Technical Program & Cross-Functional Leadership

Leading complex technical programs across teams, customers, and partners.

Connecting engineering, product, marketing, customer experience, and strategy to carry important work from ambiguity through execution.

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Keith Cunningham

How I Work

I bring structure and ownership to programs that span functions and company boundaries, connecting technical work, business priorities, and the people needed to deliver.

Understand

Build a clear picture before changing anything.

Align

Connect decisions to priorities and realities.

Execute

Resolve dependencies, remove blockers, and carry the work through delivery.

Strengthen

Build systems and cadence that scale with the company.

Endure

Leave a company better equipped for what’s ahead.

Where I Help

The work spans internal initiatives and external delivery, with ownership across four areas.

Program Definition and Delivery

Clarify the problem, define outcomes, establish ownership, and coordinate dependencies through execution.

Cross-Functional Execution

Align engineering, product, marketing, customer experience, and operations around priorities, sequencing, and decisions.

Customer and Partner Programs

Connect customer requirements and partner capabilities to technical integrations, deployments, and adoption.

Strategy and Program Decisions

Bring technical, commercial, and IP considerations into priorities and tradeoffs, working with leadership and specialists to move decisions into action.

The Pattern

The pattern has been consistent: pay attention, understand the system, find the leverage, and help the company move.

The work has centered on connecting people, priorities, and execution wherever a company needed that most. At Sylabs, that meant aligning product priorities and engineering and go-to-market sequencing, informed by customer requirements, partner opportunities, and strategic and IP considerations.

At RStor, as Business Program Manager and Senior Director of Customer Experience, I built the CX function, established onboarding and training, and led technical partner integrations. The role also included leading the Sylabs software spinout from identification through launch.

Earlier technical program leadership at EMC connected engineering, field sales, support, and customers on strategic cloud deployments, followed by product management for globally distributed cloud storage platforms. Across these roles, understanding the system and the people doing the work has shaped what happens next.

Systems thinking. Execution bias. Cross-discipline range.

The roles and engagements that work

The strongest fit is a technically complex program that needs experienced ownership across teams. That can involve an internal initiative, a product launch, a deployment, or work connecting customers and partners with engineering execution.

Open to full-time technical program and program leadership roles, plus select advisory and fractional engagements.

Company StageEarly- to growth-stage companies where the pace of work has outgrown informal coordination.

ComplexityOrganizations whose product, domain, or customers require depth to understand.

MissionMission-driven companies building the structure needed to match their ambition.

Leadership NeedProduct, engineering, and business leaders who need someone to understand the whole problem, coordinate across boundaries, and stay accountable through delivery.

Working StyleTeams that value direct communication, discretion, deep listening, and follow-through.

Reference

“Keith runs toward the problems most people walk around or try to ignore. He takes ownership without being asked and makes everyone around him better. No drama, no ego—he gets after it because it is what the organization needs to succeed.”

Jason Tuschen · Chief Executive Officer, QLAD · Command Master Chief (Ret.), U.S. Navy SEAL

Experience that travels

Experience where technology, operations, and strategy meet human needs.

⚑   Led a Launch

Led an open-source software spinout from identification through launch, building the operating foundation as the company grew.

⌘   Advanced a Technical Partnership

Work with partner DeciSym earned a DoD cyber-testing award and extended into a multi-year contract and new feature development.

⌁   Owned a Critical Deployment

Owned the customer escalation on EMC’s largest cloud storage deployment, coordinating engineering and leadership and helping earn the team the President’s Award.

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Field notes

Observations from the terrain.

Thoughts on technology, resilience, leadership, and the places that shape how we think.

Read the latest on Substack  →
A motorcyclist following a winding mountain road

Complexity is the terrain. Clarity is the path.

Keith Cunningham