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Devin Watson

Senior Operations & Chief of Staff Leader

About Me

Fractional CoS/EA to CEO & Ops for High-Growth Companies. I'm a San Francisco-based operator with 13+ years building the systems, cadences, and infrastructure that let high-growth companies move faster. My background spans Chief of Staff, Senior EA, and Director of Operations roles at companies ranging from early-stage startups to AWS. Most recently I served as Associate Director of Operations at a Series B AI company, and before that spent three years as the operational right hand to a CEO through a major acquisition, growing from Executive Assistant into full Chief of Staff scope across every function of the business. I specialize in the work that's hard to title but easy to feel when it's missing: OKR design and rollout, knowledge management overhauls, AI workflow integration, executive operating cadence, and cross-functional program management. I've led Notion migrations, stood up company-wide accountability systems, embedded AI tools into leadership workflows, and partnered directly with CEOs, COOs, and CFOs on the decisions that move companies forward. I'm currently available for fractional and contract engagements. If you're a founder or executive who needs a trusted operator without a full-time hire, I'd love to connect.

Jurisdiction

United States

Notable Employer

  • Fractional Director of Operations at Alembic
  • Chief of Staff to CEO at Tango
  • Fractional Senior Strategic Business Partner to CEO at Kokua
  • Senior Executive Assistant to VP of Marketing at Amazon | AWS
  • Senior Executive Assistant to CEO and Founder at GuestHouse Design

Experience

Seniority LevelExecutive
Years of Experience10-15 years
Current StatusActive
Fractional Director of OperationsNotableAlembic
2026 - 2026

Served as the operational right hand to the COO at a 73-person Series B Causal AI company, functioning as de facto Chief of Staff across the full leadership team. Led a team of six while owning the company's knowledge management strategy, including a ground-up Notion migration that consolidated over 200 pages of legacy documentation into a single source of truth adopted org-wide. Partnered with the executive team to design and roll out a company-wide OKR framework, then built the operating cadence to sustain it. Embedded AI tools including Claude, ChatGPT, and Notion AI into core workflows, automating meeting prep, briefing synthesis, and executive communications. Partnered with the CFO on a sensitive spend and T&E audit that surfaced over $300K in projected annualized savings. Managed the COO's full operating cadence across leadership meetings, all-hands, board prep, and cross-functional reviews.

Chief of Staff to CEONotableTango
2022 - 2025

Strategic partner to the CEO through a major acquisition, owning the company-wide operating system and driving execution across every function. Launched the company's first OKR framework, achieving 100% adoption across executive leadership, and ran the full operating cadence end-to-end including all-hands, QBRs, leadership offsites, and annual planning. Served as the primary escalation point for cross-functional blockers, resolving 25+ stuck initiatives and accelerating average timelines by four weeks. Designed Seattle Live, a quarterly customer engagement program spanning 500+ enterprise accounts that contributed to $171M in revenue and a 13% increase in existing-customer spend. Led a full overhaul of sales enablement in partnership with Sales, Product, Marketing, and Customer Success. Ghost-drafted executive communications in the CEO's voice across board updates, all-hands content, and change communications throughout diligence and integration. Onboarded and coached five incoming C-suite and VP-level leaders on operating cadence and cross-functional alignment. Built customer lifecycle dashboards in Tableau and defined health scoring KPIs in Salesforce, supporting a 7% lift in customer satisfaction.

Fractional Senior Strategic Business Partner to CEONotableKokua
2022 - 2022

Served as a strategic advisor to the CEO of an education technology startup, driving operational excellence and cross-functional alignment. Designed and implemented a quarterly OKR framework across Product, Engineering, and GTM that improved goal completion rates by 62%. Built an executive analytics suite in Tableau and Excel that surfaced underutilization patterns and enabled data-driven resource allocation. Developed an organizational health dashboard in partnership with the People team, tracking culture, engagement, and performance trends. Enhanced executive effectiveness through meeting optimization, message development, and strategic stakeholder mapping.

Senior Executive Assistant to VP of MarketingNotableAmazon | AWS
2015 - 2020

Executive business partner to VP-level marketing leadership for AWS's global marketing organization of 500+ people. Coordinated quarterly business reviews, leadership offsites, and strategic planning sessions, including full agenda design, pre-reads, and on-site logistics. Managed complex cross-functional priorities across 15+ teams in close partnership with Product Marketing and adjacent engineering and product leadership. Developed analytics dashboards tracking campaign performance, budget utilization, and team productivity. Partnered with the People team on organizational design, workforce planning, and leadership development. Streamlined executive communications and stakeholder engagement, reducing meeting overhead by 30% while improving decision velocity.

Senior Executive Assistant to CEO and FounderNotableGuestHouse Design
2012 - 2015

Trusted advisor to the founder of a boutique design agency, responsible for establishing the operational infrastructure and business intelligence systems that supported the company's growth. Implemented executive dashboards, vendor management systems, and financial reporting models that improved operational transparency across the business. Designed resource planning, travel logistics, and billing systems that increased operational efficiency by 50%. Analyzed marketing performance data and optimized channel mix, driving 65% average quarterly audience growth.

Skills

Core skills10
Interests7
Languages1

Skills

Chief of Staff
OKR Design and Implementation
Executive Operations
Notion Knowledge Management
AI Workflow Integration
Cross-functional Program Management
Executive Communications
Operating Cadence Design
Executive Assistant to C-Suite
Executive Business Partner

Interests

AI-Native Operations
Fractional Chief of Staff
High-Growth Startups
Knowledge Management Systems
Executive Partnership
Organizational Design
Business Operations Strategy

Languages

English