CP Triangle - Head of Operations

Responsibilities

• Work closely with the President and General Counsel to actualize the company vision while safeguarding compliance and risk standards
• Recruit, manage, promote, and train a team effectively, evolving the org chart to support a portfolio doubling in size
• Build the operational infrastructure needed to absorb 40 to 150 new doors per month without overwhelming the fulfillment team
• Lead the evaluation, selection, and migration of property management software (Buildium to DoorLoop or comparable platforms)
• Implement automation, AI tools, and project management systems to eliminate manual data entry and protect top performers from burnout
• Develop regional office leadership (Triangle and Triad) into strategic delegators capable of running their own teams with accountability and autonomy
• Build and oversee data dashboards that translate top-level goals into measurable individual KPIs across every department and role
• Design and execute the onboarding workflows for new portfolio acquisitions, including bulk-upload processes for large multi-unit handoffs
• Bridge domestic regional teams with offshore virtual assistant teams handling bookkeeping and maintenance functions
• Formalize HR practices, including the ongoing 1099 to W-2 conversion, compensation structures, and performance management
• Implement strict meeting cadences, communication infrastructure, and reporting rhythms across the organization
• Oversee compliance initiatives including general liability insurance, broker licensing coverage, and entity-level operational integrity

Requirements

• Proven track record scaling a property management firm through the 1,000 to 2,000+ door growth curve, including expansion into new geographic markets
• Hands-on experience auditing, selecting, and migrating legacy property management software (Buildium, DoorLoop, AppFolio, Propertyware, or similar)
• Demonstrated success implementing automation, AI tools, and project management platforms that eliminate manual workflows
• Experience managing blended teams that include domestic regional staff and offshore virtual assistants
• Track record building KPI-driven organizations out of unstructured, "fly-by" environments, including implementing formal compensation and performance structures

Core Competencies

• The "Integrator" skillset, with the ability to safely execute a visionary leader's ideas while honoring a risk-averse legal and compliance lens
• Data and KPI mastery, including building automated dashboards that translate company goals into individual measurable outcomes
• Leadership development expertise, with the ability to coach frontline doers into strategic delegators who can hire, train, and hold their teams accountable
• Change management and process engineering skills, including the ability to standardize complex transitions like onboarding 100-unit acquisitions
• Data-driven decision making, able to analyze data and make critical choices based on evidence

Benefits

• Salary Range: $120,000 to $140,000 commensurate with experience + Bonus Structure
• Employment Type: W2
• Benefits: 50% coverage on Health Benefits (Vision, Health, Dental)
• 401K: We have a $401K match available for all W2 Employees.
• Vacation: PTO is Standard 2 Weeks. Standard US Holidays observed + Week off for Christmas Holidays
• Professional Development: This role will be supported by an external Ops program that includes Ops mentorship, community, and live coaching.

How to Apply

If you are interested in this position, please submit an application at the following link. https://recruiterflow.com/db_5f712a22c33a3d8ff14e412f5e6ab747/jobs/16