Engineering Lead

Location: Remote (Ontario, Canada)

Type: Full-Time

Reports To: CEO

About FindBob

FindBob is a multi-tenant SaaS platform that powers business succession planning for financial services enterprises and SMB owners. Our clients include major enterprise institutions across Canada, the US, and the UK. We're a small, high-leverage engineering team that ships production features measured in days, not quarters.

We recently launched a new product line — a free-tools marketplace for SMB business owners navigating succession. It's built on our existing Rails infrastructure with its own design system, agentic AI, and partner monetization model. It's the most ambitious product surface we've shipped and is still in early sprint cycles. You'd be stepping into a codebase and product with real momentum.

We're looking for a senior software engineer who can operate as a technical leader and individual contributor on a small team. The role spans feature development, CI/CD, cloud infrastructure, enterprise SSO integrations, and our AI agent framework — we need someone who can cover that breadth.

About the Role

You'll own the technical direction of the FindBob platform, write code daily, mentor developers, and partner directly with the CEO on product and roadmap decisions. It's a rare opportunity to own the full technical picture of a profitable, enterprise-grade SaaS business — with the autonomy to shape how we build, what we invest in, and where we go next.

Responsibilities

• Technical Leadership: Own engineering direction, set standards, and make pragmatic architecture decisions for a multi-tenant SaaS platform serving enterprise clients.
• Full-Stack Development: Build and maintain features across a Ruby on Rails backend and React frontend, connected via a GraphQL API.
• Mentorship & Team Growth: Guide and grow the engineering team through code review, pairing, and technical coaching — and help us scale the team thoughtfully as the business grows.
• DevOps & Infrastructure: Own AWS infrastructure including RDS (PostgreSQL), ElastiCache (Redis), OpenSearch, S3, Terraform, and CI/CD (CircleCI).
• Identity & Enterprise Integrations: Own SSO, enterprise authentication, and the data integration pipelines that connect FindBob to customer systems.
• Search & Data Platform: Maintain and evolve the OpenSearch-based search and matching layer that powers advisor discovery.
• AI & Agentic Architecture: Own and extend our agentic framework and AI-powered workflows — both internal productivity and customer-facing features.
• Roadmap & Product Partnership: Partner with the CEO on roadmap, prioritization, and the technical scoping of a new adjacent product line we're investing in.
• Project Management: Help prioritize work, break down features, and keep the team shipping on a predictable cadence.

Tech Stack

• Backend: Ruby, Rails, GraphQL, Sidekiq, ActionCable
• Frontend: React, Apollo Client, Tailwind CSS, Material UI
• Database: PostgreSQL (multi-tenant), Redis
• Search: OpenSearch / Elasticsearch
• Infrastructure: AWS (EC2, RDS, S3, ElastiCache), Terraform, CircleCI
• Identity: SSO / SAML / enterprise auth
• AI: Anthropic Claude API, agentic architecture for business automation
• Monitoring: Sentry, Ahoy analytics

Qualifications

Required:

• 7+ years of professional software development experience, including at least 2 years in a lead-engineer or technical leadership capacity
• Strong proficiency in Ruby on Rails and React
• Experience with GraphQL APIs (building and consuming)
• Comfortable owning AWS infrastructure, CI/CD, and DevOps practices end-to-end
• Experience with enterprise identity (SSO/SAML) and customer data integrations
• Experience mentoring and growing engineers
• Ability to context-switch between hands-on coding, infrastructure, and team coordination
• AI-first mindset — experience using AI tools across development, code review, planning, and debugging
• Based in Ontario, Canada, and legally eligible to work in Canada

Nice to Have:

• Experience with multi-tenant SaaS architectures
• Financial services or fintech domain knowledge
• Experience with Terraform or infrastructure-as-code
• Familiarity with ActionCable / WebSocket real-time features
• Experience building AI-powered product features (agents, LLM integrations)
• Experience scaling a small engineering team as a business grows
• Comfort operating with high ownership and minimal bureaucracy

What We Value

• Bias to shipping. We measure progress in deployed features, not pull request volume.
• Comfort with breadth. In a single week you might debug a SAML certificate issue, ship a React component, write a Terraform change, and review a new agent's prompt engineering.
• Ownership mentality. When things break, you investigate — you don't wait for someone else to pick it up. When a client flags an issue, you pull the thread before it becomes a ticket.
• Pragmatism over perfection. We don't over-engineer. We ship what works, instrument it, and improve based on what we learn.
• Clear communication. We're a remote team. Written communication, async decision-making, and documenting your reasoning matter.

Why FindBob

• High ownership — you'll own the technical direction of the platform and partner directly with the CEO.
• A real growth mandate — we're expanding the team, modernizing core subsystems, and investing in a new product line. Your fingerprints will be on all of it.
• Profitable, enterprise-grade SaaS — an established platform, major enterprise clients across North America and the UK, real revenue, and no venture pressure distorting decisions.
• AI-first culture — we embrace AI as a core part of how we build, ship, and operate.
• Remote within Ontario — work from anywhere in the province.
• Small team, big surface area — no layers of bureaucracy, just shipping.