

For companies, this is incredibly attractive. AI can handle enormous amounts of research, qualification, customer service and outreach without requiring another person for every interaction.

Companies like Microsoft, Altassian, Autodesk and Saastr are cutting thousands of positions but instead of replacing people, they are deciding which human interactions still deserve a human.

Microsoft’s elimination of 4,800 roles in July 2026 explicitly described the restructuring as a reallocation of people, investment and energy toward its changing priorities.

Amazon says its AI shopping assistant generated nearly $12 billion in incremental sales last year. Walmart's Sparky can now help customers discover, compare and purchase products, including through ChatGPT.

In automotive, companies such as Rivian have gone in the opposite direction from the traditional dealership model, arguing that owning the direct customer relationship is important enough to accept potentially lost sales. Rivian CEO RJ Scaringe has said the company would "forego sales" rather than give up that direct relationship.

The common thread is control of the relationship.

→ The retailer wants to own the AI shopping experience.
→ The automaker wants to own the customer relationship.
→ The software company wants AI to handle the repetitive work while its people focus on higher-value interactions.

And the buyer wants something surprisingly contradictory: Less selling and more confidence in the products.

For me, that’s the most interesting part of all…

→ Gartner found that while 67% of B2B buyers prefer a rep-free experience, 69% still turn to sales representatives to validate information generated by AI.
→ Gartner's research describes the evolving salesperson less as a persuader and more as a verifier, someone who helps reduce uncertainty and gives the buyer confidence at critical moments.

And that indeed, is a very different job than the salesperson we’re used to.

Maybe the death of the salesman isn't the death of selling. Maybe it is the death of transactional selling.

AI is exceptionally good at the things that made traditional sales exhausting: answering the same questions, qualifying leads, sending follow-ups, comparing products, scheduling conversations and moving information from one place to another.

The question is, what do we do with the human capacity that remains?

Because the greatest salespeople are more than just about the features, benefits and cost of the products. Their value was tied to knowing you.

From understanding your needs, they would know what you like before you have a chance to articulate it.

For me, the people I value most commercially are not necessarily the ones with the biggest Rolodex or the most aggressive sales strategy.

They are the everyday connectors who remember small details.

→ The people who remember that someone mentioned wanting to enter a particular market six months ago.
→ The person who hears about an opportunity and immediately thinks of you.
→ The person who makes an introduction without needing a commission attached to it.

They are selling all the time, but they rarely feel like salespeople.

They are the curators of trust and I suspect that is where human selling is headed.

Trend Forecast
What’s Shaping The World

01

The Entry Level Sales Job Is Already Disappearing

The share of employees holding an SDR title fell from 1.9% to 1.5% in about two and a half years, roughly 8,000 fewer entry level reps. In a separate survey, 22% of sales teams say they've fully replaced their SDRs with AI. The first rung of the sales career ladder is the one quietly getting pulled up.

Source: Pave, Outreach, via sales.co

02

Buyers Would Rather Not Talk to a Salesperson at All

67% of B2B buyers now say they prefer a partly rep-free buying experience, and AI assisted self-serve now covers an estimated 70% of the typical buying journey. Even six figure and half million dollar deals are shifting toward self-serve, with 39% of buyers saying they'd complete a $500,000 purchase through a purely digital process.

Source: Gartner, via Tomba and The Smarketers

03

Some Deals Are Now Negotiated AI to AI, No Humans Involved

20% of B2B sellers report negotiating directly with an AI powered buyer agent instead of a human procurement contact. The classic image of two people hashing out terms across a table is being replaced, in a meaningful slice of deals, by two systems negotiating on their behalf.

Source: Uman.ai

04

Selling Didn't Disappear, It Got Compressed

The data is genuinely split. Some orgs cut sales headcount by 28% in 90 days, while Salesforce found teams actively using AI were more likely to add headcount than cut it, 68% versus 47% for non-AI teams. The honest read is that the same pipeline is now being produced by fewer people, more software, and a much shorter list of accounts, not that the role vanished outright.

Sources: Hathawk, Salesforce via MeetRep

05

The Salesperson Who Survives Looks Nothing Like the Old One

A typical sales pod went from 8 SDRs doing 60 dials a day in 2019 to 1 or 2 pipeline engineers running AI agents alongside live calls in 2026. Sales engineers are increasingly joining deals from the first touch instead of only showing up post-demo, because buyers expect technical proof, not just charm.

Source: Tomba Blog

Tastemaker’s Note
The trend that stuck with me this week is that sales is getting compressed. Fewer people, more software, and the same pipeline. While charm used to be enough to get someone in the room, now you need to be the reason they stay in it.

How much does a $70k hire actually cost?

A $70K salary might look straightforward on paper. But once you factor in employer taxes, statutory benefits, payroll, and country-specific employment costs, that number can skyrocket.

And those costs can vary significantly depending on where your employee is based. So before you build your hiring budget, check out Oyster's Global Hiring Cost Calculator.

The calculator can help you see the full picture by letting you compare employment costs across 120 countries and estimate what a hire could really cost your business. And unlike that new hire, it’s actually 100% free.

Perhaps, selling should never feel like selling. It should feel like trust…

Like taking this bite of crabmeat and caviar because someone who’s taste you admire told you it was worth it, without needing the pitch.

P.S. Like my style (and taste)? Work with me.