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 clientobjectives, pain points, service requirements, andvendorprocess

• 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

• Maintainaccuratepipeline 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 youremainconnected 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-locationor national accounts (automotive, fleet, insurance, or related services preferred)

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

• Proventrack recordof 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 (typically50% 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)