Founding Operations Lead

We’re hiring a Founding Operations Lead to build an AI-native operations function from the ground up at Mason ($6.5m raised, NYC-based, fast-growing AI startup).

Your job will be to design how Mason runs — using AI as a core primitive — across:

• New customer workflows: setting up scalable systems for contract generation, invoicing, and billing
   
• Onboarding & implementation: automating user onboarding, training, and support
   
• Go-to-market operations: operationalizing sales playbooks and supporting marketing execution
   
• Hiring & recruiting: supporting recruiting efforts, and building efficient recruiting processes
   
• Internal operations: creating the systems that tie everything together

This is an operations-first role at the center of the company — spanning Business Operations, Customer Success, GTM, Recruiting, and some Support. You must be a systems thinker with a track record of using AI to automate workflows and drive real operational leverage — not just experimentation.

Successful candidates will be given the opportunity to rapidly take on substantial responsibility, and to build and grow their own team.

Who You’ll Work Closely With:

You’ll work directly with Mason's founders to ensure customers are successful on Mason while also designing the internal processes and tooling that allow us to scale:

• CTO has had 3x successful startup exits: last company was YCombinator-backed HR-Tech platform that he built from 0→1 and scaled to processing 8 million+ job applications, with a highly profitable exit
   
• CEO was previously Chief of Staff at Plaid, scaled Plaid from 500 → 1,200 employees as a member of the management committee overseeing Plaid's 300+ employee GTM org; today, Plaid has been used by 1 in every 2 Americans - let's achieve the same with Mason :)

What you'll focus on:

Operations & Systems

• Design and implement how Mason operates across customer workflows, onboarding, support, and internal processes
• Build AI-native, repeatable systems that automate manual work and improve reliability
• Create lightweight infrastructure to track customers, contracts, billing, pipeline, and internal workflows
• Identify bottlenecks and inefficiencies, and continuously improve how the business runs
• Own and evolve the tooling stack across operations (e.g., CRM, support, billing, internal tools)
• Partner closely with product and engineering to translate operational needs into product improvements

Revenue & Customer Operations

• Build and scale systems for contract generation, invoicing, and billing
• Operationalize the sales process from lead → close → onboarding handoff
• Ensure clean, consistent handoffs across GTM and customer workflows

Onboarding, Implementation & Support Systems

• Design and automate onboarding and implementation workflows
• Build AI-assisted onboarding and training systems that scale
• Stand up and manage support infrastructure (Intercom, Slack, etc.)
• Define SLAs, workflows, and escalation paths
• Turn recurring issues into system and product improvements

GTM & Recruiting Operations

• Operationalize sales playbooks and workflows
• Support marketing execution and lead flow management
• Build and improve recruiting processes, pipeline tracking, and interview workflows
• Partner with founders on hiring execution

Build for Scale

• Create systems that allow Mason to grow without breaking
• Document playbooks, workflows, and best practices
• Define how the operations function evolves as the company scales
• Hire and lead team members over time

Who You Are

• 4–7 years of experience in operations, business operations, or a similar role at a high-growth startup — or an exceptional background in consulting, investment banking, or private equity
• Strong systems thinker — you instinctively turn messy processes into structured, scalable systems
• Track record of using AI to automate workflows and drive real operational leverage
• Comfortable operating across multiple functions — from revenue to internal ops to customer workflows
• Highly organized, detail-oriented, and operationally rigorous
• Strong communicator across both internal teams and external users
• Scrappy and resourceful — you move quickly and figure things out without waiting for direction
• Excited to work in-person with the team in NYC

For candidates from consulting / banking / investing backgrounds:

• Demonstrated exceptional performance (top-tier firm, rapid progression and promotion)
• Clear evidence of ownership and execution — not just analysis or advising
• Evidence of entrepreneurial drive outside your core role — ideally building or running something that generated meaningful revenue or real-world outcomes
• Already operating with high autonomy and comfort in ambiguity
• Already using AI as a default part of your day-to-day workflow

Bonus

• Experience in construction, payroll, HR, or vertical SaaS
• Experience as an early operations hire or building systems from scratch
• Experience using AI tools to automate workflows (e.g., Claude, ChatGPT, Zapier)
• Familiarity with tools like Intercom, HubSpot, or similar
• Experience working closely with product and engineering teams

Why This Role Matters

This is a foundational role at Mason.

You will define how the company operates — across revenue, onboarding and internal execution.

You won’t just run processes — you’ll build the operating system for the company as its first operations hire, working alongside top-tier operators (ex-Plaid / Brookfield / Harvard, 3x acquired CTO founder), at a stage where your impact will shape how the company scales.

Compensation & Benefits

• Competitive salary + meaningful equity
• Health, dental, and vision coverage
• Opportunity to work directly with founders and shape the company from the ground up