Senior AI Strategist

Jobtailor; California (MO); On-site; USD 180,000 - 280,000; Full time

Job summary

Jobtailor is seeking a senior strategy leader to audit and govern AI initiatives, aligning them with GTM goals and enterprise sales objectives. You will define data governance, assess vendor and tool choices, and translate business needs into scalable AI solutions that drive pipeline and cross-functional execution.

The role emphasizes building blueprints for agentic workflows, partnering with IT and sales teams, and delivering training and measurable AI impact across large, distributed sales

Qualifications

• 10+ years in mid-market or enterprise sales strategy, GTM operations, management consulting, or AI/digital transformation

Responsibilities

• Audit existing AI initiatives and build a centralized inventory
• Evaluate initiatives for performance, scalability, and strategic fit
• Define governance protocols for data usage, model risk, vendor selection, and responsible AI
• Contribute to AI portfolio intake, prioritization, build-versus-buy evaluation, and tool deprecation decisions
• Define operational blueprints for coding, configuring, and deploying agentic workflows across the sales motion
• Translate business needs into scalable, production-ready AI solutions
• Define and evolve the AI tool and architecture landscape
• Partner with GTM, sales operations, and technical teams to move strategy into execution
• Deliver AI enablement, training, and proven workflow demonstrations for the field team
• Build and run an AI Ambassador Program
• Develop role-based AI learning journeys and drive proficiency programs
• Define and implement change management and communications strategies
• Map AI deployments to pipeline growth, win rates, net revenue retention, and rep efficiency
• Build measurement infrastructure for AI adoption, workflow impact, and administrative burden reduction
• Monitor the external AI landscape and provide forward-looking perspectives to sales leadership

Skills

AI strategy

GTM operations

Management consulting

AI/digital transformation

Executive communication

LLMs knowledge

RAG pipelines

Agentic frameworks

IT collaboration

Education

Bachelor’s degree

MBA

Tools

Agentic Frameworks

RAG Pipelines

AI Enablement Tools

Job description

• Audit existing AI initiatives and build a centralized inventory
• Evaluate initiatives for performance, scalability, and strategic fit
• Define governance protocols for data usage, model risk, vendor selection, and responsible AI
• Contribute to AI portfolio intake, prioritization, build-versus-buy evaluation, and tool deprecation decisions
• Define operational blueprints for coding, configuring, and deploying agentic workflows across the sales motion
• Translate business needs into scalable, production-ready AI solutions
• Define and evolve the AI tool and architecture landscape
• Partner with GTM, sales operations, and technical teams to move strategy into execution
• Deliver AI enablement, training, and proven workflow demonstrations for the field team
• Build and run an AI Ambassador Program
• Develop role-based AI learning journeys and drive proficiency programs
• Define and implement change management and communications strategies
• Map AI deployments to pipeline growth, win rates, net revenue retention, and rep efficiency
• Build measurement infrastructure for AI adoption, workflow impact, and administrative burden reduction
• Monitor the external AI landscape and provide forward-looking perspectives to sales leadership

Requirements

• 10+ years in mid-market or enterprise sales strategy, GTM operations, management consulting, or AI/digital transformation at a leading SaaS or AI-native firm
• Demonstrated track record delivering AI or digital transformation programs with measurable behavior change in large, distributed sales organizations
• Working knowledge of LLMs, RAG pipelines, and agentic frameworks
• Comfortable evaluating and pressure-testing technical solutions
• Ability to partner with IT, data engineering, and full-stack development collaborators
• Outstanding written and verbal executive communication skills
• Bachelor’s degree required
• MBA or equivalent experience strongly preferred
• Willingness to travel approximately 20% of the time

Core Competencies

Expertise in AI strategy and digital transformation, with a focus on delivering scalable AI solutions and measurable impact in sales organizations. Proficient in governance protocols, change management, and building training programs to enhance AI adoption and proficiency.

Highest-signal resume keywords

• 10+ Years In Sales Strategy
• AI/Digital Transformation Programs
• Working Knowledge Of LLMs
• Outstanding Executive Communication Skills
• Bachelor’s Degree

ATS Optimization Keywords

Hard Skills

• AI Initiative Auditing
• Performance Evaluation
• Governance Protocol Definition
• Operational Blueprint Development
• AI Solution Translation
• AI Tool Architecture
• Change Management Implementation
• Measurement Infrastructure Building
• AI Workflow Configuration
• AI Portfolio Management

Soft Skills

• Outstanding Written Communication
• Outstanding Verbal Communication
• Collaboration With Technical Teams

Certifications & Qualifications

• MBA Or Equivalent Experience

Industry Keywords

• GTM Operations
• Sales Operations
• SaaS
• AI-Native Firm
• Mid-Market Sales

Tools & Technologies

• Agentic Frameworks
• RAG Pipelines
• AI Enablement Tools