Director of Engineering

About Aiwyn: Aiwyn (aiwyn.ai) is the first complete platform built explicitly for modern Accounting Firms. Backed by top-tier global venture investors like Bessemer, KKR, and Revolution, we are one of the fastest-growing scale-up vertical SaaS companies in the world. Building category-defining technology with world-class people, processes, and products, we partner with the majority of the Top 500 firms in the country. Aiwyn is systematically replacing 40-year-old tax engines and brittle legacy integrations with software accounting networks firms can actually trust, holding rare product-market fit in an industry about to change permanently. Aiwyn equips its core engineering squads with an AI-by-default environment built on high trust, extreme technical autonomy, and rigid execution metrics.

Position Overview

We are seeking a highly analytical, systems-minded, and execution-obsessed Director of Platform Engineering to lead, scale, and insulate the technical foundation our entire SaaS platform runs upon under a full-time, fully remote engagement framework based in the United States. Operating as a pivotal technology leader, you will step up to claim direct operational, architectural, and talent accountability over five distinct engineering squads comprising roughly thirty engineers today, managing a team of engineering managers across infrastructure, foundations, tax engine, implementation, and developer productivity domains. Shifting completely away from baseline code patch reviews, loose ticket tracking, or superficial scrum moderation, you will run an active high-throughput data ingestion, complex cloud-native architecture on GCP, and AI-native developer velocity laboratory—partnering shoulder to shoulder with product engineering groups, peer product leaders, technical support, and executive GTM teams. This position requires an engineering leader with a minimum of 2 years acting specifically as a manager of managers, who structures high-availability data normalization systems fluidly natively using DevOps and cloud infrastructure principles, evaluates engineering cadence metrics cleanly to shift deploys to a daily cadence, and establishes high technical accountability confidently to support a multi-year architecture evolution.

Key Responsibilities

• Multi-Team Technical Leadership: Coach, mentor, and develop a high-performing leadership team of Engineering Managers (EMs) across infrastructure, foundations, tax engine, client implementations, and developer productivity groups.
• Core Platform IP Ownership: Oversee the multi-year architectural optimization and scale of our core intellectual property data ingestion and normalization pipeline, ensuring absolute data calculation reliability.
• Operating Model Governance: Define, monitor, and regulate the engineering cadences, metrics, and standards that make the platform org legible and accountable, including cycle planning, design review, and on-call quality.
• Operational Excellence Reinforcement: Drive technical teams toward stable daily production deploys, pushing incident response guidelines toward rigorous root-cause remediation to make production boring.
• Infrastructure Primitive Definition: Establish well-defined internal APIs, foundational primitives, and technical \"golden paths\" that enable internal product engineers to build on top of platform systems friction-free.
• AI Productivity Championing: Lead the developer productivity unit to integrate and scale cutting-edge generative AI tooling natively into the daily engineering workflow, compounding organizational leverage.
• Cross-Functional Strategic Partnership: Coordinate closely with product leaders, customer success managers, and executive teams to ensure customer onboarding landings execute cleanly with zero recurring bugs.

Required Skills & Qualifications

• Proven professional history acting specifically as a Manager of Managers for a minimum of 2+ years, with a verified background leading multi-team technical orgs of 20+ engineers.
• Deep operational mastery managing high-availability, mission-critical cloud applications and a high bar for table-stakes operational metrics natively utilizing DevOps standards.
• Lived, practical history setting high engineering bars, conducting regular structured performance appraisals, and leading performance remediation plans cleanly.
• AI-native technical fluency, showing active personal use of cutting-edge AI development tools and a clear perspective on optimizing modern developer workflows.
• Outstanding written and spoken communication skills, enabling clear translation of highly technical platform roadmaps and tradeoffs to non-technical executive stakeholders.
• Strong background steering multi-year architectural roadmaps and database configurations on Google Cloud Platform (GCP) or comparable hyperscale environments.
• Location Context: Position features 100% remote parameters open exclusively to qualified engineering executives residing permanently within the United States.

Preferred Strategic Indicators (Nice to Have)

• Prior executive engineering tenure navigating the high-stakes compliance and data-integrity requirements of B2B SaaS, enterprise fintech, payments, accounting technology, or similar regulated fields.
• Demonstrated background scaling developer velocity or internal DevOps/SRE tooling platforms inside hyper-growth venture-backed startups.

What We Offer

• Vetted, High-Growth Vertical SaaS Blueprint: Exceptionally competitive base compensation paired with meaningful corporate equity options and clear performance-linked metrics.
• The spectacular professional canvas to lead the foundational platform underneath one of the most consequential vertical SaaS companies of the next decade.
• Profound work-from-home remote parameters providing an autonomous virtual track, 401(k) corporate matching, and uncompromised executive support structures.
• An innovative, direct, and reflective peer leadership team that actively welcomes technical debate, challenge, and technical excellence.
• A unique, culture-driven Adventure Travel Stipend credited directly to your account on each annual anniversary of your employment.