[Hiring] Director, PMO @Juniper Square

Role Description

As a Director, PMO, you will be responsible for program management across our entire engineering organization, including our largest and most strategic enterprise engagements. You will lead client-facing delivery for our most complex customers, sitting directly with executives and internal stakeholders to build project plans and drive execution in partnership with engineering, product, and go-to-market teams.

You will act as a bridge between engineering leadership and our customers, building and managing a small team of program and technical program managers while staying hands-on to personally drive delivery on our highest-stakes initiatives. You’ll report directly to our Chief Development Officer and partner closely with R&D leadership to shape PMO structure, standards, and long-term team growth.

In addition to the above, you will 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.

What you’ll do

• 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.

Qualifications

• 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, preferably with an MBA.
• 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.
• Ability to travel domestically and internationally as needed for key client engagements and team/executive meetings.
• 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.

Preferred Qualifications

• 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.

Compensation

Compensation for this position includes a base salary, annual bonus, equity and a variety of benefits. The U.S. base salary range for this role is $200,000 - $250,000 USD. Actual base salaries will be based on candidate-specific factors, including experience, skillset, and location, and local minimum pay requirements as applicable.

Benefits

• 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