Chief Operating Officer

Chief Operating Officer Holler Law Firm

LLC - 3.4

Milford, CT Job Details Full-time $125,000 - $180,000 a year 1 day ago Qualifications Performance dashboard reports Employee onboarding Financial forecasting Dashboard development Escrow Budget management Operations management Variance analysis Real estate law Legal firm experience Financial performance report preparation Managing budgets in a finance role Financial operations management Team management Profit & Loss statement Relationship management Law office Due diligence CRM system proficiency Senior level AI Onboarding process management Post-merger integration Profit and loss analysis Leadership Staffing management Full Job Description General Manager / Integrator Holler Law Firm, LLC/Mancuso Carey — Rocky Hill, CT (hybrid; regular travel to Colchester, Danielson, and Milford) • Reports to the CEO • Full-time, exempt The role in one paragraph 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. Who we are 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. What you'll own 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. Your first 90 days Days 1-30 — Learn and stabilize. Listening tour with every employee. Absorb the COGS model, overhead baseline, and financial projections. Stand up a daily 15-minute check-in with the CEO. Days 31-60 — Take the wheel. Own the L10 and Scorecard. Produce your first monthly P&L with variance analysis. Run COGS validation independently. Complete a full vendor audit. Formally assume HR. Deliver a written Current State Assessment to the

CEO:

what's working, what's broken, where we need to invest first. Days 61-90 — Build forward. Set next-quarter Rocks with the leadership team. Publish v1 of the Accountability Chart. Present a 12-month operational roadmap covering headcount, technology, process, and investor readiness. Stand up the KPI dashboard with automated data feeds wherever possible. What year one success looks like EOS fully operational. Monthly P&L on time every month with tight COGS variance. No operational disruption from the leadership transition. At least three new pipeline clients in national production. Investor-ready books. A CEO who is no longer the bottleneck on day-to-day execution. What you bring Must have 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 have 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+ We're more interested in evidence you've run this kind of operating seat than in the industry you ran it in. If you meet most of the must-haves and are curious about the rest, apply.

Compensation and logistics 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

Schedule:

full-time, exempt, hybrid, Rocky Hill primary with regular travel to the other three CT offices How to apply Send your résumé plus a short note — two paragraphs is plenty — describing one operating problem you owned end to end: what it was, what you did, what changed, and how you know it changed. That note matters more to us than the résumé. Holler Law Firm, LLC is an equal opportunity employer. We welcome applicants from non-traditional backgrounds and encourage you to apply if you meet most of the must-haves, even if your path here looks different from what we've described.