Senior Director – Strategic Operations, Program Management

Role Overview

• Build and scale the enterprise PMO.
• Establish the operating model, core rituals, and tooling to manage Sprout’s top six cross-functional company priorities.
• Create clear, lightweight visibility into progress, risks, dependencies, and decisions needed without unnecessary bureaucracy.
• Design measurement and reporting systems that provide genuine insight into initiative health and execution effectiveness.
• Use data to inform prioritization and resource allocation by analyzing effort versus impact, velocity, and cross-initiative dependencies.
• Partner closely with initiative owners to surface trade-offs, remove blockers, and accelerate decision making.
• Codify how Sprout executes major initiatives, iterating on what works and evolving the model as the business scales.
• Own end-to-end program management for six high-stakes, cross-functional initiatives.
• Translate executive vision into executable plans with clear ownership, milestones, and success metrics.
• Track leading and lagging indicators to identify early warning signs and course correct before issues escalate.
• Provide portfolio-level oversight by identifying patterns across initiatives, distinguishing systemic issues from one-off challenges, and advising on sequencing, integration, and resourcing.
• Anticipate dependencies and conflicts across initiatives and run effective operating rhythms to maintain momentum.
• Distill complex, multi-threaded work into clear updates, decisions needed, and next actions for senior leaders.
• Partner with the CPO and executive leadership team on annual and long-range strategic planning.
• Connect company strategy to day-to-day execution, ensuring leaders and teams have a clear line of sight to priorities and outcomes.
• Identify organizational friction points and capability gaps that slow execution, and design interventions that improve velocity.
• Develop frameworks and tools that strengthen decision making and execution effectiveness across the organization.
• Evolve from managing the initiative portfolio to helping shape it by making recommendations based on capacity, dependencies, and strategic value.
• Hire, coach, and develop one direct report to support program management execution.

Requirements

• 12+ years of experience in strategy, operations, program management, or management consulting, including 5+ years in a leadership role.
• Proven track record leading complex, cross-functional, high-stakes initiatives from strategy through execution.
• Deep experience building programs, operating rhythms, and execution frameworks in ambiguous, fast-moving environments.
• Strong analytical and quantitative skills, including designing measurement frameworks and translating insights into action.
• Exceptional communication skills and executive presence, with the ability to partner credibly with C-suite leaders.
• Preferred qualifications:
• Experience in high-growth technology or SaaS environments.
• PMO or program management certification (PMP, PgMP).
• MBA or relevant graduate degree.
• Experience in organizational design, change management, or organizational effectiveness.
• Background in management consulting, internal strategy, or enterprise PMO roles.
• Experience supporting executive or board-level strategic planning.

Tech Stack

• PMP

Benefits

• Comprehensive Health & Wellness: Premium BCBSIL medical, dental (high/low plans), and vision (Eyemed) insurance for you and your eligible dependents.
• Premium Mental Health Support: Full, free access to Modern Health for you and your dependents, including coaching, therapy sessions, and digital wellness resources.
• Retirement Savings: 401(k) plan with a 50% company match on your first 6% of contributions (a 3% total match).
• Financial Security: 100% employer-paid Life and Disability insurance for your peace of mind.
• Flexible Paid Time Off: A flexible PTO policy, supplemented with additional company-wide Rest & Recharge days throughout the year.
• Paid Parental Leave: Up to 16 weeks of paid leave for new parents to support you in expanding your family.
• Annual Lifestyle Stipend: A $1,000 USD annual Lifestyle Spending Account to spend on your physical, mental, and financial well-being.
• Work From Home Support: A one-time $550 USD stipend to set up your home office, plus a monthly $50 USD stipend for internet.
• Giving Back: 16 hours of paid volunteer time annually, plus a $100 annual match for your charitable donations.
• Additional Financial Perks: Access to pre-tax commuter benefits, subsidized child/eldercare (Care.com), discounted pet insurance (Figo), and no-cost personalized financial wellness support through Your Money Line.