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About the 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. This role is well suited for someone with experience in management consulting, workforce development leadership, government or education technology, or strategic enterprise customer success.

Responsibilities

Lead complex customer implementations
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.
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.

Requirements

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.
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.
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.

Skills

Workforce SaaS technology implementation
Customer lifecycle management
Strategic advisory
Platform design and implementation
Workflow mapping
User journey mapping
Program and technology decision-making
Account management
Product and Engineering liaison
Management consulting
Workforce development leadership
Government technology
Education technology
Enterprise customer success
Project management
Program management
Stakeholder management
Executive presentations
Steering committee meetings
Strategic planning
Implementation workshops
Complex information communication
Written recommendations
Status updates
Decision documents
Stakeholder alignment
Product roadmap input
Workforce ecosystem understanding
Labor-market trend analysis
Workforce policy knowledge
Platform demonstrations
Stakeholder enablement
Adoption strategy
Optimization strategy
Customer outcome measurement
Partnership growth
Problem-solving
Ambiguity navigation
Relationship building
Assumption challenging
Difficult conversation navigation
Learning agility
Public workforce system knowledge
Education-to-employment pathways knowledge
Economic development knowledge
Technology implementation
Transformation initiatives
Technical topic discussion (integrations, data exchanges, configurations)
Translating stakeholder needs into technology solutions

Location

Remote in the US
Hybrid (New York City)

Work Type

Remote
Hybrid

Experience Level

Senior

Education Level

No degree requirement, focus on curiosity, learning, overcoming hurdles, and self-awareness.

Salary/Compensations

USD $125,000 to $160,000

Benefits

Stipend for work-from-home office set-up

About the Company

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.
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
Core Principles: Be Curious, Drive to Outcomes, Raise the Bar, Speed Matters, Own It, We Over Me
Use of AI in Hiring: AI tools are used for screening support and interview support to enhance efficiency, consistency, and equity, but human judgment remains central to all hiring decisions.

Equal Opportunity

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.
At FutureFit AI, 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.