Chief of Staff to CEO at Outreach managing external engagements and strategic priorities. Requires strong experience in consulting, operations, and collaboration with C-suite leaders.
Responsibilities
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
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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