Outreach

Chief of Staff – Office of the CEO

Outreach

full-time

Posted on:

Location Type: Hybrid

Location: Seattle • California, Washington • 🇺🇸 United States

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Salary

💰 $150,000 - $220,000 per year

Job Level

Lead

About the role

  • Act as a strategic thought partner to the CEO on customer, partner, and market-facing priorities
  • Translate CEO priorities into clear objectives, agendas, and follow-through for external engagements
  • Anticipate needs, risks, and opportunities related to the CEO’s external commitments
  • Lead rigorous quantitative and qualitative analysis on complex business problems (brand awareness, growth, churn, AI adoption, GTM efficiency, etc.).
  • Develop hypothesis-driven insights, pressure-test assumptions, and turn data into clear executive recommendations.
  • Support CEO-led customer strategy, including prioritization of key accounts, partners, and strategic relationships
  • Prepare briefings, talking points, objectives, and success criteria for customer and partner meetings
  • Ensure outcomes, commitments, and next steps from engagements are clearly documented and executed
  • In partnerships with Marketing and Sales, own end-to-end coordination of CEO participation in externally facing meetings, events, conferences, and executive forums
  • Partner with Marketing, Sales, Customer Success, and Partnerships to ensure consistent messaging and positioning
  • Ensure seamless execution before, during, and after events, including internal alignment and follow-up actions
  • Serve as a connective tissue between the CEO and internal teams supporting external engagements
  • Partner closely with the Chief Business Officer to align external priorities with internal capacity, strategy, and execution
  • Provide visibility to the CEO and CBO on external trends, insights, and feedback that should inform strategy
  • Bring rigor, structure, and discipline to the CEO’s external operating rhythm
  • Drive clarity, accountability, and timely execution across externally driven initiatives
  • Ensure the CEO’s time and attention are invested where they create the greatest impact

Requirements

  • Bachelor’s degree required; MBA or advanced business degree strongly preferred.
  • 7+ years top-tier or boutique management consulting focused on sales 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 within the GTM functions
  • 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
  • Strong communicator with executive level polish
  • Highly organized, detail-oriented, and outcomes-focused
  • Energized by building, scaling, and transforming businesses
  • Take personal ownership for success
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

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
quantitative analysisqualitative analysishypothesis-driven insightsKPI designbusiness case developmentstrategic operationscorporate strategyGTM functionssales technologydigital transformation
Soft skills
executive communicationinfluence without authorityjudgment and discretionbias for actionanalytical thinkingorganizational skillsdetail-orientedoutcomes-focusedability to work with ambiguitycollaborative partner
Certifications
Bachelor's degreeMBAadvanced business degree