Head of Sales Training

Head of Sales Training & Enablement (Fully Remote, W-2)Company: Hello FundingLocation: Remote (U.S. preferred)Employment Type: Full-time (W-2)Reports to: Founder & CEOAbout Hello FundingHello Funding is a fast-growing business funding brokerage helping small business owners access working capital. We are building a world-class, performance-driven sales organization with the goal of becoming one of the most respected brokerages in the country.We scale deliberately "” with structure, accountability, and high standards.This role will have ownership over sales training and onboarding as the company scales.The RoleWe are hiring a Head of Sales Training & Enablement to build and lead our sales training, onboarding, and coaching function.This role is responsible for establishing clear standards, disciplined execution, and consistent sales behavior across the sales team "” from onboarding through ongoing development.This is a hands-on role suited for someone who prefers building, coaching, and enforcing standards in real sales environments "” not designing theory from a distance.The ideal candidate enjoys building structure, coaching for performance, and holding teams to a high bar in a fast-moving environment.This role serves as the primary point of guidance for sales reps on call execution, language, and sales conversations, ensuring consistency and quality across the salesfloor.Training & CoachingLead live group training sessions for sales repsProvide ongoing coaching focused on execution, consistency, and performanceReview live and recorded calls and deliver direct, actionable feedbackIdentify performance gaps and implement targeted retraining when neededEstablish and reinforce clear sales standards and best practicesTraining Content & Documentation OwnershipBuild, maintain, and continuously improve sales training materials and onboarding resourcesTranslate existing sales frameworks and call structures into clear, usable training documentationCollaborate with the CEO on core messaging, standards, and foundational training assets, while independently owning day-to-day documentation and updatesEnsure training materials remain practical, current, and aligned with how the sales team actually operatesProfessional Development & External CollaborationAs appropriate, this role will have access to external training resources, industry experts, and experienced operators to support ongoing development and the evolution of our sales training standards.Sales Compliance & StandardsEnsure the salesfloor presents a consistent voice and message, so customers receive the same clarity, professionalism, and positioning regardless of which sales rep they speak withOwn enforcement of approved sales language, tone, and positioning across all sales conversationsIdentify sales-level compliance risk and correct it through training and coachingPartner with leadership and operations to ensure sales practices remain aligned with company and regulatory standardsHiring & EvaluationParticipate in final-round interviews for sales repsAssess coachability, communication style, and readinessProvide performance feedback and development recommendationsFinal hiring and termination decisions remain with the CEOScope & FocusThis role owns sales training, onboarding, coaching, and sales-level compliance standards across the sales organization.What Success Looks LikeSales reps are onboarded smoothly and held to clear standardsSales conversations are professional, consistent, and compliantTraining materials and onboarding processes are documented and actively usedThe sales team receives ongoing coaching aligned with performance expectationsIdeal Candidate ProfileYou likely have:Direct experience selling or managing phone-based finance sales(MCA / business funding experience strongly preferred)A proven track record training, coaching, and developing sales repsComfort enforcing standards and delivering direct feedbackExperience building and maintaining practical sales training documentationStrong call analysis and objection-handling skillsHigh accountability and operational disciplineCompensationBase salary: $80,000 - $95,000, depending on experienceFull-time W-2 employmentPotential for additional performance-based incentives over timeGrowth OpportunityAs the sales organization scales, this role is expected to evolve, with opportunities to take on additional leadership responsibility and build supporting resources over time. Growth will be deliberate and supported by structure, not rushed or ad hoc expansion.To ApplyPlease send:A brief overview of your relevant experienceExamples of teams you've trained or scaledAny sales training systems or frameworks you've builtPay: $80, $95,000.00 per yearWork Location: Remote

Created: 2026-01-05