Director, Mid-Market Sales

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 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.

We'd Be Especially Excited If You Have

• Experience at an earlier-stage or high-growth SaaS company where you helped build or evolve the sales motion.
• Experience selling or leading teams selling into Marketing, Ecommerce, CRM, or other B2C business leaders.
• Martech, ecommerce technology, AI, or adjacent SaaS experience.
• Experience leading teams through a shift toward greater outbound/self-generated pipeline ownership.
• A track record of promoting AEs into larger segments or future leadership roles.
• Experience selling multi-product platforms or introducing new products into an existing sales motion.

You'll get competitive perks and benefits, from health & wellness to equity, to help you bring your best self to work.

For US based applicants:

• The US base salary range for this full-time position is $145,000 - $170,000 annually + commission + equity + benefits
• Our salary ranges are determined by role, level and location

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