Engineering Manager at highlightta

About Zipline

Zipline is a well-funded, rapidly growing SaaS company transforming how frontline teams work. We empower the world’s leading brands across retail, healthcare, logistics, and beyond to connect, align, and inspire their employees- from headquarters to the front lines. Our customers consistently give us best-in-class NPS and CSAT scores, and they rave about how Zipline makes their teams’ lives easier and their businesses more effective. We’re also a fully remote company, with passionate employees across the U.S., Canada, and around the globe.

About the Role

We're looking for an Engineering Manager who will build and lead high-performing Ruby on Rails teams as Zipline scales its product surface area and infrastructure. This is a hands-on leadership role. You'll own delivery outcomes, grow engineers' careers, and drive adoption of AI-powered development practices across your teams. You won't be writing production code daily, but you'll need deep technical fluency to guide your team through complex architectural decisions, keep technical debt visible and under control, and help engineers ship with confidence.

What You’ll Do

Manage and coach a team of software engineers delivering secure, scalable features for Zipline's enterprise customers.
Partner with Product and Design to scope, prioritize, and deliver solutions while balancing ongoing engineering health.
Own a technical debt roadmap for your teams. You'll identify, quantify, and sequence debt reduction work alongside feature delivery so it doesn't become an afterthought or an emergency.
Drive adoption of AI and agentic development workflows within your teams. This means getting engineers productive with tools like Claude Code, establishing quality gates and review practices for AI-assisted output, and measuring the impact on velocity and code quality.
Build and maintain team processes that support async, remote-first collaboration. You'll facilitate ceremonies, manage capacity, and ensure the right information reaches the right people at the right time.
Represent your teams to engineering leadership, cross-functional partners, and occasionally customers and partnership organizations.
Recruit, hire, and retain strong engineers. Build a diverse team and foster a collaborative, inclusive environment where people do the best work of their careers.
Pay close attention to team health, individual wellbeing, and career growth. Run regular 1:1s, give direct and specific feedback, and advocate for your people.

What We Look For

You have 2+ years of experience in an engineering management role, leading teams of senior individual contributors. Tech lead experience counts if you were responsible for people outcomes.
You have 3+ years of hands-on experience with Ruby on Rails at production scale. You don't need to be the strongest coder on the team, but you need to understand the codebase, review architecture decisions credibly, and spot when something is heading sideways.
You have demonstrated proficiency with AI-assisted and agentic development workflows. You've personally used AI coding tools and, more importantly, you've rolled them out across a team. You can speak concretely to how you measured adoption, handled quality concerns, and shifted team practices.
You maintain a technical debt roadmap and can talk about how you've balanced debt reduction against feature delivery in previous roles. You know how to make debt visible to product partners without turning every planning session into a negotiation.
Coaching is in your blood. You get energy from growing engineers, not just shipping features. You have a track record of promotions, skill development, and career progression on your teams. You give feedback that is direct, specific, and kind.
You are a clear, compelling communicator who can represent your team to audiences with varying levels of technical fluency. Written communication matters especially in a remote-first company.
You are experienced in designing and operating distributed systems, APIs, and web applications. Familiarity with robust logging, monitoring, and incident response practices is expected.
You are proactive, organized, and comfortable managing your own time as a remote employee.

Technologies You'll Work With

Ruby on Rails
Postgres, Redis, Elasticsearch
Hotwire, TypeScript, JavaScript, React, Webpack
AWS, Heroku, GCP
GitHub, Slack, Google Drive, JIRA, Confluence
Claude Code, Codex

Compensation

At Zipline, we're committed to paying our team fairly, transparently, and in a way that supports growth. This role is targeting an annual salary within Canada of $176,838 CAD to $216,138 CAD.

The broad salary ranges reflect the growth someone will experience in the role—from developing skills to reaching expertise within their career level. We've found that hiring team members with the expectation of being accomplished in the role sets them up for success, which for this position on the Canadian band is $176,838 CAD. Salaries below this point typically reflect someone with potential but still building the necessary skills, while salaries above are for individuals already excelling in the role, with a deep understanding of Zipline's impact on customers, product, and company.

At Zipline, you'll continue to have career development conversations with your manager to ensure your compensation grows as you advance.

Our salary ranges are determined by market, factoring in our revenue and employee size and paying competitively. In higher cost of living markets, we apply 5-10% multipliers on our ranges, depending on the location, to maintain competitive compensation and reflective of the increased expenses our team members face in those areas. While we primarily hire in Canada and the USA, we are a global employer, and all hiring regions will use the same methodology to determine fair and transparent pay.

Transparency is key to building trust in our compensation process. To better understand how this range is determined, we encourage you to ask as many questions as you'd like about compensation during the interview process to ensure clarity and confidence.

 What's In It For You

Remote-first culture: Join a high performing, fully remote team and work where you're comfortable
Stock Options: Get meaningful ownership in a fast-growing, venture-backed company shaping the future of retail.
Time off: We believe rest fuels great work. Our flexible time-off policy gives you the freedom to take the breaks you need, when you need them—whether it's a long weekend or a well-deserved vacation. We'll also give you a monthly coffee-shop stipend to switch up your workspace and get inspired outside the office. And when you've been with us for five years? You'll earn a fully paid one-month sabbatical to truly unplug and reflect—we call it a thank-you for your impact and dedication.
Benefits: World-class medical, dental, and vision policies.
Team Connection: Annual company off-sites in fun locations. We've done New York, Costa Rica, Whistler, Palm Springs, San Diego, and Mexico City.
Volunteering: Every quarter, Zipliners get a paid day off to volunteer for a nonprofit of their choice.
Learning: We support continuous learning and provide unlimited access to our Udemy Business account
Great humans, great work: Work with kind, collaborative teammates who care about doing meaningful work and making a real impact. We value diversity of all kinds and are committed to building a diverse and inclusive workplace where we learn from each other. We are an equal opportunity employer and welcome people of all different backgrounds, experiences, abilities, and perspectives.