Jim A.
Chief of Staff | Executive Operator
I help founders, CEOs, and busy executives spend more time working on the business and less time working in it. I’m a Fractional Chief of Staff and Executive Operator with 20+ years of experience across software, technology, operations, program management, product development, and project delivery. I’ve worked with venture-backed companies and Fortune 100 organizations across fintech, healthcare, eCommerce, energy, manufacturing, government, and nonprofit environments. My engagements commonly involve: • Strategic planning and operating rhythms • Cross-functional execution and accountability • Operational improvement • Product development and delivery • KPIs, executive reporting, and visibility • Special projects and high-priority initiatives Much of my work involves taking something important that doesn’t have a clear path forward, figuring it out, aligning the right people, and making sure it gets done. I work horizontally across the business - connecting strategy, people, priorities, and execution. Helping leadership teams create the clarity, ownership, accountability, and follow-through needed to keep important work moving. Clients typically bring me in when: • The CEO is carrying too much of the operating burden • Important initiatives cross multiple teams and don’t have a clear owner • Priorities exist, but execution is inconsistent • Leadership needs better visibility into what’s actually happening • The business is growing faster than its operating structure My goal is to understand the system before attempting to change it - then help build the structure and operating rhythm needed to make the business easier to run. If you need an experienced operator who can step into ambiguity, get oriented quickly, and take ownership of important work, I’d be glad to talk.
Earnings and projects
Last 6 months ÷ 6
Last 6 months: $13k
Billed in all: $127,331$127k
$6.7k in the last 6 months
Across 5 contracts
Across 29 contracts
Earnings, last 30 days
Skill rankings: Top 7% in Executive Coaching
Ranked by MRR among everyone on Upwork with the skill.
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