Director of Operations

Holler Law Firm LLCMilford, CT
$155,000 - $195,000Hybrid

About The Position

The CEO of Holler Law Firm, LLC/Mancuso Carey is a strategist and relationship-builder, and this role is for the operator who partners with him to run the day-to-day operations. This position involves making numbers legible, ensuring accountability, and translating strategy into reliable execution. The firm is a Connecticut professional services company with two divisions: a national title production operation and a retail real estate legal practice. They are a mid-sized firm with approximately 25 W-2 employees across four CT offices, three remote staff, and about 25 support teammates through two outside partners, and are transitioning to an EOS (Entrepreneurial Operating System).

Requirements

  • 7+ years in operations leadership, in professional services, title insurance, real estate law, or a similarly complex service business.
  • Hands-on experience implementing EOS or an equivalent operating framework.
  • Financial fluency: reading, producing, and defending P&Ls; variance analysis; unit economics.
  • Track record managing distributed teams, including offshore or outsourced.
  • Comfort with full-range people management, including performance cases and terminations.
  • Working proficiency with modern operating tools: CRM (HubSpot), production systems, process automation, and current AI tooling.

Nice To Haves

  • Connecticut real estate law or title insurance operations experience.
  • BPO relationship management experience.
  • Background in founder-led businesses preparing for institutional investment.
  • M&A integration experience, diligence through post-close.
  • Scaling a services business from $5–10M to $20M+.

Responsibilities

  • Manage the operating rhythm, including weekly Level 10 meetings, Scorecard metrics, quarterly Rocks, and the Accountability Chart.
  • Oversee financial operations, including monthly P&L statements with variance analysis, COGS model validation, annual budgeting, and monthly reforecasting.
  • Provide oversight for the national division, including the title, closing, and escrow group, BPO relationship management, and new-state entry processes.
  • Manage the retail division, ensuring coordination and consistent service standards across three offices.
  • Handle HR responsibilities for the W-2 team, including onboarding, performance management, and terminations, with a focus on automating or outsourcing before adding W-2 employees.
  • Oversee risk and compliance management, including the relationship with the Manager of Risk & Compliance, escalations, and delivery.

Benefits

  • Base salary: $155,000–$195,000
  • At-risk compensation: approximately 25% of total compensation, tied to Scorecard KPIs and quarterly Rock completion
  • 2026 Benefits Summary attached
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