W052019–21AI enablement / AutomationAIOps, enterprise26K tickets
Outcome
32%
increase in user adoption after integrating Pendo analytics and Salesforce into one AI-powered customer scoring system.
26,000support tickets migrated from Zendesk to Jira Service Management, zero security incidents
17percent increase in enterprise customer satisfaction via a Customer Advisory Board
100percent retention across a 3-person team hired and managed on performance frameworks

Migrating 26,000 tickets without a single security incident

01 / Context

Cross-functional initiatives for a cloud-native AIOps platform — event correlation, incident intelligence, automated decision support — while managing a team of direct reports and building execution frameworks that balanced AI-driven automation against security, compliance, and enterprise trust requirements.

02 / Problem

The platform automated incidents faster than enterprise customers trusted it to.

AI-driven operational capability needed to be explainable and trusted by real enterprise customers (a major airline, a large insurer) managing real incidents — plus a legacy support stack (Zendesk) fragmenting operational workflows underneath it all.

ZENDESK → JSM MIGRATION — DIAGRAM
FIG 01 — 26,000+ tickets, zero security incidents.

03 / Approach

Make automation something enterprise customers can trust, not just something that’s fast.

01Shape and execute a company-wide OKR framework tied to AI-driven operational outcomes, security posture, and platform reliability.
02Migrate the entire support operation — 26,000+ tickets — from Zendesk to Jira Service Management, without a security incident.
03Build a Customer Advisory Board as the execution bridge between technical, product, and enterprise customers.

04 / What I did

Hired and managed 3 direct reports across program management and technical operations, with performance frameworks and career development plans that held 100% retention.

Led delivery of AI-powered customer engagement and scoring systems integrating Pendo and Salesforce. Owned the full Zendesk-to-JSM migration while maintaining SOC compliance.

Role: Lead Program Manager · Cloud-native AIOps platform company · Nov 2019–2021 · 3 direct reports

05 / Outcome

40% improvement in cross-team alignment and compliance reporting from the OKR framework; 32% increase in user adoption from the scoring system; 17% increase in enterprise customer satisfaction from the Advisory Board — and the tooling consolidation landed with zero security incidents.

CUSTOMER ADVISORY LOOP — DIAGRAM
FIG 02 — Technical, product, and enterprise customers, one bridge.

06 / What I would do differently

I’d have sequenced the OKR framework before the Zendesk-to-JSM migration, not alongside it — running both at once meant the team was absorbing a new tool and a new set of metrics in the same sprint, and that’s more change than any team takes cleanly.