About Liberty HorizonsLiberty Horizons is a financial consulting and venture capital practice based in Toronto, Canada. We build and manage accounting and finance operations for founder-led startups and small businesses, handling everything from fractional CFO services and bookkeeping to AR/AP, payroll, and venture consulting.We are a small team with high standards. That means real ownership, real exposure, and real growth for the right person. If you want to own a function, work directly alongside senior leadership, and build something that matters to the businesses you serve, this is the right environment for you.Our goal is to be the leading accounting brand in Canada and the USA, leading the industry in AI and agentic operations that scales a category killer. You will be the one who works with us to envision what the future of accounting is for small business, and see that vision come to life with a team of A-players.About the RoleLiberty Horizons runs on a simple equation: a small team of senior operators, an AI production system underneath them, and output that looks like it came from a firm three times our size. The CTO owns the vision, the architecture, and the technical direction of that system.This is a leadership role with a builder's mandate. You set the technical strategy for how Liberty Horizons uses AI and automation to deliver at scale. You own the roadmap, the stack decisions, and the team that executes against them. You are the reason a small firm can deliver like a large one, and the reason that ratio improves every year.You report to the COO and work closely with the CEO and the broader leadership team. You are a member of the senior leadership team. You bring a technical point of view into every strategic conversation and you are accountable for the firm's technology advantage as a competitive asset.You do not need to be an accountant. You do need judgment and taste. Liberty Horizons wins on craft and precision, and the fastest way to break the machine is to automate the part that should stay human. The version of you we want can sit beside a Senior Controller or a fractional CFO, understand where the work lives, and build infrastructure that makes them faster without making them generic.What the First 90 Days Look LikeDays 1 to 30: Learn and OrientFully understand the firm's internal operations: how work moves from client intake to delivery across bookkeeping, payroll, reporting, tax, client interaction and CFO advisory servicesAudit the current tool stack, manual processes, and any existing automationsMap every recurring workflow and identify the highest-value targets for systemisationComplete all mandatory onboarding and compliance trainingDays 31 to 60: Contribute IndependentlyOwn the build-versus-buy assessment for the current stack and bring a prioritised recommendation to the COO and CEODefine the technical architecture for the internal AI production layerEstablish documentation and engineering standards for everything the team buildsIdentify and begin the hire or onboarding process for the Senior Full Stack AI Engineer if not already in placeDays 61 to 90: Own ItThe technical roadmap for the next two quarters is defined, documented,



and agreed with the COO and CEOThe internal AI production layer is in active development with clear milestonesOutput per person is instrumented and the baseline is establishedThe engineering function is operational with clear ownership, standards, and a build cadenceResponsibilitiesTechnical Strategy and ArchitectureSet the technical direction for how Liberty Horizons uses AI, automation, and software to deliver at scaleOwn the architecture of the internal production layer: agents, automations, integrations, and the data infrastructure underneath themOwn the build-versus-buy decision on every tool and defend the margin that comes from getting it rightStay ahead of the tooling landscape and have a plan before capabilities shift under the businessTeam Leadership and Engineering FunctionBuild and lead the engineering function from the ground up, starting with the Senior Full Stack AI EngineerSet the standard for how the team builds: documentation, quality control, shipping cadence, and code that others can maintainDevelop the engineers under you and build a team and culture that scales with the businessMake every operator in the firm more capable by raising the floor on AI fluency across the teamThought Leadership and Building Out LoudWork alongside the CEO and COO to develop yourself and the team as a thought leader in the spaceCollaborate with the marketing team to create "build out loud" content as we tell the story of a small group challenging the oligopoly of the accounting industryBuild pitch decks with the leadership team and be a part of the venture funding process when neededAI Production SystemsOwn the internal AI production layer end to end: the agents, workflow automations, and integrations that compress the distance from intake to delivered workInstrument output per person and cycle time, and show the gains in numbers every quarterBuild the quality control layer so AI-assisted work clears the bar before it affects a clientInnovation and Technical JudgmentSeparate what is real from what is hype. Run quick, cheap pilots, kill what does not earn its keep, and scale what doesSpecify problems clearly enough that a model can solve them, and identify when the output is wrongBring new capability recommendations to the COO and Founder with context, a recommendation, and a build planOperations and Internal InfrastructureFind the recurring inefficiencies across the firm and systemise themBuild and maintain the technical playbook for how Liberty Horizons works, and keep it current as the tooling shiftsEnsure every system built can be run by the team without the builder in the roomWhat an A-Player Looks Like in This RoleTechnical vision: You set the direction, not just the implementation. You think in systems and in years, not sprintsOutput quality: Everything you ship is documented, maintainable, and held to a standard the team can reproduceOwnership: You own the firm's technical advantage completely. When it falls short, you do not explain it. You fix itLeadership: You build engineers, not just systems. Your team is better because you are in the roomJudgment and taste: You know which slice of the work should never be handed to a model,



and you protect itStrategic thinking: You bring a technical point of view into business decisions, not just engineering decisionsValues: You do the right thing when no one is watchingWho This Role Is ForSomeone who has built and led engineering or AI functions, not just contributed to themSomeone who is technically deep and commercially sharp in equal measureSomeone who can sit beside a finance operator, understand the work at a craft level, and build infrastructure that makes them betterSomeone who wants equity and ownership in something being built from the ground up, not just a job, and certainly not just a titleSomeone who is energised by the constraint of a small team and the ambition of a large missionSomeone who finds the intersection of AI and professional services genuinely interestingWho This Role Is Not ForSomeone who is a strong individual contributor but has not led a technical functionSomeone who sets technical direction without staying close to the buildSomeone who treats AI as a novelty rather than a production layerSomeone who needs a fully defined brief before they can moveSomeone who finds early-stage ambiguity draining rather than motivatingQualificationsMust Have10+ years of experience building software, automation, or AI systems, with at least 5 years in a technical leadership roleHands-on technical ability: you can build when needed and you never lose touch with the stackExperience working in a venture-backed business as it scalesFluency with the modern AI stack including LLMs, prompt and context engineering, and agent frameworksA track record of building systems that a non-technical team actually depends onExperience hiring, developing, and leading engineersExceptional written communication and documentation standardsNice to HaveExperience in fintech, professional services, or a founder-led businessFamiliarity with accounting or CFO service operationsExperience building internal tooling that scaled across a growing teamA data, analytics, or machine learning backgroundWhat We Offer$250,000–$300,000 CAD base salary plus performance bonusEquity participationFull benefits packagePaid time offProfessional development budgetIn-person in Toronto working alongside the senior leadership teamThe mandate to build a technical function from zero and own it end to endA small, high-standard team where your work is visible and your contribution mattersThe Hiring ProcessThis process is deliberate. We are selective because the standard matters.Application and Values Pre-Screen: Written application including structured values questionsScreening Interview: 45-minute video call covering values, experience, and fitHiring Manager Interview: Deep dive on technical strategy, leadership, and ownershipThe Gauntlet: Multi-stage practical assessment including a take-home assignment, case study, and live presentationReference Checks: Minimum two professional references, at least one direct managerDisclaimerLiberty Horizons is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome all qualified applicants, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.#J-18808-Ljbffr

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