Remote Senior Program Manager - SaaS Delivery Leader

Ladders; United States; Remote; USD 150,000 - 175,000; Full time

Benefits offered by this job

Medical, dental & vision insurance

HSA with high-deductible plan

Flexible time off

Paid holidays

401(k) plan with employer contrib.

Career anniversary leave

Job summary

Ladders seeks a Senior Program Manager - Director, Services to lead large, complex SaaS delivery programs in the insurance and financial services space. This hands-on leader will drive cross-functional teams, maintain delivery discipline, and ensure strong business outcomes from planning through post-go-live stability. Location: Remote.

Compensation: $150,000 – $175,000 annually. You will partner with senior stakeholders to manage risk, governance, and client expectations, leveraging Agile,

Qualifications

• 10+ years of senior leadership experience in enterprise software or SaaS for insurance or financial services.
• Proven success in leading large-scale transformation programs ($5M-$20M) across multi-disciplinary teams.
• Deep understanding of Life, Health, and Annuity insurance operations, including policy administration and claims.
• Strong command of delivery governance, risk management, and financial control.
• Hands-on experience with Agile delivery models and tools like NetSuite and Jira.
• Executive presence for boardroom discussions and delivery execution forums.
• Bachelor's degree required; PMP, LOMA, FLMI, or Scrum Master certification preferred.

Responsibilities

• Own end-to-end execution of complex SaaS delivery programs, ensuring timelines and quality are met.
• Lead from the front, engaging deeply in plans and intervening early when outcomes drift.
• Drive delivery through measurable business outcomes, holding teams accountable for results.
• Take decisive ownership during high-pressure delivery moments, providing clarity and resolution.
• Anticipate risks through experience and data, acting before issues impact clients.
• Ensure production readiness and post-go-live stability for strong operational outcomes.
• Accelerate delivery performance using tooling, automation, and AI capabilities.

Skills

Leadership

Cross-functional

Delivery governance

Agile

Risk management

Education

Bachelor's degree

PMP/LOMA/FLMI/CSM

Tools

NetSuite

Jira

Job description

Ladders seeks a Senior Program Manager - Director, Services to lead large, complex SaaS delivery programs in the insurance and financial services space. This hands-on leader will drive cross-functional teams, maintain delivery discipline, and ensure strong business outcomes from planning through post-go-live stability. Location: Remote.

Compensation: $150,000 – $175,000 annually. You will partner with senior stakeholders to manage risk, governance, and client expectations, leveraging Agile,