Senior Program Manager - Director, Services

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

For our client, we are seeking a Senior Program Manager - Director, Services to join the team of a leader in the Information Technology space.

This role will oversee the execution of large, complex delivery programs within enterprise software and SaaS environments serving insurance and financial services clients. The position requires a hands-on leader who can drive cross-functional teams, maintain delivery discipline, and ensure strong business outcomes from planning through post-go-live stability. You will partner closely with senior stakeholders to manage risk, financial control, governance, and client expectations in high-pressure program environments.

Location: Remote

Compensation: $150,000 – $175,000 annually

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.

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.

Benefits

• Medical, dental & vision insurance starting Day One.
• Employer-funded HSA with a high-deductible health plan.
• Flexible time off and paid sick days.
• 11 paid holidays and paid parental/bonding leave.
• 401(k) plan with employer contributions.
• Career anniversary leave and other voluntary benefits.

Our client is an equal opportunity employer.