Technical Program Management · Product & Engineering Delivery · AI Transformation

Richard
Caliendo

I drive product and engineering programs to ship on commitment — surfacing risk early, clearing blockers before they slip a launch, and keeping cross-functional teams aligned and on-track. The result for leadership: time to plan forward instead of getting pulled into the weeds.

Get in Touch → View Experience
$120M+
ARR Portfolio Scope
1,500+
Engineers Enabled
6
Launches & AI Features Shipped
About

The TPM who ships
on commitment

I'm a Technical Program Manager who lives in the operational reality of product and engineering — roadmaps, dependencies, release trains, and the hard tradeoffs between scope, quality, and date. I run programs proactively: setting the plan, instrumenting the risk signals, and keeping multi-team delivery on-track so launches ship on commitment. And when something is already off the rails, I'm the person who diagnoses the real blocker and steers it back to GREEN.

I fluently navigate the technical roadmap and the engineering culture around it. I understand sprint mechanics, architectural dependencies, and where delivery risk actually hides — usually in the seams between teams, not inside any one of them. At Kaseya, I've driven this across a $120M+ ARR backup SaaS portfolio, partnered with Boston Consulting Group on product repositioning, delivered 2 major launches and 4 AI-powered features, and scaled AI tooling across 1,500+ engineers.

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 deeper differentiator: I built early-warning risk detection and team-recovery into a discipline because I understand the human system as well as the technical one. A graduate background in education and psychology, developed over my career into real expertise in organizational change, motivation, and performance, means I can read where a team is breaking down and intervene before the status report turns red. The result for leadership: executives get to plan forward, not react.

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.

Operating Principle
"Risk is cheapest to kill early. The job is to see it before it's on the dashboard."
The Value to Leadership
RED programs returned to GREEN — so executives spend their time planning forward, not firefighting.
Education
M.S. Education & Psychology, 3.96 GPA — The College of Saint Rose
B.A. Psychology, 3.87 GPA — SUNY Oneonta
Core Capabilities

Built to deliver
under risk

01
On-Track Program Delivery
Owning complex, multi-team programs end to end — setting the plan, holding the line on commitments, and getting launches across the line. When a program does go off-track, diagnosing the real issue and steering it back to GREEN.
02
Early Risk & Blocker Mitigation
Surfacing delivery risk before it reaches the dashboard — instrumenting dependency tracking, escalation paths, and blocker-clearing mechanics that keep release trains moving and protect committed dates.
03
Product & Engineering Roadmap Fluency
Speaking the language of product and engineering — roadmap planning, architectural dependencies, sprint and release mechanics, and the scope/quality/date tradeoffs that determine whether a launch ships.
04
Cross-Functional Delivery Orchestration
Driving execution through the seams between Product, Engineering, GTM, and Finance — where most programs stall — with the stakeholder management to align competing priorities and keep teams committed.
05
AI Enablement & Productivity Systems
Scaling AI tooling and governance across engineering orgs — deploying developer-productivity workflows, adoption frameworks, and ROI models that translate AI investment into measurable delivery velocity.
06
Team Recovery & Human Performance
Reading where a team is breaking down before it shows in the metrics — applied expertise in organizational change, motivation, and performance management that turns struggling teams into delivering ones.
Tools & Stack

Fluent in the
modern delivery stack

Program & Delivery
Jira Confluence Asana Atlassian Rovo Agile / Scrum SAFe Release Management Dependency Mapping Roadmap Planning KPI Dashboards
AI & Developer Tooling
Claude Code GitHub Copilot Cursor Lovable Codex M365 Copilot GitHub AI Governance Prompt & Workflow Design LLM Evaluation
Microsoft & Automation
Power Automate Power Apps Microsoft Studio Power Platform Power BI Microsoft 365 SharePoint Teams Zapier Process Automation
Data & Analytics
SQL Tableau Looker Snowflake Google Analytics Mixpanel Amplitude Excel / Sheets Data Modeling Cohort Analysis
Cloud & Engineering
AWS Azure SaaS Architecture GCP REST APIs CI/CD Pipelines Microservices Cloud Cost Optimization Datadog PagerDuty
Product & Collaboration
Productboard Figma Slack Notion Miro Loom Salesforce Gainsight Zendesk Customer Discovery
Experience

A career built on
measurable impact

Kaseya
Aug 2025 – Present
Associate Director, Technical Program Management
  • Orchestrated cross-functional execution across product, engineering, and GTM in partnership with Boston Consulting Group, driving market repositioning and pricing strategy for a ~$120M+ ARR backup SaaS portfolio
  • Managed senior stakeholders across competing priorities to scale AI adoption across 1,500+ engineers and product leaders, driving ~23% improvement in developer productivity
  • Delivered 2 major product launches and 4 AI-powered features, navigating shifting priorities and incomplete information to keep execution on course
  • Developed executive ROI models linking AI investment to ~20% cost reduction and innovation velocity, informing multi-million-dollar decisions
  • Drove AI-powered product strategy targeting ~25–30% efficiency gains in customer operational cost reduction
Kaseya
Aug 2024 – Aug 2025
Associate Director, Training & Development
  • Architected enterprise-wide leadership enablement strategy across a 5,000+ employee global technology organization
  • Designed the company's first enterprise goal cascading system, aligning Sales, Engineering, Support, and Operations to strategic priorities
  • Co-developed Manager Development Program in partnership with Gallup, embedding coaching-based leadership accountability across revenue-facing teams
  • Built KPI dashboards linking manager effectiveness to engagement, execution consistency, and business performance
Kaseya
Jul 2023 – Aug 2024
Manager, Training & Development
  • Led technical, compliance, and leadership development programs across global teams
  • Modernized LMS ecosystem and designed onboarding/certification frameworks improving ramp efficiency
  • Supported early-stage AI governance and education initiatives preparing workforce for emerging AI workflows
Banyan Health Systems
Sep 2021 – Jun 2023
Manager of Clinical Training
  • Directed training strategy across multidisciplinary healthcare teams
  • Built data-driven capability development programs tied to retention and performance outcomes
NY State Office of Mental Health
Jun 2020 – Aug 2021
Program Specialist
  • Led training and technical assistance for a $125M statewide initiative supporting 60+ agencies
  • Designed large-scale learning collaboratives and cross-agency programs at the policy level
Featured Work

Programs shipped,
commitments kept

Delivery & Risk Management
RED → GREEN Launch Recovery
Stepped into a backup-product roadmap misaligned with market and customer needs and at risk of slipping commitments. Reframed priorities around high-value customer use cases, surfaced and cleared cross-team blockers early, and resequenced delivery — landing 2 major product launches and 4 AI-powered features and restoring leadership confidence in the date.
2 + 4
Launches + AI Features
On Time
Committed Dates Held
AI Transformation
Enterprise AI Enablement at Scale
Led AI productivity enablement across 1,500+ engineers — deploying tools including Claude Code and Lovable with governance, adoption tracking, and executive ROI dashboards that tied tool adoption directly to feature-delivery velocity and faster time-to-value for customers.
23%
Dev Productivity Gain
1,500+
Engineers Enabled
~20%
Cost Reduction
Executive Strategy
BCG Partnership: Market Repositioning
Partnered with Boston Consulting Group on an executive task force driving market analysis, product repositioning, and pricing strategy for Kaseya's backup SaaS portfolio — grounding roadmap and monetization decisions in real enterprise buyer expectations and customer use cases at a majority-ARR scale.
$120M+
ARR Scope
BCG
Partner
Organizational Design
Enterprise Goal Cascading System
Designed and launched the company's first enterprise-wide goal cascading system at Kaseya, aligning Sales, Engineering, Support, and Operations across a 5,000+ person global organization. Built KPI dashboards linking manager effectiveness to engagement and execution outcomes.
5,000+
Employees Aligned
First
System of Its Kind
Leadership Development
Gallup Manager Development Program
Co-developed a comprehensive Manager Development Program in partnership with Gallup — embedding coaching-based leadership and performance accountability frameworks across revenue-facing teams at a global SaaS organization.
Full Case Study — Coming Soon
Gallup
Partner
Global
Scale
Consulting & Thought Leadership

Expert contributions
across sectors

SimonSez IT
Leadership Development Author
Created and published leadership development curriculum for one of the largest online software training platforms — reaching professionals across industries on management, productivity, and performance systems.
LearningMate
Psychology Subject Matter Expert
Provided expert advisory on psychology-informed learning design — bridging behavioral science and instructional design for enterprise and academic learning programs.
Foundation for Health Leadership
Integration Specialist
Supported healthcare leadership integration initiatives, applying organizational development and performance frameworks to complex, mission-driven environments.
Connect
Let's Connect

Ready to build
something exceptional?

I'm selectively exploring Director-level Technical Program Management roles — or a senior technical IC role at the right company. If you have programs that need to ship, and leadership that would rather plan forward than get pulled into the weeds, let's talk.