by Terrance Ellis | Jan 20, 2026 | Uncategorized
This isn’t a “cool demo” role. You’ll build production-grade AI infrastructure that ships into real systems affecting revenue, safety, and compliance for fleets across North America. If you want ownership, board-level visibility, and work that actually matters, this is the lane.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and efficiency platform built to simplify how fleets manage safety, tolls, inspections, and vehicle data under one unified brand. They’re building AI-native products using a deep data moat from 10+ years of toll, inspection, safety, and fleet telemetry data across all 50 states. The goal is simple: help fleets operate safer, smarter, and beyond compliant.
Schedule
Canada-based remote or hybrid.
Foundational role on a newly created AI platform team with cross-functional collaboration.
Expectation: ship production code, build core AI infrastructure, and communicate progress to executive leadership.
What You’ll Do
Build and own core AI infrastructure including feature store, model CI/CD, evaluation harnesses, and observability across AI efforts
Write and ship production code daily (Python, Go, TypeScript) while architecting scalable AI and data systems
Partner across product, design, compliance, and support, guide technical direction for others, and present roadmap and results to executives and the board
What You Need
4+ years building backend or infrastructure systems plus 2+ years production experience in AI and ML
Experience delivering AI applications in real environments, including LLMs, RAG workflows, computer vision, or real-time event processing
Strong system design and technical leadership skills, comfort moving fast in ambiguity, and a bias toward shipping working software
Benefits
Remote or hybrid flexibility within Canada
Foundational ownership on an AI platform team with visibility to executives and the board
Modern stack: Python, Go, TypeScript, GCP and AWS, Postgres, Redis, Kafka, MLFlow, dbt, Dagster, LangChain, Triton Inference Server
This is a rare chance to build the core AI engine inside a company with real data, real customers, and real stakes. If you’re ready to ship AI that moves the needle, apply now.
Build it. Ship it. Prove it in production.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 20, 2026 | Uncategorized
Build and evolve applications that help fleets move through the world safer and more efficiently. You’ll work on Drivewyze’s Smart Roadside ecosystem, owning everything from APIs and microservices to portal apps, architecture, and long-term reliability.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and efficiency platform built to simplify how fleets manage safety, tolls, weigh station bypass, and more under one unified brand. Through the Drivewyze ecosystem, they deliver technology that helps commercial fleets operate smarter, reduce risk, and stay beyond compliant.
Schedule
Edmonton, Alberta (role supports the Smart Roadside team).
Collaborative Agile environment working alongside developers, QA, product managers, and internal partners.
Expectation: design, build, test, and support production systems that continue delivering value after launch.
What You’ll Do
Design, architect, develop, and test applications across server and cloud environments, including portal apps, back-end services, APIs, and supporting tools
Build and improve web APIs and microservices, strengthen security and architecture, and document designs and integrations as needed
Evaluate and implement new technologies to improve efficiency and support new product ideas, while contributing to strong engineering practices like testing and peer reviews
What You Need
Post-secondary education in Computer Science, engineering, or equivalent experience
5+ years of application development experience across back-end services, databases, and modern application ecosystems
Strong craftsmanship and ownership mindset, including writing clean, secure code, valuing testing and code reviews, and supporting what you build beyond deployment
Benefits
High-impact product work inside a mature fleet technology ecosystem
Collaborative, cross-functional team environment with room to influence architecture and tooling
Opportunity to work across multiple stacks including C#, ASP.NET, SQL Server, Postgres, and Elixir/Erlang on Linux
If you want senior-level ownership and real product impact, don’t wait. Apply while this role is still open.
Build the systems. Ship the features. Keep fleets moving.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 19, 2026 | Uncategorized
Build the data platform that powers smarter fleet safety and compliance decisions at scale. You’ll blend data engineering with DevOps-style automation to help teams ship reliable, high-quality data products in a modern Data Mesh environment.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and efficiency platform built to simplify how fleets manage safety, tolls, weigh station bypass, and more under one unified brand. Their connected suite delivers real time insights that help customers reduce risk, improve efficiency, and save money. Supporting millions of drivers and vehicles, Fleetworthy is leading a new era in road safety and fleet technology.
Schedule
Canada-based remote or hybrid.
Distributed team environment with a fast-paced, build-and-improve mindset.
Expectation: design pipelines, automate deployments, and support teams adopting Data Mesh best practices.
What You’ll Do
Build and maintain platform tools that automate deployment and operations for data products across a Data Mesh architecture
Design and optimize ingestion and transformation pipelines using SQL, Python, and PySpark, aligned with ETL best practices and Medallion Architecture
Improve infrastructure and delivery by contributing to CI/CD workflows and infrastructure-as-code provisioning (Terraform or similar), while strengthening reliability and performance at scale
What You Need
Strong working knowledge of SQL, Python, and PySpark in data-intensive environments, plus solid fundamentals in data modeling, warehousing, and ETL concepts
Comfort collaborating in a remote, distributed team with strong communication and a mindset of enabling other teams
Interest and aptitude for platform and infrastructure work, including automation, CI/CD, and reliability practices (Terraform, observability, and cloud platforms are a plus)
Benefits
Remote or hybrid flexibility within Canada
High-impact work building a modern data platform and Data Mesh foundation
Opportunity to grow deeper into DevOps, infrastructure, and scalable platform engineering
If you want to level up from data engineering into platform engineering while working on large, complex datasets, apply now while this role is open.
Help teams ship better data products, faster, with a platform that just works.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 19, 2026 | Uncategorized
Help shape how real people experience fleet safety and compliance tools that keep millions of drivers moving. You’ll turn complex workflows into clean, accessible designs while learning fast inside a small, collaborative product team.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and efficiency platform built to simplify how fleets manage safety, tolls, weigh station bypass, and more under one unified brand. Their connected suite delivers real time insights that help customers reduce risk, improve efficiency, and save money. Supporting millions of drivers and vehicles, Fleetworthy is leading a new era in road safety and fleet technology.
Schedule
Remote in Canada.
Highly collaborative product team environment with quick iteration cycles.
Expectation: partner closely with designers, product managers, and engineers through the full design lifecycle.
What You’ll Do
Create user flows, wireframes, mockups, and prototypes that communicate interaction and design ideas clearly
Design new experiences and improve existing ones by contributing to user testing, iterating on feedback, and refining details
Collaborate with engineers and product managers in an Agile environment while helping maintain UI specs and design system consistency
What You Need
2+ years of experience in UX design (or a similar role) plus a portfolio showing strong user-centered work
Solid knowledge of usability principles, prototyping, wireframing, and basic user research methods
Strong communication and storytelling skills, plus comfort working directly with developers for implementation
Benefits
Remote role based in Canada
Small team, high ownership, and fast learning with guidance from senior designers
Product work with real-world impact across safety, compliance, and fleet efficiency
This is a strong entry point into a product org that’s actively building and evolving. If you want meaningful UX work, apply while this role is still fresh.
Come help build intuitive tools that make every trip safer and more efficient.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 16, 2026 | Uncategorized
SmithRx is building the modern PBM backbone, and this role sits right in the engine room: backend systems that power drug data for their product suite. If you like designing APIs, scaling services, and translating messy business needs into clean architecture, this is a strong fit.
About SmithRx
SmithRx is a venture-backed health tech company modernizing pharmacy benefits with a platform built for real-time insights, cost savings, and a better customer experience. They’re mission-driven, growing fast, and operating in a regulated space where reliability and accuracy matter.
Schedule
- Full-time, remote
- Collaborative, cross-functional team environment (Backend, Frontend, Product, stakeholders)
- Ongoing on-call style production support expectations (triage, RCA, mitigations)
- Work includes quarterly planning/roadmapping with leadership
What You’ll Do
- Design, build, test, and maintain backend features across Go, GraphQL, Node, and SQL
- Own backend architecture for the Drug Access team’s 1P and 3P drug data systems
- Partner with Product and Frontend to define requirements and deliver scalable solutions
- Write technical design docs, estimates, and risk assessments for features and systems
- Build and run services on AWS (Lambda, DynamoDB, SQS, RDS) including batch processing
- Troubleshoot production issues, execute mitigations, and lead root-cause analysis
- Improve availability, performance, and scalability across services and data flows
- Mentor junior engineers through code and design reviews with clear, actionable feedback
- Help translate technical vision into a quarterly roadmap with senior leadership
- Explore and share AI tools that increase delivery speed and software quality
What You Need
- BS (or higher) in Computer Science or equivalent professional experience
- 5–8 years of professional software engineering experience
- Strong experience in a compiled language (Go strongly preferred; Java/C#/C++ also relevant)
- PostgreSQL expertise: schema design, query tuning, and database monitoring
- Proven ability to design and implement scalable APIs with solid testing practices
- Strong working knowledge of GraphQL APIs, CI/CD, AWS, Docker, and Kubernetes
- Comfortable operating independently, forecasting milestones, and managing stakeholder expectations
- Team-first mindset with the ability to work in ambiguity without getting rigid about “the one true way”
- Bonus: experience using GenAI tools to ship higher-quality production code faster
Benefits
- Medical, pharmacy, dental, vision
- Life and AD&D insurance
- Flexible Spending Accounts (FSA)
- 401(k) retirement program
- Short-term and long-term disability
- Discretionary PTO
- 12 paid company holidays
- Wellness benefits
- Commuter benefits
- Paid parental leave
- Employee Assistance Program (EAP)
- Professional development and training
- Well-stocked kitchens in office locations
If you’re scanning for the real signal: this is not “just write endpoints.” They want someone who can own systems, write the designs, keep prod healthy, and elevate the team while scaling drug data services.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Jan 16, 2026 | Uncategorized
SmithRx is building ML into the core of how pharmacy benefits run: detecting anomalies, optimizing claims, validating eligibility, and layering in GenAI where it actually improves decisions. If you like shipping models that end up inside real workflows (not trapped in notebooks), this is that lane.
About SmithRx
SmithRx is a venture-backed health tech company reshaping Pharmacy Benefit Management with a modern platform built for real-time insights, cost savings, and better experiences. They’re mission-driven, growing fast, and operating in a regulated healthcare environment where accuracy and trust matter.
Schedule
- Full-time, remote
- Cross-functional work with Platform Engineering, AI, Product, Data Engineering, and SMEs
- Mix of customer-facing and internal ML tooling
- Expectations include production-grade delivery (model monitoring, iteration, and scalability)
What You’ll Do
- Design and implement end-to-end ML solutions across high-impact domains like anomaly detection, claims optimization, and eligibility validation
- Productionize models with software and data engineers and integrate them into business workflows
- Mine claims data for new ML use cases that improve decisions, operations, and outcomes
- Identify and prototype GenAI use cases that increase automation, transparency, and customer experience
- Help build scalable ML infrastructure and establish best practices for model development, evaluation, and monitoring
- Serve as a thought partner on emerging AI capabilities (especially GenAI) and evaluate fit for PBM problems
What You Need
- 5+ years in data science / machine learning / AI with a track record of leading impactful initiatives
- MS or PhD in CS, EE, Statistics, Robotics, or related field (or equivalent)
- Strong applied ML foundations: regression/classification, supervised + unsupervised learning
- Strong math fundamentals: linear algebra, calculus, probability, statistics
- Python proficiency and solid object-oriented programming
- Practical MLOps experience: deploying models, monitoring, and iterating with incremental improvements
- Experience across a broad range of ML techniques and tools
- Strong retrieval/embedding experience (RAG-style approaches, similarity search, etc.)
- Hands-on with common Python ML/DL stack: pandas, scikit-learn, TensorFlow, PyTorch, transformers, LangChain (and similar)
- Ability to drive projects independently and collaboratively across teams
- Strong communication skills, including explaining complex concepts to non-technical stakeholders
Benefits
- Medical, pharmacy, dental, vision
- Life and AD&D insurance
- Flexible Spending Accounts (FSA)
- 401(k) retirement program
- Short-term and long-term disability
- Discretionary PTO
- 12 paid company holidays
- Wellness benefits
- Commuter benefits
- Paid parental leave
- Employee Assistance Program (EAP)
- Professional development and training
- Well-stocked kitchens in office locations
Apply soon — roles like this go fast when the scope is “ML + GenAI + production + healthcare.”
If you want my blunt take: the “Senior ML Engineer” title is accurate, but the job reads like “ML tech lead who can ship.” If someone only wants to model and not productionize, they’ll struggle here.
Happy Hunting,
~Two Chicks…
