Essential Job Duties 

• Develop and execute a strategic prospecting plan to target and win new national and multi-location accounts 

• Build and manage a robust pipeline, including lead generation, qualification, discovery, solution development, and closing 

• Conduct executive-level outreach and relationship development with C-suite, VP, and Director stakeholders 

• Lead discovery to understand client objectives, pain points, service requirements, and vendor process 

• Create and present compelling proposals that align Caliber’s capabilities to client needs, including service scope, coverage, and performance expectations 

• Lead contract, pricing, and service level agreement (SLA) negotiations in partnership with internal stakeholders 

• Coordinate cross-functionally (Operations, Finance, Legal, Billing, Implementation, and other support teams) to ensure deal feasibility and smooth onboarding readiness 

• Drive internal alignment and obtain approvals for pricing, terms, and commitments 

• Maintain accurate pipeline forecasts, activity reporting, and opportunity notes in CRM 

• Represent Caliber at industry events, conferences, and client meetings to build brand credibility and generate opportunities 

• Monitor market dynamics, competitive landscape, and industry trends to refine targeting and value messaging 

• Partner with Business Account Managers / account management teams to ensure clean handoffs post-close, including documentation of commitments, scope, and success metrics 

• Participate in QBRs to ensure you remain connected to existing clients 

• Contribute to broader sales and company initiatives as needed 

Preferred Skills and Experience 

• 8+ years of B2B sales experience with proven success closing complex, multi-location or national accounts (automotive, fleet, insurance, or related services preferred) 

• Demonstrated ability to build pipeline from scratch through outbound prospecting and relationship development 

• Proven track record of meeting or exceeding new business targets (revenue, account wins, pipeline coverage) 

• Experience managing long, multi-stakeholder sales cycles and navigating procurement, legal, and operational reviews 

• Strong executive presence with the ability to influence senior decision makers 

• Experience negotiating contracts, pricing agreements, and performance-based service metrics 

• Strong analytical mindset; ability to build business cases and ROI/value narratives 

• Excellent presentation, communication, and negotiation skills 

• Highly organized, self-motivated, and results-driven; strong follow-through and urgency 

• Proficient in Microsoft Office (Excel, PowerPoint, Word) and CRM tools, Salesforce 

• Professional demeanor with a “World Class” customer service approach 

• Travel: as needed to support client meetings, onsite presentations, and industry events (typically 50% to 80%, based on territory and target account footprint) 

Performance Measures 

• New account wins (national and multi-location) 

• New revenue growth (bookings) and ramp to production volume 

• Pipeline health (coverage, stage progression, conversion rates) 

• Sales cycle effectiveness (time to close, win rate, forecast accuracy) 

• Quality of handoff and onboarding readiness (clear scope, SLAs, documentation, internal alignment)