We are looking for a strategic and innovative Senior Director of Revenue Enablement & GTM AI to transform and accelerate a high-growth B2B SaaS revenue organization. In this executive-level role, you will lead two interconnected functions: enterprise-wide Revenue Enablement and AI-powered Sales Development (AI SDR). You will drive the adoption of artificial intelligence, agentic workflows, automation, and modern sales technologies to improve prospecting efficiency, pipeline generation, and commercial performance. Working closely with Sales, Growth Marketing, Customer Success, Product Marketing, and Revenue Operations, you will build scalable processes that connect human expertise with AI-driven capabilities. You will also shape the learning, coaching, and development strategies that help revenue teams ramp faster and execute more effectively. This is an opportunity to play a pivotal role in modernizing a revenue engine and supporting sustainable growth beyond $100M in annual recurring revenue.
- AI SDR Strategy & Execution: Lead the strategy, design, implementation, and performance of AI-powered inbound and outbound prospecting programs, including lead qualification, routing, account research, personalized messaging, and automated follow-ups.
- Human-AI Collaboration: Establish an effective operating model defining responsibilities, workflows, and handoffs between AI agents, Sales Development Representatives (SDRs), and Account Executives (AEs), ensuring consistent service levels and a seamless prospect experience.
- Outbound Prospecting Optimization: Develop and oversee a unified outbound playbook covering account prioritization, buyer personas, messaging strategies, outreach channels, and performance monitoring.
- Technology & Vendor Management: Select, implement, and optimize AI SDR platforms and prospecting technologies, working with Revenue Operations to manage integrations, data quality, deliverability, automation, and conversion performance.
- Enterprise Revenue Enablement: Build and scale a comprehensive enablement function supporting Sales, Customer Success, Solutions Consulting, and Partnerships throughout the customer lifecycle, improving onboarding, productivity, retention, and expansion.
- AI Adoption & Transformation: Drive adoption of AI assistants, conversational intelligence, sales practice platforms, account intelligence, and digital sales tools. Establish governance, training, and workflows that embed AI into everyday commercial activities.
- Onboarding & Continuous Learning: Design scalable onboarding, certification, and continuous development programs that reduce ramp time and accelerate productivity for new Sales and Customer Success hires.
- Competency Development & Coaching: Establish role-specific competency frameworks, evaluate skill gaps, create individual development plans, and equip frontline managers with effective coaching methodologies.
- Sales Methodology & Playbooks: Institutionalize enterprise sales methodologies such as MEDDPICC, Challenger, and Value Selling, ensuring consistent messaging and execution across prospecting, acquisition, renewals, and expansion.
- Content Strategy & Governance: Oversee sales content development, organization, accessibility, usage, and lifecycle management. Establish structured processes for collecting field feedback, prioritizing requests, and improving enablement resources.
- Launch & Campaign Readiness: Coordinate commercial readiness for product launches, pricing updates, new target audiences, competitive initiatives, and major marketing campaigns or events.
- Pipeline Generation & GTM Alignment: Partner with Sales, Growth Marketing, Customer Success, Product Marketing, and Revenue Operations to align human-led and AI-powered prospecting strategies and generate qualified pipeline.
- Performance Measurement: Define and monitor key performance indicators, including pipeline generation, speed-to-lead, meeting conversion, show rates, quota attainment, time-to-productivity, and win rates. Translate performance insights into measurable revenue and ARR impact.
- Leadership & Team Development: Foster a collaborative, inclusive, and high-performance culture centered on accountability and continuous learning. Lead and develop the Senior Manager of Revenue Enablement, who oversees late-stage, renewal, and expansion enablement.
Requirements:
- Professional Experience: At least 8 years of progressive experience in revenue enablement, sales leadership, and/or sales development within high-growth B2B SaaS organizations, ideally supporting businesses scaling beyond $50M–$100M in ARR.
- AI SDR Expertise: Hands-on experience designing, launching, or managing AI-powered SDR programs and agentic inbound or outbound prospecting initiatives, with demonstrable results in pipeline generation and meeting conversion.
- Sales Development Leadership: Proven experience leading or partnering closely with outbound SDR teams, with a track record of achieving or exceeding pipeline and meeting generation targets.
- AI Transformation & Automation: Demonstrated ability to identify, evaluate, implement, and scale AI technologies, automation platforms, and agentic workflows while driving meaningful adoption across commercial teams.
- Broad Enablement Experience: Experience developing enablement strategies across the entire customer lifecycle, including new business acquisition, technical solution readiness, customer retention, account expansion, and renewals.
- Modern Learning & Enablement Practices: Strong knowledge of just-in-time learning, onboarding frameworks, competency assessments, certification programs, content governance, and collaboration with Product Marketing.
- Sales Methodology Expertise: Deep understanding of enterprise sales methodologies such as MEDDPICC, Challenger, and Value Selling, as well as conversational intelligence and modern sales coaching practices.
- Revenue Technology Fluency: Strong operational and administrative knowledge of CRM and revenue enablement platforms, including Salesforce, Salesloft or Outreach, Gong, Highspot, Seismic, WorkRamp, data enrichment solutions, and AI SDR technologies.
- Analytical & Commercial Acumen: Ability to connect prospecting performance, enablement initiatives, and technology adoption to measurable business outcomes, including ARR growth, conversion rates, pipeline velocity, and sales productivity.
- Executive Communication: Excellent communication, presentation, facilitation, and stakeholder management skills, with the ability to influence senior executives and cross-functional leadership teams.
- Strategic & Operational Leadership: Strong organizational and problem-solving abilities, combining a long-term transformation vision with hands-on execution and a data-driven approach to decision-making.
- Change Management: Ability to lead organizational transformation, encourage technology adoption, and build a culture of continuous improvement, collaboration, and accountability.
Benefits:
- Opportunity to lead a major revenue transformation initiative within a high-growth B2B SaaS environment.
- Strategic leadership role with significant influence over revenue operations, AI adoption, and go-to-market performance.
- Opportunity to build and scale innovative AI-powered prospecting and enterprise enablement functions.
- Close collaboration with executive leadership and cross-functional teams.
- Professional growth and development opportunities in an evolving AI-driven commercial environment.
- Inclusive and diverse workplace committed to equal employment opportunities and professional excellence.
- Remote working opportunity within the United States.
