Technical Project Manager & Product Enablement at BenchPrep

| Chicago
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We deliver the most advanced and flexible learning experience for certification, credentialing, test prep, continuing education, and training.  Our cloud-based learning platform is designed to help 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 sitting in a pivotal time in the BenchPrep history.  The number of learners on our cloud-based learning platform has reached 6 million in 2021. 

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


When the COVID-19 Pandemic hit in March of 2020, we were one of the first companies to send our people to work from home.  And since then, we’re still (mostly) working remotely.  Our first core value is “People First” and the pandemic has reinforced how true this value reigns to us.  Our office is located in the Chicago loop, and those that want to may work in-office.  For the rest of us, we have “figured out” how to work remotely and we will continue to do so until it’s safe.  We know the world is shifting and we are too.  What is the future of BenchPrep’s plans for working in-office or remote?  We haven’t figured it out exactly - but what we do know is collaboration and connection are our top priorities.   Let us know what your preferences or requirements are for being in-office, hybrid or remote only.  Welcome to BenchPrep!

What you'll do in the role:

As our Technical Project Manager reporting to the Director of Product Management, you will leverage your SaaS product enablement experience and project management expertise in leading projects culminating in the rapid and successful launch, adoption, and growth of BenchPrep products and features.  You will develop and continuously refine a repeatable, flexible, and data-driven product enablement strategy, as well as related processes, and will lead a cross-functional project team’s focused delivery of excellent resources and experiences that elevate the value and adoption of BenchPrep products and features.  Developing and utilizing in-depth customer and product knowledge, you’ll understand, convey, and oversee the delivery of enablement resources. 

You'll be joining our Product team and will work closely with all other departments, including but not limited to Engineering, Sales, Customer Success, Support, and Professional Services.


Lead the development of, and continuously refine, a repeatable, flexible, transparent, and data-driven product enablement strategy

  • Collaborate with Product Management and cross-functional stakeholders to prioritize and clearly define deliverables that advance internal, customer, and prospective customer and partner product enablement 
  • Work closely with assigned stakeholders to identify training needs for all audiences, and to ensure that training is appropriately targeted, timed, accessible and effective  
  • Project manage cross-functional workstreams and empower, motivate, and support team members across multiple internal organizations to do their best work in the creation and delivery of impactful enablement programs
  • Maintain a schedule of deliverables, contributors, dependencies, and risks, and ensure team-wide visibility 
  • Establish, measure, and report on OKRs linking enablement efforts and investment with critical outcomes, such as adoption, satisfaction, win rates, and more
  • Prepare and deliver targeted, product enablement-related communications, company-wide and to individual and group stakeholders
  • Solicit, document, and leverage data from internal and external stakeholders to inform enablement strategy shifts; such as measuring learning engagement, satisfaction, content knowledge, comprehension and retention
  • Assess customer challenges with product/feature adoption and test and implement strategies to address these challenges  
  • Engage in the entire software development lifecycle, for key projects, ensuring that key milestones are achieved, and that potential issues and risks are identified and escalated as early as possible, and work collaboratively to resolve them
  • Document all project artifacts and ensure that they are complete, organized, and stored appropriately

**Skills and experiences we value:

  • Bachelor’s degree in Business, Education, or related field.
  • Proficiency in building lasting and productive cross-organizational relationships
  • Strong collaborative nature and communication skills to work effectively and efficiently with peers, SME’s, leadership, and stakeholders.
  • Highly organized and analytical in nature with outstanding project management skills. Preference given to candidates with experience in agile methodologies and tools.
  • Excellent written communication, verbal communication and presentation skills
  • Excellent knowledge of sales technologies, processes, and best practices. Preference given to candidates with knowledge/previous experience with Salesforce and enablement platforms.
  • Excellent knowledge of training best practices and experience delivering training through a variety of delivery methods (video, documents, online, in-person, etc.)
  • Excellent program management skills.  High adaptability in flexibility, including the ability to manage multiple and competing priorities, quick deadlines, and constant change.
  • Proficiency using the Google suite of products, Confluence, Jira, and Smartsheets.
  • Relevant SaaS experience in a high-performance organization supporting marketing, sales, enablement, or learning and development.
  • Proven track record of delivering successful enablement programs, concurrently and at scale.
  • Data-driven: comfortable with data, analysis, and reporting

**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!

About the team:

Here at BenchPrep, the product management team is responsible for the growth of our business. We are strong, dynamic, and wear many hats. True to startup culture, we aren’t afraid to roll up our sleeves to get the job done. We are inspired by a shared mission to help millions learn better and faster through our unique platform.

Life at BenchPrep:  

We work at BenchPrep because we’re dedicated to the mission and each day have an opportunity to be challenged and learn.  We work hard, eat well, and have lots of fun. Culture is our lifeline at BenchPrep.  We celebrate our people, both professionally and personally. We focus on flexibility - both in work/life balance, but also everyday in operating with agility. We care about learning so much that we offer employees $1,200 annually to develop their 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 learnersJoin 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.
Fitness Subsidies
Employees have access to the FFC gym located within our building, free of charge!
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, valuable stock options, 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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