{"id":1437406,"url":"https://alion.io/job/checkbox-principal-engineer","title":"Principal Engineer","company":{"id":3796,"name":"Checkbox","domain":"checkbox.ai","url":"https://alion.io/company/checkbox","size_band":"51-200","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Ashby","truth_index":null},"role":"Industrial Engineering","role_family":"Industrial Engineering","seniority":"lead","employment_type":null,"work_mode":"hybrid","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["Sydney, Australia"],"countries":["AU"],"hiring_countries":[],"hiring_countries_total":0,"salary":null,"salary_estimate":{"min_usd":92000,"max_usd":215000,"period":"year","method":"global_role_cell_scaled_by_country","sample_n":1258},"experience_years_min":null,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"AI Agents","optional":true}],"status":"live","first_seen_at":"2026-09-29T03:56:46Z","employer_posted_date":null,"last_verified_at":"2026-09-29T03:56:46Z","board_verified":false,"closed_at":null,"days_open":0,"trust":{"level":"not_scored","repost_count":null,"flags":[],"days_open":0},"description":"Checkbox is a Series A, Sequoia-backed technology start-up with a mission to enable meaningful work for all. We are building an AI-first platform that is transforming how in-house legal teams operate, from how work enters legal through to how it is understood, routed, managed and resolved.\nOur customers include leading in-house legal teams at companies such as SAP, Coca-Cola, Allianz, BMW, Elastic and Stryker.\nWe are now expanding beyond workflow automation into AI-powered intake, matter management, triage and work orchestration. Our vision is to become the Legal Service Hub for modern organisations, responsible for how legal work is raised, allocated, managed and resolved.\nAs we scale our product, engineering organisation and AI capabilities, we need our architecture to stay coherent, secure and built for the future. This role sits at the centre of that.\nThe Role\nWe are looking for a hands-on Principal Engineer to act as the senior technical authority across Checkbox’s product engineering streams.\nThis role is accountable for making, recording and governing the key technical decisions that shape our future-state product architecture. That includes high-consequence, hard-to-reverse “one-way-door” decisions that are expensive to undo and should not be made implicitly inside a single team.\nYou will help keep our architecture sound, coherent across product streams and safe as we scale. Just as importantly, you will ensure important decisions are written down, understood and followed, rather than lost in tribal memory.\nThis is a technical leadership role, not a people-management role. You will influence through judgement, clarity and working code.\nWhat You’ll Own\nOwn key architecture decisions across Checkbox’s product engineering streams, including high-consequence one-way-door decisions\n\nDefine, document and govern the future-state product architecture\n\nEnsure architecture remains coherent across product streams, Platform, Data Engineering, QA, Enterprise IT and other technology teams\n\nIdentify, design and help build force-multiplier initiatives that help engineering teams move faster and ship higher-quality software\n\nContribute directly to production releases and set the technical bar through working code\n\nDrive engineering decisions through data, feedback loops and measurable quality signals rather than opinion alone\n\nEmbed fitness functions, architecture measures and technical feedback loops into how product engineering works\n\nPartner closely with the Data Engineering function on the data and AI reference architecture\n\nEnsure tenancy, security and compliance are designed into systems from the start\n\nWork closely with Product, Customer Success and Sales so architecture decisions reflect real customer and commercial needs\n\nSupport teams in making pragmatic technical trade-offs between speed, scale, quality, security and maintainability\n\nAbout You\nSignificant experience as a Principal Engineer, Staff Engineer, Architect or senior technical leader in a modern SaaS environment\n\nDeep systems expertise across product engineering, platform architecture, distributed systems and modern cloud-native software\n\nStrong track record of making and governing high-impact architecture decisions across multiple teams or product areas\n\nProven ability to design and ship force-multiplier technical initiatives that improve engineering velocity, quality or reliability\n\nComfortable contributing to production systems while also setting broader technical direction\n\nStrong understanding of tenancy, security, compliance and data isolation in enterprise SaaS environments\n\nExperience working closely with platform, data, QA, infrastructure or enterprise IT teams\n\nStrong product and customer judgement, with the ability to connect technical decisions to commercial and customer outcomes\n\nAbility to influence through credibility, clarity and working code rather than formal authority\n\nExcellent communication skills, with the ability to bring technical and non-technical stakeholders along\n\nPragmatic, hands-on and comfortable operating in a fast-moving scale-up environment\n\nBonus Points\nExperience working on AI-native products, agentic systems, workflow automation or enterprise legal technology\n\nExperience defining architecture across multiple product streams or a multi-product SaaS ecosystem\n\nExperience designing systems that rely on context, retrieval, eventing, integrations or AI-enabled workflows\n\nExperience partnering with data engineering teams on AI or data reference architecture\n\nExperience introducing engineering fitness functions, architectural decision records, technical standards or quality measures\n\nExperience working in a Series A, Series B or high-growth scale-up environment\n\nWhat We Offer\nCompetitive salary\n\nHybrid working with team days in our Sydney CBD office\n\nHigh ownership over architecture decisions that shape Checkbox’s product and engineering future\n\nDirect impact across product engineering, platform, data and AI systems\n\nOpportunity to help scale an AI-first SaaS platform used by leading enterprise legal teams\n\nPersonal learning and development budget\n\nFlexible leave policy\n\nExpense policy and salary sacrifice options\n\nCBD start-up hub with snacks, drinks, premium coffee and team socials\n\nCompany-wide social events and annual off-sites\n\nTransparent, flat culture where questions and feedback are welcomed","description_format":"text","description_chars":5390,"description_truncated":false,"requirements":{"experience_years_min":null,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":["Hybrid work"],"hiring_locations":[],"hiring_excludes":[],"relocation_offered":false,"industries":["Document Management","Legal AI","Legal Software"],"lifecycle":[{"event":"open","at":"2026-09-29T03:56:46Z"}],"liveness":{"score":86,"band":"hot","label":"Hiring now","p_open":1,"p_active":0.86,"p_room":1,"age_days":0,"expected_fill_days":32,"reasons":["seen:0","win:early"],"computed_at":"2026-09-29T05:45:00Z"},"pay":null,"html_url":"https://alion.io/job/checkbox-principal-engineer","json_url":"https://alion.io/job/checkbox-principal-engineer.json","meta":{"generated_at":"2026-09-30T03:25:35Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","usage":{"tier":"crawler","counted_by":"address","units_charged":1,"used_today":2428,"day_limit":5000,"remaining_today":2572,"minute_limit":60,"resets_at":"2026-10-01T00:00:00Z"}}}