Head of Sales

Why Join UsReceivables management is a $20B+ market at an inflection point. Increasing regulatory complexity, rising operating costs, and declining effectiveness of legacy outbound models are driving demand for a modern, AI-first approach. Overtime.ai is the platform to define this next generation—combining voice AI, automation, and compliance-by-design to transform how the industry recovers debt while improving the consumer experience. This is a start-up leadership opportunity to shape go-to-market strategy, build a category-defining sales motion, and drive revenue in a market ready for disruption.The Head of Sales is responsible for building pipeline through partnerships, market engagement, and early customer programs for the Overtime.ai platform.All qualified opportunities and revenue generated through this role are credited to the Sales organization and count toward the Head of Sales’ pipeline and quota. The role reports to the CEO and is tightly aligned with Sales on priorities, pipeline development, and field execution.Requirements10+ years in enterprise software, fintech, or receivables managementExperience building partnerships or new revenue channelsExperience in healthcare partnerships or go-to-market strategyStrong communication and industry presenceComfortable working across teams without direct authorityResponsibilitiesRevenue DevelopmentBuild pipeline through partnerships, industry relationships, and targeted outreachDevelop early-stage opportunities and transition them into the sales pipelineSupport new channels that strengthen overall sales performancePartnershipsDevelop and manage strategic partners (platforms, integrations, industry relationships)Create opportunities that drive distribution and embedded adoptionAct as a senior point of contact for key partnersSales CollaborationWork closely with the Head of Sales on key opportunitiesSupport early deal shaping, use cases, and positioningParticipate in select sales cycles as neededEnsure smooth handoff of opportunities to Sales for execution and closeBeta and Early CustomersBuild and manage beta and pilot programsIdentify the right early customers and use casesDrive conversion from pilot to paying customer in coordination with SalesMarket EngagementBuild relationships across agencies, healthcare, and financial servicesRepresent Overtime.ai in the market and at industry eventsIdentify new use cases and opportunitiesAlignmentPartner with Sales on target markets and prioritiesAlign with Marketing, Product, and OperationsProvide market feedback to improve positioning and executionWhat We OfferA team built from the collections industry — work alongside leaders with experience across third party collections, healthcare revenue cycle, and first party servicing.Opportunity to grow with the company — take on meaningful responsibility as the business expands.Fast moving environment with direct access to leadership — decisions get made quickly and ideas can move into execution without unnecessary layers.Build technology tied to real operational outcomes — focused on improving recovery performance, lowering operating costs, and creating a better consumer experience in regulated environments.Fully remote within the US15 days PTO + all federal holidays + 3 sick days Health insurance reimbursement (ICHRA)401(k)Laptop provided by the companyParticipation in Employee Stock Ownership Plan (ESOP)