Chief of Staff

About OpenCall

OpenCall builds AI phone agents for healthcare. We help medical groups automate the front desk: booking, rescheduling, cancellations, FAQs, routing, reminders, reactivation, and operational follow-up across calls and texts.

Healthcare practices are drowning in phone volume, staffing shortages, missed calls, inconsistent workflows, and manual admin work. OpenCall gives them a 24/7 AI operator that actually understands their scheduling rules, specialties, providers, locations, escalation paths, and patient workflows.

We are growing fast, selling into multi-location healthcare groups, and need help as we scale expansion across enterprise customers at much higher speed. The bottleneck is no longer demand. It is operational leverage.

That is where this role comes in.

About the Role

This is a high-trust, high-output role working directly with the Founding team. You will turn chaos into operating cadence, messy customer problems into clear execution plans, and repetitive founder work into scalable systems.

This is not a “take notes and follow up” Chief of Staff role. It is an operator role. You will own cross-functional execution across sales, implementation, customer operations, recruiting, internal automation, investor prep, and company operating systems.

The right person is sharp enough to sit in the room on strategy, practical enough to fix the broken process afterward, and intense enough to keep moving when the problem is ambiguous, urgent, and ugly.

What You’ll Own

• Founder leverage: Run the Founding team’s operating cadence across priorities, meetings, follow-ups, investor materials, customer escalations, recruiting, and internal execution.
• Company operating system: Build lightweight systems for goals, ownership, deadlines, metrics, dashboards, customer status, hiring pipelines, and weekly execution rhythm.
• AI-enabled internal automation: Identify manual work across the company and turn it into AI-native workflows using tools like ChatGPT, Claude, Zapier, Make, Retool, Airtable, Notion, Linear, HubSpot, Slack, Gmail, and internal scripts.
• Implementation and customer operations: Help drive enterprise customer rollouts from signed contract to live deployment, making sure owners, blockers, timelines, SOPs, and customer communication are clear.
• Special projects: Own messy, cross-functional problems where the answer is not obvious and there is no existing owner. Examples: improving implementation speed, building a customer health system, creating a new reporting process, preparing an enterprise procurement package, or standing up a new internal function.
• Executive communication: Draft crisp internal updates, investor notes, customer-facing materials, board-style memos, hiring docs, operating reviews, and decision briefs.
• Sales and GTM operations: Help tighten pipeline tracking, handoffs, deal follow-up, pricing materials, customer ROI analyses, sales scripts, and expansion motions.
• Recruiting and team scaling: Help source, screen, coordinate, and close high-quality candidates across operations, sales, implementation, support, and engineering-adjacent roles.
• Metrics and accountability: Build the reporting layer that tells us what is actually happening across sales, deployment, support, usage, customer health, and internal throughput.

Who You Are

• You are extremely organized, but not bureaucratic.
• You can write clearly and think from first principles.
• You are comfortable with spreadsheets, dashboards, workflows, automations, and lightweight scripting.
• You are not intimidated by healthcare complexity, enterprise customers, messy data, or incomplete information.
• You can operate across founders, engineers, sales, implementation, support, and customers without creating confusion.
• You can take a vague request like “deployment is too slow” and turn it into the right meetings, metrics, owners, process changes, and follow-through.
• You do not need clean swim lanes.
• You are willing to do unglamorous work if it is the highest-leverage thing.
• You have strong judgment about when to move fast, when to escalate, and when to slow down because a detail matters.
• You are AI-native and actively use modern tools to produce more output than a normal operator.

What Great Looks Like

Within your first 30 days, you understand the company’s operating rhythm, major customers, sales pipeline, implementation process, internal bottlenecks, and founder priorities.

Within 60 days, you have taken over recurring executive operations, improved follow-through across the company, and shipped at least a few internal systems or automations that save real time.

Within 90 days, you are independently owning major cross-functional initiatives, reducing founder drag, accelerating customer deployment, and making the company feel meaningfully more organized without slowing it down.

You Might Be a Fit If

• You have 3 to 8 years of experience in startups, consulting, banking, private equity, BizOps, strategy, operations, growth, product ops, or founder-facing roles.
• You have worked in a high-growth, low-process environment before.
• You are strong with written communication and can produce investor/customer/executive-quality material quickly.
• You can handle both strategy and execution.
• You like being close to the center of the company.
• You have unusually high follow-through.
• You are comfortable being measured by output, not effort.

Not for Everyone

This role will be intense.

There will be urgent customer situations, shifting priorities, imperfect information, and problems that do not come with instructions. You will be deep in implementation trackers, customer escalations, hiring loops, messy spreadsheets, or internal automation.

If you want a narrow strategy role, this is not it.
If you need heavy process, this is not it.
If you dislike operational details, this is not it.
If you wait to be told exactly what to do, this is not it.

If you want real responsibility and direct leverage on a fast-growing company, this is the job.

Compensation & Benefits

• $160k to $220k base depending on experience
• Meaningful equity
• Health, dental coverage
• High-trust working environment
• Direct exposure to founders, customers, investors, and company-defining decisions
• In-person team culture in NYC and/or SF

Homebase

NYC or San Francisco preferred.
In-person strongly preferred. We move faster when the people building the company are in the room.