Sr. Learning Technologist (Content Ingestion) - Remote at BenchPrep

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As a Sr. Learning Technologist (aka Sr. Content Automation Specialist), you handle and, when appropriate, improve and automate, BenchPrep’s ability to intake, process, and transfer to production a large quantity and wide variety of educational materials received from enterprise customers in preparation for go-live events of our EdTech SaaS offerings.

As the primary technical expert in the Professional Services department, you influence the adoption of technologies by our educational subject matter experts (Learning Technologists and Learning Content Managers) with a focus on learner experience. You’ll regularly utilize your knowledge of Content Management Systems (CMS), advanced file systems, and normalizing large volumes of structured and unstructured content. 

When appropriate, you’ll develop automation scripts using your tool of choice (Excel macros, batch scripts, Python, or Ruby). By creating these automation tools, you improve the self-service ability, delivery times and satisfaction of our customers.

The right person for this role could come from a wide range of backgrounds including a Content Manager with a technical focus, an Implementation Specialist who worked with lots of data or content, a Researcher or PhD candidate managing significant quantities of data, a Programmer focused on procedural scripting and data management, or a Data Analyst with a knowledge of a wide variety of file formats.  Ultimately, you are a technologist managing large quantities of content in a client-facing implementation role.

In the role, you will: 

  • Interface with our customers and all Professional Services teams to understand the scope and complexity of the content necessary to stand up a new learning option from content ingestion through driving the educational content into production. 
  • Develop methods for transforming various file formats (including CSV, XML, text, images, Powerpoint slides, video, PDF and form submissions) for import into our content management system. The content will be displayed on web and mobile platforms so you will utilize and understand HTML, CSS and responsive techniques to ensure an optimal learner experience.
  • When appropriate, design and implement tech-driven automation solutions using Excel macros, shell scripts, Ruby or other tools to support customer project work and internal Professional Services operations, especially as related to processing large volumes of content. Your goal is to make it easy for our customers’ Instructional Designers & Content Managers to work with our proprietary platform to load their educational collateral with the ultimate focus on empowering the Professional Services department to the point where Engineering resources are no longer required.
  • Interface with the Engineering and Product Design teams, acting as liaison for Professional Services to support easy implementation of the product, new offerings for existing customers, and modification of existing learning offerings. Translate and document findings for platform feature consideration and integration in future product roadmaps.
  • Act as subject matter expert in content management (CMS) and automation tools and techniques, including researching vendors and product offerings and bringing those findings to leadership for consideration. Train and collaborate with the Learning Technology & Conversion team and its Content Management vendors when needed. This may grow into leading Learning Technology team members.

Fundamentally, the focus of this role is to please our current customers while building scalable, efficient implementation processes and tools, including—when appropriate—automated processes for managing content.

This role allows you to use your communication skills and technical expertise to create a bridge between customers, the Professional Services teams, and the Engineering/Product teams, meaning you’ll have impact and visibility. 

Skills and experiences we value:*

  • Experience working with industry standard learning/content formats and content management systems (SCORM, Articulate Storyline, QTI, etc.) extremely helpful
  • Demonstrated ability to import content including knowledge of Content Management Systems (like Wordpress, HubSpot, Drupal, Moodle, Canvas), advanced file management, database basics, and normalizing/transforming structured & unstructured content
  • Tech savvy with examples of improving workflow efficiency through process and automation. Ability to develop and maintain effective automation scripts (Excel macros, batch scripts, Ruby, Python, or similar) incorporating regular expressions RegEx) to manage content
  • Proficiency with web languages including HTML, and ideally CSS (especially SCSS) with a clear understanding of how different data/file types display responsively on the web

*Note: We know that excellent candidates can have all sorts of backgrounds and experiences, so please don’t hesitate to apply even if you don’t meet 100% of the listed requirements! 

Nice to have and/or you’ll learn:

  • Client-facing experience with enterprise-level SaaS products, ideally in EdTech, learning management systems (LMS), or content management systems
  • Experience developing & working with XML converters and/or similar semi-structured content processing a significant plus
  • Adaptability, initiative and a love of learning; this role has significant process ideation involved, so ability and willingness to quickly pick up new tools and skills to implement those ideas are critical
  • Effective at communicating with a wide range of professionals (educators, sales, and software engineering) adapting style and content to audience
  • Experience creating CSV files to enable the import of content
  • Experience or interest in people management nice have, but not required

About BenchPrep:  

We deliver the most advanced and flexible learning experience for certification, credentialing, test prep, continuing education, and training. Our cloud-based learning platform helps training organizations, associations and the extended enterprise deliver a highly engaging and effective learning experience for individuals who are trying to advance their careers. We incorporate the latest in learner-centered technology, including personalization, gamification, data science, usability and omni-channel delivery.  

We’re at a pivotal time in BenchPrep’s history. The number of learners on our cloud-based learning platform neared 7 million in 2021. 

We’re committed to helping everyone learn better, and that starts with our own people. 


Speaking of our people, in March 2020, we put safety first and quickly moved our people to working remotely. We’ve learned that our employees are really productive working at home and still (mostly) work remotely. Our first core value is “People First” and the pandemic has reinforced how true this value reigns to us. What is the future of BenchPrep’s plans for working in-office or remote? We haven’t finalized that, but what we do know is that collaboration and connection are our top priorities. Remote, in-office (Chicago), or hybrid... employees know how they work best.  Let us know what your preferences or requirements are for being remote-only, hybrid or in-office.

Life at BenchPrep:  

We work at BenchPrep because we’re dedicated to the mission and each day we have an opportunity to be challenged and learn. We work hard and have lots of fun. Culture is our lifeline at BenchPrep. We celebrate our people, both professionally and personally. We care about learning so much that we offer employees $1,200 annually to develop their skills so they can continue to operate everyday with new skills. It’s no wonder we were selected in Inc’s Best Workplaces of 2020 and Crain’s 2020 Best Places to Work in Chicago lists.  

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

We are looking for high performing and motivated professionals who are excited about the chance to leverage technology to impact the lives of millions of learners. Join us.

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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • JavaLanguages
    • JavascriptLanguages
    • RubyLanguages
    • SqlLanguages
    • SwiftLanguages
    • Backbone.jsFrameworks
    • Node.jsFrameworks
    • Ruby on RailsFrameworks
    • vue.jsFrameworks
    • PostgreSQLDatabases
    • RedisDatabases
    • Google AnalyticsAnalytics
    • ConfluenceManagement
    • JIRAManagement
    • HubSpotCRM
    • SalesforceCRM


We are located next to the Willis Tower, right in the heart of downtown Chicago.

What are BenchPrep Perks + Benefits

BenchPrep Benefits Overview

BenchPrep provides a full suite and wide variety of benefits and perks. We offer an incredibly competitive medical plan and insurance benefits, while also fostering a culture that allows employees to have fun in the office. Scroll down to learn more about those items and see what else BenchPrep has to offer.

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Highly diverse management team
Unconscious bias training
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Pre-tax dollars can be set aside for medical, dental, and vision ($2,750/yr) for employees or dependents with or w/o enrolling in our insurance program. Daycare & elder care allows for up to $5,000/yr
Disability Insurance
Our plan coverage offers employees Short Term Disability coverage at 60% of their weekly salary with a $2,500 weekly max. Long Term = 60% of their monthly salary with a $10,000 monthly max.
Dental Benefits
BenchPrep offer 3 dental plans.
Vision Benefits
BenchPrep’s vision insurance plans provide annual eye exams for a $10 copay and a $130 allowance toward frames and/or contacts.
Health Insurance Benefits
BenchPrep’s health insurance plan with BCBS of IL has a low deductible and BenchPrep pays 90% of the monthly premium for employees AND their dependents.
Life Insurance
Up to 3x annual salary, $750K max of voluntary life insurance & accidental death & dismemberment insurance. Spouse & dependent children plans available too.
Pet Insurance
Wellness Programs
Onsite Gym
Mental Health Benefits
Retirement & Stock Options Benefits
BenchPrep’s 401k retirement plan offers a a cost effective employee retirement plan. The plan offers Roth and Pre-tax Investment options.
401(K) Matching
BenchPrep contributes 3% of an employee’s annual base salary, regardless of how much the employee contributes, which is immediately vested.
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
BenchPrep offers generous paid parental leave for new parents with at least 1 month of service, including a paid leave policy for foster parents.
Flexible Work Schedule
BenchPrep offers flexible work schedules as needed for employees.
Remote Work Program
BenchPrep offers Remote Work as an option for employees.
Family Medical Leave
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
BenchPrep closes its office for all major holidays, including MLK day, Presidents' Day, Memorial Day, 4th of July, Labor Day, Thanksgiving, and Christmas THROUGH New Years Day.
Paid Sick Days
BenchPrep employees receive 5 sick days per year.
Perks & Discounts
Beer on Tap
We've got 2 beers on tap regularly, and a refrigerator stocked with bottled brews and liquor as well that is frequently "tapped" into.
Casual Dress
BenchPrep does not have a formal dress code and encourages employees to wear whatever makes them comfortable.
Commuter Benefits
Transit and Parking benefits: Employees may elect up to $260/month for pre-tax allocation for mass transit & parking expenses for commuting to BenchPrep, including Metra, Ventra and parking facilities
Company Outings
BenchPrep has regular outings that include Cubs rooftops, boat trips on Lake Michigan, off-site happy hours, poker nights, game nights, foodie dinners, and a holiday party, among other events.
Free Daily Meals
We provide a $12.50 daily stipend for employees every day via Fooda (
Game Room
Stocked Kitchen
FULLY stocked! Beverages = Soda, Coffee, Tea, RedBull, Juice, Vitamin Water, etc. Food = if you can think of the snack, we probably have it or some variation. Employees will never go hungry here.
Some Meals Provided
Happy Hours
Fitness Subsidies
Employees have access to the FFC gym located within our building, free of charge!
Home Office Stipend for Remote Employees
New hires will receive a one time payment of $500 (after 90 days, and grossed up for taxes) and a $25 monthly recurring payment (grossed up for taxes) to aid in monthly home expenses.
Professional Development Benefits
Job Training & Conferences
Employees are provided an annual stipend to attend external training events or conferences.
Lunch and learns
Cross functional training encouraged
Promote from within
Continuing Education stipend
Time allotted for learning
Online course subscriptions available
Customized development tracks
Paid industry certifications

Additional Perks + Benefits

Competitive salary, and company-sponsored 401(k) • Fun, meritocratic, mission-driven, dynamic work culture • Commitment to fostering positive office culture (included, but not limited to, quarterly outings, an in-office ping pong table, cocktail hours, poker nights, etc.)

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