AI-Driven Engineering Manager — Lead Scalable Systems

Portland Seed Fund; United States; Remote; USD 185,000 - 215,000; Full time

Benefits offered by this job

Full medical, dental, vision coverage

Mental health coverage

16 weeks parental leave

Unlimited PTO

Remote work stipend

Wellness stipend

Professional development budget

Job summary

Customer.io is seeking an Engineering Manager to lead diverse teams ranging from customer-facing product work to scalable distributed systems. You will mentor engineers, own delivery milestones, and drive AI-native practices across squads to move fast and ship with quality.

Ideal candidates pair hands-on technical depth with strategic vision, balancing architecture discussions with people leadership. This role rewards impact, autonomy, and a proactive approach to complex priorities.

Qualifications

• 3+ years managing engineers at a SaaS company (B2B or B2C), ideally early-to-mid-stage.
• A track record of driving execution—concrete delivery outcomes with milestones, dates, and "I drove" ownership.
• A strong technical background—you can hold your own in architecture conversations and design reviews.
• Comfort operating with high autonomy and little prescribed structure.
• Demonstrated AI-native leadership—not just personal fluency, but bringing AI-first practices into how your team builds.
• Experience building high-performing, inclusive, and collaborative teams.
• Clear, concise, and direct communication, both verbal and written.

Responsibilities

• Care deeply about our customers and their outcomes.
• Lead your squad to deliver real customer value by owning projects end to end—from planning through delivery, quality, and follow-through.
• Drive execution: set milestones, keep work moving through ambiguity and competing priorities, and ship in small, observable increments.
• Make confident decisions when the path isn't obvious, and lead your team through them.
• Set the operating rhythm that helps your team move fastest, rather than defaulting to ceremony for its own sake.
• Ensure your squad's solutions are scalable, architecturally sound, flexible, and secure, with strong peer-review, QA, documentation, deployment, logging, and monitoring practices.
• Stay close to the work—jump into design reviews, architecture calls, and incidents rather than watching from a distance.
• Provide direct, timely, and specific coaching, and create meaningful development opportunities for your direct reports.
• Hire, onboard, and manage performance so the right people are in place to hit your squad's goals.
• Bring an AI-native perspective—use AI tools to accelerate the team's velocity and help everyone prototype faster and ship smarter.
• Partner across engineering and other departments to align efforts with customer success, and reach higher when our customers are having a bad day.

Skills

People management

Technical leadership

AI-native leadership

Communication

Job description

Customer.io is seeking an Engineering Manager to lead diverse teams ranging from customer-facing product work to scalable distributed systems. You will mentor engineers, own delivery milestones, and drive AI-native practices across squads to move fast and ship with quality.

Ideal candidates pair hands-on technical depth with strategic vision, balancing architecture discussions with people leadership. This role rewards impact, autonomy, and a proactive approach to complex priorities.