Director of Sales Development & 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

For our client, we are seeking a Director of Sales Development & Training to join the team of a leader in the Finance & Insurance space.

This leader will own the strategy and execution of sales development and training programs that improve agent effectiveness and support growth across multiple customer segments. The role will partner closely with sales leadership, product management, and managers to sharpen positioning, refine pricing conversations, and strengthen the overall sales motion. It is a highly visible opportunity to combine coaching, experimentation, and AI-enabled tools to elevate performance in a fast-paced, regulated environment.

Location: Remote - US based candidates only, no visa sponsorship available

Compensation: $140,000 – $223,000 annually

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

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

Benefits

• Comprehensive health, dental, and vision insurance
• Flexible work arrangements, including remote work options
• Generous paid time off and holiday policies
• Professional development opportunities and training programs
• Retirement savings plan with company matching contributions

Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.