Director, Mid-Market Sales

Attentive® is the AI marketing platform for 1:1 personalization redefining the way brands and people connect. We’re the only marketing platform that combines powerful technology with human expertise to build authentic customer relationships. By unifying SMS, RCS, email, and push notifications, our AI-powered personalization engine delivers bespoke experiences that drive performance, revenue, and loyalty through real-time behavioral insights.   Recognized as the #1 provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries. Leading global brands like Crate and Barrel, Urban Outfitters, and Carter’s work with us to enable billions of interactions that power tens of billions in revenue for our customers.   With a distributed global workforce and employee hubs in New York City, San Francisco, London, and Sydney, Attentive’s team has been consistently recognized for its performance and culture. We’re proud to be included in Deloitte’s Fast 500 (four years running!), LinkedIn’s Top Startups, Forbes’ Cloud 100 (five years running!), Inc.’s Best Workplaces, and the Human Rights Campaign Foundation's Corporate Equality Index!

About the Role

Attentive is looking for a Director, Mid-Market Sales to lead, develop, and scale a team of Mid-Market Account Executives responsible for acquiring new customers and driving revenue growth.

This is a hands-on sales leadership role for someone who knows how to build high-performing teams in outbound-driven, competitive sales environments. You'll be responsible for developing AEs who can create their own opportunities, challenge how prospects think about their business, run strategic discovery, multi-thread across stakeholders, and build urgency throughout the sales process.

We're looking for a leader who is equally comfortable coaching individual deals and building the systems, expectations, and culture that drive repeatable performance across a team.

The ideal candidate has experience leading Mid-Market SaaS sellers in a high-growth or earlier-stage environment where the playbook wasn't always fully built and success required creativity, accountability, and a bias toward action.

What You’ll Accomplish

• 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 confidently engage and multi-thread across Marketing, Ecommerce, CRM, Finance, and executive stakeholders.
• Partner closely 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, account-specific outbound strategies.
• Own team forecasting, pipeline inspection, performance management, and attainment against revenue targets.
• Use data to identify trends across conversion, pipeline coverage, sales cycles, win rates, and individual rep performance—and translate those insights into action.
• Hire, onboard, and develop high-performing AEs while building clear expectations around what great looks like at each level.
• Partner cross-functionally with SDR, Marketing, Enablement, Revenue Operations, Solutions Consulting, and Customer Success to continuously improve Attentive's Mid-Market GTM motion.
• Bring insights from customers, prospects, and the field back to Product and Marketing to strengthen our positioning and go-to-market strategy.
• Help evolve the Mid-Market sales playbook as Attentive's product portfolio and market opportunity continue to expand.

Your Expertise

• 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 are expected to 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 consistent, actionable coaching.
• Comfortable operating in a high-growth environment where processes and playbooks continue to evolve.
• Strong forecasting and pipeline-management discipline with the ability to use data to diagnose performance and prescribe solutions.
• Demonstrated ability to attract, assess, hire, and retain high-performing sales talent.
• Strong executive presence and ability to communicate clearly with customers, sellers, and senior leadership.
• High ownership mentality—you identify problems, develop solutions, and move quickly rather than waiting for perfect information.

About the Role

Attentive is looking for a Director of Sales, Mid-Market to lead, develop, and scale a team of Mid-Market Account Executives responsible for acquiring new customers and driving revenue growth.

This is a hands-on sales leadership role for someone who knows how to build high-performing teams in outbound-driven, competitive sales environments. You'll be responsible for developing AEs who can create their own opportunities, challenge how prospects think about their business, run strategic discovery, multi-thread across stakeholders, and build urgency throughout the sales process.

We're looking for a leader who is equally comfortable coaching individual deals and building the systems, expectations, and culture that drive repeatable performance across a team.

The ideal candidate has experience leading Mid-Market SaaS sellers in a high-growth or earlier-stage environment where the playbook wasn't always fully built and success required creativity, accountability, and a bias toward action.

What You’ll Accomplish

• 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 confidently engage and multi-thread across Marketing, Ecommerce, CRM, Finance, and executive stakeholders.
• Partner closely with AEs on deal