Chief Technology Officer

Location
On-Site
Job Type
Full-Time
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About Liberty Horizons

Liberty Horizons is the future of accounting for small businesses. We pair talented onshore accountants with the right business owner clients to provide a white glove service that has not been provided in the small business accounting industry. We do this through a tech-enabled approach that allows accounting professionals to provide the highest quality and fastest turnaround of accounting, bookkeeping, fractional controller, and fractional CFO services to an underserved market of small business owners.

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We are a small team with high standards. That means real ownership, real exposure, and real growth opportunities 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.

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About the Role

Liberty 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.

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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 challenger firm can deliver like a large one, and the reason that ratio improves every year.

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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.

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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.

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What the First 90 Days Look Like

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Days 1 to 30: Learn and Orient‍
  • Fully understand the firm's internal operations: how work moves from client intake to delivery across bookkeeping, payroll, reporting, tax, client interaction and CFO advisory services
  • Audit the current tool stack, manual processes, and any existing automations
  • Map every recurring workflow and identify the highest-value targets for systemisation
  • Complete all mandatory onboarding and compliance training
Days 31 to 60: Contribute Independently
  • Own the build-versus-buy assessment for the current stack and bring a prioritised recommendation to the COO and CEO
  • Define the technical architecture for the internal AI production layer
  • Establish documentation and engineering standards for everything the team builds
  • Identify and begin the hire or onboarding process for the Senior Full Stack AI Engineer if not already in place
Days 61 to 90: Own It
  • The technical roadmap for the next two quarters is defined, documented, and agreed with the COO and CEO
  • The internal AI production layer is in active development with clear milestones
  • Output per person is instrumented and the baseline is established
  • The engineering function is operational with clear ownership, standards, and a build cadence

Responsibilities

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Technical Strategy and Architecture
  • Set the technical direction for how Liberty Horizons uses AI, automation, and software to deliver at scale
  • Own the architecture of the internal production layer: agents, automations, integrations, and the data infrastructure underneath them
  • Own the build-versus-buy decision on every tool and defend the margin that comes from getting it right
  • Stay ahead of the tooling landscape and have a plan before capabilities shift under the business
Team Leadership and Engineering Function
  • Build and lead the engineering function from the ground up, starting with the Senior Full Stack AI Engineer
  • Set the standard for how the team builds: documentation, quality control, shipping cadence, and code that others can maintain
  • Develop the engineers under you and build a team and culture that scales with the business
  • Make every operator in the firm more capable by raising the floor on AI fluency across the team
Thought Leadership and Building Out Loud
  • Work alongside the CEO and COO to develop yourself and the team as a thought leader in the space
  • Collaborate 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 industry
  • Build pitch decks with the leadership team and be a part of the venture funding process when needed
AI Production Systems
  • Own the internal AI production layer end to end: the agents, workflow automations, and integrations that compress the distance from intake to delivered work
  • Instrument output per person and cycle time, and show the gains in numbers every quarter
  • Build the quality control layer so AI-assisted work clears the bar before it affects a client
Innovation and Technical Judgment
  • Separate what is real from what is hype. Run fast, cheap pilots, kill what does not earn its keep, and scale what does
  • Specify problems clearly enough that a model can solve them, and identify when the output is wrong
  • Bring new capability recommendations to the COO and Founder with context, a recommendation, and a build plan
Operations and Internal Infrastructure
  • Find the recurring inefficiencies across the firm and systemise them
  • Build and maintain the technical playbook for how Liberty Horizons works, and keep it current as the tooling shifts
  • Ensure every system built can be run by the team without the builder in the room

What an A-Player Looks Like in This Role

  • Technical vision: You set the direction, not just the implementation. You think in systems and in years, not sprints
  • Output quality: Everything you ship is documented, maintainable, and held to a standard the team can reproduce
  • Ownership: You own the firm's technical advantage completely. When it falls short, you do not explain it. You fix it
  • Leadership: You build engineers, not just systems. Your team is better because you are in the room
  • Judgment and taste: You know which slice of the work should never be handed to a model, and you protect it
  • Strategic thinking: You bring a technical point of view into business decisions, not just engineering decisions
  • Values: You do the right thing when no one is watching

Who This Role Is For

  • Someone who has built and led engineering or AI functions, not just contributed to them
  • Someone who is technically deep and commercially sharp in equal measure
  • Someone who can sit beside a finance operator, understand the work at a craft level, and build infrastructure that makes them better
  • Someone who wants equity and ownership in something being built from the ground up, not just a job, and certainly not just a title
  • Someone who is energised by the constraint of a small team and the ambition of a large mission
  • Someone who finds the intersection of AI and professional services genuinely interesting

Who This Role Is Not For

  • Someone who is a strong individual contributor but has not led a technical function
  • Someone who sets technical direction without staying close to the build
  • Someone who treats AI as a novelty rather than a production layer
  • Someone who needs a fully defined brief before they can move
  • Someone who finds early-stage ambiguity draining rather than motivating

Qualifications

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Must Have‍
  • 10+ years of experience building software, automation, or AI systems, with at least 5 years in a technical leadership role
  • Hands-on technical ability: you can build when needed and you never lose touch with the stack
  • Experience working in a venture-backed business as it scales
  • Fluency with the modern AI stack including LLMs, prompt and context engineering, and agent frameworks
  • A track record of building systems that a non-technical team actually depends on
  • Experience hiring, developing, and leading engineers
  • Exceptional written communication and documentation standards
Nice to Have
  • Experience in fintech, professional services, or a founder-led business
  • Familiarity with accounting or CFO service operations
  • Experience building internal tooling that scaled across a growing team
  • A data, analytics, or machine learning background

What We Offer

  • $250,000–$300,000 CAD base salary plus performance bonus
  • Equity participation
  • Full benefits package
  • Paid time off
  • Professional development budget
  • In-person in Toronto working alongside the senior leadership team
  • The mandate to build a technical function from zero and own it end to end
  • A small, high-standard team where your work is visible and your contribution matters

The Hiring Process

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This process is deliberate. We are selective because the standard matters, to us and to our clients.

  1. Application and Values Pre-Screen: Written application including structured values questions
  2. Screening Interview: 45-minute video call covering values, experience, and fit
  3. Hiring Manager Interview: Deep dive on technical strategy, leadership, and ownership
  4. The Gauntlet: Multi-stage practical assessment including a take-home assignment, case study, and live presentation
  5. Reference Checks: Minimum two professional references, at least one direct manager

How to Apply

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Submit your application by selecting the "Apply Now" button below. You will be asked to complete a short written values response as part of the application. This is not a cover letter; generic answers will not advance. Tell us something specific and real.

Liberty 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.

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Apply Now

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