Sr Sr Sales Enablement Lead

Chicago, IL 60607, United States
Schedule: FT
Job Type: Hybrid
Salary Type: Salary
Req #: 1991

About the Role

The Field Coaching & Manager Performance Lead is a critical role within Uber Freight’s Commercial Readiness organization. This leader will elevate frontline manager capability, strengthen coaching excellence, and improve forecast and pipeline discipline across our Transportation Management (TM) and SaaS sales teams.

This role is responsible for translating insights from Gong, Salesforce, and forecasting signals into real-time field coaching, strengthening how managers inspect deals, develop talent, and drive predictable, multi-product growth. You will partner closely with Sales Leaders, CS&O, RevOps, and Product to ensure managers operate consistently against our unified GTM system.

If you are passionate about developing high-performing commercial teams and thrive in a fast-paced, insights-driven environment, this role is for you.

What the Candidate Will Do

Manager Coaching & Field Enablement

  • Provide live, in-field coaching for frontline Sales Managers across TM and SaaS.
  • Shadow forecast calls, pipeline reviews, and deal inspection sessions to uplift manager capability.
  • Reinforce GTM expectations through targeted coaching aligned with MEDDICC, forecasting signals, and TM/SaaS selling motions.
  • Partner with leaders to standardize how managers run 1:1s, team meetings, and QBRs.

Forecasting & Pipeline Discipline

  • Use Gong, Salesforce, and insights dashboards to drive pipeline quality and forecast inspection consistency.
  • Coach managers on opportunity strategy, deal movement, risk identification, and accurate close-date management.
  • Support adoption of signal-based forecasting across all commercial teams.

Insights → Behavior Change

  • Translate Gong insights into actionable coaching plans for managers and reps.
  • Identify skill gaps across TM and SaaS teams and build reinforcement programs to address them.
  • Partner with the Enablement & GTM Ops Manager to operationalize Gong findings.

Sales Excellence & GTM System Reinforcement

  • Coach managers to improve adherence to the unified GTM operating model across TM and SaaS sales cycles.
  • Ensure field teams use MEDDICC and other qualification frameworks consistently.
  • Support multi-product pathway adoption by reinforcing consistent inspection of TM + Brokerage + Parcel + SaaS opportunities.

Cross-Functional Alignment

  • Partner with CS&O, RevOps, and Sales Leadership to inform competency models, inspection standards, and manager development priorities.
  • Collaborate with Commercial Readiness leaders on manager capability programs, role expectations, and quarterly enablement priorities.

Basic Qualifications

  • 5–7+ years in Sales Management, Sales Coaching, Sales Enablement, or Field Leadership or related titles.
  • Experience coaching managers or sellers using MEDDICC or similar qualification frameworks.
  • Proven ability to influence and coach leaders at multiple levels.
  • Strong analytical proficiency in Salesforce, Gong, or equivalent tools.

Preferred Qualifications

  • Strong understanding of SaaS and/or Transportation Management (TM) sales cycles.
  • Experience in logistics, transportation technology, or enterprise SaaS selling.
  • Background in performance coaching, leadership development, or commercial operations.
  • Ability to quickly diagnose talent gaps, deal risk, and opportunity strategy.
  • Strong executive presence with the ability to influence through insights and storytelling.
  • Comfortable working in a fast-paced, ambiguous, growth-stage environment.

 

Benefits & Compensation for U.S. Employees

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.

Illinois: The target compensation for this position is $126,750- 149,600 

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.

Candidate Privacy Notice

Uber Freight is committed to protecting the privacy of our candidates. We collect and process personal data in accordance with applicable data protection laws. For detailed information on how we handle candidate data, please review our Candidate Privacy Notice.

EEOC

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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