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Salary: USD 145,000 - 185,000 / annual
Attentive is an AI marketing platform that combines SMS, RCS, email, and push notifications with AI-powered personalization to help brands build authentic customer relationships. The company partners with 8,000+ customers across 70+ industries and is recognized as the #1 SMS marketing provider by G2. Attentive has been included in 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, 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 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
- 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 improve the Mid-Market GTM motion
- Bring insights from customers, prospects, and the field back to Product and Marketing to strengthen positioning and go-to-market strategy
- Help evolve the Mid-Market sales playbook as Attentive's product portfolio and market opportunity expand
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 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—identify problems, develop solutions, and move quickly rather than waiting for perfect information
Nice-to-haves:
- 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
- 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
