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Attentive

Director, Mid-Market Sales

Attentive

. Lead, coach, and develop a team of Mid-Market Account Executives responsible for net-new revenue generation .

Posted 10/26/2026full-timeNew York City • New York • United StatesLead💰 $145,000 - $170,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in leading and developing Mid-Market Account Executives to achieve new-business revenue targets through effective coaching, pipeline management, and strategic account planning. Proven ability to implement structured sales methodologies and leverage AI to enhance team performance and efficiency.

Highest-signal resume keywords
B2B SaaS Sales ExperienceFrontline Sales ManagementCoaching AbilityForecasting and Pipeline ManagementStructured Sales Methodology Experience

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Revenue GenerationOutbound ProspectingPipeline CreationNegotiationObjection HandlingBusiness-Value SellingSales Cycle AnalysisPerformance ManagementAccount PlanningMulti-Threading
Soft Skills
Strong Executive PresenceClear CommunicationHigh Ownership Mentality
Tools & Technologies
AI ImplementationSales Playbook DevelopmentCRM Systems
Industry Keywords
Mid-Market SalesHigh-Growth EnvironmentChallenger SalesMEDDPICCCommand of the MessageEcommerceMartechB2C Sales

About the role

Key responsibilities & impact
  • Lead, coach, and develop a team of Mid-Market Account Executives responsible for net-new revenue generation
  • Build a high-performance culture centered on outbound prospecting, pipeline creation, accountability, and consistent execution
  • Coach AEs on discovery, business pain, challenging the status quo, stakeholder multi-threading, and measurable customer outcomes
  • Partner with AEs on account planning, competitive positioning, business cases, objection handling, negotiation, and closing
  • Establish expectations for self-generated pipeline and account-specific outbound strategies
  • Own team forecasting, pipeline inspection, performance management, and revenue-target attainment
  • Analyze conversion, pipeline coverage, sales cycles, win rates, and rep performance to drive action
  • Hire, onboard, and develop high-performing AEs
  • Partner with SDR, Marketing, Enablement, Revenue Operations, Solutions Consulting, and Customer Success
  • Provide customer and field insights to Product and Marketing
  • Evolve the Mid-Market sales playbook as the product portfolio and market opportunity expand

Requirements

What you’ll need
  • 7+ years of B2B SaaS sales experience, including 3+ years of frontline sales management experience
  • Proven success leading Mid-Market Account Executives against new-business revenue targets
  • Experience in an outbound sales environment where AEs meaningfully contribute to their own pipeline
  • Strong coaching ability across prospecting, discovery, multi-threading, business-value selling, objection handling, negotiation, and closing
  • Experience implementing AI into team workflows with proven improvements in efficiency or revenue
  • Experience with Challenger, MEDDPICC, Command of the Message, or another structured value-based/consultative sales methodology
  • Track record of developing sellers and improving performance through actionable coaching
  • Experience operating in a high-growth environment with evolving processes and playbooks
  • Strong forecasting and pipeline-management discipline
  • Ability to attract, assess, hire, and retain high-performing sales talent
  • Strong executive presence and clear communication with customers, sellers, and senior leadership
  • High ownership mentality
  • Especially valued: earlier-stage or high-growth SaaS experience, Marketing/Ecommerce/CRM or B2C sales experience, martech/ecommerce/AI or adjacent SaaS experience, outbound pipeline ownership, promoting AEs, and multi-product platform sales

Benefits

Comp & perks
  • Commission
  • Equity
  • Health and wellness benefits
  • Competitive perks and benefits
  • Reasonable accommodations for candidates with disabilities
  • Employee resource groups through AWAKE