The Progressive Corporation

Senior Delivery Manager (Remote)

The Progressive Corporation$100K — $130K *
US-AnywhereRemote in Utah, US
Finance & Insurance
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of delivery management in software engineering, preferably in fintech or similar environments.
  • Ability to influence stakeholders through structure, data, and concise communication.
  • Experience building and improving delivery systems with a focus on reducing rework and increasing quality.
  • Comfortable modeling delivery trade-offs for leadership.
  • Fluent in the software development lifecycle (SDLC) with knowledge of integration and release management.
  • Strong Jira skills for tracking dependencies and delivery performance.
  • Experience in both Kanban and sprint-based team operations.

Responsibilities

  • Maintain visibility of complex delivery tasks by tracking blockers and risks across teams.
  • Model scope changes and present structured options to decision-makers to evaluate impacts.
  • Ensure backlog readiness by defining work and mapping dependencies before execution begins.
  • Proactively manage delivery risks by quantifying impacts and suggesting solutions to stakeholders.
  • Improve operational norms to minimize execution variability and rework.
  • Use AI tools to enhance operational efficiency in reporting and backlog management.
  • Influence team behavior and align stakeholder expectations through clear communication of commitments.

Benefits

  • Full Health Benefits including Medical, Dental, Vision, and Life Insurance, plus Paid Parental Leave.
  • Company Matched 401k to support long-term saving goals.
  • Paid Time Off, Paid Holidays, and Paid Volunteer Hours for work-life balance.
  • Access to Employee Resource Groups promoting diversity and inclusion.
  • Employee Stock Purchase Program for increased ownership in the company.
  • Tuition Reimbursement for continued education and professional development.
  • Charitable Gift Matching to support employee philanthropy efforts.
  • Provision of necessary job equipment and services.
Full Job Description
Senior Delivery Manager (Remote)

This role is work from home position and can be performed remotely anywhere in the continental US or in one of our corporate locations in Utah, Arizona or Colorado

YOU ARE:

A technically fluent delivery manager who operates at the team level - close to the work, the risk, and the engineers doing both. You understand the full software development lifecycle, from planning through delivery. You build systems that create predictability, surface risk early, and protect delivery integrity. You influence engineers, product managers, and stakeholders through structure, data, and clear framing.

You are comfortable operating in ambiguity. When dependencies slip, scope pressure mounts, or execution variability surfaces, your instinct is to model the impact, structure the options, and reset expectations with clarity.

You are equally at home in flow-based, service-oriented environments where work is continuous and interrupt-driven as you are in iteration-based teams. You understand that delivery discipline looks different depending on the team operating model, and you adapt your approach accordingly without losing rigor.

You treat AI tools as force multipliers for delivery work by using them to draft communications, model trade-offs, accelerate backlog synthesis, and generate operational artifacts faster than manual methods allow. You have a point of view on where AI augments delivery rigor versus where it creates false confidence, and you apply that judgment deliberately.

YOUR DAY-TO-DAY:

Delivery System Operations
  • Maintain and improve delivery visibility across complex, dependency-heavy work by tracking cross-team blockers, integration risks, and upstream/downstream exposure
  • Model the impact of scope changes, timeline shifts, and capacity constraints by presenting structured options with clear trade-offs to decision-makers
  • Drive backlog readiness discipline, ensuring work entering execution is well-defined and dependency-mapped before it starts
  • Identify and actively manage delivery risk through surfacing issues proactively, quantifying impact, and framing resolution paths for engineering and product leadership
  • Maintain and improve delivery operating norms that reduce rework, carryover, and execution variability over time
  • Leverage AI tooling to accelerate operational work, including status synthesis, risk narrative generation, and backlog readiness summarization, while maintaining human judgment on prioritization and stakeholder framing decisions.


Influence and Stakeholder Management
  • Influence engineer and product manager behavior through structure and data by driving accountability and shared clarity on delivery commitments
  • Frame delivery trade-offs clearly by presenting structured options with explicit implications on timeline, quality, and capacity
  • Partner with Product Managers to enforce readiness standards and protect delivery integrity when scope pressure mounts
  • Communicate delivery feasibility and confidence clearly to the engineering team and partnering Project Managers by providing early warning when assumptions change and surfacing recovery options when they do
  • Socialize production release schedules in advance with the development team, Product Manager, and relevant change advisory processes ensuring the team is prepared for releases


Technical Fluency
  • Maintain working fluency in the technical systems your team supports through a solid understanding of integration surfaces, API dependencies, and release risk in context
  • Coordinate across engineering, QE, architecture, and platform teams to manage cross-functional dependencies and resolve blockers at the right level
  • Apply delivery metrics (i.e. cycle time, throughput, carryover, predictability) as operational signals that drive structural change in how the team works


Service-Oriented Team Operations
  • Manage a Kanban-based delivery system for a team handling a mix of planned work and high-priority operational demand
  • Balance intake discipline with responsiveness by maintaining flow efficiency while protecting planned delivery commitments from reactive work pressure
  • Model WIP impact and context-switching costs to protect team throughput and focus
  • Maintain and improve intake and triage processes that bring structure to interrupt-driven work without creating bureaucratic overhead
  • Monitor Kanban flow metrics (i.e. lead time, cycle time, and queue depth) to identify bottlenecks and maintain healthy throughput
  • Coordinate with dependent teams and platform consumers to maintain demand visibility and set clear expectations proactively


Iteration-Based Team Operations
  • Manage sprint cadence and iteration health across one or more engineering teams with a focus on commitment reliability and sprint goal integrity
  • Enforce sprint entry discipline by ensuring stories meet sizing and readiness standards before planning begins, and holding the line when they don't
  • Track and improve sprint predictability using carryover, velocity trends, and planning accuracy as signals to adjust how the team operates
  • Manage scope pressure during active sprints through modeling the impact of additions or changes and presenting clear trade-off options to the Product Manager before commitments shift
  • Maintain cross-sprint dependency visibility across teams or workstreams, identifying what is at risk and when
  • Run retrospectives as structured operational reviews by identifying systemic delivery friction and driving follow-through on changes


YOU'LL BRING:
  • 5 to 7 years of delivery management experience embedded within software engineering teams in a fintech or similarly regulated, technically complex environment
  • Demonstrated ability to influence engineer and product manager behavior through structure, data, and clear framing
  • Proven experience building or materially improving delivery systems: reducing carryover, improving commitment reliability, or increasing planning quality through structural changes
  • Experience modeling delivery trade-offs and presenting structured options to leadership
  • Deep SDLC fluency, including integration complexity, release management, dependency modeling, and cross-team coordination
  • Strong working knowledge of Jira for dependency tracking, delivery modeling, and operational insight
  • Comfort operating in API-heavy, integration-dependent backend environments where delivery risk lives in the connections between systems
  • Prior experience managing Kanban-based teams in service-oriented or platform engineering environments
  • Demonstrated use of flow metrics (i.e. lead time, cycle time, WIP) as day-to-day operational tools for managing team health and throughput
  • Demonstrated use of AI-assisted tooling (LLMs, AI-augmented Jira workflows, or similar) to improve delivery throughput, reduce coordination overhead, or accelerate artifact generation with the discernment to know when AI output requires human review before it reaches stakeholders.
  • Calm, structured approach to ambiguity and able to reset expectations and protect delivery integrity when plans change
  • Strong written and verbal communication skills, including the ability to frame engineering consequences clearly for non-technical stakeholders
  • Bachelor's degree or equivalent experience


YOU MIGHT ALSO HAVE:
  • Prior experience managing sprint-based teams, including planning discipline, Definition of Ready enforcement, and iteration health management
  • Working knowledge of CI/CD pipelines, deployment infrastructure, or cloud services sufficiently enough to understand release risk and coordinate across platform teams
  • Experience coordinating across both iterative (sprint-based) and continuous-flow (Kanban) teams within the same organization
  • Familiarity with ServiceNow or similar change management tooling in a governed release environment
  • Experience supporting offshore or distributed engineering teams with uneven execution maturity
  • Agile, Scrum, or Kanban certification (CSM, PSM, KMP, or equivalent)


WE OFFER:
  • Competitive Compensation
  • Full Health Benefits; Medical/Dental/Vision/Life Insurance + Paid Parental Leave
  • Company Matched 401k
  • Paid Time Off + Paid Holidays + Paid Volunteer Hours
  • Employee Resource Groups (Black Inclusion Group, Women in Leadership, PRIDE, Adelante)
  • Employee Stock Purchase Program
  • Tuition Reimbursement
  • Charitable Gift Matching
  • Job required equipment and services


About The Progressive Corporation

Progressive is a place where innovation and collaboration are a way of life. Each of our employees has a role in our success and together, we continue to find new and better ways to satisfy our customers and move the insurance industry forward.

The Progressive Corporation Careers

Join the vibrant team at The Progressive Corporation, a leader in the insurance industry, and propel your career to new heights with a company known for innovation, leadership, and a commitment to diversity and growth.

Work You’ll Do

At The Progressive Corporation, we offer more than just job opportunities; we provide a platform for professional development and personal growth. As part of our team, you will contribute to transformative projects that redefine the standards of the insurance industry. Our collaborative culture ensures that every team member has the opportunity to make a significant impact.

Empower Your Career

Step into a role that challenges and excites you. At Progressive, you can navigate through a variety of career paths with the support of our extensive training and development programs. From leadership training to diversity workshops, we equip our professionals with the tools they need to excel.

Innovate with Us

Join a group of forward-thinkers who are constantly driving innovation in the insurance sector. At Progressive, your skills in technology, industry expertise, and digital innovation will help shape solutions that meet the evolving needs of our customers.

Internship Programs

Kickstart your career with The Progressive Corporation’s internship programs. Gain invaluable experience, build your resume, and develop professional networking connections that will benefit your career for years to come. Our internships offer a deep dive into the insurance industry, providing a robust foundation for future success.

Benefits and Culture

Choose a career with The Progressive Corporation and enjoy a wealth of benefits that go beyond the basics. Our inclusive culture supports our employees’ life stages and fosters a workplace where everyone can thrive. Health, wellness, financial planning, and work-life balance are just the beginning of what we offer.

Join Our Team

Explore the numerous positions available at Progressive, from entry-level to executive, and find where your expertise can make the most impact. We are continuously hiring talented individuals who are passionate about making a difference and ready to contribute to our culture of continuous improvement.

Stay Connected

Keep up to date with the latest at Progressive: - **Career Insights**: Get insider perspectives and industry-leading insights through our careers blog. - **Job Alert Emails**: Customize your subscription to receive job alerts and news tailored to your preferences. Discover the exciting and rewarding opportunities that await at The Progressive Corporation.

Explore Job Opportunities

Search open positions that match your skills and interests. We look for curious, creative, and solution-driven team players who are eager to drive progress and thrive in a dynamic environment.

SEARCH PROGRESSIVE JOBS

At The Progressive Corporation, your career is what you make of it. Grow, innovate, and lead with us as we redefine the future of insurance. Join us and be part of a team that values diversity, innovation, and the professional growth of its members.
Learn more about The Progressive Corporation
Size
49,000 employees
Market Cap
$75.6 billion
Industry
Net Income
$5.7 billion
Founded
1937
5 Year Trend
+15.3%
Revenue
$42.6 billion
NASDAQ

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