Customer Support Learning & Enablement Specialist

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About the Opportunity

Since launching in 2019, the company has grown to support over 300,000 startups, businesses, and customers worldwide. As the organization scales, so does the need to ensure its Customer Support team has the tools, knowledge, and confidence to deliver exceptional support—and continue growing in their craft.

The organization is looking for a strategic, detail-oriented Enablement Specialist to join its CS Operations team. In this role, the individual will design and scale learning and knowledge initiatives across both business and personal banking, helping teams navigate complexity with clarity and confidence. This position will own end-to-end enablement programs—from identifying needs and designing structured learning experiences to measuring impact and continuously improving how teams are enabled.

The individual will partner closely with cross-functional stakeholders to translate new products, processes, and risk requirements into clear, effective training, while ensuring consistency and quality across internal teams and BPO partners.

This role is both strategic and hands-on: the individual will shape how the organization approaches enablement at scale while building the systems, content, and programs that bring it to life. The individual will also contribute to evolving knowledge management practices, ensuring teams have access to accurate, up-to-date information when they need it.

The ideal candidate is passionate about enabling others, grounded in instructional design, and brings a systems-driven mindset to delivering learning at scale. They are equally comfortable building from scratch, improving what exists, and helping teams adapt in moments of change.

The company is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.

On the job, you will:

• Own end-to-end enablement programs: Scale existing and scope new L&D initiatives by defining timelines, setting milestones, and driving cross-functional coordination to ensure smooth, high-quality rollouts.

• Define and measure success: Build and operationalize learning metrics (e.g., training effectiveness, time to proficiency, quality impact), and continuously iterate on programs based on data, feedback, and evolving business needs.

• Design high-impact learning experiences: Apply evidence-based instructional design to create clear, engaging, creative, and compliant learning across formats — including live sessions, virtual trainings, and on-demand resources (videos, micro-learnings, SOPs, facilitator guides, and assessments).

• Build scalable learning systems: Develop structured programs and resources that support employee growth, improve confidence in role, and strengthen readiness for increased scope and responsibility.

• Help evolve knowledge management: Contribute to and improve knowledge systems to ensure teams have easy access to accurate, up-to-date information when they need it.

• Maintain content quality and relevance: Regularly audit training and documentation, proactively updating materials to reflect product, policy, and process changes.

• Partner cross-functionally to drive performance: Work closely with CS, Leadership, Quality, WFM, Strategy, and technical teams to identify performance gaps and deliver targeted, data-informed learning interventions.

You should have:

• 3+ years of experience in L&D, instructional design, or enablement — ideally in customer support and/or a regulated or high-risk environment

• End-to-end program ownership: Experience scoping, planning, executing, and iterating on programs — managing timelines, stakeholders, and outcomes from kickoff through rollout and beyond

• Data-informed approach to learning: Experience defining success metrics, building feedback loops, and using data to improve training effectiveness

• Strong instructional design and facilitation skills: Ability to design and build effective learning experiences from the ground up using proven frameworks. Comfortable leading engaging remote trainings and knowing how to keep participants involved and learning

• Clear communication, systems thinking, and ownership: Ability to translate complex ideas into simple, actionable content, partner effectively across teams to drive alignment, and think beyond one-off solutions—taking responsibility for outcomes and continuously improving how learning scales

• Enablement Techstack Experience: Familiarity with LMS and instructional design tools such as WorkRamp, Articulate, etc. Guru and Notion experience is a plus.

The total rewards package includes base salary, equity (stock options/RSUs), and benefits.

Salary and equity ranges are highly competitive within the SaaS and fintech industry and are updated regularly using the most reliable compensation survey data for the industry. New hire offers are made based on a candidate’s experience, expertise, geographic location, and internal pay equity relative to peers.

Target new hire base salary ranges for this role are the following:

• US employees in New York City, Los Angeles, Seattle, or the San Francisco Bay Area: $106,200 - $132,800

• US employees outside of New York City, Los Angeles, Seattle, or the San Francisco Bay Area: $95,600 - $119,500

• Canadian employees (any location): CAD $100,400 - $125,500

The organization values diversity & belonging and is proud to be an Equal Employment Opportunity employer. All individuals seeking employment are considered without regard to race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, sexual orientation, or any other legally protected characteristic.

The organization is committed to providing reasonable accommodations throughout the recruitment process for applicants with disabilities or special needs. If assistance or an accommodation is needed, please let the recruiter know once contacted about a role.

The organization uses Covey as part of its hiring and / or promotional process for jobs in NYC and certain features may qualify it as an AEDT. As part of the evaluation process, Covey is provided with job requirements and candidate submitted applications. Covey Scout for Inbound began use on January 22, 2024.