Pilot.com
Learning Experience Designer, Partner Enablement (Part-Time, Temporary)
Pilot.com, Myrtle Point, Oregon, United States, 97458
The Role
We’re 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 software—through clear, structured, and easy-to-follow content.
You’ll 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 skills—clear, 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 - which Pilot hires as full-time, U.S.-based employees - 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 Fintech’s 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 - we’re small enough that your work makes a big difference in Pilot’s 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 Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.
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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 software—through clear, structured, and easy-to-follow content.
You’ll 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 skills—clear, 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 - which Pilot hires as full-time, U.S.-based employees - 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 Fintech’s 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 - we’re small enough that your work makes a big difference in Pilot’s 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 Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.
#J-18808-Ljbffr