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About the Role

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, leads three senior engineers and a QA engineer, and is accountable for posting integrity. 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.

Responsibilities

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 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.
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.

Requirements

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
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.
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.

Skills

Customer-Focused Execution and Communication
Tenacious Problem-Solving
Integrity-Driven Work
Collaborative Impact
End-to-End Ownership
Dedication to Craftsmanship

Location

Remote

Work Type

Full-time
Remote

Experience Level

Principal
8+ years of software development experience
2-3+ years of application software architecture experience

Education Level

Undergraduate or graduate degree in a computer related field
Coding bootcamp certificate
Thorough demonstration of self-taught software development skills

Salary/Compensations

$164,500-$200,000/per year

Benefits

Choose from two comprehensive medical plans (including an HSA-eligible option), plus high-quality dental and vision insurance.
Company-Paid Basic Life and AD&D Insurance, Short-Term Disability (STD), and Long-Term Disability (LTD) coverage.
Discounted, employee-paid options for Voluntary Life and AD&D, Accident, Critical Illness, and Hospital Indemnity insurance, Pet Insurance, and plans offering Legal Support and Identity Theft Protection.
401(k) plan with a company match of up to 3.5% with immediate vesting.
Flexible time off with Flex PTO that can be used for vacation, personal time, personal illness, or time off to care for dependents.
Remote-friendly workplace.
Dedicated resources and access to funds for professional development, industry conferences, and certifications.

About the Company

Nerdery is a digital product consultancy. Much more than consultants, we’re allies and guides on our clients’ digital journey – helping them to grow their business and delight their customers through intuitive, thoughtfully designed technology.
As true partners, we prepare our clients for the opportunities in front of them, help them achieve their goals, and quickly deliver value for their customers.
We do this by solving problems in creative ways across strategy, design, and technology.
At Nerdery, we’re not defined by our job titles but by the impact we make.
You’ll work directly and closely with some of the world’s best brands to help create innovative digital products that serve everyone.
As Nerds, our insight, innovation, and expertise are celebrated, and our growth is not only encouraged but expected.
Being a Nerd means stepping up and pushing the boundaries of what’s possible.

Equal Opportunity

Nerdery is an equal opportunity employer and complies with all applicable federal, state and local fair employment practice laws.
Nerdery strictly prohibits and does not tolerate discrimination against employees, applicants or any other covered persons because of race, color, religion, creed, national origin or ancestry, ethnicity, sex, sexual orientation, gender (including gender nonconformity and status as a transgender or transsexual individual), pregnancy, marital status, familial status, age, physical or mental disability, citizenship, past, current or prospective service in the uniformed services, genetic information, membership or activity in a local human rights commission, status with regard to public assistance or any other characteristic protected under applicable federal, state or local law.
All employees, other workers and representatives of Nerdery are prohibited from engaging in unlawful discrimination.
Nerdery will ensure that all employment practices are free of such discrimination.
Such employment practices include, but are not limited to: hiring, promotion, demotion, transfer, recruitment or recruitment advertising, selection, layoff, disciplinary action, termination, compensation, benefits, selection for training, including apprenticeship and other terms and conditions of employment.
Nerdery will also provide reasonable accommodation to applicants and employees with disabilities pursuant to all applicable laws.