Senior Project Manager

About the role

We’re looking for a Senior Project Manager to own end-to-end delivery for our strategic and enterprise customer accounts. You’ll partner directly with clients and our internal engineering, product, and partnership teams to turn customer commitments into shipped outcomes — running the project, the relationship, and the commercial details from kickoff through launch.

Responsibilities

• Own end-to-end delivery of customer engagements from kickoff through implementation, UAT, and launch, against committed scope, timeline, and budget.
• Serve as the primary point of contact for assigned strategic and enterprise accounts, leading client meetings, status reviews, and quarterly business reviews.
• Partner with engineering managers, solutioning leads, and product to translate customer requirements into well-scoped epics and stories, and to broker tradeoffs between scope, timeline, and engineering capacity.
• Contribute to the definition, drafting, and solutioning of business requirements partnering with customers, product, and engineering to turn ambiguous needs into clear, actionable specifications.
• Participate in an agile delivery cadence, standups, sprint planning, grooming, and retros.
• Manage the dashboards and reporting that keep customers and internal teams aligned.
• Manage scope, change orders, and escalations in coordination with the Partnership team, Legal, and Finance, maintaining awareness of SOWs, milestone commitments, and invoicing requirements.
• Develop and maintain program master schedules, budgets, risk logs, and the team assets, playbooks, decks, and templates that scale how we deliver across accounts.
• Drive routine status communications to customers and executive leadership, execution vs. baseline, risks, mitigations, and recovery actions, using data to drive decisions and unblock the team.
• Additional duties and responsibilities as assigned.

Requirements

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

• 7+ years in project or program management, with a track record of delivering customer-facing engagements on time, on scope, and on margin.
• Demonstrated experience owning strategic or enterprise customer accounts with executive-level stakeholders.
• Hands-on experience in an agile delivery environment, with deep working knowledge of Jira (boards, workflows, and dashboards).
• Proven ability to partner with software engineering teams — comfortable translating between technical and business audiences.
• Insurance industry experience (carrier, broker, MGA, or Insurtech) is a strong plus.

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.

About the company

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

• 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 team through great Slack channels for work and play, regular video conferences, and all-hands "Waddles." Company swag themed after our Antarctic bird mascot is also available.