Remote Senior Delivery Lead — FinTech Delivery Systems

Prog Leasing, LLC; United States; Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

Full Health Benefits

Company Matched 401k

Paid Time Off

Paid Holidays

Volunteer Hours

Employee Stock Purchase Program

Tuition Reimbursement

Charitable Gift Matching

Job summary

Progressive Leasing is seeking a Senior Delivery Manager to lead delivery systems within a fintech-driven environment. The role focuses on predicting blockers, modeling trade-offs, and aligning engineering, product, and leadership around disciplined delivery.

You will drive readiness, manage dependencies, and leverage AI-assisted tooling to accelerate backlog synthesis while preserving human judgment and prioritization. Remote work is supported across the continental US.

Qualifications

• 5 to 7 years of delivery management experience embedded within software engineering teams in fintech or regulated environments.
• Demonstrated ability to influence engineer and product manager behavior through structure, data, and clear framing.
• Experience building or materially improving delivery systems and reducing carryover or improving planning quality.
• Strong SDLC fluency, including integration complexity, release management, and cross‑team coordination.
• Excellent written and verbal communication skills for technical and non‑technical stakeholders.
• Comfort with AI-assisted tooling to improve throughput with human oversight.

Responsibilities

• Maintain and improve delivery visibility across complex, dependency-heavy work.
• Model the impact of scope changes and capacity constraints to present structured options to decision-makers.
• Drive backlog readiness and ensure work entering execution is well-defined.
• Identify and actively manage delivery risk, surfacing issues and presenting resolution paths.
• Leverage AI tooling to accelerate operational work while keeping prioritization human‑driven.
• Socialize release schedules and coordinate with Product Managers and change advisory processes.

Skills

Delivery management

SDLC fluency

Cross-functional coordination

Communication skills

Stakeholder management

Problem solving

AI-assisted tooling

Education

Bachelor's degree or equivalent

Tools

Jira

Job description

Progressive Leasing is seeking a Senior Delivery Manager to lead delivery systems within a fintech-driven environment. The role focuses on predicting blockers, modeling trade-offs, and aligning engineering, product, and leadership around disciplined delivery.

You will drive readiness, manage dependencies, and leverage AI-assisted tooling to accelerate backlog synthesis while preserving human judgment and prioritization. Remote work is supported across the continental US.