Job Description

The Role

Were looking for a Product Training & Enablement Specialist to design an engaging self-serve learning experience for our Local Partners. This person will help our partners confidently onboard and manage their own clients using our softwarethrough clear, structured, and easy-to-follow content.

Youll create step-by-step guides, how-to videos, and explainers that walk partners through key workflows and features. Your work will help transform complex tools into intuitive learning experiences that empower partners to be self-sufficient and successful.

This role will be part-time (about 20 hours a week) for a duration of 6 months.

Key Responsibilities

• Learn our platform deeply to understand the partner and client experience.
• Develop training modules that teach Local Partners how to:
• Onboard new clients using the software
• Manage client financials month-to-month
• Navigate common workflows and product features
• Create step-by-step guides, how-to videos, and visual explainers that make complex processes simple.
• Build an intuitive self-serve experience , ensuring partners can independently learn and troubleshoot.
• Collaborate with internal stakeholders (Product, Partner Ops, Sales) to align content with product updates and partner needs.
• Establish a repeatable framework for maintaining and updating training materials
• Works closely with Partner and Product teams, but largely independent in execution

About you

Must-haves:

• 3+ years in Learning & Development, Product Enablement, or Instructional Design (preferably SaaS or startup environment)
• Strong experience creating video-based and interactive learning materials
• Ability to translate complex product workflows into accessible, engaging content
• Excellent communication skillsclear, concise, and visually oriented
• Comfortable working independently and iteratively

Nice-to-haves:

• Experience with partner or customer enablement programs
• Familiarity with learning tools (Loom, Notion, Canva, Captivate, Articulate, etc.)
• Background in finance, accounting, or business operations

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 2,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion Meet Fintechs Newest Unicorn.

Why Pilot?

• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox)
• Drive impact and change the trajectory of Pilot - were small enough that your work makes a big difference in Pilots success
• All federal holidays are observed
• 401(k) plan

The base pay range target for the role seniority described in this job description is between $39/hour - $81/hour. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilots recruiting notices, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.

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