Jessica Drumright-Cabalu

Jessica Drumright-CabaluJessica Drumright-CabaluJessica Drumright-Cabalu
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Jessica Drumright-Cabalu

Jessica Drumright-CabaluJessica Drumright-CabaluJessica Drumright-Cabalu
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About Me

I am an operations and program leader who designs the systems, operating models, and execution frameworks that help organizations scale. My work focuses on turning complex, fast-moving environments into clear, durable structures that improve visibility, execution quality, and business outcomes.


Across my career, I have led cross-functional initiatives spanning operations management, program delivery, resource planning, and technology implementation. I build planning systems, operating cadence, and workflows that reduce friction, improve efficiency, and give teams the clarity they need to do high-impact work. I am especially drawn to environments where ambiguity is high and the need for structure is critical.


I am deeply fluent in modern tools and platforms and approach technology as an enabler of better ways of working. From automation and AI-enabled workflows to planning frameworks and collaboration models, I focus on practical systems that improve how work moves from intake through delivery.


I am a San Francisco native, shaped by the pace, density, and constant evolution of the city. That environment taught me how to stay organized inside complexity, appreciate momentum, and build order without eliminating creativity. That balance shows up in how I work: structured but adaptable, rigorous but human.


Outside of work, I spend time with my family, explore new places, and stay active through yoga, Peloton, and movement that supports long-term energy and focus. Those practices keep me grounded and inform how I show up as both a leader and a partner to the teams I support.

HOW I HELP ORGANIZATIONS SCALE

I help organizations scale by designing the operating systems that sit between strategy and execution, and by ensuring those systems are measurable, trackable, and continuously improved. I work with leadership teams to establish clear goals, define success metrics, and build operating cadence that keeps teams aligned and accountable as complexity increases.


My work focuses on creating clarity through strong planning systems, well-defined operating models, and KPI- and OKR-driven execution frameworks that improve visibility, prioritization, and delivery quality across the organization.


What this looks like in practice:

  • Designing operating models that translate strategy into clear ownership, execution paths, and measurable outcomes
  • Establishing OKRs, KPIs, and executive reporting cadence to track progress, surface risks, and support timely decision making
  • Strengthening cross-functional delivery across complex, multi-workstream portfolios through shared metrics and dependencies
  • Reducing operational friction through workflow design, tooling, automation, and continuous performance review

Skills

Operating Model & Strategy

Operating Model & Strategy

Operating Model & Strategy

Design and execution of scalable operating models, planning systems, and governance frameworks that translate strategy into measurable priorities and outcomes.

Process & Workflow Design

Operating Model & Strategy

Operating Model & Strategy

Identification of bottlenecks and design of streamlined workflows that improve execution quality, reduce friction, and increase organizational throughput.

Cross-Functional Delivery

Operating Model & Strategy

Program & Portfolio Management

Leadership of complex, multi-workstream initiatives across technical, creative, and business teams, aligning dependencies, timelines, and ownership.

Program & Portfolio Management

Program & Portfolio Management

Program & Portfolio Management

End-to-end ownership of programs and portfolios, including planning, prioritization, risk management, and delivery cadence across global teams.

Data & Performance Insights

Program & Portfolio Management

Financial & Resource Planning

Design of KPI frameworks, dashboards, and reporting cadences that improve visibility, surface leading indicators, and support executive decision making.

Financial & Resource Planning

Program & Portfolio Management

Financial & Resource Planning

Oversight of budgeting, forecasting, and capacity planning to strengthen cost visibility, profitability tracking, and resourcing accuracy.

Tooling & Systems Enablement

Tooling & Systems Enablement

Tooling & Systems Enablement

Implementation and adoption of planning platforms, operational tools, and automation systems that improve how work moves from intake through delivery.

Change & Adoption

Tooling & Systems Enablement

Tooling & Systems Enablement

Operational rollout of new systems and ways of working, focusing on clarity, enablement, and sustained adoption rather than one-time change efforts.

Continuous Improvement

Tooling & Systems Enablement

Continuous Improvement

Ongoing refinement of operating cadence, workflows, and systems based on data, feedback, and evolving organizational needs.

Experience & Education

Experience

First Person, Inc., San Francisco Bay Area — Director of Operations

Nov 2022-Nov 2025


Led company-wide operations with ownership of operating cadence, planning systems, and cross-functional delivery across high-visibility initiatives. Designed and implemented scalable operating models that improved financial visibility, execution discipline, and organizational efficiency.


  • Reduced operating costs by 25% through improved governance, planning systems, and workflow optimization
  • Led multiple platform implementations across project management and budgeting, achieving 100% adoption and doubling visibility into forecasting and profitability
  • Partnered with executive leadership to align marketing, sales, and operations through unified pipeline and reporting systems
  • Built and scaled the project management function, strengthening execution quality and delivery predictability
  • Designed automation and AI-enabled workflows that reclaimed 10+ hours per week across teams



First Person, Inc., San Francisco Bay Area — Studio & Operations Manager

Jul 2016-Nov 2022


Led global program delivery and built early operational systems that improved execution predictability, resource visibility, and cross-functional alignment during periods of rapid growth.


  • Delivered large-scale, global B2B programs with 100% on-time execution
  • Built resource and staffing systems that reduced wasted effort by 20%
  • Streamlined workflows across creative, account, and production teams to improve consistency and delivery clarity



Camp Creative, San Francisco Bay Area — Project Manager

Aug 2012-Jul 2016


Delivered cross-functional marketing and digital projects while building foundational systems and execution discipline.


  • Led integrated projects across brand, content, design, video, and web with 100% on-time delivery
  • Implemented a project management system that improved workflow clarity and collaboration
  • Supported operational coordination that improved scheduling efficiency and team productivity

Education

Emerson College, Boston 

BA Post Production, Minor in Photography

Aug 2008-Jun 2012


Activities and societies: Varsity Volleyball Team, Emerson Independent Video. 

Contact ME

Drop me a line!

If you are building or scaling an operations function and need stronger execution systems, planning cadence, or delivery clarity, I would welcome a conversation.

Contact Me

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