{"id":3136527,"url":"https://alion.io/job/ledgebrook-director-of-engineering","title":"Director of Engineering","company":{"id":3793660,"name":"Ledgebrook","domain":"ledgebrook.com","url":"https://alion.io/company/ledgebrook","size_band":"11-50","is_staffing_agency":true,"employer_type":"agency","is_intermediary":false,"listed_via":null,"ats_vendor":"Comeet","truth_index":null},"role":"Leadership","role_family":"Leadership","seniority":"head","employment_type":"full_time","work_mode":"remote","remote_scope":"stated_countries","remote_scope_basis":"posting_text","remote_working_hours":null,"hiring_geo_confidence":"explicit","locations":[],"countries":[],"hiring_countries":["US","CA"],"hiring_countries_total":2,"salary":null,"salary_estimate":{"min_usd":166000,"max_usd":333000,"period":"year","method":"global_role_seniority_cell","sample_n":3940},"experience_years_min":12,"visa_sponsorship":true,"relocation_package":false,"has_equity":true,"technologies":[{"name":"AWS","optional":false},{"name":"CI/CD","optional":false},{"name":"Incident Management","optional":false},{"name":"Outlook","optional":false},{"name":"Amazon ECS","optional":true},{"name":"Amazon Kinesis","optional":true},{"name":"Confluence","optional":true},{"name":"Docker","optional":true},{"name":"FastAPI","optional":true},{"name":"GitHub","optional":true},{"name":"GitHub Actions","optional":true},{"name":"JavaScript","optional":true},{"name":"Jenkins","optional":true},{"name":"Jira","optional":true},{"name":"Kubernetes","optional":true},{"name":"LLM","optional":true},{"name":"MySQL","optional":true},{"name":"Node JS","optional":true},{"name":"PostgreSQL","optional":true},{"name":"Python","optional":true},{"name":"React.js","optional":true},{"name":"Slack","optional":true},{"name":"SOC 2","optional":true},{"name":"Terraform","optional":true},{"name":"TypeScript","optional":true}],"status":"live","first_seen_at":"2026-10-23T04:03:48Z","employer_posted_date":"2026-10-23","last_verified_at":"2026-10-25T04:03:34Z","board_verified":true,"closed_at":null,"days_open":2,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":2},"description":"Description\nAt Ledgebrook, we are building an Excess & Surplus (E&S) lines insurance company that combines deep underwriting and pricing expertise with a modern technology platform fit for the future of insurance - truly a best-of-both-worlds approach. Our speed and service underpin every decision we make, and our rapidly growing team is a testament to our value proposition resonating with the market.\nYou bring the passion, leadership, and entrepreneurial spirit, and we’ll provide the opportunity to unleash the very best of your talents and skills. Apply now to advance your career at Ledgebrook.\nAbout the Role\nWe’re looking for an experienced Director of Engineering to lead and scale multiple engineering teams responsible for the technology powering Ledgebrook’s underwriting, policy, rating, data, and operational systems.\nThe ideal candidate combines strong technical judgment, organizational leadership, and business acumen. You are someone who can develop Engineering Managers and senior technical leaders, shape technology strategy and architecture, create operating discipline across teams, and ensure engineering investments translate into meaningful business outcomes.\nYou will be accountable not only for what engineering delivers, but also for building the organization, systems, processes, and leadership capability that allow teams to execute predictably and scale as Ledgebrook grows.\nYou’ll partner closely with Product, Data, Infrastructure, Security, Finance, Operations, and business leaders to translate company priorities into technology roadmaps and execution plans while maintaining the reliability, scalability, security, and long-term health of our technology platform.\nWhat You'll Do:\nLead, coach, and develop Engineering Managers, Technical Leads, and senior individual contributors across multiple engineering teams.\nOwn organizational health across your engineering domain, including staffing, structure, technical delivery, capacity, performance, team engagement, retention, and succession planning. \nPartner with Product and business leaders to translate company strategy and priorities into technology roadmaps, investment decisions and executable delivery plans.\nDrive execution across multiple teams, ensuring initiatives have clear ownership, milestones, dependencies, success measures, and accountability.\nOwn the technology strategy and long-term health of systems and services within your domain, including architecture integrations, scalability, reliability, security, performance, and cost.\nPartner with Principal Engineers, Architects, Engineering Managers, and Technical Leads to establish technical direction, architecture standards, and engineering best practices.\nMaintain sufficient technical depth to challenge designs, evaluate trade-offs, identify systemic risks, and guide significant technology and architecture decisions.\nBalance product delivery with platform investment, technical debt reduction, reliability, security, compliance, and modernization.\nEstablish strong data-driven engineering operating practices across development, testing, CI/CD, observability, incident management, documentation, release management, and production support.\nProvide leadership during critical incidents, ensuring effective escalation, communication, resolution, root-cause analysis, and follow-through on preventative improvements.\nLead quarterly and annual technology planning, including roadmap prioritization, capacity planning, organizational design, and headcount projections.\nMaintain productive relationships with strategic technology vendors and external partners, including involvement in evaluations, renewals, integrations, and build-versus-buy decisions.\nIdentify opportunities to leverage emerging technologies, AI, automation, and modern engineering practices to create meaningful business or operational advantage.\nRepresent Engineering in leadership discussions, planning forums, operating reviews, and cross-functional initiatives.\nAbout you\nWe love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building and scaling a company from the ground up.\nAs a Director, you are comfortable operating at multiple levels. You can discuss architecture with senior engineers, coach an Engineering Manager through an organizational challenge, work with Product on roadmap trade-offs, and explain technology investments and risks clearly to business and executive leaders.\nYou’ll be a great fit if you bring:\nA Strong Moral Compass: You believe in doing the right thing, period. We have a strict zero-tolerance policy for toxic behaviors.\nCustomer-First Empathy: You are passionate about delivering an exceptional experience to everyone you work with, both inside and outside the company.\nLeadership Through Others: You understand that your impact as a Director comes from building strong leaders, teams, systems, and organizational capability rather than personally owning every decision.\nBusiness Acumen: You connect engineering decisions to business outcomes and understand how technology investments affect customers, operations, cost, growth, and risk.\nTechnical Judgment: You can operate comfortably in architectural and technical discussions, ask the right questions, understand trade-offs, and provide direction without becoming a bottleneck.\nIntellectual Curiosity: You naturally question the status quo and love finding innovative ways to solve problems.\nA Growth Mindset: You possess a hunger for continuous learning and actively seek ways to improve yourself, your leaders, and the organization.\nUrgency & Prioritization: You can make thoughtful decisions quickly and balance long-term technology health with the realities of a fast-moving business.\nA Solution-Oriented Outlook: When things go wrong, you focus on solving the problem, understanding the root cause, and improving the system rather than assigning blame.\nTransparent Communication: You value honesty, clarity, direct feedback, and early communication of risks and trade-offs.\nTeam-First Energy: You want to win together as a high-performing team and actively build strong connections across teams, functions, and remote locations.\nOrganizational Thinking: You look beyond individual teams and identify patterns, bottlenecks, and opportunities that improve the broader engineering organization.\nRequirements\nMust haves\n12+ years of professional software engineering experience, including significant experience leading engineering teams and managers.\n5+ years of engineering leadership experience, including experience managing Engineering Managers or leading multiple engineering teams.\nDemonstrated success building, scaling, and developing high-performing engineering organizations.\nStrong technical background in software architecture, distributed systems, APIs, cloud platforms, data-integrated applications, and production systems.\nExperience leading architecture and technology strategy across multiple services, systems, or product areas.\nDemonstrated ability to translate business strategy and product priorities into technology roadmaps and executable engineering plans.\nExperience partnering closely with Product, business stakeholders, and senior leadership on ambiguous and complex business problems.\nStrong understanding of software development lifecycle practices, CI/CD, testing, observability, reliability, incident management, and operational excellence.\nExperience designing and delivering scalable, production-grade systems in cloud environments, preferably AWS.\nProven experience managing cross-team dependencies, complex initiatives, and competing priorities in a high-growth environment.\nProven ability to recruit, coach, mentor, and develop Engineering Managers, senior engineers, and technical leaders.\nExperience with workforce planning, organizational design, capacity planning, and headcount prioritization.\nStrong communication, with the ability to explain complex technical issues, risks, investments, and trade-offs to technical and non-technical audiences.\nStrong sense of ownership and accountability for technology outcomes from strategy and architecture through delivery and production operations.\nNice to haves\nPrior startup or scale-up experience in a high-growth, high-velocity environment.\nExperience scaling engineering organizations through significant company growth.\nExperience with insurance, fintech, financial services, or another highly regulated industry.\nExperience with underwriting, rating, policy administration, claims, financial, or insurance data systems.\nExperience with cloud-native architectures and platforms using AWS, Terraform, Docker, ECS, or Kubernetes.\nExperience with modern CI/CD tooling such as GitHub Actions, AWS CodePipeline, or Jenkins.\nExposure to AI/ML systems, generative AI, LLM-driven workflows, and intelligent automation.\nExperience developing engineering operating models, career frameworks, technical governance, or organizational maturity practices.\nExperience managing cloud, vendor, infrastructure, and technology investment costs.\nExperience supporting SOC 2, security, compliance, or other regulated technology environments.\nThe Tech Stack for this role:\nLanguages: Python, TypeScript\nFrontend: React\nBackend: Python, Node.js, FastAPI and related frameworks\nData Stack: PostgreSQL, MySQL, Kinesis\nCloud Infrastructure: AWS, Terraform\nDevOps: GitHub Actions, Docker, CI/CD automation\nTools: GitHub, Jira, Confluence, Jellyfish, Slack\nEmerging Technologies: AI/ML, LLM-enabled workflows, intelligent automation\nBenefits\nUS & Canada Benefits\nCompetitive salary + meaningful equity ownership\n100% employer-paid health insurance\n100% remote work, flexible hours\nUnlimited paid time off\nWork with an ambitious, smart, fun team to transform a $1T global industry\nSignificant ownership, autonomy, and opportunity to shape the engineering organization\nDirect influence on technology strategy and company growth\nFor Candidates Applying From The U.S. and Canada:\nPlease note: This position is open only to candidates who are authorized to work in the United States or Canada without the need for current or future employer-sponsored work authorization. We are unable to offer sponsorship at this time.\nLedgebrook may use Artificial Intelligence (“AI”) as part of the job application process, including to assist us in evaluating your application. AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact . Requesting an accommodation will not negatively affect your application.","description_format":"text","description_chars":10837,"description_truncated":false,"requirements":{"experience_years_min":12,"management_years_min":5,"team_size_min":null,"manages_managers":true,"education":null,"security_clearance":false,"languages":[]},"benefits":["Continuous learning","Equity","Health insurance"],"hiring_locations":[{"name":"United States","iso":"US","kind":"country"},{"name":"Canada","iso":"CA","kind":"country"}],"hiring_excludes":[],"relocation_offered":false,"industries":[],"lifecycle":[{"event":"open","at":"2026-10-23T06:03:45Z"}],"visa":[],"liveness":{"score":54,"band":"ok","label":"Likely open","p_open":1,"p_active":0.542,"p_room":1,"age_days":1,"expected_fill_days":8,"reasons":["conf:1","agency","velocity","win:early"],"computed_at":"2026-10-24T06:02:35Z"},"pay":null,"html_url":"https://alion.io/job/ledgebrook-director-of-engineering","json_url":"https://alion.io/job/ledgebrook-director-of-engineering.json","meta":{"generated_at":"2026-10-25T04:10:29Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":5391,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-10-26T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":3793660},"rest":"https://alion.io/mcp/rest/get_company?id=3793660"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fledgebrook-director-of-engineering"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fledgebrook-director-of-engineering"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fledgebrook-director-of-engineering"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/ledgebrook-director-of-engineering\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fledgebrook-director-of-engineering"}]}