Strategic Program Director

About Outreach

Outreach, founded in 2014, is the only complete AI Revenue Workflow Platform that helps sales leaders benefit from connected account visibility, performance insights, and higher forecasting accuracy across every GTM team. Outreach infuses agentic AI to power 100s of use cases across sales motions. From new logo prospecting to renewal and expansion, Outreach AI automates workflows and frees sellers to focus on more strategic conversations and actions. Global organisations use Outreach to power their revenue teams, including SAP, Siemens, Snowflake, ZoomInfo, and Verizon to name a few. To learn more, please visit www.outreach.io.

The Role 

Operating as a core member of the Office of the CEO, this individual will lead the company’s most critical, cross-functional initiatives from concept through execution, working directly with the Chief Executive Officer , Chief Business Officer and executive leadership team. The Director of Strategic Programs is a highly analytical, execution-oriented leader responsible for turning enterprise strategy into measurable business outcomes. This role is designed for a former management consultant with preferred operating experience in technology companies who thrives at the intersection of strategy and execution. Someone who can ideate at the executive level, build a plan, orchestrate work streams across departments, and then personally drive it to completion. 

 This is a hands-on role for a strategic operator who is equally comfortable in models, board materials, working sessions, and execution trenches.

Location: We’re looking to hire in Seattle or the Bay Area. 

• 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. 

• Bachelor’s degree required; MBA or advanced business degree strongly preferred. 
• 5+ 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. 
• Experience with Excel and Asana.

#LI-SC1

Why You’ll Love It Here

• 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

Outreach is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.

Our success is reliant on building teams that include people from different backgrounds and experiences who can elevate assumptions and ideas with fresh perspectives. We're dedicated to hiring the whole human, not just a resume. To that end, we look for a diverse pool of applicants-including those from historically marginalized groups. We would like to invite you to apply even if you don't think you meet all of the requirements listed below. We don't want a few lines in a job description to get between us and the opportunity to meet you.