Remote Director of AI-Driven Sales Enablement & Training

Ladders; United States; Remote; USD 140,000 - 223,000; Full time

Benefits offered by this job

Comprehensive health coverage

Flexible remote work

Generous PTO

Professional development

Retirement savings plan

Job summary

Ladders is seeking a Director of Sales Development & Training to lead strategy and execution of sales enablement programs in a highly regulated Finance & Insurance space. This leader will coach, experiment with AI-enabled tools, and partner with sales, product, and leadership to raise agent effectiveness across segments.

The role is remote for US-based candidates, offering a competitive compensation range and a path to shape how we position and price offerings while driving scalable growth

Qualifications

• 5-7 years of experience in sales training or enablement, preferably in a regulated environment.
• Proven track record of developing and implementing successful sales strategies.
• Strong analytical skills with a scientific approach to testing and iterating scripts.
• Experience with AI tools and their application in sales processes.
• Ability to collaborate effectively with cross-functional teams, particularly in sales and product management.
• Passion for coaching and developing sales talent.
• Comfortable taking ownership and making bold decisions in a fast-paced environment.

Responsibilities

• Own and evolve sales scripts across multiple verticals in collaboration with sales leaders.
• Develop AI tools to assist agents in real-time during customer interactions.
• Create a performance tracking suite using AI for agent performance analysis.
• Conduct structured pilots and A/B testing to refine sales methodologies.
• Design onboarding and remedial training programs for agents.
• Establish coaching programs for managers to enhance their effectiveness.
• Collaborate with product and sales leadership to influence product positioning and pricing.

Skills

Sales enablement

Cross-functional collaboration

AI tools in sales

Analytical mindset

Coaching & development

Regulated environment

Ownership & decision-making

Job description

Ladders is seeking a Director of Sales Development & Training to lead strategy and execution of sales enablement programs in a highly regulated Finance & Insurance space. This leader will coach, experiment with AI-enabled tools, and partner with sales, product, and leadership to raise agent effectiveness across segments.

The role is remote for US-based candidates, offering a competitive compensation range and a path to shape how we position and price offerings while driving scalable growth