Director, Engineering

Hi, I'm Paul, VP of Engineering at Customer.io. I'm looking for an experienced engineering leader to own Customer.io's product development engineering teams. The most important near-term project is delivering our new billing platform from the ground up. This is a high-priority, zero-to-one initiative with direct executive visibility — the kind of role where you'll set the vision, build the team, and drive the execution yourself. If you're energized by taking complex, ambiguous problems from near-zero to production and building the org to sustain them, this role is for you. About Customer.io Over 9,000 companies — from scrappy startups to global brands — use our platform to send billions of emails, push notifications, in-app messages, and SMS every day. Customer.io powers automated communication that people actually want to receive. We help teams send smarter, more relevant messages using real-time behavioral data. Under the hood: Go, React and AI help us ship fast and scale with confidence. What We Value Ownership You set direction and see initiatives through. You've led complex, zero-to-one engineering efforts — not just maintained and scaled existing systems — and you know what it takes to drive them to completion across an organization. Engineering leaders who can do both You operate at the strategic level and stay close to the technical work. You can align executives on a roadmap and earn an engineering team's respect in the same day. You don't choose between vision and execution — you hold both. A healthy skepticism for "the way things are done" You bring rigor and pragmatism. Best practices matter — but never more than forward motion. You know when to build, when to buy, and when to wait. An AI-first engineering mindset AI is central to how you build and how you lead your team to build. You've developed a real point of view on AI-native development, you can speak to it concretely, and you bring it into how your org operates. What You'll Do • Own the vision, roadmap, and execution for Customer.io's billing platform: a custom, in-house system built for real SaaS complexity — usage-based billing, subscription management, and multi-tier pricing • Partner with Product, Finance, and Engineering leadership to align billing strategy with company goals and unlock Customer.io's next phase of growth • Make build-vs-buy decisions with conviction, and lead the team through them • Mentor and develop engineering managers and senior technical leaders on your team • Drive a culture of accountability, transparency, and continuous improvement across the org • Leverage AI tools to accelerate team velocity and bring an AI-native perspective to how the team builds What We're Looking For • 12+ years of software engineering experience, with 8+ years leading engineering teams • At least 4+ years managing engineering managers and/or directors • Proven track record of taking complex, custom platform initiatives from zero-to-one at a SaaS or marketplace company — you've built something from near-nothing and seen it through to production at scale • Deep understanding of SaaS software architecture, cloud-native infrastructure, and the tradeoffs that come with building in-house vs. buying • Experience in domains requiring real platform complexity — not just feature development, but systems that other parts of the business depend on • Ability to translate technical complexity into clear strategy and communicate effectively with both engineers and executives • Strong track record building high-performing teams: hiring, developing talent, creating career paths, and navigating team transitions with care • Demonstrated AI-native leadership — not just personal fluency, but a track record of bringing AI-first development practices into how your team works • Comfort operating in ambiguity and making difficult tradeoffs between competing priorities Bonus points for: • Experience at high-growth SaaS companies; you have delivered results at a startup • Track record of shipping in high-velocity product orgs where your domain was treated as a first-class engineering concern • Experience in the domains of audience segmentation, customer data platforms (CDPs), self-service or growth Compensation & Benefits We believe in transparency. Starting salary for this role is $230,000-$270,000 USD (or equivalent in local currency) depending on experience and subject to market rate adjustment. We know our people are what make us great, and we're committed to taking great care of them. Our inclusive benefits package supports your well-being and growth, including 100% coverage of medical, dental, vision, mental health, and supplemental insurance premiums for you and your family. We also offer 16 weeks paid parental leave, unlimited PTO, stipends for remote work and wellness, a professional development budget, and more. See full benefits here → Our Process No gotchas, no trick questions - just a clear, human process desig