Task Order Project Manager overseeing IT service contracts for CACI. Driving leadership in a complex IT environment with opportunities for growth and development.
About the role
- Director of Strategic Programs overseeing critical initiatives and strategy execution at Outreach AI Revenue Workflow Platform. Collaborating with C-suite leaders to ensure impactful business outcomes.
Responsibilities
- Lead CEO-sponsored, enterprise-wide strategic initiatives from problem definition through delivery and measurable impact.
- Translate strategic priorities into structured programs with clear business cases, operating plans, milestones, owners, and KPIs.
- Move fluidly between high-level strategy and day-to-day execution to ensure results, not just recommendations.
- Partner effectively and closely with C-Suite level leaders to understand their current state of business and how potentially new directives may affect their current operations – eventually, be able to speak on their behalf with the CEO & CBO when new ideas or initiatives are brought to the table so that the first discussion is fruitful.
- Lead rigorous quantitative and qualitative analysis on complex business problems (brand awareness, growth, churn, AI adoption, GTM efficiency, operating leverage, etc.).
- Build financial, operational, and scenario models to support executive decision-making.
- Develop hypothesis-driven insights, pressure-test assumptions, and turn data into clear executive recommendations.
- Drive execution across Sales, Marketing, Product, Engineering, Finance, People, and Customer Success.
- Influence senior leaders without direct authority through structured problem-solving, clarity, trust, and credibility.
- Identify risks, dependencies, and resource constraints early and actively remove roadblocks.
- Be able to push new ideas that may not be popular by identifying how it could work for each C-Suite Leader (coming to the table with a solution versus a directive only).
- Act as a strategic extension of the Chief Executive Officer.
- Collaborate in developing executive-level and board-ready materials including strategy narratives, program updates, operating reviews, KPI dashboards, and decision frameworks.
- Support the Office of the CEO with strategic planning cycles, operating cadence reviews, transformation milestones, and executive offsites.
- Give feedback to CEO on why ideas may or may not be worth pursuing by providing solid data and evidence, inclusive of considering financial and operational restrictions.
- Establish disciplined operating rhythms, governance structures, and escalation paths for critical, cross—functional initiatives.
- Track results against commitments with transparency and urgency.
- Lead stakeholder communication and change management to ensure organizational alignment and adoption.
Requirements
- Bachelor’s degree required; MBA or advanced business degree strongly preferred.
- 12+ years Top-tier or boutique management consulting focused on technology, SaaS, AI, or digital transformation and/or
- Strategic operations, corporate strategy, Office of the CEO or Chief of Staff roles within a scaling technology company.
- Proven track record of leading complex, cross-functional initiatives from strategy through execution.
- History of successful relationships with visionary start up CEOs
- Direct experience working with C-suite leaders and presenting to executive and board audiences.
- Experience in startup companies who are high-growth, fast-changing environments where priorities shift and ambiguity is constant.
- Strategic & Tactical Execution: Can zoom out to enterprise strategy and zoom in to operational detail seamlessly.
- Advanced Analytical Thinking: Expert in structured problem-solving, KPI design, and business case development.
- Executive Communication: Exceptional ability to synthesize complexity into clear, compelling executive narratives.
- Influence Without Authority: Trusted partner to senior leaders across functions. Works collaboratively to achieve desired outcomes.
- Program & Operating Rigor: Brings structure, discipline, and momentum to ambiguous initiatives.
- Judgment & Discretion: Trusted with highly sensitive leadership and company matters.
- Bias for Action: Not just an advisor, personally accountable for results.
- Thinker and doer with strong intellectual horsepower.
- Comfortable with ambiguity, pace, and pressure.
- Confident but humble; challenges ideas with data and respect.
- Highly organized, detail-oriented, and outcomes-focused.
- Energized by building, scaling, and transforming businesses.
Benefits
- Flexible time off
- 401k to help you save for the future
- Generous medical, dental, and vision coverage for full-time employees and their dependents
- A parental leave program that includes options for a paid night nurse, and a gradual return to work
- Infertility/ assisted reproductive services benefit
- Employee referral bonuses to encourage the addition of great new people to the team
- Snacks and beverages in the Office, along with fun events to celebrate
- Diversity and inclusion programs that promote employee resource groups like Outreach Women's Network, Latinx community, Outreach Black Connection, AAPI community, Pride/LGBTQIA+, Gender+, Disability Community, and Veterans/Military
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