ClickUp's New Roadmap: Gray's Top Picks for 2026

ClickUp AI: New Interface and Model Picker

The AI button inside ClickUp now opens a redesigned experience with an Ask tab and an Agents tab. The biggest change is the model picker. You can now choose Opus, GPT, ClickUp Brain, or other models directly from the prompt, which answers a feature request Gray covered a few weeks back.

Saved prompts and web search toggles live in the same panel. Gray’s honest workflow note: the in-product saved prompts are useful, but he reaches for a text expansion tool more often because of the dynamic variable support.

Both patterns work. Pick whichever fits your day. The search speed has also noticeably improved, which makes “ask the full question” a more reliable pattern than “find the message and dig through it.”

The 2026 Roadmap: Three Features That Actually Matter

The roadmap document is long and packed with AI buzzwords. Gray is splitting the deep dive across two episodes. Alex is joining next week for scheduling, resource management, and super agents.

Three roadmap items stood out in this preview.

AI form builder. Today, building complex forms with conditional logic is tedious. ClickUp forms are one of the most powerful features in the platform, but building them at scale is a grind. AI-assisted form building would be a meaningful quality-of-life upgrade.

Thread replies to channels and DMs. Today, you can’t cleanly surface a thread decision back to the main channel. This ships table-stakes parity with Slack and Microsoft Teams. The more interesting angle is what it unlocks for agents, like a decision-documenting agent that reads a long thread and posts a wrap-up reply automatically.

List-level properties. Today, if you want every task in a client list to carry a “client name” or “budget” field, you either set it manually or run an automation. Native list properties eliminate that workaround. Portfolio-style views get much easier to set up, especially for non-power users.

No-Bot Meeting Notetaker

ClickUp is building a notetaker that captures meeting audio and transcribes it without joining the call, similar to how Granola works. No bot icon. No “ClickUp Notetaker has joined the meeting” message.

That changes the social dynamic of recorded calls. Meetings feel more personal without a third party visibly in the room.

There is a tradeoff. When a notetaker bot joins a call, everyone sees it and implicitly consents. A silent transcription tool puts the legal and ethical obligation squarely on the organizer to disclose.

For internal one-on-ones, that’s a clear win. For external calls with clients or prospects, you still need to tell people. Ask Elephant and Notion already ship this pattern.

ClickUp in the Wild: Scrappy ABM’s Transparent Case Study

Gray spends a few minutes highlighting Mason Cosby and the team at Scrappy ABM. They just launched a public Scrappy ABM success story with real numbers. $50K to $200K MRR, 30% net profit margin.

Gray calls out how rare that kind of transparency is, especially from agencies still in their growth phase. Most large ClickUp customers won’t let you share their logo, let alone their revenue. Early-stage operators often feel embarrassed about their numbers.

Mason’s willingness to put it all out there is a gift to every other agency founder trying to benchmark themselves against reality instead of marketing.

Chaos to Clarity (Not Chaos to Calm)

Gray also shares why ZenPilot’s mission landed on “chaos to clarity” instead of something softer. The word operators kept using when describing their agencies was “chaos,” in a dozen different synonyms.

The instinctive fix sounds like “calm,” but running a real business with real clients is never calm. The actual antidote is clarity. Knowing what’s working, who has bandwidth, which clients are healthy, and where the risks are.

That framing is the backbone of the ZenPilot methodology. It’s the reason the new website leans so hard into transparency around process and pricing.

The New ZenPilot Website (Built with Claude Code)

ZenPilot was on HubSpot before, working with Lean Labs. Great team, great platform. But HubSpot was slow to update and most of the content needs didn’t match the features they were paying for.

Over three weeks, Gray and Ian on the marketing ops side rebuilt the entire site using Claude Code.

Start with brand guidelines

Before touching any page, write out the brand voice, visual system, and how social proof should appear. Feed that into Claude Code first so every subsequent prompt inherits the same direction.

Without this step, the output looks generic. It’s the same AI-flavored layout every other site is shipping.

Lean into humanity

When prospects book a call, they should know they’re talking to Alex, the head of delivery, not a nameless SDR. The new site leads with actual team members, actual quotes, and actual case studies instead of stock phrasing.

Make the methodology visible

The ClickUp Blueprint page shows the real price, the real process, and the real guarantee. Very few agencies in the ClickUp space are willing to publish that level of detail.

Gray thinks that’s a competitive advantage rather than a liability.

Clean up content debt. The old blog had posts from 2013 still floating around. The rebuild was the right moment to consolidate and retire the stale material instead of carrying it forward.

Trivia

Last week: ClickUp AI launched in February 2023 and was rebranded in 2024. To what name? ClickUp Mind, ClickUp Brain, ClickUp Intelligence, or ClickUp Assist? Answer: ClickUp Brain.

This week: How much funding did ClickUp raise in its October 2021 Series C round, led by Andreessen Horowitz? $200 million, $300 million, $400 million, or $500 million? Lock in your guess and we’ll reveal the answer next week.