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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 — establishing AI-driven workflows to automate operations — across:
- New customer signups: setting up scalable systems for contract generation, invoicing, and billing
- User onboarding & implementation: automating new user setup, training, and support
- Internal operations: creating the systems that tie everything together (Slack → Hubspot → Billing)
- Go-to-market operations: operationalizing sales playbooks and supporting marketing execution
- Hiring & recruiting: supporting recruiting efforts, and building efficient recruiting processes
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:
In your first 6–12 months, you’ll:
- Stand up the core operational systems behind contracts, billing, onboarding, support, recruiting— moving from manual workflows to structured, reliable processes
- Own day-to-day execution across our operations — ensuring things run smoothly, and stepping in wherever needed to unblock issues
- Identify and automate high-friction workflows — replacing manual, error-prone processes with AI-native systems
- Fix root causes, not symptoms — turning recurring issues into scalable solutions across systems, tooling, or product
- Connect and streamline tools and data across CRM, billing, support, and internal workflows
- Lay the foundation for scale — documenting playbooks, improving processes, and beginning to define how the function grows 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
Skills Required
- 4–7 years of experience in operations or a similar role
- Track record of using AI to automate workflows
- Strong systems thinking abilities
- Experience in a high-growth startup or consulting
What We Do
Mason is building the AI workforce management platform for construction. We help contractors run their entire back office — time tracking, HR, payroll, compliance, and communication — without the manual work that slows teams down. Today, managing labor in construction is fragmented across paper field notes, spreadsheets, text messages, emails, HR platforms, payroll systems, benefits websites, and accounting tools. These workflows are ripe for unification and automation through AI and modern, cloud-based systems that connect the field and back office. Mason replaces firms' siloed tools with a single platform that connects the field to the office in real time — capturing hours, simplifying HR, running payroll, and ensuring compliance automatically. Our platform saves teams 20+ hours per week by eliminating repetitive data entry and reducing errors across HR, payroll and accounting. Workers get a modern, intuitive way to track time and manage their pay, while office teams receive clean, structured data that flows directly into payroll and job costing systems. Construction is the least-digitized major industry in the U.S. — and we’re changing that. Mason is a NYC-based, venture-backed company on a mission to bring AI-first workflows to the field. Come build the future with us!
Why Work With Us
This is a rare opportunity to be one of the first hires at a well-funded, fast-growing startup with a repeat founder disrupting a large US industry. Our team is led by Jef Chedeville (3x acquired/exited founder - previously co-founded YC-backed HigherMe) and Matt Kozlowski (former Chief of Staff at Plaid, scaled Plaid from 500 → 1,200 employees).
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