Working Ranch Manager Jobs in Chicago, IL (NOW HIRING)

Company

Farm Family specializes in farm and ranch protection with a wide range of products including flexible farm packages, business owner policies, commercial package, workers compensation, commercial auto and select personal auto coverage. Farm Family is a leader in serving the Northeast and Mid-Atlantic markets and is pursuing growth across the U.S. The Farm Family entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc.

Job Description

Head of Small Commercial (P&L Owner - Build & Scale)

Mission

Own full financial and strategic performance of the Small Commercial business, balancing growth, underwriting profitability, and capital efficiency while building a scalable, market-leading franchise over time.

This leader will initially operate as a matrixed business owner, shaping strategy and execution across underwriting, pricing, claims, and distribution-then design, justify, and stand up a dedicated operating model and team to accelerate performance.

Role Evolution (Critical to Success)

Phase 1: Diagnose, Align, and Shape (0-6 months)

Objective: Establish control through influence; define the opportunity and roadmap

• Own small commercial P&L visibility (baseline performance, segmentation, profitability drivers)
• Diagnose portfolio health:
  • Segment profitability (class, size band, tenure, state, channel)
  • Rate adequacy
  • Expense evaluation
  • Claims drivers (severity, litigation, leakage)
• Evaluate current capabilities:
  • Underwriting (authority, consistency, referral patterns, talent quality)
  • Pricing (rating plans, segmentation depth, data gaps)
  • Distribution (producer mix, productivity, concentration, appetite clarity)
  • Operations (cycle time, STP, scalability constraints)
• Identify structural gaps vs. best-in-class small commercial models (speed, simplicity, segmentation, digital enablement)
• Build and socialize Small Commercial Strategy & Operating Model Blueprint:
  • Target segments and appetite
  • Go-to-market and channel strategy
  • Required pricing sophistication
  • Underwriting model (rules vs. judgment)
  • Technology and workflow needs
• Begin influencing:
  • Appetite clarity and tightening/expansion
  • Early pricing or segmentation fixes
  • Distribution focus adjustments

Key Output: business case for investment and operating model evolution

Phase 2: Build & Prove (6-18 months)

Objective: Stand up capabilities and demonstrate measurable improvement

• Execute approved investment roadmap:
  • Talent (initial hires: product/portfolio, analytics, underwriting leadership as needed)
  • Pricing/segmentation improvements
  • Workflow/STP enhancements
• Begin formalizing P&L ownership mechanisms:
  • Portfolio steering cadence
  • Rate adequacy governance
  • Exception and authority frameworks
• Deliver early wins:
  • Improved loss ratio through segmentation/pricing
  • Increased quote-to-bind and retention where targeted
  • Reduced cycle times and referral friction
• Establish:
  • Underwriting guidelines and authority aligned to small commercial speed
  • Producer segmentation and targeted growth strategy
  • Claims feedback loop for loss drivers and leakage
• Start building a dedicated small commercial identity internally and externally

Key Output: Demonstrated P&L momentum + validation of the model

Phase 3: Scale & Own (18+ months)

Objective: Transition to full organizational ownership with reporting structure

• Build and lead a dedicated Small Commercial organization, including:
  • Product / Portfolio Management (fully or partially aligned to the vertical)
  • Underwriting teams (fully or partially aligned to the vertical)
  • Analytics / pricing partnership structure
  • Dedicated ops alignment (where scale warrants)
• Assume formal authority over underwriting execution for the segment
• Mature capabilities:
  • Advanced segmentation / pricing sophistication
  • Automated underwriting / STP expansion
  • Digital distribution and platform strategy
• Optimize capital deployment:
  • Reinsurance usage
  • Mix management
  • Expansion into adjacent segments or geographies
• Deliver sustained outperformance vs. plan and market

Key Output: Fully scaled, profitable, and differentiated small commercial franchise

Primary Responsibilities

Portfolio & Financial Performance

• Own Small Commercial P&L:
  • GWP, Earned Premium, Loss Ratio, Expense Ratio, Combined Ratio
  • Growth, retention, mix/segmentation
• Set and continuously refine appetite:
  • By class, size (micro vs. small), industry, geography, channel
• Drive rate adequacy and pricing sophistication with actuarial:
  • Ensure alignment to loss trend and target returns
• Actively manage:
  • Concentration risk
  • Cat exposure
  • Litigation-prone segments
• Define and outperform annual business plan

Operations & Experience

• Partner with Ops/IT to build a fit-for-purpose small commercial engine:
  • Straight-through processing (STP)
  • Simplified workflows
  • Pre-bind rules and controls
• Improve:
  • Cycle times and responsiveness
  • Data capture quality
• Monitor:
  • NPS / CSAT
  • Referral SLAs
  • Ease-of-doing-business

Claims & Risk Feedback Loop

• Partner closely with Claims to:
  • Understand severity drivers and emerging trends
  • Reduce leakage and improve outcomes
• Embed claims insights into:
  • Pricing
  • Appetite
  • Underwriting rules

People & Organizational Build

• Phase 1:
  • Assess talent across underwriting, product, and analytics
• Phase 2:
  • Define hiring plan and capability requirements
  • Justify ROI of organizational build-out
• Phase 3:
  • Lead Small Commercial team:
    • Product / Portfolio Leads
    • Underwriting leaders/teams
    • Analytics (direct or aligned)
• Build a culture of:
  • Ownership
  • Data-driven decision-making
  • Speed + discipline

Decision Rights (Evolving)

Early (Matrix Authority)

• Influence appetite, pricing, and underwriting decisions
• Recommend investment priorities
• Drive alignment across functions

Mid (Shared Authority)

• Co-own appetite, pricing direction, and underwriting frameworks
• Formal role in governance committees

Late (Full P&L Authority)

• Final decision on:
  • Appetite and segmentation
  • Product roadmap
  • Underwriting framework
• Direct control over dedicated small commercial resources

Salary range: $269,178 - $389,000

PLEASE NOTE:

Applicants must be legally authorized to work in the United States. At this time, we are not able to sponsor or assume sponsorship of employment visas.

If you have a disability under the Americans with Disabilities Act or similar state or local law and you wish to discuss potential reasonable accommodations related to applying for employment with us, please contact our Benefits Department at 210-321-8400.

Benefits and Compensation

We offer a competitive compensation package, performance-based incentives, and a comprehensive benefits program-including health, dental, vision, 401(k) with company match, paid time off, and professional development opportunities.

Core Values

At Clearbrook our Core Values are Integrity, Collaboration, Pursuit of Excellence and Forward Thinking. These values reflect who we are today and who we aspire to be - guiding how we work, how we lead and how we succeed.