Show recap — Monday, June 22, 2026

Another Orange Morning Recap: June 22, 2026

Monday morning, and the updates board was empty. HubSpot took Friday off for the holiday weekend, so there was nothing fresh to run through. Chris opened the show, welcomed Casey, and welcomed Joshua Oakes back after a stretch away. The running joke about Chris losing track of the date in the middle of saying the date made its usual appearance. Then the room did the sensible thing with an open Monday and turned the floor over to Oakes to hear what had landed for him since his last appearance.

Here is what we got into: the one update worth revisiting, a long and useful detour into Breeze and the context problem, a live look at the AI Context area inside Breeze Studio, the segment formerly known as Will It Workflow, and the conversation every admin eventually has about proving the value of HubSpot. Revenue Hub got a passing nod near the top and a promise to come back to it another day.

The One Update Worth Revisiting

New Formula Options in the Custom Report Builder

Oakes brought this one forward, and it was the closest thing to news on a no-news day. The Custom Report Builder picked up guided ways to write formulas alongside the existing syntax approach, including conditional logic that handles if-then-else cases through an interface rather than hand-written syntax. If a deal is over a certain amount, return high value, otherwise return low value, without writing the formula by hand. It has been on Oakes's radar for a while. He has been posting about case statements in formula builders every couple of months, asking for exactly this.

Why it matters: The quiet win is keeping reporting logic inside the report instead of spinning up a calculation property you do not otherwise need. A lot of portals carry tech debt from the opposite reflex, where every bit of report logic turned into a new property. There is still a real place for a property, like folding several integration fields into one durable value. For one-off reporting, this keeps the logic where it belongs and the property count lower. As Casey put it, the amount of tech debt this kind of thing clears is kind of incredible.

This same update came up on the June 19 show, so for the fuller breakdown, it is in that recap: the June 19 Another Orange Morning recap. For the update itself: conditional logic and summary measure in the Custom Report Builder public beta.

Breeze, and the Context Problem Underneath Everything

The formula conversation opened a door, and the show walked all the way through it. The live demo started with a question a lot of stakeholders ask: can you give me a pie chart of high value deals versus low value deals? The catch, which is the catch in most real portals, is that nobody had defined what high or low value actually means. So Breeze gave it the old college try. Its first instinct was to find the median, which means the split comes back close to fifty-fifty every time, because that is what the math does when there is no definition to work from.

When the prompt shifted to something more open, asking whether there was a qualitative story to tell rather than a dollar threshold, Breeze did something more honest. It flagged that the qualitative fields were patchy, tightened its query to open deals only, and told the story the data actually supported. This was a pipeline discipline story, not a buyer intent story. The process was the issue, not the deals. Breeze even described the data as having "mixed pipeline hygiene," which the room agreed was about the most generous review of pipeline data anyone had heard.

Why it matters: The useful realization is that AI is easy to bias, and not always on purpose. If you ask Breeze to show you the deals that really matter, it will show you those and stop looking, because it wants to please. The harder and better question is the open one: is there a story here, and what is it? That keeps you from accidentally defining value in the middle of a chat with the assistant instead of with your team. It also lets Breeze do something people struggle to do under pressure, which is look at messy data without taking it personally.

The conversation added the piece that ties it together. What is missing when AI weighs deals is not data, it is intuition: the sales leader who knows the VP has been quietly worried about one segment, or excited about a product, and reads the room accordingly. That is bias in the technical sense, but it is the good kind, built on context the system cannot see. The long-term question is how you bring that context in without it living only in one person's head.

The example that made the stakes clear was the CFO meeting. The last thing you want walking into a finance conversation is for the AI to use its training data to decide what a CFO cares about, because then you sound like an intern talking about ROI while the CFO wants to talk about the price of the subscription. The fix is context that belongs to the business: time-bound priorities, historicals, how the org actually operates. HubSpot has started building toward this with brand context and ICP for Breeze and the customer agent. The room's wish was for HubSpot to be more aggressive about the rest of it.

A Live Look at AI Context in Breeze Studio

This was the part where the conversation met the product. Chris clicked into the AI Context area inside Breeze Studio, which organizes things into business, customers, and team and processes. Anyone who has been through Value-First scoping will recognize those buckets right away, because they are the same three things you have to understand before you can implement HubSpot well, tool-agnostic and all.

It is early. The team and processes section is, in the show's words, a stub right now. Products recently moved under business, and the depth is not there yet. But the motion is real, and that was the point. A lot of this context already exists in the background. The open question is how to surface it in a way that helps rather than creates more heartache.

Where Chris wants this to go: deeper sub-tabs, process definitions that connect to skills Breeze can run with a human in the loop, or tie into workflows and the AI automation beta. Right now it sits under Breeze. It would not be surprising to see it move into settings eventually. For now, products being there is a good start.

Will It Workflow Is Now Will It Breeze

The segment picked up a quiet rename to Will It Breeze, mostly because Chris has not updated the website yet. The bit holds up either way, because the marketing trick is that the answer is always yes. Will it Breeze mermaid diagrams? Yes.

The real advice underneath the joke is worth keeping. Most people are not good at documenting process, and there have not been great places to do it inside the CRM anyway. Context ends up scattered across Miro, Lucid, Visio, and a dozen other tools, which is its own problem, and to be clear, nobody was knocking Miro. Asking Breeze or Claude to draft mermaid diagrams of your processes is a low-stakes way to start pulling that context back into one place. You do not have to chew on these things alone anymore. Ask for the diagram, see what comes back, and tell it to show you the same thing a different way if the first pass does not land.

The Conversation Every Admin Has Eventually

The throughline of the whole morning was the value conversation. The annual or quarterly review where someone asks whether HubSpot is worth what it costs, and you want to walk in with the answer already built rather than scramble to assemble it after the fact.

The honest read from years of client work is that showing up with real deliverables, the process maps, the right report, the clear story, changes the conversation. Trust in you goes up tenfold, because most teams do not have that level of documentation. The next ask gets easier instead of turning into "great, now make me something ten times more impressive by Monday." And the sentiment from that meeting travels further than the meeting itself, in both directions.

Which brings it full circle. With the new formula options and a little help from Breeze, you can jump ahead to the exact report or calculated property you need instead of building, testing, and finding the gaps the hard way. Then the value is assumed, and you spend the meeting solving an actual business problem. That is what anyone in the C-suite actually wants to know: how is this helping me with what I am trying to do.

The Sign-Off

A no-updates Monday turned into one of the more useful conversations the show has had in a while, and it got there without ever pulling up Revenue Hub. That one is still waiting in the wings for another morning.

You probably already own the value you are looking for in HubSpot. You just need to wake up to it. We will see you tomorrow morning.