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VP of Sales

| Chicago

BenchPrep VP of Sales

Based in Chicago, BenchPrep is the leading provider of an advanced white label online learning platform and enables the world's leading education and training companies to deliver best-in-class digital learning programs. The company’s modern cloud-based platform is transforming the professional education space, with many of the largest credentialing bodies, associations, and training organizations in the world now delivering learning programs through BenchPrep. Customers include ACT, Becker Professional Education, AAMC, CFA Institute, CompTIA, GMAC, Institute for Supply Management, ASCM, Hewlett Packard Enterprise, NCBE, ProLiteracy, HR Certification Institute, Richardson Sales Training, Hobsons, McGraw Hill Education, OnCourse Learning, and Houghton Mifflin Harcourt. More than 4 million learners have used BenchPrep’s platform to attain academic and professional success. To discover more about BenchPrep, please visit www.benchprep.com.

Job Description:

BenchPrep is looking for an ambitious, metrics-driven sales leader who is seeking to scale a B2B sales organization and drive revenue. As the head of sales, you will advocate for your team while working to support our broader mission. You will own all aspects of revenue generation processes, go to market strategies and execution. You have a proven track record of success with defining the sales playbook, sales execution, recruiting, management and operations while exceeding growth expectations year over year

Duties and Responsibilities:

Managing & Coaching

  • Manage all aspects of the sales effort including prospecting, opportunity qualification, contract negotiation and handoff to customer success
  • Build and lead a high performing sales team via strategic guidance, industry insights, and sales training; while focusing on quantitative results
  • Ensure the attainment of assigned sales quotas by leading the sales process, providing direction and recommendations to improve sales close ratios
  • Coach and mentor a growing sales team by delegating responsibility, empowering decision making, and fostering collaborative communications

Sales Strategy & Operations

  • Build a scalable, repeatable, and predictable revenue engine
  • Develop the organizations go-to-market strategy. Lead the Sales organization in the acquisition of new customers and the retention of existing customers
  • Establish performance metrics and utilize reporting tools to monitor the results of direct reports, while providing concise forecasting and reporting
  • Develop annual business plans for key accounts across all sales channels, including pricing, comprehensive account plans, and forecasts
  • Support the sales team in negotiating contract terms, manage deals to a successful closing, and ensure a smooth transition to the customer success team
  • Maintain high level of pipeline, funnel and CRM discipline by including accurate forecasting around revenue; i.e. ensuring entire team records meeting activity, opportunity value and close/won dates, etc.
  • Drive annual planning process across the sales organization, including business modeling, white space analysis, territory planning, compensation design, in close partnership with cross-functional leadership team.
  • Maintain impeccable sales data quality in our CRM for tracking leads and opportunities, generating regular reports and forecasts for the CEO and our Board.
  • Develop a growing, talented salesforce through the creation of a sales training program to quickly ramp new folks while maintaining a high level of sales acumen for new products.
  • Work closely with our product team to develop a deep understanding of our product, competitive positioning and how it integrates with our clients’ needs
  • Help drive alignment between sales and marketing. Work with Head of Marketing to ensure sales strategy is integrated with marketing roadmap, plan and programs.


  • 10+ years of sales leadership experience in a fast-paced, high-growth SaaS startup, experience establishing a successful and scalable Enterprise Sales team
  • Demonstrates ability to generate and manage $25M+ ARR
  • Strong understanding of B2B SaaS or subscription business model
  • Strong track record of achieving and exceeding revenue goals
  • Possesses a strategic vision and an ability to execute
  • Showcases entrepreneurial spirit with strong relationship management and negotiation skills
  • Proven track record of recruiting, training, and motivating top-tier sales and account management talent
  • Passion for developing and mentoring sales talent
  • Natural results-oriented leader with inherent personal drive; ability to navigate ambiguity, operate effectively in a hyper-growth, start-up environment, and motivate a team of high performing individuals.
  • Exceptional communication and presentation skills with the ability to clearly articulate compelling value propositions of our products.
Read Full Job Description

Technology we use

  • Engineering
  • Product
  • Sales & Marketing
    • JavaLanguages
    • JavascriptLanguages
    • RubyLanguages
    • SwiftLanguages
    • Backbone.jsFrameworks
    • Node.jsFrameworks
    • Ruby on RailsFrameworks
    • vue.jsFrameworks
    • PostgreSQLDatabases
    • RedisDatabases
    • Google AnalyticsAnalytics
    • TrelloManagement
    • HubSpotCRM
    • ZohoCRM


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 (https://www.fooda.com/resources/case-study/how-tech-startup-benchprep-made-lunch-powerful-part-its-culture).
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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