A little bit about us…
FIVE19 is a full-service advertising and marketing agency based in Richmond, Virginia, that specializes in the senior living sector. We focus on putting people first - whether that’s our clients, the communities those clients serve, or our internal team. Our approach combines strategy, storytelling, website design and digital campaigns to reshape perceptions of senior living and build meaningful partnerships.
A little bit about the role!
We are seeking a Chief of Staff who operates as both strategic partner and tactical executor - someone who thrives at the intersection of vision, operations, and accountability. This role serves as the CEO’s integrative force and operational counterpart, translating big ideas into disciplined execution, structured priorities, and measurable outcomes.As the Yin to a visionary CEO’s Yang, you bring structure, calm, and clarity to creativity and momentum. You absorb ideas, organize priorities, and drive the systems, processes, and metrics that support healthy scale, alignment, and profitability.
You serve as a trusted partner with the calm precision of an operator, the strategic acumen of an advisor, and the emotional intelligence required to influence, guide, and elevate teams.You will report directly to the CEO and ensure the business moves with focus, accountability, and operational excellence. Day-to-day responsibilities include:
Operational Leadership & Accountability
- Serve as the Integrator within the EOS framework, owning cross-functional accountability, team alignment, and performance tracking.
- Facilitate scoping, resourcing, and project profitability reviews - leading scope meetings and driving billability.
- Build, maintain, and analyze operational KPIs in dashboard format to ensure the team stays focused on top priorities.
- Identify and synthesize issues; provide the issue → solution → recommendation framework with concise rationale to the CEO.
- Responsible for management and maintenance of the office.
Finance & Business Operations
- Partner closely with Finance to ensure real-time visibility into forecasts, budgets, utilization, and profitability.
- Oversee and improve processes related to job scoping, time tracking, and performance reporting.
- Build and manage dashboards that track the metrics that matter, driving operational insights and executive visibility.
- Oversee estimates, invoicing, contracts, and process discipline, ensuring smooth operational flow and consistent profitability.
Strategic Planning & Cross-Functional Alignment
- Facilitate leadership and planning meetings, ensuring decisions are documented, communicated, and executed.
- Oversee change management efforts to strengthen clarity, consistency, and buy-in across the organization.
- Translate the CEO’s ideas into structured strategies, action plans, and measurable milestones.
- Lead cross-departmental initiatives to ensure alignment and eliminate silos.
Leadership, Communication & Culture
- Serve as a trusted confidant and strategic sounding board to the CEO.
- Promote a culture of accountability, collaboration, clarity, and transparency across all directors and their departments.
- Navigate conflict and manage sensitive dynamics with professionalism and calm authority.
- Communicate clearly and consistently across the leadership team; drive alignment through concise, actionable messaging.
We are excited about you because you…
- Bring a strategic (40%) and tactical (60%) mindset. You can operate at both the vision-setting and execution levels.
- Operate as an Integrator - building discipline, focus, and clarity across a fast-moving organization.
- Are proactive and anticipatory - spotting gaps, risks, and needs before they’re raised.
- Translate ideas and complexity into clear systems, plans, and priorities.
- Communicate directly, confidently, and with executive presence.
- Think critically and make thoughtful, structured, well-reasoned decisions.
- Navigate complexity and sensitive conversations with emotional intelligence.
- Bring financial acumen - experience with forecasting, utilization, margins, and cost structures.
- Are advanced in Excel and comfortable building dashboards and operational models.
- Are proficient in using Mac and Google Suite products.
- Have agency experience (corporate training or foundation is a plus).
- Understand account and project delivery environments, resource planning, and operational rigor.
- Earn trust quickly and operate with discretion, maturity, and independence.
- Thrive working with a visionary, creative leader - balancing energy with clarity and calm.
Reasons it pays to work at FIVE19 (in addition to the pay itself)...
- Medical, dental and vision insurance
- Employee assistance program (EAP)
- PTO and sick leave, in addition to 8 paid Agency holidays
- 401(k) retirement plan, with company contributions
- Profit sharing plan
- Pet Insurance
- Short-term and long-term disability insurance
- Life insurance
Sandbox and FIVE19 are Equal Opportunity Employers committed to diversity and inclusion in the workplace. All qualified applicants will receive consideration for employment without regard to sex, race, color, age, national origin, religion, physical and mental disability, genetic information, marital status, sexual orientation, gender identity/assignment, citizenship, pregnancy or maternity, protected veteran status, or any other status prohibited by applicable national, federal, state or local law.
