Pilla vs UpKeep (2026): AI that acts inside the work, or a CMMS for assets, parts and PMs

I ask the same twelve questions on every comparison. For Pilla I describe what the product does today. For UpKeep I went back to their help, product pages and the live pricing page on 16 September 2026. Where they stay quiet, I stay quiet.

I am Liam Jones. I founded Pilla after more than ten years running hospitality operations, food safety and frontline teams. On 16 September 2026 I sat with UpKeep help: checklist templates, conditional logic, how to edit a checklist template, required tasks, work-order photos and files, Nova modes, Nova Workflows, work-order Activity, External Chat, the public API and the live pricing page. I have not lived in a paid UpKeep account for this write-up. I am telling you what their docs say.

I built Pilla for AI work management on the floor. UpKeep sells a CMMS for work orders, assets, parts and preventive maintenance.

You open Pilla on the phone you already carry. You see the next step, read how to do it, take the photo or sign, and move on. The record lands while you work. Pilla checks it against the rules you set and follows up when something needs you.

I hear the same thing from managers: they draw the process once and stop asking all day whether it happened. The team likes it because they can see what good looks like before they start.

A paid seat is anyone assigned work or who configures the system. Admin and technician cost the same. Requesters and view-only users are unlimited and free. Essential is $24 per user per month. Premium is $55. Professional and Enterprise are quoted. Every listed plan includes a Nova credit bundle: 250 on Essential, 500 on Premium, 750 on Professional and 1,000 on Enterprise. Custom checklists and preventive maintenance sit on Premium. Offline, the external request portal, full analytics history and work-order signature capture sit on Professional. API, SSO, purchase orders and the workflow automation row sit on Enterprise. Help labels Zapier as Enterprise. I could not find whether Zapier is broader. Implementation packages are $500, $1,500, $5,000 or custom. The SAP connector is $5,000 per year. Safety, Learn, Edge and Fleet are separate products. I could not find whether $24 and $55 are billed monthly only, or cheaper annually. I could not find Professional or Enterprise dollar rates, or a day count on the live trial form. Help says all plans can create one classic Automated Workflow and that Nova Workflows are on all paid plans for admins. I could not find how those nest with the Enterprise workflow-automation row.

You can open Pilla the same day. Every new account gets a 14-day trial of Pro, with no card. I usually see a first workflow take an afternoon. UpKeep advertises Try for free with no credit card, and you can invite the full team. I could not find a length in days on the live trial form. Professional, Enterprise, implementation packages and Edge sensors take a real rollout.

If you move, you rebuild the checklists on the canvas. Photos and history stay in UpKeep unless you export them by hand. Run both for a while. Keep the asset register, spare parts, purchase orders, preventive maintenance and sensors on UpKeep or another vendor. I did not build Pilla to be a CMMS.

If you want a process on a canvas today, start with Pilla. If you need assets, parts and preventive maintenance from one vendor, stay with UpKeep. If money is tight, I publish prices, and UpKeep publishes Essential and Premium. If you want AI in the run and an MCP server, I would pick Pilla even in a small team.

UpKeep keeps physical assets running. You take a request, turn it into a work order, attach an inspection checklist, schedule calendar or meter PMs, hold spare parts, and prove the job with photos, signatures and timestamps. I would stay on UpKeep for that CMMS depth: asset records, meters, parts, purchase orders, a PM calendar, and optional Edge sensors, Safety and Fleet. Labour timers and iOS GPS arrival prompts are why some teams stay.

I built Pilla so you can turn the processes you already know into workflows on a canvas. Your team follows them on a phone, tablet or the web app. Pilla checks completed work and handles the follow-up you configured. You keep judgement, coaching and the awkward calls. I left shift scheduling, payroll and HR out on purpose.

If I needed a real CMMS, with asset records, spare parts, purchase orders and preventive maintenance, I would keep UpKeep. That stack, plus optional Safety, Fleet and Edge sensors, is a fair reason to stay. If I wanted the work drawn on a canvas and AI acting inside the run, with DMs and MCP, I would use Pilla, and I would keep assets, parts and PMs somewhere else.