Regional Manager, Sales Enablement

Posted:
3/4/2026, 3:54:24 AM

Location(s):
Chicago, Illinois, United States ⋅ Illinois, United States

Experience Level(s):
Expert or higher ⋅ Mid Level ⋅ Senior

Field(s):
Sales & Account Management

The Regional Manager, Sales Enablement is accountable for driving regional revenue performance by operationalizing sales enablement strategy at the field level. This role ensures disciplined execution of sales methodology, consistent frontline leader coaching, including pipeline maintenance, accelerated rep productivity, and predictable growth outcomes across assigned office locations.

The role operates with direct accountability to the Sales Enablement function and dotted-line influence over Sales Leaders via collaboration with Training and Development. This is not a training delivery role. It is a field leadership coaching and performance role responsible for translating strategy into execution, discipline, and delivering measurable revenue impact at the regional level. 

Essential Duties and Responsibilities:

Regional Enablement Execution

  • Translate corporate sales enablement strategy into actionable field-level execution plans.
  • Standardize adoption of sales methodology, deal qualification framework, and opportunity progression.
  • Ensure standardized pipeline management and forecast discipline across office locations.
  • Establish structured business practices (pipeline reviews, QBRs, forecast calls) aligned to organizational expectations.

Sales Leader Effectiveness (Dotted-Line Leadership)

  • Partner with Sales Leaders to implement consistent coaching frameworks and performance cadence.
  • Equip Leaders with structured tools for deal reviews, qualification enforcement, and opportunity advancement.
  • Establish measurable coaching standards and hold leaders accountable to execution expectations.
  • Improve leader capability in diagnosing stalled deals and driving accountability within teams.

Revenue Performance & Analytics Ownership

  • Own and measure impact of regional visibility and performance tracking over Sales Leaders through key metrics including:
    • Revenue vs. plan
    • YoY growth
    • Office contribution margin
    • Attrition/Retention
    • Ramp-to-quota timing
    • Multi-modal portfolio coverage
  • Ensure CRM compliance, understanding, and data integrity.
  • Partner with General Managers and Training and Development to maintain accurate reporting and dashboards.
  • Partner with General Managers and Training and Development and identify performance gaps using data and deploy targeted enablement interventions.

Training Support, Onboarding & Ramp Acceleration

  • Support structured ongoing education programs to reduce time-to-productivity.
  • Reinforce product knowledge, value-based selling, negotiation effectiveness, and role-based workflows.
  • Monitor ramp curves and intervene where productivity lags.
  • Partner with HR, Training and Development, and Sales Leadership on retention-focused development initiatives.

Cross-Functional Alignment

  • Serve as liaison between Sales, Operations, Training and Development,  and Finance to ensure field alignment on:
    • Messaging updates
    • Pricing changes
    • Go-to-market shifts
    • Product launches
  • Ensure new initiatives are operationalized at the office level with clear execution standards.

Change Management & Best Practice Scaling

  • Partner with Training and Development to lead regional adoption of new tools, processes, and systems.
  • Facilitate Quarterly Business Reviews and structured performance sessions.
  • Establish scalable, repeatable sales behaviors to reduce variability across locations.

Talent & Organizational Impact

  • Coach Sales Leaders through dotted-line authority to elevate team performance.
  • Contribute to hiring decisions and talent recommendations within the region.
  • Influence succession planning and capability development discussions.

JOB REQUIREMENTS

  • Experience: 3-5+ years in B2B sales leadership; experience in 3PL, transportation, logistics, or supply-chain selling strongly preferred.
  • Proven track record: consistently achieving regional revenue targets, improving forecast accuracy, and scaling sales teams.
  • Technical: strong CRM (Salesforce preferred) and sales analytics experience; comfortable with BI tools (Tableau, Power BI) and Excel modeling.
  • Education: Bachelor’s degree in Business, Logistics, Supply Chain, or related field; MBA or advanced degree a plus.

KNOWLEDGE, SKILLS, AND ABILITIES

  • Leadership: ability to influence through a dotted-line relationship and drive accountability without direct headcount control.
  • Analytical: data-driven mindset; ability to translate metrics into action plans.
  • Communication: clear presenter to executives and field teams; strong written skills for reports and playbooks.
  • Coaching: experienced in coaching managers to improve owner sales behaviors and outcomes.
  • Negotiation & commercial acumen: understands contract terms, pricing levers, margin impacts, and go-to-market strategies.
  • Change agent: comfortable leading cross-functional initiatives and driving adoption.

OUR BENEFITS:

  • Competitive base salary ($80,000-$120,000) + bonus potential
  • Paid time off
  • Paid health days
  • Company paid Holidays and Floating Holidays
  • Paid parental leave
  • Competitive Benefit Package, including Medical, Dental, Vision, and Pet insurance!
  • 401(k) with Company Matching

**MAY PERFORM OTHER DUTIES AS ASSIGNED** 

WORK ENVIRONMENT 

Standard office environment, usually indoors away from the elements with moderate noise. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. 

PHYSICAL EFFORT 

Maintain a stationary position for extended periods; move about the office, operate computers and files, as needed; and frequently communicate with others. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to sit and talk or hear. The employee is required to stand, walk, and reach with hands and arms. Occasionally, the employee is required to lift boxes up to 20 pounds.   

SCHEDULING 

This is a full-time benefits-eligible position, working Monday through Friday; 8:00 a.m. – 5:00 p.m. An employee in this position must be available to work occasionally on weekends and evenings, during peak periods.  

TRAVEL 

Local and cross state travel is required.

DISCLAIMER 

The above statements are intended to describe the general nature and level of work being performed. They are not intended to be an exhaustive list of all responsibilities, duties, and skills required. 

EEOC/ADA STATEMENT:

We are an Equal Opportunity employer. All qualified applicants will receive consideration for employment without regard to race, gender, sexual orientation, age, religion, disability, veteran, or any other status prohibited by applicable national, federal, state or local law. In an effort to recruit, develop and retain top talent, we are committed to a policy of nondiscrimination in all personnel practices to ensure equal opportunity for employment, promotion, and training for a more inclusive workforce.

RECRUITMENT SCAM NOTICE:

Transportation Insight/Nolan Transportation Group is aware of scams involving fake job interviews and offers. Our hiring process includes a formal interview with a member of our recruitment team. We do not conduct interviews exclusively through text or instant messaging platforms. TI/NTG does not require candidates to pay for training, equipment, or any other fees as a condition of employment. Any request for payment is a scam. Official communication from our recruitment team about your application will only come from emails ending in ‘@ntgfreight.com’ or from ‘[email protected].' 

Transportation Insight

Website: https://transportationinsight.com/

Headquarter Location: Hickory, North Carolina, United States

Employee Count: 1001-5000

Year Founded: 1999

IPO Status: Private

Last Funding Type: Private Equity

Industries: Logistics ⋅ Supply Chain Management ⋅ Transportation