Webhook delivery retries

Reliability
Aligned with:Reliability

Webhook delivery is the #1 reliability complaint this quarter. Customers report missed events with no retry. Eng has a clean fix scoped at 1 sprint with dead-letter queue.

Evidence

Recommendation

Defer· Q4 Sprint 1· 1 sprint· high confidence

I recommend deferring this. Real pain but capped impact. $92k ARR mentioned vs $2M+ in Q3 priorities (Enterprise + SOC2). Recommend Q4 — keeps Reliability OKR alive without crowding out higher-ROI work.

Reliability OKR partial credit — but the ticket-volume KR depends on this.

· AI picked this — click to switch
Predicted outcome: If deferred to Q4: 18 open tickets accumulate ~+30% in Q3 (CS friction). $92k ARR remains exposed. If volume spikes mid-Q3, AI will resurface for review.

Trade-offs · what shifts in the roadmap

  • Deferring Q3 → Q4 frees 1 sprint-effort in Sprint 2, providing buffer for Bulk CSV slippage.
  • CS team will push back — they've been promising customers a Q3 fix.
  • If support volume keeps climbing, we may need to revisit mid-Q3.

Q3 sprint context · where this lands

Sprint 1· Jul 1
0/6
Open · 6 capacity available
Sprint 2· Jul 15
0/6
Open · 6 capacity available
Sprint 3· Jul 29
0/6
Open · 6 capacity available
Sprint 4· Aug 12
2/6
  • Permission groups (vs individual ACLs)(2sp)
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