Head of Engineering

Rebrandly

14d • Remote

About The Position

Rebrandly has been recognized as one of the leading software companies globally by G2. The company's branded link-management platform ensures that links are safe, secure, and engaging for individuals, agencies, businesses, and developers, driving optimal performance. Rebrandly follows a product-led growth (PLG) model, where the product plays a central role in user acquisition, retention, and revenue expansion.
With a diverse and global team spanning the US, Ireland, Italy, Germany, and Spain, Rebrandly caters to tens of thousands of customers in over 30 countries. Established in Italy in 2015, Rebrandly has operated as a remote-first company since its inception. Headquartered in the US, with an office in Rome, Rebrandly serves millions of users and global brands worldwide, including Versace, Toyota, PayPal, and Zillow. For more information, please visit www.rebrandly.com.

At Rebrandly, we embrace a serverless-first approach to development, leveraging AWS services to maximize scalability, reduce operational overhead, and ensure rapid deployment. This allows our team to focus on delivering high-quality features while maintaining robust, cost-effective systems. Our serverless architecture underpins our commitment to innovation and efficiency, providing a reliable foundation for our link management platform.
We're at an exciting stage in our growth. The business is strong: GTM and operations are strong, we have a world-class product and design team led by industry experts, and we've built modern data infrastructure, including a data warehouse, BI tools, and observability. What we need now is an engineering leader who can transform a talented team into a high-velocity, AI-native engineering organization.

We're seeking an exceptional Head of Engineering to own our engineering strategy, execution, and culture. Reporting directly to the CEO, you'll lead a distributed EU-based team (with flexibility to add resources in the US or Ireland) and partner closely with Product and Design to ship faster and better. You'll combine deep technical expertise with strong leadership skills, driving both architectural decisions and cultural transformation in a fast-paced, high-scale environment.

Requirements

• Scaled API infrastructure experience: Proven track record operating or building systems handling millions of requests with strict uptime requirements
• Architecture simplification: Successfully rationalized sprawling service architectures, knowing when to consolidate, rewrite, or leave alone
• Modern engineering practices: Built or transformed teams with contemporary DevOps, CI/CD, testing, and deployment practices representing 2025 standards
• Player-coach capability: Can read code and participate in code reviews, but primary leverage comes through people and systems, not personal commits
• Exceptional hiring skills: Track record of spotting and assessing talent, with humility to hire people ahead of you in specific areas (particularly AI-native engineers)
• AI fluency: Understand how to leverage AI in engineering workflows, build AI-powered product features, and structure data as a strategic asset
• Distributed team leadership: Successfully led remote/distributed engineering teams with strong async communication and documentation practices
• Coaching orientation: Demonstrated ability to develop promising ICs into leaders, meeting teams where they are and helping them level up
• Cultural transformation experience: Shifted engineering cultures from reactive to proactive. You know how to make reliability work feel meaningful
• Exceptional communication: Ability to communicate frequently, transparently, and precisely across all formats—strategy docs, team syncs, technical decisions
• Experience with Python, Node.js, and TypeScript (preferred but not required)
• AWS infrastructure experience, particularly multi-region data residency
• Understanding of high-throughput redirect infrastructure and uptime requirements
• Security and spam/abuse prevention knowledge for exposed products

Nice To Haves

• Experience in PLG/SLG hybrid businesses serving both self-serve scale and enterprise requirements
• Background in link management, martech, or high-volume B2B API platforms
• Comfort with EU team timezones (or willingness to flex schedule)
• Experience with SOC2 Type II, HIPAA, and GDPR compliance requirements
• Track record leading engineering in companies at similar scale ($10M ARR, 1M+ users)

Responsibilities

• Own the engineering strategy, execution, and culture for the entire organization
• Partner closely with Product and Design leadership to drive company-wide technical roadmap
• Drive the AI transformation initiative, making engineering AI-native within 60 days while infusing AI features into our product using our data assets
• Continue to modernize our engineering practices
• Lead and develop a distributed EU-based engineering team,
• Grow and develop the team by coaching the current members and bringing in top talent to add to the team 4 full-time hires and 2 contractors within 6 months
• Coach and mentor the team our leaders on the eng team, building leadership depth across the organization
• Create an environment where engineers are inspired by impact, not just interesting problems
• Accelerate both velocity AND quality—shipping faster with fewer defects and less firefighting
• Oversee high-scale infrastructure maintaining 99.99% uptime
• Lead tech debt remediation efforts with dedicated budget and contractor support
• Establish modern DevOps, CI/CD, testing, and deployment practices across the organization
• Drive the team to simplify the codebase and build sustainable practices
• Work closely with CEO (product/EPD background) on strategic technical decisions
• Collaborate with world-class Product and Design partners (industry/domain experts) to accelerate delivery
• Lead incident response and drive root cause analysis for production issues
• Champion technical documentation, knowledge sharing, and engineering best practices
• Communicate frequently and transparently with both technical and non-technical stakeholders

Benefits

• Inflection point opportunity: The hard foundational work is done—business model works, product-market fit is proven, data infrastructure is built, and compliance is handled. You're here to unlock the next level.
• Real resources: Full budget for AI transformation and tech debt contractors. This isn't a "do more with less" situation.
• Exceptional product partners: Work with genuine experts who know this space and are AI-forward thinkers. You won't be fighting product—you'll be racing together.
• CEO partnership: Our CEO comes from product/EPD, speaks your language, and will be genuinely supportive while staying out of day-to-day decisions. Direct, engaged, outcome-oriented leadership style.
• Hungry team: Our engineering team is fantastic and hungry to continue to grow and learn.
• Career acceleration: Drive measurable impact in a rapidly scaling SaaS platform with true autonomy and executive support
• Work-life harmony: Remote-first culture that balances innovation with sustainable work practices
• Periodic travel: Leadership offsites and team gatherings (in both USA and Europe)

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 11-50 employees