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 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 - $185,000 annually + commission + equity + benefits - Our salary ranges are determined by role, level and location #LI-SJ1 By applying for this position, your data will be processed as per Attentive's Privacy Policy. Attentive Company Values Default to Action - Move swiftly and with purpose Be One Unstoppable Team - Rally as each other’s champions Champion the Customer - Our success is defined by our customers' success Act Like an Owner - Take responsibility for Attentive’s success Learn more about AWAKE, Attentive’s collective of employee resource groups. If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience. At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation. Attentive is also committed to providing reasonable accommodations for candidates with disabilities. If you need any assistance or reasonable accommodations, please let your recruiter know.