Chief Operating Officer

Holler Law Firm LLC • Milford, CT

9d • Hybrid

About The Position

Our CEO is a strategist and relationship-builder — that's his strength, and he'll tell you it's also his ceiling. We're hiring the operator who partners with him: the person who runs the day-to-day, makes the numbers legible, holds people to what they committed to, and turns a good strategy into reliable execution. Holler Law Firm, LLC is a Connecticut professional services firm with two divisions: a national title production operation serving institutional clients across multiple states, and our retail real estate legal practice running across three offices. We're a midsized firm ready to scale, with about 25 W-2 employees across four CT offices, three remote staff, plus ~25 support teammates through two BPO partners. We run on EOS.

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 (you've owned a Scorecard, not just attended L10s)
• Financial fluency — reading, producing, and defending P&Ls; variance analysis; unit economics
• Track record managing distributed teams, including offshore or outsourced
• Comfort with the full range of people management, including performance cases and terminations
• Working proficiency with modern operating tools — CRM (we use 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

• The operating rhythm. The weekly Level 10 meeting, a live Scorecard of 5–15 metrics, quarterly Rocks with named owners, and the Accountability Chart.
• The numbers. Monthly P&L by the 15th with variance analysis, monthly validation of our detailed COGS model against BPO invoices, annual budget and monthly reforecast, board-ready reporting. Accounting runs independently — your job is to extract truth from the numbers.
• National division. Oversight of title, closing and escrow group, BPO relationship ownership, and the new-state entry process.
• Retail division. Oversight, coordination, and consistent service standards across three offices handling ~150-200 orders/month.
• People. HR for the W-2 team — onboarding, performance, hard conversations, and terminations, including the ones the founder has historically avoided. Headcount planning that defaults to automate or outsource before adding W-2s.
• Risk and compliance. Our Manager of Risk & Compliance owns day-to-day execution; you own the management relationship, escalations, and delivery.

Benefits

• Base salary: $125,000–$180,000, benchmarked to the Connecticut market for a General Manager seat at a firm this size and complexity
• At-risk: approximately 25% of total compensation, tied to Scorecard KPIs and quarterly Rock completion
• Benefits: See 2026 Benefits Summary attached

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed