Chief of Staff, Office of the CEO

Outreach•San Francisco, WA

10d•$150,000 - $220,000

About The Position

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 organizations 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 The Chief of Staff (CoS) to the CEO is a senior, trusted partner who enables the CEO to operate at maximum effectiveness in externally facing priorities including customers, partners, investors, and key ecosystem relationships. This role is highly execution-oriented working with the GTM teams, ensuring that the CEO’s customer strategy, engagements, and external commitments are thoughtfully planned, tightly aligned to company priorities, and flawlessly executed. The Chief of Staff is a critical member of the CEO’s Office and serves as the orchestrator of the CEO’s external agenda, working in close partnership with the Chief Business Officer to ensure cohesion between external commitments and internal priorities. Location: We’re looking to hire in Seattle or the Bay Area.

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

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

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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