Obsidian

When to negotiate Obsidian

Vendor sales pressure is non-uniform — quarter-close, year-end, and post-funding-round are your high-leverage windows.

Low pressure window. Reps have time on their side. If you can wait, target the last 30 days of Q3 for materially better economics.

1. 1
   PRICING

   Obsidian starts on the free tier. What forces an upgrade — specific feature gates, usage caps, or support tier? Give me the realistic monthly bill at small scale.
2. 2
   CONTRACT

   Auto-renewal: how many days notice is required to terminate, and what happens if we miss the window? Will you commit to a renewal-reminder email at 90 and 60 days?
3. 3
   MIGRATION

   Data export: what's the complete spec — format, frequency, and what data does the export NOT include? After contract end, how long do we have read-only access?
4. 4
   MIGRATION

   Implementation runs Same day for basic use; weeks to tune a personal system. Who from your team is included by default, and who do we add at additional cost? Is a CSM assigned?
5. 5
   FIT

   Connect us with 2-3 reference customers at our company size in your industry — not the case-study list, customers who've been live for 18+ months.
6. 6
   INTEGRATION

   Obsidian lists 4 integrations including GitHub, iCloud Drive, Readwise. Which of OUR existing tools — bring our list — have you confirmed shipping integration with versus "on roadmap"? Show me the actual status.
7. 7
   VENDOR

   Track record over the last 18 months: any pricing model changes, executive departures, layoffs, M&A activity, or material customer churn we should know about?
8. 8
   VENDOR

   If you're acquired or shut down, what's the contractual continuity — source-code escrow, data portability, transition period? Show me the actual clause.

1. 1
   PERFORMANCE

   Bring YOUR data, not their demo data. Insist on running the demo workflow against a sample of your real records, files, or queries. If they refuse — that's a signal.
2. 2
   PERFORMANCE

   Obsidian demo will be built around the happy path. Ask: "Show me what happens when [the most common failure mode in our context]" — make them improvise.
3. 3
   EDGE CASES

   Push the limits live: largest dataset, longest workflow, most users concurrent. Vendors prep demos for medium loads — your real-world usage might 10x what they show.
4. 4
   EDGE CASES

   Mobile and offline behavior: how does Obsidian degrade on slow connections, on iPad, in airplane mode? Test in the demo if your team uses these surfaces.
5. 5
   PRICING

   Find the upgrade triggers. Which features force a paid plan? Which usage limits trigger overage? Get the rep to demo your team hitting each cap.
6. 6
   INTEGRATION

   Vendors love their integration logo wall. Test the actual depth: pick the 2-3 (GitHub, iCloud Drive-style) integrations you depend on most, and ask the rep to demo a real two-way data sync, not a marketing screenshot.
7. 7
   INTEGRATION

   API and webhook reality check: rate limits, payload size limits, retry behavior, auth refresh handling. Ask for actual API docs in the demo, not "we'll send those."
8. 8
   MIGRATION

   Demo the full data export workflow. Even with low lock-in, you want to see how clean the exit looks before signing.
9. 9
   SUPPORT

   Submit a real support ticket DURING the demo. Use the actual support channel customers use, not the rep's email. Time the response. This is your most honest data point about post-sale reality.
10. 10
    SUPPORT

    Ask to be connected with a customer in the demo who you can email TODAY (not "we'll arrange a reference call next week"). The vendor's confidence in their references is a tell.