Job description

COME JOIN OUR CUSTOMER SUCCESS TEAM! High velocity, high trust, and high impact with a will to win. If those words resonate deeply with you, this could be your next career move. We're seeking someone who leads with humility, pursues audacious goals, and is motivated by meaningful impact on people and the world. At FutureFit AI, our core mission is to help more people get to better jobs faster and cheaper, with a specific focus on those facing barriers to opportunity. Our work helps resolve the growing issue of economic inequality, ensuring that no one is left behind in the future of work. Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale. Ready to make an impact? Apply today. Important note: Data shows that men typically apply when meeting 3/10 requirements, while women often wait until it's 10/10. We encourage you to apply if you see a strong (not necessarily perfect) fit. YOUR ROLE We are seeking a strategic, highly consultative leader to guide complex workforce SaaS technology implementations and help our customers translate ambitious workforce goals into effective, scalable solutions throughout the customer lifecycle. In this role, you will serve as a trusted advisor to senior leaders across government, education, and industry. You will lead customers through platform design and implementation, helping them define their strategy, map workflows and user journeys, make critical program and technology decisions, and successfully launch and scale their platforms. You will also own ongoing account management through renewal and expansion. You will also serve as a key bridge between our customers and our Product and Engineering teams. You will relay customer goals and operational needs internally, while also communicating product capabilities in an accessible, audience-appropriate language externally. This role is well suited for someone with experience in management consulting, workforce development leadership, government or education technology, or strategic enterprise customer success. WHAT YOU’LL DO LEAD COMPLEX CUSTOMER IMPLEMENTATIONS - Lead the end-to-end implementation of complex workforce technology solutions. - Develop implementation strategies, work plans, decision frameworks, timelines, and governance structures. - Facilitate discovery sessions to understand customers’ goals, policies, programs, stakeholders, technology environments, and operational constraints. - Be able to lead discussions on current- and future-state workflows, user journeys, service-delivery models, and data flows. - Identify risks, dependencies, and unresolved decisions, and proactively drive them toward resolution. ADVISE AND ENGAGE EXECUTIVE STAKEHOLDERS - Build trusted relationships with executive sponsors, program leaders, technical stakeholders, and frontline teams. - Lead executive presentations, steering committee meetings, strategic planning sessions, and implementation workshops. - Communicate complex information clearly and concisely through presentations, written recommendations, status updates, and decision documents. - Help customers connect platform decisions to their broader workforce, economic-development, and organizational strategies. - Navigate competing stakeholder priorities and build alignment across complex customer organizations and partners. SERVE AS THE BRIDGE BETWEEN CUSTOMERS AND PRODUCT - Partner closely with Product, Engineering, Data, and Design to clarify customer needs, evaluate potential solutions, and communicate tradeoffs. - Provide customers with clear updates on integrations, data exchanges, configuration work, and other technical deliverables. - Explain technical concepts to audiences with varying levels of technical expertise. - Represent the customer perspective while balancing individual requests with scalable product strategy. - Identify recurring customer needs and market trends that should inform the product roadmap. PROVIDE WORKFORCE EXPERTISE AND STRATEGIC INSIGHT - Develop a strong understanding of each customer’s workforce ecosystem, target populations, programs, partners, and policy environment. - Stay informed about workforce policy, labor-market trends, funding developments, economic conditions, and other external factors that may affect customers. - Help customers anticipate changes and adapt their strategy, implementation, or platform experience accordingly. - Apply knowledge of workforce systems and terminology to build credibility and provide relevant, practical guidance. DRIVE ADOPTION AND LONG-TERM SUCCESS - Deliver compelling platform demonstrations tailored to executive, programmatic, technical, and end-user audiences. - Guide customers through launch planning, stakeholder enablement, adoption, and ongoing optimization. - Establish clear measures of success and help customers connect platform activity to program and workforce outcomes. - Identify opportunities to deepen customer impact, expand platform usage, and strengthen long-term partnerships. WHAT YOU BRING - Significant experience in strategic customer success, management consulting, workforce development, education technology, government technology, implementation, or a related field. - Strong project and program management skills, with the ability to manage multiple work-streams, dependencies, and stakeholders. - Demonstrated ability to advise and present to senior executives and other high-level stakeholders. - Exceptional verbal and written communication skills, including the ability to turn complex information into clear recommendations and next steps. - Strong problem-solving skills and comfort operating in ambiguous, evolving environments. - A consultative approach to relationship building, with the ability to challenge assumptions, navigate difficult conversations, and build stakeholder alignment. - Ability to quickly learn new policies, programs, technical concepts, and market dynamics. Nice to Have - Strong knowledge of the public workforce system, education-to-employment pathways, economic development, or adjacent workforce topics. - Experience leading complex, multi-stakeholder technology implementations or transformation initiatives. - Confidence discussing technical topics such as integrations, data exchanges, system configurations, and product development—even if you are not an engineer. PARTICULARLY RELEVANT BACKGROUNDS We recognize that the right candidate may come from several different professional paths. Relevant backgrounds may include: - A consultant who has led workforce, education, government, digital transformation, or technology implementation engagements. - A workforce development leader who has managed complex programs, partnerships, systems, or modernization initiatives. - A senior customer success or implementation leader from an ed-tech, gov-tech, workforce-tech, or enterprise SaaS organization. - A program or product strategist experienced in translating stakeholder needs into scalable technology solutions. WHAT SUCCESS LOOKS LIKE Within your first year, you will have: - Established credibility and trusted-advisor relationships with executive and operational customer stakeholders. - Led complex implementations from discovery and solution design through launch and optimization. - Created clarity and momentum across ambiguous, multi-stakeholder initiatives. - Improved how customer requirements are documented, prioritized, and communicated to Product and Engineering. - Contributed to stronger platform adoption, customer outcomes, and long-term partnership growth. YOUR EDUCATION We don't think degrees should block talent from finding pathways to opportunity so this won't be a factor in how we look at candidates. We do care that you are naturally curious, constantly learning, have overcome hurdles/challenges, and have a good handle on your strengths and gaps. LOCATION Remote across the US and Canada. We are open to candidates living anywhere in either country, with at least 5 to 6 hours of daily overlap with our EST-based team required. For candidates living in Toronto, our office is conveniently located at 325 Front St West (a short walk from Union Station), and you are welcome to drop by, though it is entirely optional and not a hybrid requirement. COMPENSATION The base salary range for this role is USD $125,000 to $160,000 for candidates based in the United States, regardless of location. As a remote-first company, we benchmark compensation to the national market for comparable roles at institutionally-funded startups, targeting the middle of the market. Bands are designed for the lifecycle of the role — where you enter the band reflects your applied experience and other criteria established by the hiring committee, with room to grow through the band as you grow in the role. 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: 1. Online Application 2. Initial Screen/Checkpoint 3. Performance Challenge and Debrief 4. Final 1:1 Interviews 5. Reference Checks 6. Final Decision Generally, this entire process takes around 4 weeks, although the timing can vary due to specific candidate circumstances. READY TO SHAPE THE FUTURE OF WORK? At FutureFit AI, we're not just building a company—we're transforming how talent and opportunity connect. Join our driven team united by a commitment to job seekers and the workforce ecosystems we serve. COMPANY SNAPSHOT: - Team: 30-50 across US and Canada (hubs in NYC and Toronto) - Customers: Workforce development agencies and intermediaries, government agencies, employers - Industry: SaaS/AI technology - Funding: Bootstrapped 0-1, then raised funding led by JP Morgan - Structure: Growth, Customer Success, Product, Engineering, Data, People & Culture, Finance & Operations OUR CORE PRINCIPLES - Be Curious - Drive to Outcomes - Raise the Bar - Speed Matters - Own It - We Over Me USE OF AI IN HIRING At FutureFit, we use artificial intelligence (AI) tools to make our hiring process more efficient, consistent, and equitable—never to replace human judgment. We use AI in the following ways: - Screening support: AI may help us compare applications against the skills and experience required for a specific role. These skills are defined by the hiring team for each position. A human reviews each application, with the AI assessment as just one input. - Interview support: In some interviews, we may use an AI notetaker to summarize the discussion so interviewers can focus on being present in the conversation. - Insights, not decisions: AI provides data points to support our team’s evaluation but does not make or recommend final hiring decisions. Every hiring decision is made by people. 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.

Requirements

Must-haves

COME JOIN OUR CUSTOMER SUCCESS TEAM!
High velocity, high trust, and high impact with a will to win.
If those words resonate deeply with you, this could be your next career move. We're seeking someone who leads with humility, pursues audacious goals, and is motivated by meaningful impact on people and the world.
Ready to make an impact? Apply today.
Important note: Data shows that men typically apply when meeting 3/10 requirements, while women often wait until it's 10/10. We encourage you to apply if you see a strong (not necessarily perfect) fit.
This role is well suited for someone with experience in management consulting, workforce development leadership, government or education technology, or strategic enterprise customer success.
Lead the end-to-end implementation of complex workforce technology solutions.
Develop implementation strategies, work plans, decision frameworks, timelines, and governance structures.
Facilitate discovery sessions to understand customers’ goals, policies, programs, stakeholders, technology environments, and operational constraints.
Be able to lead discussions on current- and future-state workflows, user journeys, service-delivery models, and data flows.
Identify risks, dependencies, and unresolved decisions, and proactively drive them toward resolution.
Build trusted relationships with executive sponsors, program leaders, technical stakeholders, and frontline teams.
Lead executive presentations, steering committee meetings, strategic planning sessions, and implementation workshops.
Communicate complex information clearly and concisely through presentations, written recommendations, status updates, and decision documents.
Help customers connect platform decisions to their broader workforce, economic-development, and organizational strategies.
Navigate competing stakeholder priorities and build alignment across complex customer organizations and partners.
SERVE AS THE BRIDGE BETWEEN CUSTOMERS AND PRODUCT
Partner closely with Product, Engineering, Data, and Design to clarify customer needs, evaluate potential solutions, and communicate tradeoffs.
Provide customers with clear updates on integrations, data exchanges, configuration work, and other technical deliverables.
Explain technical concepts to audiences with varying levels of technical expertise.
Represent the customer perspective while balancing individual requests with scalable product strategy.

Nice-to-haves

Strong knowledge of the public workforce system, education-to-employment pathways, economic development, or adjacent workforce topics.
Experience leading complex, multi-stakeholder technology implementations or transformation initiatives.
Confidence discussing technical topics such as integrations, data exchanges, system configurations, and product development—even if you are not an engineer.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

Platform: ashby
Effort: quick