Learning and Development Lead

Company: Cardless
Location: San Francisco
Posted on: April 1, 2026

Job Description:

We're looking for a builder to own Learning and Development at Cardless from the ground up. You'll design the systems that turn new hires into confident specialists, close skill gaps across the CS team, and make sure our training keeps pace with fast-moving fintech. It's cross-functional, high-ownership work, and the impact is visible. The Job This isn't a "maintain the existing program" role. You'll build the L&D function from scratch (i.e. onboarding, ongoing training, performance coaching, and knowledge management). You'll partner directly with Product, Compliance, and Operations to translate complexity into training that actually sticks, and you'll measure whether it's working. Before You Apply A few things worth knowing: We work in the office 5 days a week. We know that's a dealbreaker for some people, and that's okay. You'll be building, not inheriting. There's only a nascent program to plug into. You'll be starting from a blank canvas — and that should excite you, not unsettle you. Fintech complexity is real. Credit cards sit at the intersection of product, compliance, fraud, and banking. You'll need to get fluent quickly and build that fluency into everything you create. Speed matters. Our product, policies, and team evolve fast. Training materials and documentation have a short shelf life if you're not staying ahead of them. If that sounds like your kind of work, keep reading. Why This Role Is Cool You own the whole function. There's no L&D team above you. You're setting the strategy, building the content, and measuring the results. High autonomy, high impact. Your work compounds. A great onboarding program pays dividends every time a new hire ramps faster. A well-written SOP reduces escalations for months. The work you do here has a long tail. The team is motivated. These are people who want to grow. Building for an engaged team makes the work more rewarding. Responsibilities Design the L&D function end-to-end: onboarding, ongoing training, performance coaching, and knowledge management. Identify skill gaps across the CS team and build targeted training to close them. Create and maintain SOPs, process guides, and customer-facing resources. Partner with Product, Compliance, and Operations to translate complexity into usable training. Define and track KPIs for L&D effectiveness — ramp time, CSAT correlation, assessment scores. Requirements 3–5 years in L&D, training, customer service enablement, or a related field. Proven experience building or significantly rebuilding a training program (not just maintaining one). Strong writing and communication skills. You'll produce a lot of content and quality matters. Comfortable with QA frameworks and data-driven iteration. Fintech, financial services, or regulated industry experience is a strong plus. Startup experience or demonstrable comfort with fast-moving, resource-constrained environments. Availability to travel up to 25% of time to outsourced BPO locations for training. San Francisco-based and in-office 5 days a week. Compensation This role has an annual starting salary range of $140k-$170k equity benefits. Actual compensation is influenced by a wide array of factors including but not limited to skills, experience, and specific work location. Benefits We're proud to offer our team excellent benefits: Meaningful Start-up equity 100% health, vision & dental primary coverage ? 75% health, vision & dental dependent coverage Catered lunches $250/month Commuter benefit Parental leave ?? Team building events & happy hours Flexible PTO with a minimum of 15 days off per year ? Apple equipment 401k plan Location We're headquartered in San Francisco, CA. This role is in-office 5 days a week.

Keywords: Cardless, Santa Cruz , Learning and Development Lead, Human Resources , San Francisco, California