Director Loadsmart Jobs in Illinois (NOW HIRING)

Join Our Team as Senior Solution Sales Director

Loadsmart is an innovative logistics technology company that uses cutting‑edge technology to reinvent freight. Our remote team is headquartered in Chicago and we pride ourselves on curiosity, clarity, results, commitment and teamwork.

About the Role

We are seeking a Sr. Solution Sales Director to lead solution sales for the Shipper Solutions group. This role focuses on listening, consulting, and creating integrated platform solutions for new customers and driving expansion within existing accounts. It is an individual‑contributor position that requires strong matrixed collaboration across internal sales teams, external decision‑makers and leadership to pursue qualified leads.

Reporting to

Joel Rosenblatt, Vice President, Strategic Sales & Enterprise Account Management

Location

Remote – anywhere in the US with regular travel to meet prospects and clients.

What you get to do

• Acquire and grow shipper accounts from SMB to large enterprise with a focus on small‑to‑mid‑size customers (~$20M Freight Under Management).
• Own end‑to‑end consultative sales cycles from initial engagement through close, building long‑term customer relationships.
• Drive revenue growth through strategic upsell and cross‑sell initiatives across new and existing accounts.
• Sell Loadsmart’s full suite of digital and brokerage solutions, articulating value to complex logistics organizations.
• Develop and execute new business growth strategies that increase account growth and profitability.
• Manage sales pipeline, quota attainment, outreach activity, conversion rates, and key performance metrics.
• Partner closely with Marketing to drive outbound and inbound customer acquisition and onboarding.
• Collaborate with Shipper Solutions, Implementation and Operations teams to retain, expand, and successfully launch customers.
• Qualify, vet, and propose new Shipper Solutions opportunities from inbound and outbound leads.
• Lead customer sales engagements, presentations and formal proposals to customer leadership teams.
• Develop customer‑specific value propositions and pricing; negotiate contracts and commercial terms.
• Serve as an escalation point for customer and internal stakeholder needs.
• Oversee smooth handoff from sales to implementation, including scope definition, project planning and delivery alignment.
• Maintain executive‑level communication with customer leadership as required.
• Aggregate customer feedback and market insights to inform sales strategy, product direction, and collateral.
• Utilize sales enablement tools (Salesforce, SalesLoft) to document activity, manage pipeline and track OKRs.
• Report on pipeline health, forecast accuracy and initiative performance.
• Streamline communication across Sales, Customer and Shipper Solutions teams to ensure alignment and execution.

You have experience

• Demonstrated P&L experience in a multi‑modal managed transportation services environment.
• Extensive familiarity with the North American multimodal carrier base (FTL, drayage, LTL; parcel and flatbed a plus).
• Demonstrated program and project management skills.
• Effective cross‑functional collaboration that drives results.
• Comfortable creating project roadmaps, scopes and timelines.
• Focused on driving measurable results or key deliverables within ambitious timelines.
• Experience at a fast‑paced tech or logistics startup undergoing rapid change and growth.
• Excellent track record of successfully partnering with C‑level executives.
• 10+ years experience building and running a high performance managed transportation operation.

Your colleagues would describe you as

• Market focused with a strong familiarity with industry issues and trends.
• Passionate about delivering a fantastic customer experience.
• Genuine, respected and able to establish credibility quickly.
• An individual who interacts effectively with colleagues in other departments and business lines.
• An individual who constantly looks at things with a visionary eye and offers creative suggestions and solutions; energized by challenge and welcomes change.

Salary, Incentives & Equity

$140,000 – $170,000 a year. Compensation is based on location, scope, and experience. Eligible for incentive bonus, stock options and benefits listed below.

Benefits

Prosperity

• Competitive base salary.
• 401k match up to $5,000 regardless of salary.
• Commuter benefits and Divvy bike membership.

Happiness

• Unlimited PTO.
• Inclusive global community of Loadies across 15 countries.
• Regular recognition, feedback and transparency across all levels (monthly business updates, AMA with CEO, quarterly equity updates).
• Opportunities to join community service initiatives and donation drives.
• Employee engagement activities (offsite and onsite). If you’re in Chicago we host happy hours, free lunches, breakfast, games and regular social events.

Additional Benefits

• Extremely competitive equity package.
• Loadie Time Off – unlimited PTO and sick days.
• Comprehensive Medical, Dental and Vision insurance plans.

Equal Opportunity Employer

We are proud to be an equal‑opportunity employer, hiring and developing individuals from diverse backgrounds. Loadsmart treats all candidates and employees with respect and does not discriminate based on race, color, religion, sex, age, sexual orientation, gender identity or expression, national origin, veteran status or disability.

Background Check & AI Tools

All offers of employment are contingent upon successful electronic background checks conducted by a vendor in accordance with all applicable laws. We may use AI tools to support parts of the hiring process, but final decisions are made by humans.

Job Type

Exempt – Full‑time

Are you up to the challenge? Apply today!