Quick take: Terra Security raised $30M Series A (led by Felicis with Dell Technologies Capital, SVCI, SYN Ventures, LAMA Partners, Underscore VC) and added Gerhard Eschelbeck (ex‑Google CISO) to its board.
Terra’s big idea: a continuous, agentic‑AI penetration testing platform with a human‑in‑the‑loop—so findings are exploited, validated, and mapped to business risk, not just scored.
What’s New (And Different)
Always‑On, Not Annual. Terra runs all the time, reducing blind spots between point‑in‑time tests.
Exploit‑Driven Proof. Agents validate real exposure before flagging it, so your team isn’t drowning in hypotheticals.
Business‑Context Aware. Results land with impact, not just CVSS numbers.
Human Oversight. Expert pentesters guide the swarm for depth, safety, and precision.
Translation for CS leaders: fewer security fire drills, cleaner launches, and stronger renewal stories.
If you want the broader context for the agent era, my analysis in Databricks Hits $4B—What CS Leaders Should Do Now explains how agentic workflows are going mainstream and how to turn reliability into NRR proof. It’s worth a skim before you set your 2025 plan (see ).
Why This Matters For Customer Success
1. Faster, Safer Onboarding.
Continuous testing finds blockers before go‑live, which cuts time‑to‑first‑value. If you’re standing up CS from scratch, use my Build Customer Success From Zero: 7‑Day Plan + Checklists to wire basic security guardrails from day one.
2. Fewer Incidents, Calmer QBRs.
Validated findings and safe fixes mean fewer escalations right before renewals. For a practical security lens, compare with my breakdown of device posture automation in Remedio Raises $65M: Why Device Posture Management Matters To Customer Success.
3. Credible Revenue Stories.
Tie “risk removed → launch on time → adoption ↑ → renewal probability ↑.” My 15 Churn Alerts Every CS Leader Needs shows how to turn security and usage signals into renewal saves and expansion plays.
4. AI Readiness Needs Clean Data.
Agent workflows fall down without governed, real‑time data. See the agentic MDM approach in Syncari Series B: Agentic MDM For AI-Ready Customer Data—then mirror those data hygiene habits in your CS plans.
What To Do In 90 Days (Copy/Paste)
Days 0–30 — Make Security A Lane In Your Success Plan
Add a “Security & Resilience” section to every Success Plan (exceptions, owners, SLAs, go/no‑go gates). Steal the structure from my Free Customer Success Plan Template | Boost Your CS Strategy.
Baseline: onboarding days, security exceptions per go‑live, P0/P1 incident rate, and rework hours.
Create a shared Slack/Teams channel with SecOps for pre‑launch triage.
Days 31–60 — Pilot Continuous Testing With 3 Accounts
Pick one high‑stakes launch per segment. Ask Security to mirror Terra‑style continuous tests across app, infra, and identity.
Turn top 3 recurring findings into preventive checklists and in‑product nudges.
Update health scores with a Resilience signal (e.g., “no open criticals 14 days pre‑launch”).
Days 61–90 — Prove It In The QBR
Show a one‑slide before/after:
“Exceptions ↓, onboarding days ↓, P0/P1 ↓, adoption ↑.”
Link those deltas to pipeline unlocked and renewal risk reduced.
If you need alert wiring for the story, the 15 Churn Alerts post gives exact patterns.
Metrics That Move NRR (Track These)
Time‑to‑first‑value (TTFV) per segment
Security exceptions per launch (and time‑to‑close)
P0/P1 incidents per 30 days after go‑live
Change failure rate tied to releases
Renewal probability shift when “no open criticals” at T‑14
For more background on making AI & security measurable inside CS, see Databricks Hits $4B—What CS Leaders Should Do Now and Syncari Series B: Agentic MDM For AI-Ready Customer Data.
My Takeaway
Pen tests that behave like real attackers—and never sleep—turn security from a compliance exercise into a customer experience advantage.
CS should co‑own this with Security: fewer delays, fewer surprises, and clearer business outcomes.
If you want help packaging this motion—playbooks, talk tracks, and the one‑slide QBR story—my weekly briefings walk you through it step by step.
—Hakan | Founder, The Customer Success Café Weekly Newsletter