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Director, Commercial Enablement

Chicago, IL 60607, United States
Schedule: FT
Job Type: Hybrid
Salary Type: Salary
Job Level: E1
Req #: 2374

About the Role

Uber Freight is on a mission to transform global logistics. As part of this journey, we are building a world-class Commercial Strategy & Operations (CS&O) organization that directly fuels revenue growth and productivity.

We are seeking a Director, Commercial Enablement to design and lead our global enablement function. This role will directly impact pipeline creation, win-velocity, and win rate by equipping our sales, account management, and specialist teams with the right skills, content, tools, and coaching to consistently win in the market.

The ideal candidate is both strategic and execution-oriented: a leader who can set a bold enablement vision, build measurable programs, and partner closely with Sales, Marketing, Product, and CS to accelerate outcomes.

What the Candidate Will Do

Enablement Strategy & Leadership

  • Build and lead a world-class enablement function tied directly to revenue outcomes.
  • Define the enablement roadmap across onboarding, continuous learning, sales methodology, and deal coaching.
  • Partner with Sales, Marketing, and CS leadership to align enablement priorities with GTM strategy.

Pipeline Creation

  • Drive programs that elevate prospecting and pipeline discipline (e.g., MEDDPICC, early-stage qualification, champion-building).
  • Equip SDRs, AEs, and AMs with playbooks, talk tracks, and customer-facing content to accelerate demand generation.
  • Partner with Marketing to embed enablement into campaign execution and lead conversion.

Win Velocity & Win Rate

  • Institutionalize sales methodologies (e.g., MEDDPICC, Challenger, SPIN) into daily execution.
  • Build certification and coaching programs to ensure consistent discovery, qualification, and negotiation excellence.
  • Deliver deal coaching and win-loss analysis to inform content and training improvements.
  • Partner with Deal Desk, Pricing, and Product to enable field teams on value articulation, competitive positioning, and solution packaging.

Tools, Tech, & Measurement

  • Own the enablement tech stack (LMS, Gong, SFDC integrations, knowledge management).
  • Define KPIs for enablement effectiveness tied to revenue impact, not activity.
  • Use data to drive continuous improvement in enablement programs.

Basic Qualifications

  • 10+ years of experience in Sales Enablement, GTM Strategy, or Commercial Operations, with at least 5+ years leading enablement at scale.
  • Proven track record of driving measurable improvements in pipeline, win rate, and sales productivity.
  • Deep knowledge of B2B sales methodologies and SaaS/tech-enabled sales cycles.
  • Strong stakeholder management experience with senior sales, marketing, and product leaders. 
  • Data-driven operator who can design KPIs, measure impact, and adjust strategy accordingly.

Preferred Qualifications

  • Experience in logistics, transportation, or enterprise SaaS industries.
  • Track record of building global enablement teams and scaling programs across geographies.
  • Comfort operating in a high-growth, fast-paced environment where priorities evolve.
  • Strong executive presence and ability to influence at the C-level.

Success in this Role Looks Like

  • Pipeline Creation: ≥15% lift in sourced/qualified pipeline within 12 months.
  • Win Velocity: ≥20% reduction in average sales cycle for deals >$50K FUM.
  • Win Rate: 2–3% increase in win rate in H1 FY26 through consistent methodology adoption.
  • Productivity: ≥90% of reps certified on core selling motions within 6 months of onboarding.

Benefits & Compensation for U.S. Employees

(CHI) Base: $175,000 - $210,000 + 18%
Equity: $70,000 - $200,000

Employees working more than 30 hours in the US at Uber Freight are eligible for benefits like a company sponsored health plan, dental and vision benefits, 401k match, financial and mental wellness benefits, parental leave, short- and long-term disability coverage, life insurance and more.  US based employees may also be eligible for a performance or sales incentive bonus program, participation in Uber Freight equity awards, and other types of compensation depending upon the role.

About Uber Freight 

Uber Freight is a market-leading enterprise technology company powering intelligent logistics. With a suite of end-to-end logistics applications, managed services and an expansive carrier network, Uber Freight advances supply chains and moves the world’s goods. Today, the company manages nearly $20B of freight and one of the largest networks of carriers. It is backed by best-in-class investors and provides services for 1 in 3 Fortune 500 companies, including Del Monte Foods, Nestle, Anheuser-Busch InBev, and more. For more, visit www.uberfreight.com.

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Uber Freight is proud to be an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regards to sex, gender identity, sexual orientation, race, color, religion, national origin, disability, protected Veteran status, age, or any other characteristic protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. 

 

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