Senior Project Manager

Bold Penguin is a digital broker for commercial insurance that uses technology, digital distribution, wholesale capabilities, and AI-driven insights to transform insurance risk management. The Senior Project Manager will lead end-to-end delivery for strategic and enterprise customer engagements, partnering with clients and internal engineering, product, and partnership teams to manage scope, timelines, budgets, relationships, and launches.

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, 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
• 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
• Insurance industry experience (carrier, broker, MGA, or Insurtech) is a strong plus