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#110: Why AI makes systems thinking the most valuable skill for PMs | Apurva Garware (ex-VP Product at Upwork, ex-Amazon)

May 11, 2026
Apurva Garware, VP Product with leadership at Invisible Technologies, Upwork, Amazon and Microsoft. He argues systems thinking beats evals or prompt skills for AI products. Short takes cover handling non-determinism, designing guardrails, escalation heuristics, and building internal operational systems alongside customer products. Practical advice on starting with internal workflows and avoiding needless AI complexity.
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ANECDOTE

Beyonce Lemonade Exposed Contextual Blindspots

  • Apurva recalled a Beyonce Lemonade spike where search queries returned drink pages, crashing conversion despite the algorithm working as designed.
  • The team added classifiers and a cold-start boost to detect media queries and surface the correct media ASINs, fixing the conversion drop.
INSIGHT

Non-Determinism Makes Systems Thinking Essential

  • Non-deterministic AI systems require systems thinking because components can behave probabilistically and fail at runtime in ways you didn't design for.
  • You must design guardrails, monitoring, and escalation paths to catch runtime issues like unsafe multi-turn conversations or refund spikes.
ADVICE

Govern AI With Three Phase Controls

  • Split AI product work into design, deployment, and production phases and require must-have checks at each stage before advancing.
  • Define agent contracts, run benchmarks during deploy, and create runtime human-in-the-loop escalations for anomalies like refund thresholds.
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