Senior Program Manager, Enablement

Summary

Join Twilio as a Senior Program Manager and lead the design, launch, and evolution of programs that enhance the People Partnerships team. Partner with team members and business leaders to identify and address enablement gaps. Design and deliver engaging training experiences, develop enablement materials, and drive change management strategies. Measure program impact and continuously seek improvement opportunities. Act as a trusted advisor to stakeholders, influencing enablement across teams. This remote role, based in Canada, requires occasional travel.

Requirements

• 5+ years of experience in program or project management, with demonstrated experience leading enablement, learning, or talent-focused initiatives
• Proven ability to design, manage, and scale cross-functional enablement programs in a matrixed, fast-paced environment
• Experience creating engaging content and enablement materials (e.g., playbooks, onboarding guides, presentation decks, toolkits), with a focus on adult learning principles, internal comms, and behavior change
• Strong facilitation skills and experience delivering live and asynchronous trainings to diverse audiences
• Demonstrated ability to influence without authority and build trusted partnerships with stakeholders at all levels, including senior leadership
• Excellent communication skills, with experience crafting clear, compelling messaging to support enablement, change management, and adoption
• Highly organized and detail-oriented, with the ability to manage multiple programs simultaneously, prioritize effectively, and drive execution through ambiguity
• Comfortable using project and content management tools
• Experience creating engaging content and enablement materials (e.g., playbooks, onboarding guides, presentation decks, toolkits), with a focus on instructional design, adult learning principles, internal comms, and behavior change

Responsibilities

• Lead the strategy, roadmap, and execution of Twilio’s cross-functional enablement programs (e.g., team enablement, role clarity frameworks, onboarding playbooks, tools adoption)
• Partner with your team and business leaders to identify enablement gaps and build scalable, repeatable solutions that drive behavior change and performance
• Design and deliver engaging, learner-centered training experiences — from live sessions to self-guided toolkits — ensuring content is actionable, relevant, and aligned with business priorities
• Develop enablement materials and resources such as presentations, job aids, playbooks, onboarding guides, and tool walkthroughs to support knowledge transfer at scale
• Drive change management and communication strategies that promote awareness, engagement, and adoption of new programs and ways of working
• Implement structured program and project plans, including timelines, resource needs, milestones, and success metrics
• Measure and evaluate the impact of enablement programs using both qualitative feedback and quantitative performance data; adjust content and delivery based on insights
• Continuously scan for enablement opportunities, risks, and inefficiencies; surface recommendations and drive improvements across the enablement portfolio
• Act as a trusted advisor and thought partner to stakeholders, influencing how enablement is embedded and scaled across teams

Preferred Qualifications

• Experience in a high-growth, fast-paced tech or SaaS environment
• Program Management certification(s) (PMP) a plus
• Change Management certification (e.g., Prosci, CCMP) is a plus

Benefits

• Competitive pay
• Generous time off
• Ample parental and wellness leave
• Healthcare
• A retirement savings program