Senior Director

Paciolan operates across multiple business segments with distinct client needs and growth trajectories. As the organization accelerates investment in new products, shared product, engineering, and design, capacity has become its most constrained and strategically valuable resource. The Senior Director, Portfolio & Program Management establishes and leads the enterprise portfolio function that governs how this capacity is allocated and deployed. This role provides end-to-end visibility into the product development portfolio, ensuring alignment between strategic priorities and execution while enabling leadership to make informed, data-driven investment decisions.
This is a charter-level role, serving as the connective layer between segment demand and engineering supply, and acting as the single source of truth on the state of the development portfolio for the President, CTO, CPO, and CFO.

Essential Duties & Responsibilities:

Portfolio Governance & Visibility 

• Own and deliver the enterprise capacity scorecard, providing a clear and recurring view of how shared resources are allocated and whether deployment aligns with business priorities. 
• Build and maintain the single source of truth for all product development initiatives, including scope, ownership, dependencies, risk, status, and forecasts. 
• Surface insights on misalignment, overcommitment, and emerging delivery risks. 

Team Leadership & Function Build 

• Build and lead the program management function, aligning resources to product domains and business segments. 
• Recruit, develop, and scale a high-performing team of program managers. 
• Establish a durable operating model that evolves with growth. 

Executive Decision Support 

• Lead the recurring portfolio review forum with executive leadership, structuring discussions, framing tradeoffs, and enabling prioritization decisions. 
• Present clear, data-backed options when demand exceeds available capacity. 
• Capture decisions and ensure alignment and follow-through across stakeholders. 

Resource Allocation & Capacity Planning 

• Operate the enterprise resource allocation process across segments and product initiatives, making both supply and demand transparent and actionable. 
• Identify and escalate capacity conflicts, dependency risks, and delivery constraints early. 
• Ensure ongoing alignment between strategic direction and weekly/monthly capacity deployment. 

Operating Model & Delivery Discipline 

• Establish scalable, lightweight standards for status reporting, risk management, and forecasting across delivery teams. 
• Drive a consistent operating cadence that enables decision-making without introducing unnecessary process overhead. 
• Clearly distinguish between portfolio governance and delivery execution reporting. 

Financial Integration & Investment Management 

• Partner with Finance to integrate engineering investment tracking into portfolio reporting, including cost-per-initiative, capex/opex classification, and domain-level spend. 
• Enable visibility into ROI and benefits realization for completed initiatives and incorporate learnings into prioritization. 
• Link capacity allocation decisions to financial outcomes and investment performance. 

Minimum Qualifications:

• 8+ years of proven experience leading a portfolio or PMO function within a product-led, software-driven organization, with an emphasis on outcomes over process compliance. 
• Demonstrated success in converting business priorities into actionable portfolio decisions, including resource allocation, sequencing, and tradeoffs. 
• Executive Influence: Strong presence with senior leadership; skilled at communicating complex tradeoffs clearly and influencing decisions without direct authority. 
• Financial Acumen: Demonstrated understanding of engineering investment economics, including capex/opex treatment, cost modeling, and ROI analysis. 
• Data & Systems Discipline: Experience building accurate, scalable portfolio reporting using tools such as Jira, Azure DevOps, or portfolio management platforms, with pragmatic use of AI-supported insights. 
• Operating Cadence: Ability to design and sustain governance rhythms that drive decisions and accountability. 
• Build & Scale Mindset: Experience standing up new functions and evolving them into scalable organizational capabilities. 

Preferred Qualifications:

• Experience in ticketing, sports technology, live entertainment, or comparable multi-segment B2B SaaS environments. 

Pay Transparency:

The approximate national base pay range for this position is $172,000 to $215,000. Please note that this is a good faith estimate for the position at the time of posting. Individuals may also be eligible for an annual discretionary bonus and/or sales compensation based on individual and company performance. Placement on the range may vary based on factors including but not limited to job-related knowledge, skills, and experience, and geographic location.The pay rate will comply with all minimum federal, state, and local wage/salary requirements.

Learfield offers a full spectrum of benefits for eligible employees including Medical, Dental, Vision, Health Savings Account, Life Insurance and Other Insurance Plans, Flexible Paid Time Off (minimum 10+ days annually), including Parental Leave, 20 Paid Holidays, 401(k) + Match, and Short/Long Term Disability. Leave benefits are consistent with state and local laws, including the Colorado Health Families and Workplaces Act.

Learfield is an Equal Opportunity Employer. We provide equal employment opportunities to applicants and employees without regard to race; color; sex; gender identity; sexual orientation; religious practices and observances; national origin; pregnancy, childbirth, or related medical conditions; status as a protected veteran or spouse/family member of a protected veteran; or disability.