rc.Richard Caliendo

Technical program leadership

Richard
Caliendo.

Complex strategy.
Executable systems.

I connect strategy to Product and Engineering execution across SaaS transformation, Cyber Resilience, and enterprise AI.

View resume Explore the work

Staff Technical Program ManagerProduct & Engineering, Kaseya

Hollywood, FloridaRemote US-wide / South Florida

Selected evidence

Scope, delivery & program scale

Enterprise AI enablement

1,500+

Engineers and product leaders in the adoption program.

AI transformation

Cyber Resilience delivery

7

Customer-facing launches in 2026, including Portal alpha and early access.

Release record

FY26 revenue program

Multi-million

Targeted revenue impact across retention and reactivation.

Portfolio execution

01 Selected transformation work

The complexity is real.
So is the execution.

Three views into the work: align a portfolio, enable an organization, and connect delivery to business priorities.

01 / Portfolio & platform In progress

A shared foundation.
A coordinated migration.

Turning a multi-product Backup portfolio strategy into sequenced execution toward a natively built object-storage data plane.

My role
Program leadership across Product, Engineering, and cross-functional dependencies.
The execution system
Migration workstreams. Jira-aligned roadmaps. Source-linked dashboards. Clear escalation paths.

Cyber Resilience / Backup SaaS / Cloud readiness

Portfolio transformationExecution view
ProductsPlatformsCustomers
Program orchestrationDefine. Sequence. Align.

Workstreams · Roadmaps · Decisions

Shared technical foundationObject-storage data plane
Platform
simplificationPublic-cloud
readinessInfrastructure
cost objectives

Target direction. Migration is in progress.

Inside the program

Where the ambiguity lived

Teams did not yet share migration definitions, ownership, sequencing, or roadmap maturity. Some Product and Engineering leads were unclear how their work mapped to the broader migration.

What I put in place

Migration workstreams, epic hygiene standards for Product Owners, a portfolio dashboard tied to source epics, per-product migration sessions, office hours, and escalation paths for unresolved decisions.

The decisions around delivery

Sequencing depends on Architecture, Infrastructure, Security, Finance, cloud-provider strategy, customer migration, and regulatory requirements. I distinguish executable commitments from milestones contingent on upstream decisions.

The strategic context

The shared foundation supports objectives for lower infrastructure cost, fewer strategic platforms, public-cloud deployment, and FedRAMP and regulated-market readiness. These are program objectives, not claims of achieved savings or certification.

02 / Enterprise AI enablementGovernance to adoption

From access to tools.
To organizational capability.

Led AI adoption and enablement for 1,500+ engineers and product leaders, connecting tooling, responsible use, workflow integration, and measurement.

My role
Adoption and enablement leadership, tool consolidation, governance, and executive ROI models.
Evidence
Dashboard-tracked productivity lift and ROI models informing multi-million-dollar funding decisions.
1,500+

Engineers &
product leaders

  1. 01
    Consolidate

    Claude, Codex, Cursor, Lovable

  2. 02
    Enable

    Peer community, workflow integration, onboarding

  3. 03
    Govern & measure

    Responsible use, adoption tracking, executive ROI

Inside the enablement system

The organizational problem

AI coding tools were arriving quickly, but adoption was inconsistent and difficult to connect to business value. Tool access alone did not establish effective use.

From experimentation to practice

Consolidated tooling with Claude as the primary adoption focus. Built a peer-led AI Enablement community with best practices, responsible-use principles, and MCP showcases. Built the governance and an automated AI tool onboarding workflow in Jira that brought speed and precision to provisioning. Newly hired engineers and product leaders started with the right tools and guardrails in their first week.

A measurement layer

With no established velocity baseline in a Jira environment and SDLC not set up to track it, designed a framework using Atlassian Rovo agents and Claude via MCP to cross-analyze Jira telemetry across Product and Engineering teams against AI tool usage. Rolled the findings into ROI metrics for leadership, including a measurable productivity lift.

03 / Revenue & portfolio executionBusiness priorities to delivery

The business objective
needs an operating system.

Program-managed the H1 strategic initiatives portfolio targeting multi-million-dollar FY26 revenue impact across retention, evergreen, and customer reactivation.

My role
Cross-enterprise program execution and partnership with Marketing leadership on customer-centered positioning.
Strategy partnership
Partnered with BCG and executive leadership on Backup portfolio analysis, repositioning, and pricing, translating recommendations into roadmap, GTM, and delivery execution.

FY26 targeted impact

Multi-milliondollar revenue portfolio
  • 01 Churn reduction
  • 02 Evergreen
  • 03 Customer reactivation

Program targets, not realized revenue.

What execution readiness reveals

A separate growth-readiness diagnosis

A company growth objective for a cloud backup offering was not converting into meaningful new revenue. I investigated gaps in seller awareness, CRM data quality, incentive alignment, and GTM activation.

The finding

The objective had been treated as an execution commitment before the commercial operating system required to deliver it was validated. The dependencies spanned Product, Marketing, RevOps, Sales, and Compensation.

Delivery record / 2026

7 launches.
Connected execution.

Cross-team dependencies, launch risk, and GTM readiness across Cyber Resilience.

Selected capabilities shown. The count includes released customer-facing capabilities only, including Portal alpha and early access. Future targets, POCs, internal validations, and in-progress work are excluded.

  • AI-powered backup screenshot verificationReleased
  • Azure Files backup and restoreReleased
  • Azure Blob backup and restoreReleased
  • Agentless Hyper-V backup and restoreReleased
  • Unified Cyber Resilience PortalAlpha + EA
Portal release progression
  1. H1 2026AlphaAnnounced at Kaseya Connect
  2. June 2026Early accessEarly-access release
  3. Next phasePath to GAOngoing refinement and release readiness

02 How I operate

Make the dependencies visible.
Make the decisions possible.

I work where executive strategy meets Product and Engineering reality. The job is to build the structure that lets teams move together.

  1. 01 / Ambiguity

    Find the gaps.

    Surface unclear ownership, competing priorities, and hidden dependencies.

  2. 02 / Structure

    Build the system.

    Define workstreams, roadmaps, source-linked dashboards, and escalation paths.

  3. 03 / Alignment

    Connect the teams.

    Bring Product, Engineering, Infrastructure, Finance, GTM, and leadership into the plan.

  4. 04 / Execution

    Make it deliverable.

    Separate commitments from contingencies. Keep delivery risk and decisions visible.

Engineering onboarding & enablement

Help new practices take hold.

I launched Kaseya's first global New Employee Orientation and ran its self-paced learning ecosystem. In Product & Engineering, I built governance and a Jira workflow for AI tool provisioning, helping new engineers and product leaders start with access and guardrails in their first week. Peer guidance and feedback helped turn access into daily practice for 1,500+ engineers and product leaders.

Hands-on, I build with Claude Code and Codex, mostly in TypeScript and JavaScript. Projects include a multi-agent desktop orchestration app built with Electron and React and running a local open-weight model via llama.cpp, a Jira MCP server, this site built with Codex and deployed on Netlify, an e-commerce agent, and an AI lesson-plan engine for StandardCraft.

  • New-hire orientation
  • First-week AI access
  • SME-led guidance

Adoption, incentives, and cross-team friction belong in the plan from day one.

The human systems matter, too.

03 Career trajectory

A consistent discipline.
An expanding scope.

From human and organizational systems to enterprise transformation, technical programs, and SaaS execution.

KaseyaAug 2025 – Present

Staff Technical Program Manager,
Product & Engineering

Formerly Associate Director, Technical Program Management

Product and Engineering execution across Backup portfolio consolidation, object-storage migration, Cyber Resilience launches, and enterprise AI adoption.

Explore the programs
KaseyaAug 2024 – Aug 2025

Associate Director,
Training & Development

Enterprise goal cascading and manager enablement across a 5,000+ employee global technology organization.

Organizational operating systems
  • Designed and launched the company's first enterprise goal-cascading system across Sales, Engineering, Support, and Operations.
  • Co-developed the first leadership development program with Gallup, embedding coaching-based accountability across revenue-facing teams.
  • Built KPI dashboards connecting manager effectiveness to engagement, execution, and revenue.
KaseyaJul 2023 – Aug 2024

Manager, Training & Development

Launched the first global New Employee Orientation program and operationalized the self-paced learning ecosystem.

Workforce enablement

Designed mandatory and role-based e-learning across Code of Conduct, AI literacy and policy, cybersecurity, and product knowledge. These early AI governance programs prepared the workforce for the enterprise AI rollout that followed.

Administered the learning system and built 30-60-90 development plans, using learner data to improve programs.

Banyan Health SystemsAug 2021 – Jul 2023

Manager of Clinical Training and Development

Led the clinical training lifecycle across multidisciplinary teams and the implementation of WELLE Behavioral Emergency Safety Training.

New York State Office of Mental HealthJun 2020 – Aug 2021

Program Specialist

Research Foundation for Mental Hygiene

Designed training for 55 provider agencies launching a statewide FEMA Crisis Counseling Program. Served as SME to the NYS Psychiatric Institute and Center for Practice Innovations; co-authored reports to NYS and FEMA.

Education & selected authorship

Education

M.Ed., Community Mental Health Counseling
The College of Saint Rose · GPA 3.96

B.A., Psychology
SUNY Oneonta · GPA 3.87

Selected authorship & subject-matter work

SimonSez IT / Leadership Development Author
Published leadership development curriculum on management, productivity, and performance systems.

LearningMate / Psychology Subject Matter Expert
Advised on psychology-informed learning design for enterprise and academic programs.

04 Tools in context

Capability first.
Tools in service.

Tools used for program delivery, enablement, and measurement. Technical domains reflect the programs I lead.

Program systems
Jira, Jira Plans, Confluence, Asana, Atlassian Rovo agents
Product & Engineering
Agile / Scrum, SAFe, launch governance, dependency mapping, release management
AI enablement
Claude Code, Codex, GitHub Copilot, Cursor, Lovable, M365 Copilot, MCP
Hands-on build stack (AI-assisted)
TypeScript, JavaScript, React, Electron, llama.cpp (local inference), Git and GitHub, Netlify
Onboarding systems
Global new-hire orientation, role-based learning, LMS administration, 30-60-90 plans, Jira-based AI tool onboarding
Analytics & automation
Power BI, Excel, Power Automate, Power Apps, Zapier
Cloud & SaaS domains
Object-storage migration, public-cloud migration, Microsoft Azure, Backup & BCDR, FedRAMP readiness
Collaboration
Microsoft 365, SharePoint, cross-functional operating cadences

05 The full record

The context.
The career.
The resume.

Experience, education, and program delivery in one document.

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06 The next conversation

Let's discuss
what comes next.

Exploring Staff and Principal TPM roles and Director-level technical program leadership across SaaS, enterprise software, cloud, and AI.

Hollywood, Florida · Remote US-wide or South Florida

EmailRichard.Caliendo@outlook.comLinkedInConnect with RichardPhone(518) 944-1138