Sr. Solution Sales Director

Loadsmart • Chicago, IL

1d • $140,000 - $180,000 • Remote

About The Position

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 to 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. If so, nice to meet you! 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. Not pushing a product or specific service, but rather listening, consulting and creating solutions across platforms and/or services, leveraging SMEs. This position is an individual contributor role, however, it 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.

Requirements

• 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 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

Nice To Haves

• parcel and flatbed nice to have

Responsibilities

• 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, 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

Benefits

• Competitive base salaries - we believe in rewarding top talent
• 401k match up to $5,000 regardless of salary
• Commuter benefits and membership with Divvy bike
• Unlimited PTO
• An opportunity to work with an inclusive, global community of Loadies across 15 countries united by our core value of Teamwork
• Regular recognition, feedback, and transparency across all levels; we offer monthly Business Updates, monthly "Ask Me Anything" Sessions with the CEO and Quarterly Equity updates
• Opportunities for you to join our community service initiatives and donation drives
• Lots of employee engagement activities both offsite and onsite; if you’re in Chicago expect to have an amazing time at our new 35,000 sq foot office where we host happy hours, free lunches, free breakfast, lots of games (ping pong, pool, arcade, etc) plus get out of the office regularly for company social events (i.e. bowling, baseball games, golf outings)
• Extremely competitive Equity package - become a shareholder in our company!
• Loadie Time Off - PTO and sick days without a limit
• Comprehensive Medical, Dental, and Vision insurance plans
• 401k Match

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees