[Hiring] Principal Software Engineer @Nerdery

Role Description

The Principal Software Engineer is the technical lead and a full-time hands-on builder for a multi-tenant ERP connector framework for Fleetio, a fleet maintenance SaaS platform. The first adapters are SAP S/4HANA Cloud and Microsoft Dynamics 365 Business Central. The Principal owns the architecture and its early decisions (platform, stack, cloud setup), leads three senior engineers and a QA engineer, and is accountable for posting integrity: financial data moves between Fleetio and customer ERPs with no duplicates and a complete audit trail. They are the main technical voice to Fleetio’s product, integrations and infrastructure teams, and hand the framework over to Fleetio’s integrations team at the end of the engagement.

Qualifications

• Undergraduate or graduate degree in a computer related field, coding bootcamp certificate, OR a thorough demonstration of self-taught software development skills
• 8+ years of software development experience
• 2-3+ years of application software architecture experience, including familiarity with common design patterns and approaches for solving typical application problems for their discipline
• Ability to write complex software and demonstrated proficiency in explaining the “why” behind code
• Strong technical communication acumen; can explain complex technical problems to technical and non-technical audiences (clients, project members, team members, peers, etc.)
• Strong understanding of the development process and ability to maintain an iterative approach throughout the project lifecycle
• Architected and shipped production system-to-system integrations or an integration platform. A web-app architect isn’t enough.
• Deep data-integrity design: idempotency, outbox/ledger patterns, at-least-once delivery, reconciliation.
• Multi-tenant SaaS design: tenant isolation (row-level security), per-tenant secrets, kill switches.
• AWS and IaC design responsibility, not just usage.
• Fluent in Python and/or TypeScript/Node, and comfortable reading Ruby/Rails.
• Has led a client-facing technical engagement under a hard date.
• Demonstrated experience designing and architecting scalable, reliable, and maintainable backend systems and system-to-system integrations, with a strong understanding of distributed systems, architectural trade-offs, and production-level design decisions.
• Demonstrated hands-on experience integrating AI-assisted development tools into daily software engineering workflows, including code generation, debugging, testing, refactoring, and technical problem-solving.
• Ability to effectively leverage AI development tools through structured context management, clear technical specifications, prompt engineering, and iterative validation of AI-generated solutions.

Requirements

• Has experience or demonstrates the ability to participate in client pitches
• Exposure to full stack applications and coding skills outside of your specialization
• SAP S/4HANA APIs (OData/SOAP, communication arrangements, SAP Cloud SDK) and/or Dynamics 365 Business Central
• ERP accounting flows (journal entries, PO → goods receipt → supplier invoice, three-way match)
• iPaaS platforms (Paragon, Workato)
• Framework or SDK design meant for reuse by another team
• Experience designing, building, or integrating AI-powered applications, autonomous agents, or agentic workflows using LLM APIs, AI orchestration frameworks, or related technologies.

What You'll Do

• Own and evolve the existing design: framework module boundaries, adapter interface, idempotency ledger, posting matrix, Postgres-as-queue with the managed-queue upgrade path, and tenant configuration.
• Run the early decision spikes and write the decision records: Paragon vs. standalone, language and SDK choices, AWS environment layout, Fleetio API gaps, and SAP journal-entry timeout recovery.
• Gate the canonical data models with Fleetio. If Fleetio’s models arrive late, define interim models and get sign-off on them.
• Translate accounting requirements into design. Run the finance review of posting defaults (journal-entry mode, company code, tax, currency, posting dates) with Fleetio’s SAP-literate accounting lead.
• Build core framework code alongside the team, especially the ledger and posting-integrity paths.
• Sequence work across the SAP and Dynamics lanes. Keep the “SAP ready by end of January” scope honest using the agreed cut order, and raise early when scope and capacity diverge.
• Set the engineering standards, aligned with Fleetio’s quality guidelines and IaC standard (Terraform/Pulumi). Review code and set test strategy with QA, including duplicate-posting and fault-injection tests.
• Lead the technical side of the demo for Fleetio’s Feb 1–4 kickoff, and the knowledge transfer and runbooks for Fleetio’s integrations team.
• Set how the team uses AI-assisted development within the SOW’s AI clause. The plan assumes those efficiency gains.
• Provide ad-hoc technical support to other practitioners in the domain as needed
• Assist with sales requests as needed by providing technical recommendations and estimates to prospective clients
• Participate in other duties as assigned

Benefits

• Choose from two comprehensive medical plans (including an HSA-eligible option), plus high-quality dental and vision insurance.
• We provide peace of mind by fully covering the cost of several essential plans: Basic Life and AD&D Insurance, Short-Term Disability (STD), and Long-Term Disability (LTD) coverage.
• Take advantage of discounted, employee-paid options to protect your family, pets, and assets, including Voluntary Life and AD&D, Accident, Critical Illness, and Hospital Indemnity insurance, Pet Insurance, and plans offering Legal Support and Identity Theft Protection.
• We offer a 401(k) plan with a company match of up to 3.5% with immediate vesting.
• Nerds enjoy flexible time off with Flex PTO that can be used for vacation, personal time, personal illness, or time off to care for dependents.
• Nerdery is a remote-friendly workplace. Our Minnesota office space is available for Nerds who prefer an in-office environment or collaborative setting.
• All Nerds have dedicated resources and access to funds to pursue professional development, attend industry conferences, and obtain certifications.

Physical Demands and Work Environment

• Sitting for extended periods: will spend significant time in meetings, presentations, and computer use.
• Occasional standing and walking: will need to move around during presentations and client interactions.
• Computer Use: Extensive use of a keyboard, mouse, and computer screen for extended periods. Ability to adjust focus between screen and documents.
• Public Speaking: requires public speaking, including presenting to clients.
• Reaching: Reaching for items on a desk, retrieving documents, or working with equipment is required.
• Lifting: Occasional lifting of light objects (e.g., laptops, peripherals) may be necessary.
• Office Environment: The work environment is primarily an office setting, with typical office equipment and noise levels.
• On-site client work: some work might involve on-site client visits and demonstrations, possibly requiring some walking and standing for extended periods.