Director of Engineering, Operations Planning

HelloFresh; Toronto (OH); On-site; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Meal kit discounts (75% off HelloFresh

Chefs Plate discounts

Fact discount 50%

Job summary

HelloFresh is seeking a senior engineering leader to head an engineering squad (10–15 engineers and managers) across multiple offices. You will own the GenAI transformation roadmap, drive AI-enabled development and reliable planning infrastructure, and align engineering priorities with business outcomes.

You will guide architecture across Python, Go, PostgreSQL, Kafka, React, and AWS, while fostering strong cross-functional collaboration.

Qualifications

• AI proficiency and advocacy with a track record of adoption.
• Deep technical expertise across planning systems and data/engineering.
• Experience leading distributed engineering teams and PMs.
• Strong SRE practices: SLOs/SLIs, incident management, on-call.
• Ability to translate business goals into engineering priorities.

Responsibilities

• Lead an engineering squad of 10–15 engineers and managers across locations.
• Own GenAI transformation roadmap and AI-native tooling adoption.
• Ensure availability and reliability of planning infrastructure and services.
• Set technical direction across core technologies and cloud platforms.
• Partner with Product, Operations, Marketing, and Procurement to align priorities.
• Coach and develop Engineering Managers and engineers; maintain high standards.
• Navigate organizational change while keeping teams focused.

Skills

GenAI proficiency

Engineering leadership

SRE/Observability

Distributed teams management

Systems thinking

Cross-functional collaboration

Technical communication

Owner mindset

Tools

Grafana

PostgreSQL

Kafka

Python

Go

React

React Native

AWS

Job description

S'more about the team

The Operations Data and Decisions Tribe at HelloFresh is responsible for driving operations planning by creating high quality, reusable data assets, data science models, and algorithmic solutions. Additionally, the tribe. This team has a direct impact on the customer experience and is constantly optimising for various Business KPIs. They build in-house products using modern technologies to handle a massive scale of transactions (>8.5 million active customers) and continuously improve the SDLC for fast flow and continuous delivery.

- Lettuce share what this role will be responsible for

• Lead an engineering squad comprising 10-15 engineers, managing Engineering Managers and Staff Engineers across Warsaw, Berlin, & USA.
• Own the GenAI transformation - define and drive a concrete roadmap for becoming a genuinely AI-native engineering organisation: from AI-assisted development and automated incident response, to agentic workflows and LLM-powered tooling embedded in day-to-day operations.
• Own the availability and reliability of HelloFresh's planning infrastructure - drive SRE practices, incident management, SLOs/SLIs, and on-call maturity across high-throughput systems serving multiple markets.
• Set technical direction across Python, GoLang, PostgreSQL, Kafka, React, and React Native services on AWS, ensuring systems.
• Partner with Product, Operations, Marketing, and Procurement providers to align engineering priorities with business outcomes.
• Manage , coach, and develop Engineering Managers & Engineers - holding them accountable for team health, delivery, and engineering standards.
• Navigate organisational change with maturity, keeping teams focused and motivated through evolving priorities.

Sound a-peeling? Here's what we're looking for

• AI proficiency and advocacy. Hands-on familiarity with AI technologies and a demonstrable track record of championing their adoption - whether through AI-assisted development workflows, LLM-powered tooling, or driving team-wide GenAI-native ways of working.
• Deep Technical Expertise. Mastery of a broad range of technical skills relevant to Operations Planning - including planning systems, data science modeling, data engineering, database systems, distributed computing, and backend development frameworks. Hands-on familiarity with full stack application development.
• Systems Thinking. The ability to understand complex systems holistically, recognising how components interact and impact each other, and leveraging this to design scalable, resilient solutions in a high-throughput environment where downtime means direct revenue loss.
• Proven Leadership at Scale. 10+ years in software engineering with 4+ years managing Engineering Managers - not just individual contributors. Demonstrated ability to lead distributed teams across multiple offices, building trust and maintaining high engineering standards without daily co-location.
• Operational Excellence Mindset. Strong grounding in SRE practices - SLOs/SLIs, incident management, on-call culture, and observability tooling (Grafana or similar). Experience owning payments infrastructure in regulated, multi-market environments is a strong plus.
• Cross-Functional Collaboration. Exceptional ability to work across engineering disciplines, Product, business stakeholders, and external service providers - fostering alignment towards common goals and translating business outcomes into engineering priorities.
• Effective Communication Across Disciplines. Strong ability to articulate complex technical concepts clearly to diverse audiences, from engineers to senior business stakeholders.
• Low ego, high ownership, and a bias toward clarity over complexity.

Let’s cut to the cheese, this is why you’ll love it here

• Shape the future of food: Play a key role in transforming how millions of people eat as we grow into a global food solutions company.
• Drive transformational change: Your decisions will have a direct and immediate impact, helping to shape strategy, scale teams, and redefine leadership in a rapidly evolving business.
• Build a global brand: Create deeper, more sustainable connections with our customers, putting them at the heart of every decision.
• Compensation & Financial Wellbeing: Enjoy amazing discounts: 75% off weekly HelloFresh/Chefs Plate meal kits plus 50% off weekly Fact