Richard Caliendo

I'm a Technical Program Manager who lives in the operational reality of product and engineering — roadmaps, dependencies, release trains, and the scope-quality-date tradeoffs that decide whether a launch ships. I run programs end to end: set the plan, instrument the risk signals, hold multi-team delivery on commitment, and ship.

At Kaseya, I run cross-cutting programs across the Cyber Resilience / Backup SaaS portfolio: a majority-ARR portfolio realignment in partnership with Boston Consulting Group, an H1 strategic initiatives portfolio targeting $6.4M in FY26 revenue impact across churn reduction, evergreen, and customer reactivation, 7 Cyber Resilience product launches shipped in 2026 YTD, and AI tooling rolled out to 1,500+ engineers with a measurable, dashboard-tracked productivity lift. The work that actually moves these programs forward happens in the seams between teams — that's where delivery risk hides, and that's where I operate.

Everything I do is customer-centric by default — roadmap priorities trace back to real customer use cases, compliance demands, and the value the product actually realizes in the field. The point of program rigor isn't process for its own sake; it's shipping the right thing, on time, that customers feel.

The differentiator most TPMs don't have: a graduate background in counseling and organizational change, converted over a decade into operator instinct for the human system inside every technical program. It doesn't show up as a credential on my resume. It shows up in how I read a stuck team, how I broker alignment between leaders with competing priorities, and how I see a program breaking down before the metrics catch up. The result for leadership: time to plan forward instead of getting pulled into the weeds.

I'm based in South Florida and actively exploring Director-level Technical Program Management roles, or a senior technical individual-contributor role at the right tech company — in SaaS, enterprise software, and AI-native environments.