Project Manager / Executive Business Operations Partner

Company Overview
Keystone Advisors is a full-service marketing company aligned with Top Health Insurance Carriers to provide our partners and clients a broad and competitive portfolio of Insurance Options. We have over 20 years of experience in Insurance marketing while serving our local communities with Medicare, Individual, Group Health, Life, and Annuity products. Our core values are Customer service, integrity, compassion, tenacity, and collaboration. 

Position Summary 

We are seeking a high-caliber, execution-obsessed Project Manager / Executive Business Operations Partner to support a fast-moving multi-business entrepreneur overseeing organizations across: 

• Insurance Brokerage & BPO Operations 

• Healthcare & Data Technology Platform 

• Non-Profit / Community Impact Initiatives / Events and Annual Exec/Sales Summits 

This role serves as a force multiplier for the CEO — translating strategy into execution, keeping multiple companies aligned, and ensuring projects move from idea → launch → scale without chaos. 

This is not a traditional admin role. This is a hybrid of: 

• Project Manager 

• Operations Integrator 

• Executive Partner 

Some travel will be required to support executive initiatives, partnerships, site visits, and key events. 

Core Responsibilities 

Enterprise Project Management 

• Manage cross-company projects across insurance, BPO, tech, nonprofit, and real estate 

• Build and maintain project plans, timelines, risk trackers, and milestone dashboards 

• Coordinate cross-functional teams (Sales, Ops, Tech, Finance, Compliance, Community Partners) 

• Drive accountability on deliverables and deadlines 

• Track KPIs and provide executive-ready status reporting 

Executive Operations Support 

• Act as execution extension of CEO priorities 

• Prepare briefing materials, talking points, and executive summaries 

• Support partnership launches, acquisitions, and new market expansion initiatives 

• Assist with vendor selection, contract coordination, and implementation timelines 

• Anticipate needs before they become fires  

Business Line Support 

Insurance Brokerage / BPO 

• Support membership growth initiatives 

• Coordinate call center launches, staffing models, and vendor integrations 

• Track performance metrics and service level standards 

• Assist with carrier and partner implementation projects 

Technology Platform 

• Support product rollout coordination 

• Assist with implementation timelines and client onboarding projects 

• Track sprint deliverables and cross-team dependencies 

Non-Profit / Community Programs 

• Coordinate event planning and community initiatives 

• Support grant tracking and partnership deliverables 

• Help manage volunteer and outreach programs 

Real Estate / International Assets 

• Coordinate vendors, property management, and project improvements 

• Track investment timelines and documentation 

• Assist with international coordination when applicable 

Travel Expectations 

• Estimated 10–25% travel includes: Conferences, Partner meetings, Community events, Property visits and, Executive planning sessions 

Required Qualifications 

• 5+ years Project Management, Operations, or Chief of Staff support experience 

• Experience supporting executives or founders preferred 

• Strong multi-project management across different industries 

• High discretion and professionalism (you’ll see everything) 

• Advanced organizational and prioritization skills 

• Strong written and executive communication skills 

• Comfortable in high-growth, fast-change environments 

Preferred Experience 

• Healthcare, Insurance, or BPO operations exposure 

• Technology implementation or SaaS environment experience 

• Non-profit or community program coordination 

• Real estate or asset management exposure 

• Experience working in founder-led or high-growth companies 

Tech Stack Familiarity (Preferred) 

• CRM platforms (Salesforce or similar) 

• Project tools (Jira, Monday, Confluence, Smartsheet) 

• Data dashboards / reporting tools 

• Microsoft Office + Google Workspace 

• AI productivity tools (working smarter, not harder) 

Success Profile 

You will thrive here if you: 

• Move fast but don’t break important things 

• Love turning messy ideas into clean execution plans 

• Can talk strategy with executives and logistics with operators 

• Stay calm when everything is “priority #1” 

• Are wildly trustworthy 

Compensation 

• Competitive salary based on experience 

• Performance bonus potential 

• Travel expense coverage 

• Growth path into senior operations or chief of staff leadership 

• Full Benefits Package: Health, Dental, Vision, 401K, Gym Membership / wellness, PTO and Paid Holidays. 

Why This Role Matters 

You will directly help scale multiple businesses impacting: 

• Healthcare access 

• Community outcomes 

• Technology innovation 

You are not just supporting operations.  You are helping build an ecosystem.