About the role

Role Overview

The Senior Technical Project Manager leads complex, cross-functional software engineering initiatives from inception to delivery. You will connect engineering teams with product stakeholders to ensure work ships on time, within scope, and with high quality in a fast-paced fully remote environment.

What You’ll Do

Project Leadership
- Own end-to-end delivery of complex, multi-team software/integration projects
- Define scope, milestones, success metrics, and risk mitigation strategies
- Drive alignment across engineering, product, design, and business stakeholders
- Identify blockers early and remove impediments to keep delivery on track
Agile & Process Management
- Lead agile ceremonies: sprint planning, stand-ups, retrospectives, and demos
- Manage epics/stories/tasks and prioritize work in Jira
- Improve team processes to optimize velocity and quality
- Track and report project health, velocity, and delivery metrics to leadership
Stakeholder Communication
- Provide clear status updates, roadmaps, and executive briefings
- Manage expectations and escalate risks/decisions appropriately
- Serve as the primary point of contact for project status across levels
Technical Collaboration
- Partner with engineering leads to understand architecture, dependencies, and constraints
- Translate technical concepts for non-technical stakeholders
- Collaborate with teams building on Ruby on Rails and .NET platforms

Requirements

7+ years in project/program management within a software/engineering organization
Track record delivering large-scale software products in an agile environment
Proficiency with Jira/Confluence and modern agile tooling for backlog management and reporting
Hands-on experience with cloud platforms and CI/CD pipelines (AWS, Azure, or GCP)
Strong written and verbal communication; able to synthesize complexity for any audience
Solid risk management and proactive, solutions-oriented mindset
Fully remote across distributed time zones (with onboarding and optional in-office events)
PMP, PMI-ACP, CSM, or equivalent preferred

Preferred Qualifications

Experience with Ruby on Rails
.NET / C# background or familiarity
Background in InsurTech, FinTech, or B2B SaaS
Familiarity with AWS services such as EC2, RDS, S3, Lambda
Experience managing third-party vendor integrations and API-driven projects
Fluency in Insurance Tech / Integrations

About Bold Penguin

Bold Penguin is a digital broker focused on commercial insurance. Its technology supports digital distribution, wholesale capabilities, and AI-driven insights to transform the insurance risk lifecycle from prospecting through placement for enterprise partners.