Director of People & Culture

Come join our People & Culture Team!

High velocity, high intensity, high trust, high bar, high impact, and a will to win.

FutureFit AI could be the right next step in your career journey if reading those words resonates deeply with you, full stop. You live and lead with humility, pursue audacious goals, and are motivated by having a meaningful and positive impact on the people and the world around you.

First, an important note: Data shows that men on average apply for a role if they meet 3/10 requirements while women often only do so if it’s 10/10. We work hard to be clear and specific about what our roles include and demand and encourage you to apply if you see a strong (but not necessarily perfect) fit between you and the opportunity.

Your Role

This is a high-ownership, high-impact individual contributor role. As the sole People team member, you will be responsible for the full employee lifecycle—from hiring to offboarding. You’ll oversee payroll, benefits, compliance, employee relations, talent acquisition, and culture initiatives while equipping managers to lead effectively, ensuring our People function evolves alongside our company’s growth.

Key Functional Areas:

People Operations & Compliance

• Own and manage all HR policies, documentation, and compliance across the U.S. and Canada.
• Maintain and update the employee handbook, create company policies, and ensure legal alignment.
• Handle employee contracts, visa processes, and confidential HR matters.
• Oversee onboarding and offboarding logistics, including account setup and system access.
  
  

Compensation, Benefits & Payroll

• Manage payroll and benefits strategy across the U.S. and Canada.
• Oversee vendor relationships and serve as the primary point of contact for payroll, benefits, and compensation matters.
• Ensure competitive and equitable total rewards programs.
• Partner with leadership to define and execute our compensation philosophy.
  
  

Talent Acquisition & Recruiting

• Lead and support hiring efforts, including sourcing, interviewing, and offer processes.
• Develop best practices and scalable processes to improve hiring efficiency.
• Train and support hiring managers in interview techniques, candidate evaluation, and company hiring processes.
• Manage ATS systems to ensure a structured and fair hiring process.
  
  

Employee Experience & Culture

• Design and execute initiatives that drive engagement, recognition, and team culture.
• Plan and execute annual offsites, weekly All Hands, and team events (both in-person and virtual).
• Champion internal communications that reflect company principles.
• Leverage data from monthly employee pulse surveys to enhance the workplace experience.
  
  

Performance & Leadership Enablement

• Own quarterly performance management processes, including reviews and feedback loops.
• Develop and implement a manager enablement program to equip leaders with the tools and skills to grow and support their teams.
• Provide coaching and guidance on employee relations matters.
• Utilize data-driven insights to enhance People programs and policies.
  
  

Your Skills & Experience

• People & Culture Leadership – 3+ years of experience in People Ops, HR, or related roles, ideally in a high-growth, early-stage startup (Series A/B ideal) with ownership over key People functions.
• HR Strategy & Execution – Strong balance of strategy and execution across People programs.
• Compensation & Benefits – Expertise in payroll and benefits administration.
• HR Compliance & Policy Management – Deep understanding of employment law and compliance.
• Talent Development & Leadership Enablement – Experience supporting and equipping managers in performance, feedback, and leadership development.
• Process Optimization & Tech – Proficiency with HR tech, ATS, and payroll systems (e.g., Rippling, Ashby).
• Confidential & High-Stakes HR Matters – Ability to handle sensitive employee issues with discretion.
• Fast-Paced Execution & Prioritization – Strong organizational skills to manage multiple priorities.
• Communication & Influence – Excellent ability to engage employees at all levels.
  
  

Your Education

Your alma mater isn’t our focus. Your grit, hunger, and drive are. If you're someone who learns continuously, tackles challenges head-on, and knows your strengths and growth areas, you’re our person.

Job Benefits

• Work directly with the founding team
• Unlimited PTO
• Healthcare & 401(K)
• Career development budget
• Technology reimbursement
• Flexible schedules built on trust
  
  

Location

This role is based in New York City or Toronto. We are a hybrid-friendly environment but place a high value on weekly in-person collaboration and team building. Our team typically works from our office 2-3 days per week.

Our Offices:

• New York City: Located near Union Square
• Toronto: Located near Union Station
  
  

Compensation

The salary range for this role is $120k-$150k, variable based on experience and other factors identified by the hiring committee.

Role Logistics - Hiring Journey

At FutureFit AI, we believe in designing intentional and rigorous hiring journeys to help you determine if this is the best role and organization for you, based on your unique skills, mindset, and experiences. We operate at high velocity with high intensity and want an accurate taste of what that feels like before you get through the door.

Every hiring journey at FutureFit AI consists of thoughtfully crafted steps including a performance challenge and rounds of interviews with team members. For this role, that might look like:

• Online Application – Includes a 2-minute video submission on why you’re a great fit.
• Initial Screen
• Performance Challenge & Debrief
• Panel Interviews
• Final 1:1 Interviews
• Final Decision
  
  

This process generally takes around 4 weeks but may vary based on candidate availability.

Our Company

In looking at a job posting, it’s often hard to get a basic picture of the company profile (size, stage, structure, etc.) which is why we are sharing it with you upfront. This helps you quickly decide and helps us focus any time we spend together on going beyond the basics:

• Problem Domain: Future of Work / Workforce Development - important that the problem domain interests you even if you haven’t worked in the space before.
• Industry: SaaS / AI - technology and data are at the core of what we build.
• Customers: We partner with workforce development agencies, government agencies, and employers/enterprises.
• Structure: We are organized around the following key departments: Growth, Customer Success, Product, Engineering, Data, People & Culture, Finance & Operations.
• Team: We are a team of 30-50 across US and Canada with main hubs in New York and Toronto.
• Funding: We built the company from 0 to 1 with no external capital (a rare feat for tech startups) and have subsequently raised one round of funding led by JP Morgan which fueled a significant growth trajectory for us.
  
  

Our Core Principles

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

About FutureFit AI

At FutureFit AI, we’re on a mission to unlock pathways between talent and opportunity using the power of AI. We focus on personalized, AI-powered career guidance for job seekers, emphasizing skills over extensive resumes, and partner with workforce development partners, governments, and employers to level access to opportunity.

FutureFit AI is a growing, venture-backed company focused on using technology to improve the lives and outcomes for people going through career transitions. We’re a small, driven team, united by our commitment to the job seekers and workforce ecosystems we serve. We're not just building a company; we're shaping the future of work.

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request an accommodation.

FutureFit AI All rights reserved, we are proud to be an equal opportunity workplace. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, religion, color, gender identity, sexual orientation, age, disability, veteran status, or other applicable legally protected characteristics. We encourage people of different backgrounds, experiences, abilities, and perspectives to apply.