Principal, Product Learning & Development
Segment
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Remote (US) · $171k–$252k a year · Posted November 13, 2026
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About the job
Who we are
At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower millions of developers worldwide to craft personalized customer experiences.
Our dedication to remote-first work , and strong culture of connection and global inclusion means that no matter your location, you’re part of a vibrant team with diverse experiences making a global impact each day. As we continue to revolutionize how the world interacts, we’re acquiring new skills and experiences that make work feel truly rewarding. Your career at Twilio is in your hands. .
Hiring and how we work
We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions!
Also, while we are a remote-first company, you may be asked to report in person on an ad-hoc basis for team gatherings, functional off-sites or customer meetings. .
See yourself at Twilio
Join the team as Twilio’s next Principal, Product Learning & Development
About the job
Twilio is the world’s leading customer engagement platform empowering developers to build modern communication applications and experiences designed to be trusted, simple and smart. Twilio is looking for a Principal, Product Learning & Development to bring our AI first PDLC vision to life and build the capability our product organization needs to deliver it.
Reporting to the Director of Product Strategy & Operations, this role owns how our PMs get better at their craft, and how they learn to do that craft with AI. You'll build the competency model and curriculum that define "how we do product here," then go beyond curriculum by designing and shipping the internal tooling (prompt libraries, agents, PRD generators) that makes a PM measurably faster and sharper. You'll bring our AI first PDLC vision to life, partnering with product and engineering leaders to find where AI genuinely changes the work, and coaching the org through the change.
Responsibilities
We are looking for a leader who brings product, learning, and hands on AI expertise to help:
Design and deliver the PM Academy, covering onboarding and ongoing curriculum across PRD writing, discovery, prioritization, roadmapping, and stakeholder influence, each taught with AI in the workflow.
Design and help build and facilitate adoption of "PM in a box": ship internal AI tooling such as prompt libraries, agents, and PRD and research generators, as products with users, feedback loops, and adoption targets.
Bring the AI first PDLC vision to life and execute against it, partnering with Product leaders to map current workflows and identify the AI and automation opportunities worth pursuing.
Run cohort programs for new PMs and newly promoted PM managers, and design tailored programming for different parts of the organization rather than one generic track.
Curate the internal playbooks, templates, and documentation that carry "how we do product here," and keep them current as practice changes.
Facilitate workshops, office hours, and 1:1 coaching for PMs and PM leaders, building the credibility to coach senior people.
Drive AI adoption across the PM org through a champion network that surfaces use cases from inside each team.
Measure impact against baselines captured before rollout.
Qualifications
Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table!
Required:
Bachelor’s degree in Business, Computer Science, a related field or equivalent practical experience.
8+ years of experience across product management, consulting, program management, L&D or enablement
Experience leading programs or product operations for B2B SaaS, PaaS or equivalent
Outstanding written and verbal communication that drives executional impact at scale, distilling complex detail into an executive narrative, and explaining technical concepts to audiences without technical backgrounds.
Strong facilitation, and the ability to build trust and exchange ideas across organizational boundaries in service of a broader goal.
Excellent problem solving and organizational skills.
Ability to thrive in a fast paced, evolving, ambiguous environment, with a default to action in order to adapt quickly to changing priorities and requirements.
Desired:
Master’s in computer science or engineering or business administration
Hands on experience building AI agents, automated workflows, and internal tooling.
Experience leading change management in B2B SaaS
Location
This role will be remote and based in the USA.
Travel
We prioritize connection and opportunities to build relationships with our customers and each other. For this role, approximately 5-10% travel is anticipated to help you connect in-person in a meaningful way.
What We Offer
Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location.
The estimated pay ranges for this role are as follows:
Based in Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, Vermont or Washington D.C. : $171,120 - $ 213,900
Based in New York, New Jersey, Washington State, or California (outside of the San Francisco Bay area): $181,200 - $226,500
Based in the San Francisco Bay area, California: $201,280 - $251,600
This role may be eligible to participate in Twilio’s equity plan and corporate bonus plan. All roles are generally eligible for the following benefits: health care insurance, 401(k) retirement account, paid sick time, paid personal time off, paid parental leave.
The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.
Applications for this role are intended to be accepted until March 1, 2027, but may change based on business needs.
Twilio thinks big. Do you?
We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values — something we call Twilio Magic . Additionally, we empower employees to build positive change in their communities by supporting their volunteering and donation efforts.
So, if you're ready to unleash your full potential, do your best work, and be the best version of yourself, apply now! If this role isn't what you're looking for, please consider other open positions.
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