• Own the end‑to‑end development lifecycle for our platform and unified client gateway—collaborating with engineering, design, and subject matter experts. • Define and drive the team’s product strategy and roadmap, aligning with business goals, user needs, and technical feasibility. • Facilitate transparent, cross‑functional prioritization to maintain and communicate a living roadmap that balances new capabilities, technical debt, and operational reliability. • Understand business requirements and translate them into clear, actionable product requirements and user stories, organizing and prioritizing the development backlog for engineering teams. • Collaborate closely with technical teams, business stakeholders, and process owners to identify and drive the change necessary to deliver impact, regardless of where it needs to happen. • Lead effective integrations between our products and other enterprise systems, including vendor offerings. • Drive effective decisions on when to build vs buy vs partner to deliver results. • Own production validation, feature testing, and bug verification to ensure high‑quality, reliable releases. • Support change management and go‑to‑market efforts for new platform capabilities, including documentation, release notes, and help center content. • Partner with customer enablement, marketing, and change management teams to support demos, training, onboarding, and adoption. • Manage feature flags and release gating, determining which users gain access to which capabilities and when. • Conduct structured beta testing and usability research, synthesizing feedback and prioritizing improvements ahead of general availability. • Research market trends, competitor offerings, and emerging technologies to identify opportunities to improve platform capabilities. • Collaborate with product analytics to define and track success metrics, interpret usage data, and communicate outcomes to stakeholders. • Mentor and guide other product managers, fostering their growth and raising the bar for product management practices across the team. • Keep business unit leaders and executive stakeholders informed and aligned on strategy, progress, and risks. • Support business unit technology strategy, including architecture alignment and integration of third‑party solutions. • Stay current with product management best practices and AI trends, incorporating modern tools, frameworks, and capabilities into the platform and delivery process. • Hold a high bar for security, user experience, reliability, quality, and ways of working.

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space. We're looking for a Senior Product Manager to lead strategy and delivery of a clinical decision support platform for the Department of Veterans Affairs, working at the intersection of healthcare interoperability, clinical workflows, and modern product development. What you'll be doing: - Own the end-to-end product roadmap for CDS capabilities from discovery through launch and iteration - Lead requirements gathering with clinical stakeholders including physicians, nurses, and pharmacists - Translate clinical and technical requirements into actionable user stories and acceptance criteria - Define and monitor KPIs tied to adoption, safety, and workflow efficiency - Manage Agile ceremonies across two engineering teams and contribute to team-wide product practices - Collaborate with engineering on FHIR, CDS Hooks, and EHR integration features What you’ll bring: - 5+ years of product management experience, with 2+ years in health IT or digital health - Working knowledge of FHIR R4/R4B, CDS Hooks, and HL7 standards - Experience shipping products that integrate with EHR platforms - Strong ability to translate clinical needs into clear, buildable product requirements - Experience with VA systems such as VistA or Oracle Health is a plus - Familiarity with SMART on FHIR or Clinical Quality Language (CQL) is a plus - Thrives in a remote, collaborative Agile environment and genuinely enjoys working closely with a cross-functional team - Communicates clearly and openly across both clinical and technical audiences - Performs other related duties as assigned. Requirements: - Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance. Education: - Bachelor’s degree Benefits: - Fully remote - Yearly stipend - Comprehensive Benefits Package - Company Match 401(k) plan - Flexible PTO, Paid Holidays Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hello@Oddball.io Compensation: At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level. United States Wage Range: $100,000 – $140,000

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. We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions! . See yourself at Twilio Join us as a Principal Product Manager on the Console & API team, leading product development for Console Copilot backend services and AI agent platforms. About the job This position is a high-leverage leadership role designed to drive the strategy and execution of Twilio’s Copilot Backend Services. You will build the foundational AI orchestration engines that power Twilio’s own intelligent agents—the virtual experts that serve our customers across the Twilio Console and various support channels. As a Principal PM, you will define how our backend services ingest vast amounts of Twilio-specific product knowledge, documentation, and real-time telemetry to provide proactive "nudges" and conversational assistance. Your goal is to move beyond static help docs to a world where our backend predicts customer friction and solves it autonomously. You will ensure these agents are performant, context-aware, and seamlessly integrated into the customer’s journey from sign-up to global scale. Responsibilities In this role, you’ll: - Design the "Twilio Brain": Lead the strategy for backend services that aggregate Twilio’s proprietary data (docs, support tickets, API logs) into a unified knowledge layer for our internal agents. - Drive Proactive Engagement: Define the logic and triggers for AI "nudges"—real-time, backend-driven interventions that guide customers when they encounter errors or configuration hurdles. - Omnichannel Agent Orchestration: Ensure the Copilot backend provides a consistent "memory" and personality for agents, whether the customer is interacting via the Console, SMS, or Slack. - Optimize Agent Accuracy: Establish the frameworks for RAG (Retrieval-Augmented Generation) and fine-tuning to ensure the Copilot provides technically accurate, "hallucination-free" advice on Twilio’s complex product suite. - Cross-Functional Integration: Partner with Product, Engineering, and Growth teams to embed intelligent assistance directly into the core user flows of every Twilio product. - Performance & Reliability: Manage the infrastructure costs and latency of LLM calls to ensure that Twilio’s agents respond in real-time without compromising the snappiness of the Console. 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: - Extensive Experience: 8+ years of Product Management experience, with a focus on backend services, internal platforms, or intelligent automation. - Contextual AI Expertise: Deep understanding of how to build AI systems that utilize contextual data (user state, account history, real-time logs) to provide relevant, personalized assistance. - Experience with RAG & Tooling: Familiarity with building RAG pipelines and giving agents "tools" (e.g., the ability to look up a customer's recent SID errors or billing status) to solve problems. - Growth-Oriented Mindset: Proven ability to use AI to drive business metrics like time-to-first-hello, churn reduction, and support ticket deflection. - Technical Acumen: Ability to design backend systems that can handle high-concurrency AI interactions while maintaining strict data privacy and security. - Storytelling & Influence: Experience convincing product teams to integrate centralized AI services into their specific product silos. Desired: - Conversational UX for Tech: Experience building chatbots or assistants specifically for technical/developer personas (e.g., GitHub Copilot, AWS Q). - Behavioral Analytics: Experience using data to identify "friction points" in a user journey and designing automated interventions to solve them. - Multi-Modal Experience: Knowledge of how to transition a customer conversation from a web-based chat to a live support ticket or a phone call with full context. Location - This role will be remote, but is not eligible to be hired in San Francisco, CA, Oakland, CA, San Jose, CA, or the surrounding areas. Travel We prioritize connection and opportunities to build relationships with our customers and each other. For this role, you may be required to travel occasionally to participate in project or team in-person meetings. 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. Compensation *Please note this role is open to candidates outside of California. The information below is provided for candidates hired in those locations only. 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. Application deadline information Applications for this role are intended to be accepted until March 2nd, 2026 , 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. Twilio is proud to be an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.

• Lead the engineering platform roadmap, ensuring the product remains secure, performant, and sustainable as it evolves. • Drive initiatives related to stack modernization, component lifecycle management, and architectural improvements. • Own Product Operability, improving how the product is installed, upgraded, monitored, and troubleshooted in real customer environments — including air-gapped and restricted deployments. • Ensure engineering investments translate into clear product outcomes such as faster deployments, lower operational overhead, and improved supportability. • Translate technical platform initiatives into structured roadmaps, clear priorities, and measurable outcomes. • Work closely with Engineering, Support, Security, and Solution Architecture teams to identify operational friction and systematically remove it. • Provide strong execution leadership across complex initiatives that span multiple engineering teams. • Bring clarity and structure to technical trade-offs, balancing innovation with long-term maintainability.