Director, PMO (Engineering)

Juniper Square is hiring a Director, PMO (Engineering) to lead program management across its engineering organization and oversee delivery for complex enterprise engagements. The role builds and manages the PMO team, establishes company-wide reporting and governance standards, and drives execution with customers and cross-functional leaders.

Responsibilities:

• Own program management across the whole engineering organization, serving as the single point of accountability for program health across multiple engineering leaders' portfolios
• Lead client-facing delivery for our largest and most complex enterprise engagements, representing engineering directly with customers and partnering with Sales, Customer Success, and Product from pre-close through implementation and go-live
• Build and run a company-wide program reporting standard, including a common dashboard for R&D leadership, so every program has consistent, trustworthy visibility into status, risk, and milestones
• Manage and grow a team of program and technical program managers, setting the bar for program rigor, governance, and documentation across the function
• Build trusted partnerships with R&D leadership and drive cross-functional alignment so every major initiative has a program manager embedded and accountable from the start, rather than looped in late
• Partner with the Chief Development Officer and R&D leadership to shape PMO structure, standards, and delivery governance, and drive long-term team growth
• Stay hands-on: in addition to setting direction, personally drive day-to-day execution on the highest-stakes programs. This is a doer role, not a pure oversight layer
• Design, run, and administer multi-step AI-powered workflows and PMO tooling (for example, Cowork skills or scripted Jira and Confluence reporting) to keep program tracking and executive reporting fast and current as the team scales
• Demonstrate strong executive communication skills, with the ability to present effectively and convey key updates, risks, and strategic initiatives to senior leadership
• Partner with product and engineering leaders on roadmap, resource planning, and capacity allocation to keep program milestones and deliverable timelines on track
• Proactively identify, track, and mitigate risks and issues across strategic initiatives

Requirements:

• 12+ years of program management experience, including 4+ years leading a SaaS PMO or program function at the director level
• Bachelor's or Master's degree in Computer Science, a related technical field
• Proven track record leading complex, client-facing enterprise software implementations, directly engaging with enterprise customers and executives, not just internal stakeholders
• Experience managing and developing a team of program or technical program managers
• Demonstrated ability to build trust and drive outcomes across engineering leadership without direct authority over delivery teams
• Real, hands-on AI-workflow experience: has built and run a multi-step AI or Cowork workflow, not just used ChatGPT to draft documents
• Experience managing and aligning program management functions and engineering squads across multiple geographies (such as North America, Latin America, India, and Europe)
• Direct experience driving high-stakes, large-scale enterprise deployments and managing complex, multi-million-dollar strategic customer engagements with executive stakeholders
• Experience scaling PMO operations, governance standards, and delivery frameworks through periods of rapid organizational growth or structural transformation
• preferably with an MBA
• Background in fintech, private markets, fund administration, or other regulated enterprise SaaS
• Experience building executive or company-wide reporting and dashboarding standards
• Experience identifying and turning around an at-risk enterprise implementation before it affected the customer relationship, rather than catching the problem after the fact
• PMP, PMI-ACP, or equivalent certification