Sr. Solution Sales Director, Managed Transportation

About Loadsmart

Are you interested in joining an innovative logistics technology company?

Loadsmart is a growth‑stage technology company valued at over $1 billion (a true Tech Unicorn)! We are a collection of industry veterans and user‑centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers move more with less. With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change.

We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.

We are Loadsmart and we are adding an additional Sr. Solution Sales Director to continue to fuel our growth. This position is responsible for developing and executing new business growth strategies aimed at long‑term growth and profitability within Loadsmart’s Shipper Solutions group. This person leads solution sales efforts for new customers and cross/upsell expansion of existing customers. We focus on listening, consulting and creating solutions across platforms and/or services, leveraging SMEs.

This individual contributor role requires strong matrixed collaboration skills to drive engagement across internal sales teams (Digital, Managed Transportation and Brokerage), external decision makers, and Loadsmart leadership teams (including, but not limited to, sales, implementation, operations, product, and engineering) to ensure qualified leads are identified and pursued properly. You will obsess about delighting our customers to achieve breakout revenue growth.

You will create a culture of sales success and lead by example.

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

• Acquire and grow shipper accounts from SMB to Large Enterprise, with primary focus on small to mid‑sized 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 by clearly articulating value to complex logistics organizations
• Develop and execute new business growth strategies to 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, Sales Loft) 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

• Demonstrated P&L experience in a multi‑modal, managed transportation services environment
• Extensive familiarity with the North American multimodal carrier base including FTL, drayage and LTL; parcel and flatbed nice to have
• Demonstrated program and project management skills
• Effective and proven cross‑functional collaboration that drives results
• Comfortable creating project…