Senior Manager/Director, Sales Enablement & Operations, Downers Grove

Senior Manager/Director, Sales Enablement & Operations

83 Days Old

Job Description Summary:

We're looking for a data-driven, execution-focused Senior Manager or Director of Sales Enablement & Operations to elevate the performance of our commercial organization in the LTL transportation industry. In this high-impact leadership role, you'll be responsible for building and leading a high-performing team, while establishing systems of accountability and performance management across sales operations and enablement.

You will drive execution with urgency and discipline, delivering process improvements, actionable analytics, and scalable programs that directly impact revenue growth, customer experience, and margin performance. This is an ideal opportunity for a builder who thrives on turning vision into structured, measurable action.

Critical Job Functions:

Build and lead a best-in-class sales operations and enablement team, fostering a culture of high performance, accountability, and continuous improvement.
Define team goals, KPIs, and development paths aligned with organizational priorities.
Establish clear ownership, execution rhythms, and cross-functional collaboration processes to drive accountability and follow-through.
Act as a performance multiplier-empowering team members to deliver impact across sales productivity, efficiency, and results.
Design and execute onboarding, training, and enablement programs that reduce ramp time and increase win rates.
Develop and maintain sales playbooks, messaging frameworks, and training materials tailored to LTL-specific market dynamics.
Partner with Product, Pricing, and Operations to ensure sales teams are trained on services, capabilities, and go-to-market strategies.
Reinforce selling methodologies and ensure consistent execution across all sales roles.
Build accurate, scalable reporting and dashboards that monitor revenue, margin, pipeline health, and sales efficiency.
Lead territory planning, quota setting, and performance management-anchored in data and aligned with operational capacity.
Identify bottlenecks in the sales process and implement technology- and process-based solutions.
Drive adoption and optimization of Zoho CRM and HubSpot, ensuring robust reporting, user engagement, and integration with other systems.
Translate commercial goals into structured execution plans with defined metrics, owners, and deadlines.
Lead cross-functional GTM initiatives, including pricing execution, retention strategies, and account expansion programs.
Use advanced analytics to uncover performance gaps, customer trends, and margin improvement opportunities.
Serve as a trusted advisor to sales leadership-providing insights and driving disciplined execution against strategic objectives.

Job Requirements:

Bachelor's degree in Engineering, Mathematics, Finance, Business, or another analytical field is required.
Advanced degree (MBA or similar) strongly preferred.
7-10+ years of experience in Sales Enablement, Sales Operations, or Revenue Operations, preferably in LTL, 3PL, or transportation/logistics.
Proven experience in building and leading high-performing teams, with a strong record of driving execution and delivering measurable impact.
Demonstrated ability to establish accountability systems and manage through KPIs and performance metrics.
Deep expertise in Zoho CRM and HubSpot, with the ability to design, optimize, and drive adoption.
Strong analytical skills; fluent in Excel and BI tools like Tableau, Power BI, or Looker.
Experience in high-growth or transformation environments, ideally within transportation or logistics.
Familiarity with sales enablement platforms like Gong, Outreach, Clari, or Seismic.
Solid understanding of LTL-specific operational metrics (e.g., Revenue Per Hundredweight, Cost Per Shipment, Transit Time).
Comfortable working in dynamic, fast-paced environments with shifting priorities.

Physical Demands and Work Environment: The physical demands and work environment described here are representative of those an employee encounters while performing the essential functions of this position. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.

Physical Demands:
- Sedentary physical activity performing non- strenuous daily activities of an administrative nature.
- While performing the duties of the job, the employee is regularly required to sit, walk, stand, reach/handle items, work with the fingers, and talk and hear others in conversations via the phone or in person.
Work Environment:
- The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job.
- The noise level in the work environment is usually moderate.

Compensation:

The estimated compensation for this role is $120,000 to $150,000 per year.

Job Location:

Remote

Benefits:

PTO
Paid Holidays
Medical Insurance
Dental Insurance
Vision Insurance
Life Insurance
401k

Why Join Us

This is a unique opportunity to build, lead, and scale a critical function in a fast-moving LTL business. You'll shape how we go to market, drive sales performance, and unlock growth. If you're passionate about turning data into action, building high-impact teams, and delivering executional excellence-this is the role for you.

Roadrunner Freight is building something special with great people, a winning culture and a differentiated service offering in the marketplace. Join us today to grow your career!

*We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!

Additional Requirements:

Summary:
Roadrunner's Smart Long Haul is revolutionizing the industry with significant investments in technology, a culture of continuous improvement, and intelligent and efficient direct routing. A Top 100 Trucking company by Inbound Logistics and a Top Tier Service Carrier by Mastio, Roadrunner is an LTL industry leader on the rise.

As a long-haul, metro-to-metro LTL carrier, Roadrunner offers more direct routes than any other nationwide Less-than-Truckload carrier in the United States. With a nationwide presence, terminals across 40+ markets, and more than $400 million in revenue, the company's Smart Long-Haul Network is the preferred choice for shippers looking to move freight quickly and reliably.

Roadrunner is growing and looking for a highly motivated Senior Manager/Director, Sales Enablement & Operations, to join our winning team. If you are results-driven and looking for a rapidly growing company with high growth and earnings potential, apply today!

We Run Safe. We Run Smart. We Run Together.

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Location:: Downers Grove

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