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Salary: USD 145,000 - 185,000 / annual
Attentive is the AI marketing platform for 1:1 personalization, combining SMS, RCS, email, and push notifications with an AI-powered personalization engine. The company partners with over 8,000 customers across 70+ industries, including major brands like Crate and Barrel, Urban Outfitters, and Carter's. Attentive has been recognized by Deloitte's Fast 500 (four years running), Forbes' Cloud 100 (five years running), and LinkedIn's Top Startups.
You will 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 in an outbound-driven, competitive environment. You'll be responsible for developing AEs who can create their own opportunities, challenge prospect thinking, run strategic discovery, multi-thread across stakeholders, and build urgency throughout the sales process.
Key responsibilities include:
- Lead, coach, and develop a team of Mid-Market Account Executives on net-new revenue generation
- Build a high-performance culture centered around outbound prospecting, pipeline creation, accountability, and consistent execution
- Coach AEs on effective discovery, uncovering business pain, challenging the status quo, and connecting Attentive's platform to measurable outcomes
- Develop sellers who can confidently engage and multi-thread across Marketing, Ecommerce, CRM, Finance, and executive stakeholders
- Partner 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 revenue target attainment
- Use data to identify trends in conversion, pipeline coverage, sales cycles, win rates, and individual rep performance
- Hire, onboard, and develop high-performing AEs with clear expectations at each level
- Partner cross-functionally with SDR, Marketing, Enablement, Revenue Operations, Solutions Consulting, and Customer Success
- Bring field insights back to Product and Marketing to strengthen positioning and go-to-market strategy
- Help evolve the Mid-Market sales playbook as the product portfolio and market opportunity expand
Attentive has distributed global workforce with employee hubs in New York City, San Francisco, London, and Sydney.
REQUIREMENTS:
- 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 outbound sales environments 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
- Familiarity 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 high-growth environments where processes and playbooks continue to evolve
- Strong forecasting and pipeline-management discipline with ability to use data to diagnose 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—identify problems, develop solutions, and move quickly
PREFERRED:
- Experience at 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
- Track record of promoting AEs into larger segments or future leadership roles
- Experience selling multi-product platforms or introducing new products into existing sales motion
