← All jobs in Canada

Remote · Unlimited leave

Forward Deployed Engineer

Feathery · Toronto · Canada

Remote Full time CAD 100k–135k / year Posted Open until 31 Oct 2026

The job, in the employer's words

About Feathery

Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader in financial agentic automation. Industry leaders like Tokio Marine, Sequoia Financial, and Cerity Partners run their client-facing workflows on Feathery, from onboarding and risk assessment to reconciling systems and generating proposals and reports.

At the center of it all is Robin, our AI operations assistant. Robin scans client documents, configures and deploys workflows, assists users in their day-to-day work, takes notes during meetings, and supports a growing range of operational tasks across the client lifecycle.

We're building a future where financial operations shift from paperwork, manual data entry, and disconnected systems to intelligent, automated workflows that let firms spend their time on clients instead of process. We're proud to be backed by world-class investors who share that vision, including Portage Ventures, Allstate Ventures, and Index Ventures, among others.

We're driven by a shared commitment to excellence and velocity. Our values — Own the Problem, Grit Beats Gloss, Say It Straight — shape how we work and grow as a team.

Why We're Hiring

As Feathery grows, we're partnering with larger, more sophisticated customers who rely on our platform for critical workflows.

We're hiring a Forward Deployed Engineer to work directly with enterprise customers to design, implement, and scale workflows on the Feathery platform. This role is ideal for someone who enjoys solving technical problems, working directly with customers, and shaping how a product is adopted in real-world environments.

You’ll partner closely with customers, product, engineering and sales to deliver successful customer implementations while helping shape the future direction of the Feathery platform.

About the Role

This is a high-ownership role that blends:

  • Customer-facing technical architecture and implementation

  • Technical partnership across the customer lifecycle

  • Workflow design, deployment, and problem solving

  • Cross-functional collaboration with Product, Engineering, and Go-to-Market teams

As an early member of the Forward Deployed Engineering team, you'll help define how we deliver and scale end-to-end customer implementations—from technical discovery and proof-of-concept through production deployment and long-term adoption.

What You'll Do

Customer Solutions & Implementation

  • Own technical delivery across customer implementations—from technical discovery and proof-of-concept through successful deployment and onboarding

  • Partner with customers to architect, implement, and optimize complex workflows on the Feathery platform

  • Guide customers on best practices for building scalable, maintainable workflow solutions

  • Measure success through successful customer adoption and long-term customer success

Technical Partnership & Solution Design

  • Partner closely with Sales to understand technical requirements and deliver scalable workflow solutions

  • Translate customer requirements into scalable workflow solutions

  • Build demos, prototypes, and implementation examples that showcase Feathery's flexibility and power

  • Serve as a trusted technical advisor to prospects and customers from evaluation through implementation

Product Feedback & Platform Enablement

  • Share customer implementation insights and feature requests that help shape the evolution of the Feathery platform

  • Create technical content, including implementation guides, documentation, and example applications

  • Help customers and internal teams maximize the capabilities of the Feathery platform

  • Contribute to improving onboarding and implementation best practices

Team & Function Building

  • Help turn successful customer implementations into repeatable playbooks, documentation, and best practices

  • Contribute to hiring and mentoring future team members

  • Improve internal processes, tooling, and implementation playbooks as the team scales

About You

  • Experience in a customer-facing technical role (Forward Deployed Engineering, Solutions Engineering, Sales Engineering, Customer Success, or similar)

  • Strong problem-solving skills, especially in workflow automation and data-intensive environments

  • Strong working knowledge of JavaScript, including writing and troubleshooting scripts and implementation logic

  • Basic familiarity with Python (able to build/debug APIs)

  • Strong communication skills with the ability to work across technical and non-technical teams

  • Comfortable owning customer implementations from discovery through deployment

  • Proactive, resourceful, and comfortable in a fast-paced startup environment

  • Strong sense of ownership with a focus on delivering exceptional customer outcomes

Bonus

  • Experience with B2B SaaS fintech platform or workflow automation tools

  • Familiarity with low-code/no-code platforms

  • Experience delivering enterprise customer implementations

  • Background in financial services (insurance, wealth management, lending)

  • Experience creating technical documentation, demos, or implementation guides

What We Offer

  • Competitive compensation and equity

  • Health, dental, and vision coverage

  • Unlimited PTO

  • Downtown Toronto office location

  • Stocked office pantry with snacks and ready-to-eat meals

  • A supportive, low-ego team that values ownership and growth

  • Company offsite to connect and recharge

If you’re excited about helping enterprise customers successfully implement and scale mission-critical workflows — and want to play a key role in shaping the customer experience at a fast-growing startup — we’d love to hear from you.

Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.

Benefits mentioned

  • Competitive compensation and equity
  • Health, dental, and vision coverage
  • Unlimited PTO
  • Downtown Toronto office location
  • Stocked office pantry with snacks and ready-to-eat meals
  • A supportive, low-ego team that values ownership and growth
  • Company offsite to connect and recharge
  • If you’re excited about helping enterprise customers successfully implement and scale mission-critical workflows — and want to play a key role in shaping the customer experience at a fast-growing startup — we’d love to hear from you.
  • Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.

Requirements mentioned

  • Experience in a customer-facing technical role (Forward Deployed Engineering, Solutions Engineering, Sales Engineering, Customer Success, or similar)
  • Strong problem-solving skills, especially in workflow automation and data-intensive environments
  • Strong working knowledge of JavaScript, including writing and troubleshooting scripts and implementation logic
  • Basic familiarity with Python (able to build/debug APIs)
  • Strong communication skills with the ability to work across technical and non-technical teams
  • Comfortable owning customer implementations from discovery through deployment
  • Proactive, resourceful, and comfortable in a fast-paced startup environment
  • Strong sense of ownership with a focus on delivering exceptional customer outcomes

No Mondays shows this listing as the employer published it. Check the details on the employer's site before you apply.

More unlimited leave jobs in Canada

Kepler Group · Toronto · today

Senior Analyst - Activation

Kepler executes engineered marketing, where every message and ad delivered helps create a more personalized and productive relationship between brands and their consumers…

RemoteUnlimited leaveCAD 64k–78k / month
Veterinary Emergency Group (VEG) · Leaside · 4 days ago

Medical Director - ON

Position: Emergency Medical Director Location: Onsite, in hospital, Full Time, Salary Reason for Job Posting: New Vacancy ABOUT VEG In 2014, VEG was born with a mission t…

Unlimited leave
Celonis · Remote, Canada · 5 days ago

Senior AI Applied Value Architect

Celonis is the trusted platform to industrialize Enterprise AI. At our core is the Celonis Context Model — which combines process data, business knowledge, and intelligen…

RemoteUnlimited leaveCAD 179k–204k / year
Celonis · Remote, Canada · 5 days ago

Applied AI Value Architect

Celonis is the trusted platform to industrialize Enterprise AI. At our core is the Celonis Context Model — which combines process data, business knowledge, and intelligen…

RemoteUnlimited leaveCAD 132k–151k / year
Bridgit · Canada · 6 days ago

Customer Education Manager

Bridgit is looking for a Customer Education Manager to serve as the connective tissue between our customers and the product. Helping them get the most out of Bridgit thro…

Unlimited leaveCAD 70k–100k / year
Coalition, Inc. · Any location, Canada · 7 days ago

Complex Cyber Claim Specialist

About us Coalition is the world's first Active Insurance provider designed to help prevent digital risk before it strikes. Founded in 2017, Coalition combines comprehensi…

RemoteUnlimited leave

176 live roles · See all →

Other roles at Feathery

Feathery · Toronto · 30 days ago

Field Marketing Specialist - North America

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader i…

RemoteUnlimited leaveCAD 90k–100k / year
Feathery · United States · 33 days ago

Field Marketing Specialist - North America - US Remote

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader i…

RemoteUnlimited leaveUSD 90k–100k / year
Feathery · United States · 40 days ago

Product Marketing Manager - US Remote

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader i…

RemoteUnlimited leaveUSD 110k–150k / year
Feathery · Toronto · 40 days ago

Product Marketing Manager

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader i…

RemoteUnlimited leaveCAD 110k–150k / year
Feathery · United States · 2 months ago

Business Development Representative

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader i…

RemoteUnlimited leave
Feathery · Toronto · 2 months ago

Business Development Representative

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader i…

Unlimited leave

15 live roles · See all →