← All roles

Director, Mid-Market Sales

Attentive· Sales
Apply on company site
Remote$145k - $185kfull-timePosted 2w ago

About the role

Director-level sales leadership role responsible for leading and scaling a team of Mid-Market Account Executives focused on net-new revenue, outbound-driven prospecting, and cross-functional collaboration to drive Attentive’s growth.

Responsibilities

  • Lead, coach, and develop a team of Mid-Market Account Executives responsible for net-new revenue generation.
  • Build a high-performance culture centered around outbound prospecting, pipeline creation, accountability, and consistent execution.
  • Coach AEs to run effective discovery, uncover meaningful business pain, challenge the status quo, and connect Attentive's platform to measurable customer outcomes.
  • Develop sellers who can engage across Marketing, Ecommerce, CRM, Finance, and executive stakeholders.
  • Partner with AEs on deal strategy including account planning, discovery, competitive positioning, business cases, objection handling, negotiation, and closing.
  • Establish clear expectations around self-generated pipeline and coach reps on creative outbound strategies.
  • Own team forecasting, pipeline inspection, performance management, and attainment against revenue targets.
  • Use data to identify trends in conversion, pipeline coverage, sales cycles, win rates, and rep performance; translate insights into action.
  • Hire, onboard, and develop high-performing AEs with clear expectations of performance at each level.
  • Partner cross-functionally with SDR, Marketing, Enablement, Revenue Operations, Solutions Consulting, and Customer Success to improve Mid-Market GTM.
  • Bring insights from customers and field back to Product and Marketing to strengthen positioning and GTM strategy.
  • Help evolve the Mid-Market sales playbook as product portfolio and market opportunity expand.

Qualifications

  • 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 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 other structured value-based/consultative sales methodologies.
  • Track record of developing sellers and improving performance through coaching.
  • Comfortable in a high-growth environment with evolving processes and playbooks.
  • Strong forecasting and pipeline-management discipline with data-driven diagnosis and solution prescription.
  • Demonstrated 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.

Skills

Required:Leadership and people managementStrategic sellingForecasting and pipeline management

Benefits

  • Health & wellness benefits
  • Equity
  • Other competitive perks referenced by link
Last updated Oct 8, 2026. Interested? Apply on the company site.

About Attentive

AI-Powered SMS and Email Marketing Platform

Learn more about Attentive—the SMS and email platform that brings your customer interactions to life with advanced AI.

SMSEmailAIMarketing AutomationData ActivationCustomer Engagement
Company profileWebsite

More open roles at Attentive