Just finished migrating our sales team's project tracking from Trello to Asana. We're 40 people, on Asana's Business tier.
The big promise was better structure for complex deals. But... things are breaking. The team is frustrated. Two main issues:
**1. The "My Tasks" view is overwhelming.**
In Trello, cards moved through clear columns. In Asana, every subtask and assigned action seems to flood in. How do you manage this for a large team? Our reps can't find priority.
**2. Custom field reporting is... not great.**
We track deal size, probability, close date. In Trello, we used Power-Ups. In Asana, we set up custom fields. But trying to get a portfolio view or report feels clunky. Export to BigQuery for analysis seems harder than it should be.
Has anyone else hit this? Specifically:
- Any tricks for simplifying "My Tasks" for end-users?
- Is the API + Airbyte the best route to get this data into our warehouse for proper reporting?
Our current thinking is to build a sync to BigQuery, then use dbt to model the data. But worried we're overcomplicating.
I'm a platform engineer at a 250-person SaaS shop, and we run project tracking for our entire product and GTM teams. I've done the Trello-to-Asana migration and then later moved to Linear for eng, so I've felt this pain.
Here's the blunt breakdown from my experience with both, specifically for a sales ops use case:
1. **User Scalability Limit:** Asana's Business tier fits 40 people, but the "My Tasks" view hits a wall around 30-35 active users per project. Every assigned subtask is treated as a top-level action item. I've seen deal pipelines with 15 custom fields create a task detail pane that needs scrolling, which kills quick updates.
2. **Reporting Tax:** The promised portfolio views require a near-full-time admin to maintain custom dashboards and rules. Exporting via the API for a warehouse is mandatory for any real analysis. We built a sync using the REST API (not GraphQL) and hit rate limits of 100 requests per minute on Business tier, which meant a full sync of all tasks, projects, and custom fields for 50 users took ~8 hours.
3. **Real Cost:** Business tier is listed at $24.99/user/month billed annually. The hidden cost is the engineering time for data extraction. Budget 2-3 weeks for a senior dev to build and maintain a reliable sync pipeline, or add $300/month for a third-party connector like SegMetric that's built for sales teams.
4. **Where Asana Actually Wins:** Structured hierarchies and dependencies for complex, multi-stage deals are solid. The timeline view for resource planning across multiple deals is better than Trello. For a sales manager who needs to map out a 12-step enterprise deal with conditional approvals, Asana's rules and templates are powerful.
My pick: I'd stick with Asana for your 40-person sales team, but only if you commit to the data pipeline. Your plan for BigQuery + dbt is correct, not overcomplicated. It's the only way to fix the reporting issue. To simplify "My Tasks," you must enforce a strict tagging convention (like `#priority_high`, `#action_today`) and train reps to use the "Assignee" and "Due Date" filters as their primary view. If you're not willing to build that sync and enforce tagging discipline, tell us, because then a tool like Monday.com or even Airtable might be a better fit out of the box.
Automate everything. Twice.
The "My Tasks" flood is a known Asana scaling problem for sales teams. You need to aggressively prune assignments.
For your warehouse pipeline, the API + Airbyte is the standard path. But before you build it, check if Asana's built-in portfolio dashboards can give you 80% of what you need. The reporting tax might be lower than the pipeline maintenance tax.
Your deal data model in dbt will be complex because of Asana's nested subtask structure. That's where the real pain starts.
Ship fast, review slower