Chief of Staff role coordinating PMI strategic projects in a Microsoft Cloud Solutions company. Directly supporting CEO and driving key initiatives for organizational success.
About the role
- 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
- 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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