Estimator (Winnnipeg)

POSITION SUMMARY

The Estimator is the full financial owner of every assigned file, responsible for driving profitability from first notice of loss through final closeout. This role controls scope, pricing strategy, negotiations, and documentation integrity while leading execution teams to deliver clean, audit-ready outcomes.

This is a performance-driven position where success is measured by gross profit, disciplined execution, and the ability to maintain control across multiple concurrent projects. The Estimator serves as the primary decision-maker on file-level financial outcomes, ensuring margin protection, scope accuracy, and operational alignment.

This role requires a high level of accountability, ownership, and precision. The Estimator is not a support function, they are the authority on performance, profitability, and execution.

ABOUT US

WINMAR® is a leader in property restoration and emergency response services, specializing in mitigation, reconstruction, and full-cycle project delivery. Our work operates in high-stakes environments where performance, precision, and accountability directly impact financial outcomes and client trust.

We are a standards-driven organization built on discipline, ownership, and execution. Every file matters, and every decision impacts profitability, client relationships, and long-term growth.

At WINMAR®, we reward performance, not tenure. Our team is composed of operators who take ownership, protect margin, and deliver results without compromise.

WINMAR® – We Do It Right.

WHAT SUCCESS LOOKS LIKE

• Files are managed with full control from intake to closeout with no loss of visibility
• Gross profit targets are consistently met or exceeded across all assigned projects
• Scope and pricing are accurate, strategic, and defensible in all negotiations
• Change orders are tightly controlled and executed without margin erosion
• Documentation is complete, clean, and audit-ready at all times
• Client and insurer relationships are managed professionally and effectively
• Multiple files are handled simultaneously without operational breakdown
• Project teams execute with clarity, accountability, and alignment
• Margin leakage is prevented through disciplined decision-making
• Communication across stakeholders is proactive, clear, and consistent
• Opportunities for upsell and relationship expansion are identified and executed
• Files close cleanly with strong financial outcomes and no audit issues

PERFORMANCE OBJECTIVES

• Own and manage the full lifecycle of each file from first notice of loss through final closeout
• Achieve or exceed gross profit targets across all assigned projects
• Develop and execute accurate scopes of work aligned with project requirements
• Establish pricing strategies that maximize profitability while remaining competitive
• Lead insurer and client negotiations to secure favorable outcomes
• Maintain strict control over change orders to prevent scope creep and margin loss
• Ensure all files maintain audit-ready documentation at every stage
• Manage multiple concurrent projects without loss of control or performance
• Lead project teams to execute work aligned with scope, budget, and timeline
• Protect margin by identifying and eliminating inefficiencies, waste, and rework
• Maintain strong client and adjuster relationships to support long-term growth
• Contribute to business growth through upselling, cross-selling, and brand representation

CORE COMPETENCIES

• Financial Ownership & Accountability – Takes full responsibility for file-level P&L outcomes
• Gross Profit Management – Deep understanding of margin control and profitability drivers
• Scope Development & Control – Builds accurate scopes and enforces discipline throughout execution
• Negotiation Skills – Effectively negotiates with insurers and clients to maximize outcomes
• Project Leadership – Leads teams to execute with clarity, alignment, and accountability
• Documentation Discipline – Maintains consistent, accurate, and audit-ready records
• Operational Control – Manages multiple projects simultaneously without loss of performance
• Decision-Making – Makes timely, informed decisions that protect financial outcomes
• Client Relationship Management – Builds trust and maintains strong external relationships
• Attention to Detail – Ensures precision in scope, pricing, and execution
• Results Orientation – Driven by performance, outcomes, and measurable success
• Adaptability Under Pressure – Thrives in fast-paced, high-stakes environments

EDUCATION & EXPERIENCE

• 3–5+ years of estimating experience in restoration and construction
• Proven experience in both emergency mitigation and reconstruction project delivery
• Strong insurance industry experience, including proficiency in Xactimate and/or Symbility
• Demonstrated ability to scope, price, and negotiate insurance claims and approvals
• Proven history of gross profit accountability and financial ownership
• Experience contributing to or managing $2M+ in annual revenue
• Strong ability to manage multiple concurrent projects with high performance standards
• Consistent track record of maintaining audit-ready documentation
• Client-facing, sales-capable, and confident communicator
• Experience operating in a performance-driven, accountability-focused environment
• Ability to think like a business owner, not just an estimator
• Valid driver’s license required
• Must be bondable (mandatory requirement)

COMPENSATION STRUCTURE

• Base Salary: $85,000–$95,000
• On-Target Earnings: $110,000-120,000 (Bonus Performance)
• Incentives: Quarterly, uncapped, gross profit-based
• Requirements for Incentive Eligibility:
• Documentation compliance
• Communication standards
• Margin discipline
• Audit approval (non-negotiable)
• Benefits: Health Benefits, RRSP Matching