About your roleAs a Senior Program Manager, PMO, you will own program management for Juniper Square's most complex, cross-functional software initiatives, driving execution from planning through release while acting as a senior voice inside our Program Management Office (PMO). You will partner closely with engineering, product, design, QA, platform, and operations leadership to build program plans, resolve dependencies, and keep delivery on track against customer commitments. You will act as a bridge between engineering, product management, and other cross-functional partners, translating ambiguous, high-stakes problems into a program plan that accounts for internal and external dependencies.
Beyond your own programs, you will help set the standard for how the PMO runs: contributing to governance, process standardization, metrics, and, critically, how the team uses AI. This role carries a heavy AI focus. You are expected to operate at the Workflow Orchestrator level on Juniper Square's AI fluency ladder. That means you do not just use AI tools yourself; you design and deploy multi-step workflows that span multiple tools or data sources and replace manual coordination, and you build the reusable systems (prompt libraries, Cowork skills and plugins, scripted Jira/Confluence data extraction) that other program and technical program managers across the org rely on. You will be looked to as the AI thought leader for the PMO organization, actively raising the AI fluency floor for the team.
What you'll do- Own program management for Juniper Square's most complex, multi-team software initiatives, partnering with engineering, product, design, QA, platform, and operations to build program plans, resolve cross-functional dependencies, and drive execution through every stage of the software development lifecycle.
- Act as a senior bridge between engineering and product management, translating ambiguous, cross-functional problems into a concrete program plan with clear milestones, owners, and dependencies, including with third-party teams where relevant.
- Establish and evolve the execution framework (agile/scrum ceremonies, artifacts, governance cadence) for your programs, and contribute those improvements back into PMO-wide standards and processes.
- Provide regular, senior-leadership-ready status reporting; proactively identify, monitor, and mitigate risk; apply change management discipline when scope or timelines shift.
- Contribute to PMO governance, including metrics definitions, process standardization, and adherence tracking, across the broader program management team.
- Design and deploy multi-step, AI-powered workflows, such as Cowork skills and plugins and scripted Jira/Confluence extraction and analysis, that replace manual PMO coordination, built as systems other PMs and TPMs can reuse rather than one-off personal shortcuts.
- Maintain a working library of reusable prompts, templates, and automations for high-frequency PMO work (status reporting, metrics dashboards, roadmap artifacts) and proactively share them across the team.
- Serve as an AI thought leader for the PMO org: define what "good" looks like before automating a workflow, build in validation steps, and own the accuracy of anything you ship. You can delegate the work, never the accountability.
- Mentor and coach TPMs and PMs on day-to-day program management practice, PMO goals, and their own AI fluency; contribute to roadmap planning and help anticipate delivery challenges across the organization.
- Ensure program documentation, status reporting, and delivery metrics are maintained on a regular, reliable cadence.
Qualifications- Bachelor's degree in Computer Science or equivalent practical experience.
- 15+ years of total industry experience, including 8+ years of technical program management on complex, large programs spanning multiple cross-functional teams.
- Deep understanding of the product development lifecycle and technical program management at scale, with a track record of driving programs from concept through release across multiple teams.
- Demonstrated AI fluency at the Workflow Orchestrator level: you have designed and deployed at least one multi-step AI or Cowork workflow spanning multiple tools or data sources, with a measurable time or quality improvement you can speak to specifically. Not just personal, ad hoc prompting.
- Comfortable maintaining a working library of reusable prompts, skills, or workflow templates, and configuring Cowork skills, connectors, and plugins without needing engineering support.
- Hands-on experience automating program-management workflows with AI, for example scripting or using AI tools to extract and analyze data from Jira and Confluence, generate status reports, or build reusable prompt libraries and templates that others rely on.
- Comfort defining quality criteria before deploying AI-assisted workflows, validating outputs, and owning the accuracy of anything you automate.
- Experience with project management tooling (Atlassian suite, Microsoft Project, Smartsheet, or equivalent) and Agile/Scrum; working familiarity with SAFe.
- Experience partnering cross-functionally with product management, design and UX, customer success, customer support, and other functions such as sales, marketing, and legal as needed.
- Experience with program and project governance: budgeting, vendor management, compliance, and metrics.
- Professional credentials (PMI PMP, ACP, CSM) a plus.
- Experience with fintech platforms, cloud platforms (AWS), Docker, and Kubernetes a plus.
- Self-driven and adaptable, comfortable mentoring peers, and flexible working with counterparts across geographies and time zones.
CompensationCompensation for this position includes a base salary and equity, and a variety of benefits. The U.S. base salary range for this role is $150,000 to $190,000 USD. The Canadian base salary range for this role is $120,000 to $150,000 CAD. Actual base salaries will be based on candidate-specific factors, including experience, skillset, and location, and local minimum pay requirements as applicable.
Benefits include:
- Health, dental, and vision care for you and your family
- Life insurance
- Mental wellness coverage
- Fertility and growing family support
- Flex Time Off in addition to company-paid holidays
- Paid family leave, medical leave, and bereavement leave policies
- Retirement saving plans
- Allowance to customize your work and technology setup at home
- Annual professional development stipend
Your recruiter can provide additional details about compensation and benefits.
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