Regional Manager, Sales Enablement

Transportation Insight • Chicago, IL

2d • $80,000 - $120,000

About The Position

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.

Requirements

• 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.
• Bachelor’s degree in Business, Logistics, Supply Chain, or related field; MBA or advanced degree a plus.
• 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.

Nice To Haves

• MBA or advanced degree a plus.
• experience in 3PL, transportation, logistics, or supply-chain selling strongly preferred.

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.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level