Job description

About UpSmith UpSmith is an AI-powered platform for home services companies. Our AI agents automate customer outreach at scale - booking maintenance appointments, following up on estimates, confirming jobs, and re-engaging lapsed customers on behalf of HVAC, plumbing, and electrical companies across the US. We're a small engineering team where every system we build directly drives revenue for our clients. The feedback loop is tight and the stakes are real - something breaks or underperforms, clients notice the same day. The Role We're hiring Software Engineers to own core platform systems as we scale. This is a high-ownership role on a small team. You'll shape technical direction, make architectural decisions, and ship end-to-end. The specific problems will shift as we grow - what stays constant is that you'll own technically complex systems with direct, measurable business impact. You'll work closely with the rest of the engineering team as well as the ops team that manages client relationships. The Kind of Work You'll Do To give you a sense of the problems on - not an exhaustive list, but representative of the type and complexity of work at this level: Decision systems. Building the logic that determines which customers to contact, when, and why - and making that logic configurable, auditable, and increasingly intelligent over time. Data infrastructure. Making our data trustworthy, queryable, and actionable - the analytics foundation that powers targeting, reporting, and client-facing products. Supply and demand. Connecting real-time technician availability to outreach decisions, agent conversations, and client reporting so the platform responds to what's actually happening on the ground. Client-facing visibility. Our clients need to see what's happening with their campaigns without emailing us. That means dashboards, attribution, full-funnel tracking, and alerting - built on the analytics layer and designed for people who aren't technical. System evolution. We have production systems serving real clients that need to be replaced incrementally. You'll design migration strategies, run parallel validation, and cut over without disrupting active campaigns. What We're Looking For You drive impact. You work to find the next thing big thing that will bring value to the team and company. You influence the team and company in an honest and positive way. You build up and support your teammates. You've built systems that make decisions at scale. Whether that's ad targeting, recommendation engines, marketplace matching, or campaign orchestration - you've designed pipelines where the system decides who gets what, and you've dealt with the operational complexity that comes with it. You think in data models. You know how to design schemas that absorb business complexity without becoming unmaintainable. You're comfortable with the tradeoffs between normalized relational models, EAV patterns, and JSONB escape hatches - and you know when each is appropriate. You're pragmatic about shipping. You design for incremental delivery, not big-bang rewrites. You've migrated production systems while they were running and know what it takes to do that safely. You close the loop. You don't just build the pipeline - you think about how to measure whether it's working, how to surface failures before clients notice, and how to use outcome data to improve the system over time. You write clearly. Engineers at UpSmith write design docs that the team can build from. You'll spend meaningful time articulating your approach before you start coding. Technical Environment • Backend: Python, PostgreSQL, SQLAlchemy • Data: dbt, Prefect, incremental models, SCD Type 2 snapshots • Infrastructure: Kubernetes, AWS (S3, SQS, EventBridge) • AI/ML: LLM-powered conversational agents, with growing opportunities to introduce ML-based optimization into targeting and prioritization • Integrations: ServiceTitan (field service management), CRM systems • Early-stage equity in a company with strong revenue growth and a clear path to scale • High ownership - you'll shape technical direction, not implement someone else's spec • A small team where your work has visible, measurable impact on client outcomes • Remote-first with flexibility to work where you're most productive

Requirements

Must-haves

The Kind of Work You'll Do
To give you a sense of the problems on - not an exhaustive list, but representative of the type and complexity of work at this level:
Decision systems. Building the logic that determines which customers to contact, when, and why - and making that logic configurable, auditable, and increasingly intelligent over time.
Data infrastructure. Making our data trustworthy, queryable, and actionable - the analytics foundation that powers targeting, reporting, and client-facing products.
Supply and demand. Connecting real-time technician availability to outreach decisions, agent conversations, and client reporting so the platform responds to what's actually happening on the ground.
System evolution. We have production systems serving real clients that need to be replaced incrementally. You'll design migration strategies, run parallel validation, and cut over without disrupting active campaigns.
You drive impact. You work to find the next thing big thing that will bring value to the team and company. You influence the team and company in an honest and positive way. You build up and support your teammates.
You're pragmatic about shipping. You design for incremental delivery, not big-bang rewrites. You've migrated production systems while they were running and know what it takes to do that safely.
You close the loop. You don't just build the pipeline - you think about how to measure whether it's working, how to surface failures before clients notice, and how to use outcome data to improve the system over time.
You write clearly. Engineers at UpSmith write design docs that the team can build from. You'll spend meaningful time articulating your approach before you start coding.
Technical Environment
Backend: Python, PostgreSQL, SQLAlchemy
Data: dbt, Prefect, incremental models, SCD Type 2 snapshots
Infrastructure: Kubernetes, AWS (S3, SQS, EventBridge)
AI/ML: LLM-powered conversational agents, with growing opportunities to introduce ML-based optimization into targeting and prioritization
Integrations: ServiceTitan (field service management), CRM systems
Early-stage equity in a company with strong revenue growth and a clear path to scale
High ownership - you'll shape technical direction, not implement someone else's spec
A small team where your work has visible, measurable impact on client outcomes
Remote-first with flexibility to work where you're most productive

Nice-to-haves

None flagged.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

airestpythonkubernetesawsmlllm

Platform: workable
Effort: medium