Chief of Staff to the CEO

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

About the Role

OpenLoop Health is seeking a strategic, entrepreneurial and execution-oriented Chief of Staff to serve as a trusted partner to the CEO while leading some of the company's most important strategic initiatives. This is not a traditional Chief of Staff role. It combines two distinct responsibilities: driving strategic alignment and operational effectiveness within the Office of the CEO, and independently building and operationalizing new businesses, subsidiaries and strategic initiatives from zero to one.

What You'll Do

• Act as the CEO's strategic partner on enterprise decisions across strategy, finance, operations and organization.
• Translate the CEO's top priorities into an enterprise plan with clear owners, and drive them to measurable outcomes.
• Own Board meeting planning, materials and follow-up with the CEO, CFO, COO and General Counsel.
• Own the executive operating cadence and hold leaders to key decisions and commitments.
• Design the operating mechanisms that close gaps in ownership, decision-making and cross-functional execution.
• Set the vision and execution roadmap for new businesses, and lead them from concept to launch with full accountability for results.
• Lead the operational establishment of new and acquired entities, aligning Legal, Finance, HR, IT, Compliance and Operations.
• Own post-acquisition integration and cross-company alignment after close, partnering with Corporate Development on diligence and planning.
• Define success metrics and governance for each new business, and transition it to a permanent leader once it runs.

Who You Are

• Accountable for strategic, financial and operational outcomes, not only recommendations.
• Self-directed, turning the CEO’s direction into action with minimal oversight.
• Comfortable with ambiguous, high-stakes problems where neither the answer nor the infrastructure exists yet.
• Trusted advisor to founders and executives, with builder experience at high-growth companies.
• Investor-trained operator who has valued businesses and then built them.
• Board-ready communicator who frames decisions, trade-offs and recommendations for the CEO, Board and investors.
• Discreet with sensitive matters across deals, governance and people.

Qualifications

• 7 to 12+ years of experience across finance, investing, corporate development and business operations.
• A first chapter in investment banking, private equity, venture capital or M&A advisory, with strong modeling, analytical and transaction-evaluation skills.
• Hands-on operating experience at an early-stage or high-growth startup, ideally launching, scaling or transforming a business or function. As a co-founder, GM, head of operations or similar.
• A track record of leading complex, ambiguous initiatives from concept to execution.
• Experience working directly with senior executives and influencing cross-functional leaders without formal authority.
• Exceptional written and verbal communication, including Board-level presentations.

Our Benefits

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans
• Flexible Spending/Health Savings Accounts
• Flexible PTO
• 401(k) + Company Match
• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.