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In this live presentation from Accelerate 2024, Ivy Grant, SVP of Strategy and Operations at Twilio, explores Twilio’s cultural evolution, the challenges of scaling a “teenage company,” and how her team transformed the enterprise planning process by moving from homegrown BPM goal setting to a structured OKR and WorkBoard-enabled operating rhythm. She outlines the cultural obstacles, integration complexities, and strategic drivers that shaped Twilio’s shift toward focus, transparency, and collaborative execution.
The Challenge
- Fragmented, Siloed Operations Due to Rapid, Inorganic Growth:
Twilio’s fast expansion and multiple acquisitions—ranging from small companies to the multi-billion-dollar Segment acquisition—left the organization with siloed teams, disconnected processes, and limited integration across business units.
- Ineffective BPM Goal-Setting Process That Lacked Measurability and Visibility:
The legacy BPM system was home-grown, nonfunctional beyond storing text, encouraged storytelling instead of measurable goal setting, and provided no mechanisms for tracking progress or enabling cross-team visibility.
- Highly Autonomous Two-Pizza Team Culture That Impeded Strategic Alignment:
Small, independent teams excelled at ownership and speed but operated with minimal collaboration or shared standards, resulting in abundant activity without coherence toward company-level priorities.
- Misaligned Functional Structures and No Cross-Organizational Governance:
Product and sales organizations operated in conflicting matrices without effective governance, making coordinated planning and joint decision-making extremely difficult.
The WorkBoardAI Solution
- Established Company-Wide Focus on a Small Set of Strategic Outcomes:
Twilio replaced 10 disparate BPM priorities with three to five top-down company OKRs, enabling unified direction and reducing the proliferation of unaligned initiatives.
- Created a Shared, Scalable Planning Language Across the Enterprise:
Adopting OKR methodology—after a year of practicing without tooling—gave teams a common framework that replaced inconsistent storytelling approaches and supported disciplined, measurable planning.
- Enabled Transparency and Executive–Team Engagement Through System Visibility:
Broad read-only access and executive mid-quarter reviews encouraged real-time updates, fostered accountability, and increased engagement as leaders could directly observe progress and interact with teams via the platform.
- Accelerated Organizational Maturity and Change Adoption Through Structured Enablement:
Deep enablement—including certification programs, OKR champions, training cohorts, and iterative quarterly learning—helped embed the methodology, strengthened cross-functional collaboration, and prepared the company for a transformative new strategy.
Conclusion
By implementing WorkBoardAI and fully embracing OKRs, Twilio achieved a significant shift from scattered, bottom-up goal setting to an aligned, transparent, and focused enterprise cadence. The organization streamlined its strategic priorities, improved accountability through visible progress tracking, strengthened cross-team collaboration, and built the operational discipline required to support a more ambitious transformation strategy. Improved focus, engagement, and enterprise-wide clarity.
