Software Engineer - Ruby / Product Engineering

Overview
SendOwl is a small, venture-backed software company helping creators and digital businesses sell products online.
Our customers rely on SendOwl to run meaningful parts of their businesses and livelihoods. We power digital commerce for creators, educators, software companies, and online businesses around the world.
We are a very small engineering team operating at high velocity. Engineers deploy to production daily, own meaningful parts of the product, and work directly on problems that impact revenue, customer experience, and platform reliability.
We’re looking for a pragmatic, product-oriented engineer who thrives in high-autonomy environments, is looking to be on the cutting edge of AI development, and wants outsized ownership and impact.
This is not a role for someone looking for heavy process, perfectly defined requirements, or narrow specialization. You will work across product development, architecture, debugging, infrastructure, AI tooling, customer problems, operational workflows, and legacy systems.
Ruby and Rails experience is preferred, but we care more about engineering judgment, learning velocity, product thinking, and execution.
How We Think About Engineering
We believe AI fundamentally changes software engineering.
Small teams using strong tooling should outperform much larger organizations.
At SendOwl, AI-assisted development is not experimental or optional. It is part of our daily workflow. We are actively redesigning how software gets built by combining strong engineering judgment with AI tooling, automation, testing, and high-leverage development workflows.
We care deeply about increasing engineering velocity without sacrificing quality, reliability, or maintainability.
We want engineers who are excited to help shape that future.
What You’ll Own
Build and ship customer-facing product features
Work across Ruby and Rails systems powering the SendOwl platform
Help improve architecture, reliability, testing, and developer workflows
Contribute to AI-first engineering workflows and internal tooling
Continuously find ways to accelerate our engineering velocity
Debug production issues and improve operational stability
Work directly with leadership, support, and product discussions
Operate with high autonomy and ownership
Ship production code frequently
Navigate ambiguity and make pragmatic technical decisions
Help modernize and improve legacy systems where appropriate
What We’re Looking ForRequired
Strong Ruby engineering experience in production environments
Experience operating effectively in startups or small engineering teams
Ability to work independently with minimal oversight
Strong product and customer intuition
Comfortable navigating ambiguity, legacy systems, and incomplete information
Strong debugging and problem-solving skills
Strong written communication skills
High curiosity and fast learning velocity
Pragmatic engineering judgment
Experience using AI-assisted development tools as part of daily engineering work
Desire to rethink how software engineering operates in an AI-first world
Nice to Have
Ruby on Rails experience
SaaS, ecommerce, subscription, or payments experience
Experience improving CI/CD and developer workflows
Experience with AI-assisted software development workflows
Frontend experience
Experience supporting live production systems
What Success Looks Like
Within the first few months, a successful engineer in this role will likely:
Ship meaningful production features independently
Become productive quickly in an established Ruby/Rails codebase
Improve at least one important engineering or operational workflow
Demonstrate strong judgment in ambiguous situations
Increase engineering throughput using AI-assisted workflows
Contribute ideas that improve architecture, tooling, or developer velocity
Operate effectively with a high degree of ownership and autonomy
Who Thrives Here
This role is likely a strong fit if you:
Like small teams with high ownership
Prefer shipping over process theater
Are excited about AI-first engineering workflows
Enjoy solving messy real-world problems
Learn quickly and operate with urgency
Take ownership, make pragmatic trade-offs, and ship high-quality work
Want direct visibility into the impact of your work
Can balance speed with strong engineering judgment
Are comfortable wearing multiple hats
This role is probably not a fit if you:
Need highly structured requirements and planning processes
Prefer narrowly scoped roles in large organizations
Avoid operational responsibility or production debugging
Want extensive management layers and process overhead
Are uncomfortable with ambiguity, legacy systems, or fast iteration
Compensation & Environment
Strong compensation and meaningful equity
Remote-friendly
Small, experienced engineering team
Venture-backed company with established customers and real scale
Daily production shipping cadence
Direct influence on product direction, architecture, and engineering workflows
Opportunity to help define how AI-first software engineering operates inside a real business

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