The result is a program that does two things at once:

1. Deflects questionnaires by answering common questions up front
2. Builds buyer confidence by making proof easy to find (and easy to trust)

It’s a subtle shift, but a powerful one: transparency isn’t a compliance output; it’s a buyer enablement strategy. And in competitive deals, that matters.

2) Build the internal “village” to power customer trust

Jon’s first takeaway was simple, and it’s exactly why it works:

1. Build tight relationships with GRC, product security, product, HR, legal, and other teams.
2. Treat them like partners in the outcome, not ticket-closers.
3. Establish “champions” across functions so you can pull the right experts in fast.

This is how you turn customer assurance into an actual program (not heroics). It’s also how you avoid the common trap where customer trust work becomes a bottleneck because only one person knows how to get things done.

3) Measure customer assurance like a revenue function

One of the strongest parts of the discussion was how Cribl frames impact in business terms. This is especially helpful for leadership that doesn’t want a report of “tasks completed.”

Here are top 3 clear metrics that Cribl uses to track customer assurance work:

1. % of closed-won deals touched by the assurance team
2. SLA performance for questionnaire turnaround (P1/P2/P3-style responsiveness)
3. Cycle-time reduction from weeks of back-and-forth down to days (and sometimes faster)

80% of all closed deals at Cribl go through my team.

– Jon Zayicek (Customer Security Assurance Leader, Cribl)

When you connect assurance activity to pipeline stages and closed-won outcomes, you stop debating whether the work is “important.” The numbers make the case.

4) Start with a strong baseline questionnaire (AI depends on it)

Myke’s message was clear: AI doesn’t save you from foundational work; it rewards it.

His recommendation:

1. Start with a baseline questionnaire you believe asks the right questions for your business.
2. Build and maintain a knowledge system behind it.
3. Keep it fresh, because in fast-growing companies, answers change quickly.

If your answers are inconsistent or scattered across docs, AI will amplify the mess. But if your knowledge is curated and governed, AI becomes a force multiplier.

5) Use AI to scale the work through software, not headcount

Cribl’s team talked about AI in the most pragmatic way possible: customer trust is one of the lowest-risk, highest-leverage places to deploy it.

Why?

1. Questionnaire work is repetitive and pattern-based.
2. The “ground truth” can be anchored in approved evidence.
3. The output is measurable (answer rate, accuracy, reuse, time saved).

Myke’s underlying point was strategic: organizations are being pushed to “do AI,” but the smart move is to apply it where it creates real business value, and customer assurance is a perfect starting point.

6) Integrate assurance into sales for maximum recognition

Sravish added the importance of integrating customer assurance into the sales function.

“If you want customer assurance to be taken seriously, integrate it into the sales function, not as a handoff, but as part of how deals move forward.”

– Sravish Sridhar, CEO, TrustCloud

This isn’t just about reporting. It’s about operational integration:

1. Assurance signals flowing into the CRM
2. Sellers knowing when and how to route requests
3. Leaders seeing assurance as part of the revenue engine, not an external dependency

This is how customer assurance teams get recognized! In the webinar, Cribl shared how customer assurance contributions were visible enough to earn real recognition from revenue leadership (like an invite to the President’s Club and a trip to Hawaii).

Questions from the audience

Q: How should teams think about tiering vendors and what to share at different stages?

A: The guidance was to keep tiering practical (often 3 tiers works), focus on “crown jewels” and use cases, and standardize wherever possible, especially for repeatable assessments.

Q: How do you go beyond documents and move toward continuous proof (especially for audits)?

A: The direction was clear: move toward automated control testing where it makes sense, and provide “status-style” indicators (think traffic lights) that show how controls are performing, without dumping sensitive internals.

Q: What belongs in a trust portal if you want buyers to actually use it?

A: Substance: real artifacts, current evidence, and proactive updates (including vulnerability communications). The point is to reduce buyer effort and prevent “one more email / one more questionnaire.”