Job Description

Locations

• Boston, Massachusetts, United States
• Austin, Texas, United States
• Bellevue, Washington, United States
• New York, New York, United States
• Santa Monica, California, United States
• Irvine, California, United States
• Chicago, Illinois, United States

Salary

Skills Required

• dataintermediate
• Learning & Development with a sales enablement focusintermediate
• Challenger Sale-based curriculum—not just familiarityintermediate
• AI-powered practice toolsintermediate
• Kirkpatrickintermediate
• LMS administrationintermediate

Required Qualifications

• 5+ years of program or project management experience (experience, 5 years)
• Experience using data and metrics to determine and drive improvements (experience)
• Experience owning program strategy, end to end delivery, and communicating results to senior leadership (experience)
• 5+ years of experience in Learning & Development with a sales enablement focus (BD, inside sales, or field sales context) (experience, 5 years)
• Demonstrated experience building Challenger Sale-based curriculum—not just familiarity, but actual design work. Candidates should be able to articulate the distinction between Teach-Tailor-Take Control and demonstrate how they've operationalized it in past curriculum. (experience)
• Strong instructional design capabilities: scenario-based learning, Bloom's-aligned objectives, meaningful assessment design (experience)
• Experience facilitating live training with sales audiences who will push back—including tenured, quota-carrying sellers, not only new hires (experience)

Preferred Qualifications

• Master's degree, or MBA in business, operations, human resources, adult education, organizational development, instructional design or related field (degree in mba in business)
• Experience with AI-powered practice tools (e.g., Hyperbound, Second Nature, Pitch Monster) (experience)
• Familiarity with Kirkpatrick or similar measurement frameworks, particularly L3 (behavior change) and L4 (business impact) approaches (experience)
• Track record of measurable impact on deal economics (e.g., reduced discounting, improved margin, higher average deal value) (experience)
• Experience with LMS administration and learner engagement analytics (experience)
• Los Angeles County applicants: Job duties for this position include: work safely and cooperatively with other employees, supervisors, and staff; adhere to standards of excellence despite stressful conditions; communicate effectively and respectfully with employees, supervisors, and staff to ensure exceptional customer service; and follow all federal, state, and local laws and Company policies. Criminal history may have a direct, adverse, and negative relationship with some of the material job duties of this position. These include the duties and responsibilities listed above, as well as the abilities to adhere to company policies, exercise sound judgment, effectively manage stress and work safely and respectfully with others, exhibit trustworthiness and professionalism, and safeguard business operations and the Company’s reputation. Pursuant to the Los Angeles County Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. (experience)

Responsibilities

• Design and facilitate scenario-based training on pricing (rate cards, DIM weight, surcharges, value-based framing) and negotiation on a quarterly cadence.
• Build and iterate on Challenger Take Control curriculum—including tension tolerance, reframing price conversations, and holding ground under pushback.
• Develop and maintain Hyperbound AI roleplay scenarios focused on pricing conversations, objection handling, and commitment negotiations with structured scoring rubrics.
• Develop role play simulations, practice briefs, and assessments tied to real sales scenarios that escalate from positioning through objection handling to pricing/commitment conversations.
• Administer and manage pricing and negotiation content within Learn (LMS), including course assignments, certifications, and completion tracking.
• Collect and analyze L1–L2 data; connect training outcomes to business metrics including discount rates, average deal value, and margin hold rates.
• Partner with the Pricing team and Finance to ensure training content reflects current rate strategies, margin expectations, and shipper behavior patterns.
• Partner with sales leadership to identify know-do gaps and translate them into targeted interventions.
• Continuously improve programs as market conditions, pricing structures, or competitive dynamics shift.

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