Director of Product Management

| Chicago

About the role:

We are looking for a dynamic and talented Director of Product Management to join our growing team. As the Director of Product Management, you are prepared to roll up your sleeves to foster high rates of annual recurring revenue growth for an assigned portfolio of SaaS products. You have hands-on product management and managerial experience in a true B2B SaaS company. You’re a critical thinker who is analytical, and you thrive on leading the product lifecycle management process from beginning to end. You have experience working with agile product development teams, senior level leadership, and cross-functional project teams, demonstrating expertise in managing a portfolio of products and leading innovative development projects from problem definition to commercial release.

BenchPrep is looking for a talented and seasoned Director of Product Management to join our growing team. The ideal candidate for the role of Director of Product Management will have had demonstrable experience in the following areas:

Portfolio Growth 

  • Successfully and consistently growing the revenue of the product portfolio by at least, meeting new sales, retention, and upsell targets
  • Performing market analysis, successfully positioning his or her products in growth opportunity areas
  • Developing and presenting business cases that resulted in greenlit development projects.
  • Developing a partner ecosystem of complementary services and products for a platform solution.
  • Experience interacting with and persuading C-level executives to take on new project opportunities based on data analytics driven strategy.
  • Defining and achieving annual portfolio goals – growth, revenue, annual recurring revenue, utilization, and others
  • Report on the portfolio health, roadmap progress, market activity, and customer research to executive team on a regular cadence.

Customer Intelligence

  • Increasing the customer IQ of the product management, technology/R&D teams, and customer facing departments.
  • Conduct onsite customer discovery interviews

Launch Coordination

  • Demonstrated experience launching new products in high growth markets, achieving high growth with existing product releases, and rationalization of underperforming products.
  • Support the Go-To-Market strategy and execution of the Go-To-Market plan.
  • Conduct retrospectives on the commercial success of project releases


  • Developed and manage the execution of roadmaps that had a high impact on customer business and the company in new sales and high retention percentages.
  • Define Program/Project KPIs and Success Metrics to support annual product and market goals in collaboration with product manager.
  • Communicate roadmaps to internal stakeholders and customers

Innovation Pipeline Management

  • Developed and manage the execution of roadmaps that had a high impact on customer business and the company in new sales and high retention percentages.
  • Improve / implement defect processes and product enhancements processes to support the commercial objectives for your portfolio 

Coaching and Managing Reports

  • Managing direct reports to achieve performance goals.
  • Experience in successfully building teams and department processes

You Should Have:

  • (7+) years of experience with strong technical or product expertise including the ability to manage multiple Product teams
  • (5+) years of experience managing direct product management reports
  • Experience with Agile and OKR product development methodologies, preferably with squad or tribe structures
  • Ability to weigh competing priorities, manage tradeoffs and evaluate opportunistic new ideas with stakeholders, driving to consensus while maintaining a clear focus on overarching business priorities.
  • Superior communication skills in the following situations: within teams, presenting to senior leadership, and company-wide.
  • Comfort in communicating regular updates on portfolio and roadmap progress to executives and internal departments
  • Having the ability to crystallize and broadly socialize insights into customer needs that customers themselves may not be able to articulate
  • Analytical skills 
  • Data Driven Decision-Making abilities 
  • Experience in Field Research and qualitative modeling techniques
  • BA required
  • Experience working in an established Product Management framework like Pragmatic Marketing 

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 tend to eat our (free) lunch together - not because we have to, but because we want to. We celebrate our people, both professionally and personally. We focus on flexibility - both in work/life balance, but also every day in operating with agility. We care about professional development so much that we offer employees $1,200 annually to build their skills. And of course, we have all the La Croix and snacks that you’d expect to keep you moving. It’s no wonder we were selected in Built in Chicago’s 50 Best Small Companies to Work For in 2019, and Crain’s 2019 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.

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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 in 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. Do things like a ping-pong table, casual dress, fully-stocked kitchen, and regular Friday Happy Hour interest you? Scroll down to learn more about those items and see what else BenchPrep has to offer.

Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Pre-tax dollars can be set aside for medical, dental, and vision ($2,650/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
We offer employees Short Term Disability coverage at 60% of their weekly salary with a $1500 weekly max. Long Term = 60% of their monthly salary with a $10,000 monthly max.
Dental Benefits
BenchPrep offer 3 dental plans--all of which cover 100% of the cost of preventative care including cleanings twice a year and exams.
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, $500k max of voluntary life insurance & accidental death & dismemberment insurance. Spouse & dependent children plans available too.
Onsite Gym
Employees have access to the Willis Tower's exclusive 35,000 sq. ft gym for $10/month.
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.
Child Care & Parental Leave Benefits
Generous Parental Leave
BenchPrep offers generous paid parental leave for new parents with at least 6 months 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.
Vacation & Time Off Benefits
Generous PTO
BenchPrep’s offers 12 days off in year 1, increasing each year & going up to 24 days for employees of five years or longer. The office closes for major holidays and the entire week of Xmas-New Years
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 in addition to their PTO.
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 (
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.
Happy Hours
We have a standing in-office happy hour that starts at 4:00 PM on Fridays, but never feel constrained to limit this into being a once a week occurrence.
Fitness Subsidies
Employees have access to the Willis Tower's exclusive 35,000 sq. ft gym for $10/month.
Professional Development Benefits
Job Training & Conferences
Employees are provided an annual stipend to attend external training evens or conferences.

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, monthly company dinners, quarterly outings, an in-office ping pong table, cocktail hours, poker nights, etc.)

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