Customer Success & Professional Services Operations

About the Role

FutureFit AI is hiring a Customer Success Operations Associate to strengthen the Customer Success function. This position suits someone who wants to become deeply familiar with the product, understand how customers actually use it, and help improve the experience by connecting customer needs with internal execution.

The company is driven by a fast-moving, high-trust, high-accountability culture focused on meaningful impact. Its mission is to help more people access better jobs more quickly and at lower cost, with a strong emphasis on people facing barriers to opportunity. The platform is designed to modernize workforce development, reduce reliance on outdated systems, and create better outcomes at scale.

This role is hands-on and customer-facing in a support sense: you will spend time inside the product, validate workflows, investigate issues, capture friction points, and turn observations into clear follow-up actions for Customer Success, Product, and Build.

Candidates are encouraged to apply even if they do not meet every requirement, as the team values potential, learning mindset, and strong alignment with the work.

What You Will Do

You will act as a bridge between customers and internal teams, helping make sure product behavior, implementation needs, and customer feedback are understood and acted on.

• Build deep product knowledge and keep pace with product changes so you can serve as an internal reference on how the platform works in real customer scenarios.
• Represent customer perspective in internal discussions so decisions reflect real usage patterns, workflows, and constraints.
• Test new and existing features from a customer point of view to identify bugs, confusing behavior, and edge cases before they affect users.
• Take ownership of clear, reproducible issue reports and route them with enough context and urgency for the Build team to act efficiently.
• Support professional services work by assisting with implementations, workflow guidance, training preparation, documentation, and light troubleshooting.
• Create reusable support materials such as how-to guides, FAQs, templates, and internal notes to reduce repetitive questions and improve scalability.
• Look across customers, regions, and use cases to identify recurring blockers and common improvement areas in the product experience.
• Coordinate closely with Customer Success, Product, and Build so customer feedback and implementation learnings are shared clearly and followed through.

Required Experience and Strengths

The ideal candidate brings experience from a SaaS environment and is comfortable working at the intersection of customer success, product operations, professional services, and quality assurance.

• Background in customer success, professional services, product operations, QA, or a closely related role within a SaaS company.
• Strong QA instincts: you can spot issues, reproduce them, and document them clearly.
• High curiosity about products and a willingness to become highly fluent in how a platform operates.
• Empathy for customers and an ability to think through software from the perspective of real users, especially people facing barriers to opportunity.
• Technical comfort working alongside engineers and product managers, reading roadmaps, and understanding how features connect.
• Self-directed work style with strong written communication and the ability to move issues forward without heavy supervision.

Nice-to-Have Experience

• Exposure to workforce development, government, or mission-driven SaaS environments.
• Experience with structured QA processes or bug-tracking systems.
• Comfort using lightweight scripts or queries to reproduce and investigate problems.

Tools You May Work With

The Customer Success team uses Intercom for product communication, Slack, Canny, Clarify, and Miro for internal collaboration, Lovable, Figma, and Canva for design-related work, and Heap and Looker for analytics.

Location and Travel

This role is open to candidates anywhere in Canada or the United States. Toronto-based candidates may work from the office at 325 Front St West, near Union Station, and can use a hybrid schedule if they choose.

Although the position is remote, occasional travel of up to once per quarter may be required for offsites and team gatherings.

Compensation

The salary range for candidates based in New York is USD 90,000 to USD 120,000. For candidates based in Toronto, the range is CAD 105,000 to CAD 135,000. Compensation is benchmarked to the middle of the market for comparable venture-backed companies and may vary by level of experience and responsibility.

Hiring Process

The hiring process is designed to help both sides evaluate fit. It usually includes an online application, an initial screen with the Director of People & Culture, an interview with the hiring manager, a panel interview, final 1:1 interviews, and a final decision. The full process generally takes about 6 weeks, though timing can vary.

Team and Company Snapshot

• Team size: 30 to 50 people across the United States and Canada, with hubs in New York City and Toronto.
• Customer base: workforce development agencies, intermediaries, government agencies, and employers.
• Industry: SaaS and AI technology.
• Funding: bootstrapped initially, then later funded with leadership from JP Morgan.
• Functions across the business: Growth, Customer Success, Product, Engineering, Data, People & Culture, and Finance & Operations.

Core Principles

• Be Curious
• Drive to Outcomes
• Raise the Bar
• Speed Matters
• Own It
• We Over Me

AI in Hiring

FutureFit AI uses artificial intelligence tools to support, but not replace, human judgment in hiring. AI may assist with application screening, interview note-taking, and generating insights for reviewers, while people make all final decisions.

Accessibility and Equal Opportunity

The company provides reasonable accommodation for applicants and employees with disabilities so they can participate in the hiring process, perform essential job functions, and access employment benefits. FutureFit AI is an equal opportunity employer and welcomes applicants from all backgrounds and identities.