Head of Product Engineering
Location: Cambridge, Ontario
Job type: Full-time
Working model: Cambridge-based and in person
Base salary: CA$200,000 to CA$250,000
Target annual performance incentive: CA$50,000 at target achievement
Target total cash compensation: CA$250,000 to CA$300,000
//The Mandate
Cash 4 You is a 25 year, mid-cap financial-services company with an 100M+ balance sheet and 77 physical locations across Ontario.
We have real customers, real transactions, existing technology, imperfect workflows and consequential business problems.
We are rebuilding how customer acquisition, lending, collections, compliance, branch execution and internal operations work using software, data, automation and AI.
Your mandate is to turn momentum into a coherent product, data and engineering capability capable of supporting national growth.
We are not hiring a conventional IT director, vendor manager or engineering executive who manages software development from a distance. If your primary outputs are roadmaps, architecture presentations and meetings about what other people are building, this is not your role.
We are hiring a founder-grade product engineer who can personally take an unresolved business problem through discovery, product definition, architecture, data modelling, coding, testing, deployment, adoption and measurable economic impact.
During the initial phase, this will be a predominantly hands-on mandate. Approximately 70 to 80 percent of your time will be spent directly designing, building, shipping and improving production systems.
You may eventually build a small, exceptional engineering team. You will not begin by creating departments, management layers or a requisition list for every capability you do not personally possess.
You will report directly to the CEO/Founder and have substantial authority over product priorities, architecture, technology choices, build-versus-buy decisions and engineering investment. You will be expected to challenge assumptions, including the CEO’s, using evidence and shipped results.
//What You Will Own
- Turn problems into products: Work directly with the Founder, operators, frontline employees and customers to understand consequential problems and determine what should be built, purchased, automated, simplified or eliminated.
- Build production software: Personally architect, code, test and ship customer-facing applications, internal operating systems, APIs, integrations, data pipelines and automation.
- Own the data layer: Design transactional schemas, queries, reporting structures, data controls, migrations, performance improvements, backup and recovery practices.
- Own the complete release path: Establish practical standards for automated testing, quality assurance, deployment, monitoring, observability, security, incident response and recovery.
- Use AI as engineering leverage: Use AI-assisted development, models and agents to compress build cycles and automate work. Establish the evaluations and controls required to prevent inaccurate outputs and weak AI-generated code from reaching production.
- Connect engineering to economics: Instrument adoption, conversion, customer acquisition, revenue, contribution, cost, productivity and risk so engineering output can be connected to business results.
- Work with imperfect reality: Integrate with existing systems, operational constraints and regulated financial-services workflows. This is not a pristine greenfield laboratory.
- Build the future physical customer experience: Our product surface will increasingly extend into branches through self-service kiosks and connected devices. You will own the system across customer experience, application software, device management, identity and document capture, payments and peripherals, remote provisioning, telemetry, secure updates, uptime and failure recovery.
- Add capacity intelligently: Bring in employees or specialist expertise only when a demonstrated bottleneck, control requirement or material risk justifies it.
You are not expected to personally design circuit boards. You are expected to make sound build, buy or integration decisions and bring in specialist hardware, security or payments expertise where necessary.
//What Success Looks Like
Within your first 30 days, you will be expected to:
- Understand our critical customer journeys, operating workflows, systems and data.
- Establish direct working relationships with the people using the systems.
- Identify the highest-value product and engineering opportunities.
- Ship at least one useful production improvement.
Within your first 90 days, you will be expected to:
- Deliver a substantial product, automation or system improvement used in live operations.
- Demonstrate adoption and an initial measurable business result.
- Establish a practical release, testing, monitoring and user-feedback cadence.
- Produce a coherent view of the architecture, data foundation and highest-priority technical liabilities.
Within your first year, you will be expected to:
- Deliver multiple production capabilities with demonstrated adoption and financial or operating impact.
- Reduce manual work, fragmented tools and unnecessary vendor dependence.
- Establish a repeatable path from business problem to deployed product to measured outcome.
- Build an architecture and data foundation capable of supporting national growth.
- Define the technical and product architecture for increasingly automated and self-service retail locations.
- Determine whether additional engineering capacity is justified and recruit selectively where required.
//Required Proof of Creation and Scale
This role will own technology capable of materially affecting a large scale $100+ million balance sheet enterprise.
This is not the role in which you receive your first opportunity to build commercially consequential technology or operate systems with significant financial exposure.
To qualify, you must demonstrate both creation and enterprise-scale production ownership.
1. Creation
You must have personally taken at least one product or core system from an unresolved customer or operating problem through product definition, architecture, hands-on implementation, deployment and sustained production use.
While you remained a material hands-on technical and product owner, that product or system must have produced at least one of the following:
- CA$10 million or more in recognized annual revenue or contribution directly attributable to the product.
- CA$5 million or more in verified annual contribution improvement, cost reduction or loss avoidance.
- Another quantified and documented outcome demonstrably equivalent to at least CA$5 million in annual economic impact.
2. Enterprise Scale
You must also have held direct production accountability for a core system operating at consequential scale, such as:
- A customer product serving at least 100,000 active customers or users.
- A core system whose failure could materially interrupt a business or product line generating at least CA$50 million in annual revenue or contribution.
- A core regulated system managing a business with a balance sheet or financial exposure of at least CA$100 million.
- A system processing or managing at least CA$500 million in annual lending, payment, transaction or other regulated financial volume.
- Another core system carrying a quantified level of financial, operational, security or regulatory exposure of comparable magnitude.
Enterprise-scale ownership qualifies only where you personally made consequential architectural decisions, wrote or materially changed critical production code, owned releases and production incidents, and remained accountable for reliability as the system scaled.
The creation and enterprise-scale evidence may come from the same product or from separate products. In either case, you must explain what you personally designed, coded, deployed and operated.
Working at a company of this size does not qualify by itself. Managing a team that produced these results does not qualify unless you remained materially involved in the architecture, code, deployment and production operation.
We will distinguish:
- Product-attributable revenue from total company revenue.
- Recognized revenue and contribution from transaction or loan volume.
- Your personal contribution from the output of the broader company or team.
- Technology that caused an outcome from technology that merely existed near it.
- A system you built and scaled from a successful platform you joined afterward.
All material claims must be supportable through a confidential product and architecture walkthrough, permitted operating or financial evidence, and references from people who directly observed the work.
//Required Capabilities
Apply only if you can demonstrate most of the following:
- You can currently demonstrate the ability to personally write, ship and support meaningful production code.
- You have taken multiple products or substantial capabilities from unresolved problems to real-world usage.
- You have deep capability in backend engineering, relational databases, SQL, systems architecture and data modelling.
- You can build enough of the frontend experience to deliver a complete, usable product.
- You understand APIs, integrations, cloud infrastructure, testing, deployment, monitoring, security and production recovery.
- You have personally spoken with users or customers and changed what you built based on what you learned.
- You understand adoption, conversion, customer acquisition, revenue, contribution, cost and unit economics.
- You use AI materially in your engineering workflow or products and understand where it fails.
- You can make sound technical tradeoffs without hiding behind unnecessary complexity or fashionable architecture.
- You know when independent security, privacy, compliance or specialist review is necessary.
- You can explain precisely what you built, what you inherited, what you delegated and what measurable outcome followed.
Experience as a technical founder, founding engineer, early-stage product engineer, principal product engineer or independent software builder is particularly relevant.
Experience with kiosks, point-of-sale systems, payment devices, identity systems, connected devices or managed device fleets is valuable but not mandatory.
Formal pedigree, prestige employers and a public GitHub profile are not required. Evidence of shipped work is required.
//This Role Is Unlikely to Fit If
Your recent experience has primarily involved:
- Corporate IT operations, helpdesk, device administration or enterprise application support.
- Managing vendors, budgets or engineering teams without personally building production software.
- Producing architecture presentations while other people make the system work.
- Operating within one narrow technical specialty while depending on separate product, database, quality assurance and deployment departments.
- Producing AI demonstrations that never reached sustained production use.
- Delivering agency or consulting projects without owning adoption, iteration, production reliability or economic results.
- Joining an already successful product and claiming the scale of the entire platform as your personal result.
//Location and Working Model
This position is based at our Cambridge, Ontario headquarters and is a primarily in-person operating role.
Candidates may apply from anywhere. The successful candidate must be able to work regularly in person at Cambridge HQ and be reliably available on site within approximately 45 minutes when the role genuinely requires it. Relocation may therefore be necessary before starting employment.
Regular in-person work with the CEO, operating teams and users is fundamental to the role. Periodic visits to branches, vendors and new markets will also be required.
This is an intensive, founder-like operating mandate requiring periodic branch travel and high availability.
This is not a remote position.
//How We Will Assess You
Traditional cover letters are not required. We care more about demonstrated work than polished interviewing.
Qualified candidates should expect:
- A review of the products and outcomes they personally owned.
- A confidential live product, architecture and technical walkthrough. Public source code is not required.
- A discussion of production failures, technical tradeoffs and economic results.
- Live working exercises. AI tools are allowed and expected.
- References from founders, customers or direct collaborators who personally observed the candidate building.
Do not provide proprietary source code or confidential information you are not authorized to share.
Generic application answers, company-level numbers presented as personal results and claims that cannot be substantiated will not proceed.
Vacancy Status: This posting is for an existing vacancy.
AI Disclosure: Cash 4 You uses AI-based tools to assist in screening and assessing applicants. Final hiring decisions are made by people.
Pay: $200,000.00-$250,000.00 per year
Application question(s):
- This position requires regular in-person work at Cambridge HQ. If hired, will you either live within practical commuting distance of Cambridge by your start date or have an agreed relocation plan?
YES OR NO
- Can you currently demonstrate the ability to personally design, code, test, deploy and support a meaningful production product end to end, including its backend, data model, integrations, release process and production incidents?
YES OR NO
- In no more than five short bullets, state:
- The product and company.
- What you personally designed and coded.
- The largest active-user or financial scale reached.
- The annual revenue, contribution, cost reduction or loss avoidance attributable to the product.
- A public product link, if available. If private, write “private walkthrough available.”
Use ranges or percentages if exact information is confidential. Do not provide a narrative.
Work Location: In person
