The Roles I’m Filling Right Now

Role one: a shipping search backed by a major US airline

Confirmed open as of August 22, 2026

Every AI company in your feed is racing to prove it’ll still exist after the next model release. This is the opposite of that. It’s a parcel delivery program run in partnership with one of the major US airlines — a carrier you’ve almost certainly flown. It moves physical packages across the country on planes that are already in the air. It makes money. It grew from $0 to roughly $30M in four years. And the thing it’s built on — a nationwide passenger flight network — is not something a competitor can spin up next quarter.

Here’s the part that makes it a role worth talking about. The majority of that $30M was closed by executives selling on the side of their day jobs — revenue that arrived more by pull than by any repeatable motion. The company would tell you the same. They put their first dedicated seller on it recently and that seller is producing, which tells you the motion works when someone actually runs it. This seat is the second.

Why this is structurally different

Three reasons this isn’t a normal logistics sales job:

The product rides infrastructure no one else can replicate. The program uses the airline’s passenger flights — roughly 4,000 a day — to carry packages on the long cross-country leg. Those planes are flying anyway. You and I could go buy a truck tomorrow; you and I are never going to go buy an airplane. The result is 2-to-3-day delivery anywhere in the country at ground prices, with flat weight-based pricing and no zone-based surcharges or accessorial fees. It wins hardest on the long, expensive lanes — the ones where the legacy carriers get slow and pricey.

It’s a switch sale, not a rip-and-replace. This is positioned as carrier diversification — an alternative you add on for redundancy, not a system you tear out. Nobody gets fired for using FedEx or UPS, so the whole game is creating urgency around a change people don’t feel forced to make. That’s why the industry lifers haven’t been the answer. The pattern has been hiring FedEx and UPS veterans who know the industry cold but sell like order-takers — not sellers who can navigate to a COO or CFO and make the case for change. The explicit read from leadership is that the gap has always been selling, not industry expertise — and they’ll teach you the industry.

It’s a mature program that has never been run like one. The revenue is real, the product fit is proven, and a structured process is being built out. Dedicated selling only started recently, and the first full-time closer is already having success. The second seat exists because one person cannot cover a national market — not because anything needs fixing. This isn’t a blank slate and it isn’t a cookie-cutter sale — it’s a real program with real infrastructure that needs someone who can both run the play and call an audible when a deal stalls.

That combination — irreplaceable infrastructure, a genuine change-sale, and a proven-but-under-sold program — is why the upside here is unusual.

Where the upside is

This is the part I’d underline. A $30M program where the majority was closed by executives on the side means the ceiling on this role hasn’t been tested. One dedicated seller is on it now and producing, which is proof the seat works and nowhere near enough coverage for a market this size — you are not walking into a mature org where the good accounts are already claimed and your job is to defend a number. You’re walking into a proven product with a wide-open field in front of it.

Deals run from roughly $100K to $6M. A single large logo can reshape your year. When a program this size has been carried mostly by executives selling part-time, the deals a dedicated closer can actually run at, multi-thread, and pull forward are the whole story. That’s what to focus on, not an “average.”

And this isn’t a first-seller lottery ticket. There’s already revenue, already product fit, already momentum. You get the open field of an early role with a business that’s already working underneath you.

If you’re looking for a sexy, of-the-moment product to put in your LinkedIn headline, this isn’t it. If you’re looking to make real money selling something that already works, in a role where your ceiling hasn’t been set, take a look.

The Role

Who fits

The profile is specific. A true hunter with a real sales methodology and 8–15 years of quota-carrying B2B experience with a record of closing complex deals. Someone who knows how to get into an org, find the right buyer, and orchestrate a multi-stakeholder switch. Experience in eCommerce, retail, SaaS, or logistics tech is a plus — selling ability is non-negotiable.

Less obviously: this role rewards someone comfortable inside a defined process but not beholden to it — you follow the playbook on a normal deal and know which lever to pull when one stalls. It’s built for a builder who wants real fingerprints on a business but doesn’t want to bet the mortgage on a pre-revenue idea. You get a proven $30M program under you and a comp plan that pays right away — your variable is guaranteed for the first three months.

Who it isn’t for: the career FedEx/UPS account manager looking to work a Rolodex. Leadership has been explicit that the order-taker profile is exactly what hasn’t worked here.

My read

I’ve been working directly with the President to redefine this role — what it should own, how it’s leveled, where a senior closer creates the most value. So I have a close view of what’s real. And what’s real is unusually good on the two things that are hardest to fake: product fit and market pull. The program works, the customers who fit love it, and the airline has its own reason to want this to grow. In the three-legged stool of product, people, and process, the product leg is solid. That’s the leg you can’t fix by hiring.

What I’d push on in a call: this is a program that got to $30M without ever really building a sales engine — executives pitching in, a process still being tightened. That’s a feature and a caveat at once. The feature is enormous room to run and genuine influence over how the commercial function gets built. The caveat is that some of the scaffolding is being poured while you’re standing on it. The right candidate reads that as the whole point; the wrong one reads it as chaos.

If you’re a senior enterprise seller who likes building but wants proven product fit and real upside from day one, this is a role worth 15 minutes. I can give you my read on the GTM side and where I’d push for clarity before signing.

Role two: an early US seat at a healthcare AI company

Confirmed open as of August 22, 2026

The first wave of clinical AI documentation went to physicians. There are now hundreds of AI scribe products built for physician workflows. That market is crowded and largely commoditized.

The nurse market looks completely different. Despite vastly larger headcount — nurses outnumber physicians several times over in the US — the AI scribe count for nurses is in the single digits. The buyers are different. The workflows are different. The technical requirements are different. That gap is not accidental; it’s structural.

Here’s the part that makes it a role worth talking about, and the reason I’m featuring it a second time. I placed one of the sellers who started in August. He called me unsolicited — not because anything was wrong, but to say thank you, that he loves the company, the product, and the people, and to give me a heads-up that they need more people in the US. That is the most useful signal I get in this job, and it is not one I can manufacture.

Why nurse AI is structurally different

Three reasons the physician scribe playbook doesn’t port to nurses:

Documentation volume per shift. A physician generates roughly one substantive documentation entry per patient per visit. A nurse generates dozens to nearly a hundred — care plans, medication logs, vitals, observations, incident notes — across an entire shift. The product surface a physician scribe needs to cover and the product surface a nurse needs are different categories of software.

Connectivity constraints. Physicians document in offices, exam rooms, and on hospital floors with reliable wifi. Nurses document inside patient rooms and care facilities, in environments where cloud-based AI structurally cannot run reliably. The AI has to be on-device, offline-capable, and sync when connection returns. Most physician-scribe architectures cannot retrofit to this. They’d have to rebuild.

Buyer composition. Physician scribes sell to medical practices, hospital systems, and individual physicians. Nurse documentation sells to skilled nursing facility operators and large care chains — a different procurement profile, different ROI math, different sales cycle.

That combination — different workflows, different architecture, different buyers — is why the physician scribe companies haven’t expanded into nurses. They can’t do it with their existing stack, and the buyer relationships don’t transfer.

Where the upside is — and where the risk is

I want to be precise here, because this one is earlier than it looks. Two sellers started in August 2026. In a procurement-heavy enterprise cycle, that means nobody has ramped and nobody has closed yet. You would not be inheriting a worn path; you’d be running roughly in parallel with two peers who are weeks ahead of you at most.

That’s better than being the only rep in a new market, and it is not the same as a proven US motion. What is proven is the business underneath: significant ARR in the company’s home market, thousands of care facilities, hundreds of thousands of frontline users, hundreds of millions of records through the platform. The product works at scale somewhere. The open question is how fast the US converts, and you would be one of the people answering it.

The upside is that the US territory is genuinely open at a stage where opening it still counts for something. The risk is that early enterprise cycles are long, and the first year is judged on pipeline built more than revenue closed. If you need a covered number in year one, this is the wrong seat. If you want a market to open, it’s a rare one.

The role

Who fits

Five-plus years of enterprise B2B SaaS sales with a real closing track record on complex deals. Within commuting distance of NYC and ready to be in the office regularly. Comfortable building pipeline from scratch without heavy enablement or SDR support. Strong executive presence with experience in procurement-heavy environments. The moat is in selling complex software to non-software buyers.

Less obviously: this is an international company opening the US, and the GTM context largely sits overseas. You need to be an independent operator who is strong with ambiguity and able to translate what you’re seeing in the US market back to a leadership team that isn’t in the room.

My read

My original view into this business came from working alongside the VP Global Sales. What I have now is better: a seller I placed, in the seat, who called me unprompted to tell me it’s good and that they need more people. He’s weeks in, so he’s telling me something real about the product, the founders, and what he’s seeing in early conversations — not that the motion converts. Nobody knows that yet.

What I’d push on in a call: how the company defines a successful first year for a US seller, and whether that definition is pipeline or closed revenue. In a market this early, with cycles this long, the answer to that question is the difference between a great seat and a frustrating one. It’s a fair question and a well-run company will have an answer.

If you’re an enterprise AE in the New York area who wants a genuinely open market, this is worth 15 minutes. I can give you my read on the GTM side, the comp structure, and where I’d push for clarity before signing.