Senior Technical Project Manager

YOUR ROLE

We are seeking an experienced Senior Technical Project Manager to lead complex, cross-functional software engineering initiatives from inception to delivery. In this role, you will serve as the connective tissue between engineering teams and product stakeholders - ensuring projects are delivered on time, within scope, and with exceptional quality.

You will thrive in a fast-paced, fully remote environment and bring deep technical fluency, a bias for action, and a track record of delivering large-scale software projects.

WHAT YOU'LL DO

Project Leadership

• Own the end-to-end delivery of complex, multi-team commercial insurance integration projects
• Define project scope, milestones, success metrics, and risk mitigation strategies
• Drive alignment across engineering, product, design, and business stakeholders
• Proactively identify blockers and remove impediments to maintain delivery momentum

Agile & Process Management

• Thought leader during agile ceremonies including sprint planning, stand-ups, retrospectives, and demos.
• Manage project backlogs in Jira, ensuring epics, stories, and tasks are well-defined and prioritized.
• Continuously improve team processes to optimize velocity and quality.
• Track and report on project health, velocity, and delivery metrics to leadership.

Stakeholder Communication

• Produce clear, concise status reports, roadmaps, and executive briefings.
• Manage stakeholder expectations and escalate risks and decisions with appropriate urgency.
• Act as the primary point of contact for project status across all levels of the organization.

Technical Collaboration

• Partner closely with engineering leads to understand technical architecture, dependencies, and constraints.
• Translate complex technical concepts into clear business language for non-technical audiences.
• Work alongside teams building on Ruby on Rails and .NET platforms.

YOUR LOCATION

This is a fully remote role, with the exception of onboarding and optional in-office events.

Skills & Experience

• 7+ years of project/program management experience in a software or engineering organization.
• Proven track record delivering large-scale software products in an agile environment.
• Expertise with Jira/Confluence and modern agile tooling for backlog management and reporting.
• Hands-on experience with cloud platforms (AWS, Azure, or GCP) and CI/CD pipelines.
• Exceptional written and verbal communication skills; able to synthesize complexity for any audience.
• Strong risk management and problem-solving skills with a proactive, solutions-oriented mindset.
• PMP, PMI-ACP, CSM, or equivalent certification preferred.
• Comfortable operating in a fully remote environment across distributed time zones.

Preferred Qualifications

• Experience working with Ruby on Rails engineering teams.
• .NET / C# background or familiarity is a plus.
• Prior experience in InsurTech, FinTech, or B2B SaaS environments
• Familiarity with AWS services (EC2, RDS, S3, Lambda) or equivalent cloud infrastructure
• Experience managing third-party vendor integrations and API-driven projects.
• Fluency in Insurance Tech/Integrations highly desired.

Physical Requirements

• Must be able to sit/stand/walk for prolonged periods of time, (up to 8 hours per day) at a desk working on a computer.
• Must be able to use standard office equipment for extended periods of time, including but not limited to, a mouse, keyboard, phone and video conferencing.

Bold Penguin is the premier digital broker for commercial insurance. Their technology expands top-of-funnel demand and increases yield for enterprise partners. Through digital distribution, wholesale capabilities, and AI-driven insights, they transform the lifecycle of both simple and complex risks, from prospecting to placement.

Benefits

We offer competitive compensation and progressive benefits that include:

• Medical, Dental, and Vision
• Flexible PTO Policy
• 401(k) with a company match
• Employee Assistance Program
• Parental Leave
• Disability and Life Benefits

Stay connected to the Glacier. We have great SLACK channels for work and play. We also like to video conference and hold all-hands "Waddles" regularly.

Penguin bling. Like swag themed after a certain Antarctic bird? Just. You. Wait.

Bold Penguin believes in inclusion. That's why we're proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. To learn more about our results-focused culture and employee-focused perks, read more on our careers page.