Hybrid Strategic Program Director

Posted 3 weeks ago

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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

Job title

Strategic Program Director

Job type

Experience level

Lead

Salary

$150,000 - $200,000 per year

Degree requirement

Bachelor's Degree

Location requirements

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