Founding Customer Success Lead

The role

We’re hiring a Founding Customer Success Lead to build an AI-native customer success & 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 onboarding, setup, training, support, and internal workflows. This is a hybrid role across Customer Success, Business Operations & Support — ideal for someone who thrives in ambiguity, loves building from scratch, and wants to be deeply embedded in the company’s growth.

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 :)

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

What You’ll Do

Customer Success & Onboarding

• Own customer onboarding end-to-end — from kickoff to successful go-live
• Act as the primary point of contact for customers, ensuring a high-quality experience
• Develop playbooks for onboarding, training, and ongoing success
• Build AI-assisted repeatable systems for onboarding
• Proactively identify and solve customer issues before they become problems

Support & Customer Experience

• Set up and manage our support function (Intercom, Slack, etc.)
• Respond to customer questions and issues with urgency and clarity
• Turn repeated issues into product and process improvements
• Define SLAs, support workflows, and escalation paths

Internal Operations

• Design and implement internal processes across onboarding, support, and operations
• Build lightweight systems to track customers, issues, and workflows
• Work closely with product and engineering to translate customer feedback into roadmap insights
• Improve operational efficiency across the company

Build for Scale

• Create repeatable systems that allow Mason to grow without breaking
• Document everything — playbooks, workflows, and best practices
• Help define what Customer Success and Operations look like at Mason long-term

Who You Are

• 4–7 years of experience in operations, customer success, or a similar role at a high-growth startup
• Comfortable working directly with customers — especially in complex or technical environments
• Highly organized, detail-oriented, and systems-minded
• Strong communicator — able to work with both field users and office teams
• Scrappy and resourceful — you figure things out without waiting for direction
• Excited to work in-person with the team in NYC

Bonus:

• Experience in construction, payroll, HR, or vertical SaaS
• Experience setting up CS/support from scratch
• Experience using AI tools to automate workflows (e.g., Claude, ChatGPT, Zapier)
• Familiarity with tools like Intercom, HubSpot, etc.

Why This Role Matters

This is a foundational role at Mason. You’ll define how we onboard customers, support them, and operate internally — and your work will directly shape the company’s trajectory.

You won’t just run processes — you’ll build the customer success operating system for the company as its first Customer Success 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