Head of Retail Operations & Field Execution
Location: Ontario, field-based with regular presence at Cambridge HQ
Base salary: $140,000 to $180,000
Target annual performance incentive: $40,000 at target achievement
Target total cash compensation: $180,000 to $220,000, with additional above-target upside for exceptional performance.
//The Mandate
Cash 4 You operates 77 financial-services locations across Ontario.
We have built live branch reporting, automated compliance and collections workflows, and much stronger visibility into what is happening across the network. We do not need another executive to observe the data and circulate commentary.
We need a proven multi-unit operator who can turn that visibility into consistent execution across 77 physical locations.
You will inherit an uneven field network. Some locations and employees execute exceptionally well. Others require stronger leadership, clearer expectations, direct coaching or decisive people changes.
Your job is to build the field leadership system that makes execution visible, measurable and repeatable.
This is not a remote oversight position. It is not a conventional corporate VP role. You will spend substantial time in branches, work directly with the CEO and Operations Builders, and be accountable for what customers and employees experience on the floor.
//What You Will Own
- Rebuild field leadership: Design, recruit and lead a lean team of Field Operators capable of managing performance across the province.
- Turn data into action: Convert daily branch-level information into specific field priorities, interventions and follow-through.
- Improve commercial performance: Drive measurable improvement in revenue generation, customer conversion, collections, productivity and branch-level contribution.
- Enforce operating standards: Own the physical condition, hospitality, urgency and execution quality of every location.
- Build stronger operators: Identify high-potential frontline employees, develop internal leaders and create a credible succession bench.
- Make difficult people decisions: Coach employees who can improve and act decisively where ability, effort or integrity does not meet the required standard.
- Partner with technology: Work directly with internal Operations Builders to improve the dashboards, workflows and controls used to manage the network.
- Reduce organizational drag: Replace unnecessary reporting layers and human routing with clear ownership, live evidence and disciplined operating cadence.
//What Success Looks Like
Within your first six months, you will be expected to:
- Establish a fact-based assessment of all 77 locations and their leadership requirements.
- Install a clear daily, weekly and monthly operating cadence.
- Build or restructure the Field Operator layer.
- Improve execution consistency across branch standards, sales activity and collections.
- Reduce repeated failures, missed deadlines and management rework.
- Produce measurable financial improvement that can be traced to specific operating changes.
- Develop a bench of internal operators capable of taking responsibility for larger groups of locations.
//Required Experience
You should apply only if you can demonstrate the following:
- You have personally led a network of at least 50 physical locations.
- You directly managed the regional, district or area leaders responsible for those locations.
- You held measurable accountability for revenue, labour, profitability or another meaningful financial outcome.
- You inherited an underperforming or inconsistent network and materially improved it.
- You have hired, developed, reorganized and, when necessary, replaced field leaders.
- You regularly used location-level data to determine where leaders went, what they inspected and what changed next.
- You are comfortable operating in branches, speaking directly with frontline employees and personally inspecting execution.
- You can distinguish a real operating mechanism from a presentation describing one.
Experience in high-volume retail, QSR, telecom, automotive services, rental operations, branch financial services or another distributed consumer network is particularly relevant.
Candidates whose experience has primarily been in strategy, consulting, support functions or dashboard-based oversight without direct field accountability are unlikely to be successful in this role.
//Travel and Working Model
This is a field-first leadership role, initially accountable for Ontario and expected to build the field operating model that will support Cash 4 You’s expansion across Canada.
You must live, or be prepared to relocate, within approximately 90 minutes of our Cambridge headquarters. Regular presence at Cambridge HQ, frequent branch visits and overnight travel throughout Ontario are required.
As the company enters additional provinces, you will be expected to lead field execution during market launches. This may include recruiting and establishing local leadership, implementing the operating cadence, and spending sustained periods in new markets to validate execution personally.
This role is not suitable for someone seeking a fixed Ontario-only mandate or a predictable remote or office-based executive schedule.
//How to Apply
Answer the indeed questions: Generic responses, unverified title claims and answers without specific numbers will not proceed.
Final-stage candidates should expect their claimed operating scope and results to be verified through references.
Vacancy Status: This posting is for an existing vacancy.
AI Disclosure: We use AI-based tools to assist with applicant screening and assessment.
Pay: $140,000.00-$180,000.00 per year
Application question(s):
- Have you personally held direct operating accountability for at least 50 physical customer-facing locations, including managing the district, area or regional leaders responsible for those locations and owning measurable revenue, contribution or P&L results? YES OR NO? **If NO, please do not apply. **
- Describe the largest physical network or business for which you held direct operating accountability during a period of expansion. State the company, your exact title, dates, starting and ending number of locations, starting and ending revenue or contribution, timeframe, capital invested, direct and indirect headcount, and management headcount added. Explain the operating system you built or changed to support that growth and clearly distinguish your personal decisions from work performed by your team or corporate support functions. If you supported the expansion but did not directly own the result, state that clearly.
- Describe the most underperforming or inconsistent multi-location network you directly inherited. State the number of locations, the two or three most important baseline financial or operating measures, the first change you made to the field leadership structure or operating cadence, and the measurable result over a defined period. Include which decisions you personally made concerning leadership, accountability or talent. If exact financial information is confidential, provide percentages or indexed results.
- This position requires living, or relocating, within approximately 90 minutes of Cambridge headquarters; regular in-person presence at HQ; frequent branch visits; overnight travel throughout Ontario; and multi-day periods in other provinces during market launches. Are you able and willing to meet all these requirements? YES OR NO? **If NO, please do not apply. **
Work Location: On the road
