Executive Project Manager Jobs in Oregon (NOW HIRING)

Portland , USA Full Time Healthcare Posted May 29, 2026

Skypoint is a HITRUST r2–certified Agentic AI platform for healthcare operations, designed to accelerate productivity and operational efficiency across healthcare organizations. Our platform enables healthcare providers, payers, and senior care organizations to unify fragmented data, model industry-specific ontologies, and deploy AI agents that automate workflows and support better, faster decision-making.

Founded in 2020 in Portland, Oregon, Skypoint has grown to a team of over 75 employees and now serves more than 100 customers. We are proud to be recognized on Deloitte’s 2024 and 2025 Technology Fast 500™, celebrating the fastest-growing technology companies in North America, and to be featured on the INC. 5000 list in 2025, reflecting our strong and sustained revenue growth over the past three years.

Location: Life Time Work, 500 SW 116th Ave., Suite 152, Portland, OR 97225.

We are seeking an experienced Technical Project Manager to lead the successful planning, execution, and delivery of strategic customer and product initiatives across Skypoint’s AI-powered healthcare platform.

This role sits at the intersection of technology, product, engineering, and customer success. You will partner closely with customers, product managers, engineers, data teams, and business stakeholders to ensure projects are delivered on time, within scope, and aligned with business objectives.

The ideal candidate combines strong project management discipline with technical fluency, excellent communication skills, and the ability to navigate complex, fast-paced environments.

• Lead end-to-end project execution for customer implementations, platform deployments, integrations, and strategic initiatives.
• Develop project plans, timelines, milestones, resource allocation strategies, and risk mitigation plans.
• Drive project governance, status reporting, stakeholder communication, and executive updates.
• Ensure projects are delivered on time, within scope, and meet quality expectations.
• Identify project risks, dependencies, and blockers while proactively driving resolution.

• Partner with Product, Engineering, Data, AI, Customer Success, and Operations teams to align priorities and execution plans.
• Facilitate sprint planning, project reviews, standups, retrospectives, and stakeholder meetings.
• Coordinate multiple concurrent projects while managing competing priorities and deadlines.
• Ensure clear ownership, accountability, and visibility across all project stakeholders.
• Translate business requirements into actionable project plans and technical workstreams.
• Serve as a trusted point of contact for customers throughout project delivery.
• Lead customer onboarding, implementation planning, progress reviews, and project governance meetings.
• Manage customer expectations while ensuring alignment between customer goals and project deliverables.
• Communicate project status, risks, timelines, and outcomes to technical and non-technical audiences.
• Build strong relationships with internal and external stakeholders to drive successful outcomes.

• Work closely with engineering and data teams to understand system architecture, integrations, APIs, data pipelines, and deployment requirements.
• Coordinate technical implementation activities across cloud, data, AI, and application teams.
• Track technical dependencies and ensure successful delivery of platform enhancements and customer solutions.
• Support release planning, deployment coordination, and change management activities.
• Drive continuous improvement of project management processes, tools, and best practices.

• Establish project management standards, templates, reporting frameworks, and operational rhythms.
• Monitor project performance using KPIs, dashboards, and success metrics.
• Drive process improvements that enhance team productivity, predictability, and delivery quality.
• Contribute to building a scalable project delivery organization as Skypoint continues to grow.

• 5+ years of experience managing technical projects, software implementations, or SaaS deployments.
• Proven experience leading cross-functional projects involving engineering, product, data, and customer-facing teams.
• Strong understanding of Agile, Scrum, and modern software development methodologies.
• Experience managing project plans, timelines, risks, budgets, and stakeholder communications.
• Excellent verbal and written communication skills with the ability to engage executives, customers, and technical teams.
• Strong organizational skills with exceptional attention to detail and follow-through.
• Experience using project management tools such as Jira, Azure DevOps, Asana, Monday.com , or equivalent.

• Ability to understand technical concepts, APIs, integrations, cloud platforms, data pipelines, and software architecture.
• Experience working with SaaS products, enterprise software, or technology implementation projects.
• Comfortable collaborating with engineers and translating technical discussions into business-friendly communication.
• Familiarity with AI, analytics, healthcare technology, or data platforms is highly desirable.

• Experience in healthcare technology, healthcare operations, payer, provider, or senior care environments.
• Experience managing customer-facing software implementations.
• Exposure to AI, machine learning, data engineering, or cloud technologies.
• Experience working in high-growth startup or scale-up environments.

• Lead high-impact initiatives that directly improve healthcare operations and outcomes.
• Work alongside talented product, engineering, AI, and customer success teams.
• Be part of a fast-growing company recognized on Deloitte Fast 500™ and INC. 5000.
• Gain exposure to cutting-edge Agentic AI technologies transforming healthcare operations.
• Competitive compensation, comprehensive benefits, and a flexible work environment.

Skypoint is an Equal Opportunity Employer. We do not discriminate based on race, color, religion, sex, national origin, age, disability, veteran status, or any other protected characteristic.