Deputy Chief of Staff

Calling all operations-minded strategists! A confidential growing organization in Silicon Valley, CA is looking for a resourceful, execution-driven Deputy Chief of Staff to lead a small team and take ownership of financial operations, workflow design, and data infrastructure. In this role, you'll act as the bridge between executive vision and day-to-day execution, keeping financial systems sound, operational processes running smoothly, and organizational data clean and useful. This is a hands-on, in-person role for someone who thrives in a lean environment, loves solving problems independently, and isn't afraid to roll up their sleeves wherever work takes them. Key Responsibilities: Manage and supervise a small team, fostering collaboration and positivity. Drive organizational initiatives from kickoff to delivery, holding the line on deadlines and scope. Act as the glue in a small team, catching friction points early and clearing the path forward. Take ownership of financial oversight from processing invoices, monitoring inflows and outflows financial balances, and tracking spend, to managing expenses. Dig into vendor contracts and resources used to find smarter, leaner ways to spend. Take the lead on database and CRM health, from routine clean-up to long-term data governance and security. Connect the dots across the organization's tech stack, linking financial, communication, and project tools into one smoother workflow. Turn raw numbers into dashboards and reports leadership can actually act on. Push the organization forward on AI adoption, spotting where automation can cut busywork and sharpen efficiency. Be the first call for tech questions, quick to learn new tools, and roll them out across the team. Why You'll Love Working Here: An in-person role with direct exposure to executive leadership and real influence over how the organization runs. Join a close-knit team where your ideas and initiative directly shape outcomes. A confidential, unique role supporting ultra-high-net-worth principles with opportunity for increased responsibility built through trust. What We're Looking For: Experienced. You bring at least seven years of experience in operations, management, and ideally have spent time managing others. Analytical and resourceful. You bring order to ambiguity, transform messy data into clean processes, and don't wait around for someone else to hand you the answer. Polished communicator. You have the judgment, discretion, and gravitas to work closely with senior leadership, translating complexity into clarity while staying hands-on behind the scenes. Team-oriented and humble. You're energized by a lean, do-it-yourself environment and are willing to step outside your job description when the moment calls for it. Adaptable. You stay steady and sound-minded when priorities shift quickly. Systems-savvy. You area advanced across technology, generally curious about AI functions and productivity, and pick up new tools quickly. The salary listed reflects the anticipated compensation range for this position. Actual compensation will be determined based on relevant experience, qualifications, location, business considerations, and internal equity. Final offer amounts are determined at the employer’s discretion. Essential to Hawthorne Lane’s success is our ability to attract talent from a range of backgrounds. Our network reflects the diverse community around us, and we believe in a workplace where everyone feels valued and empowered to succeed. Applicants will not be discriminated against on the basis of race, color, creed, religion, sex, national origin, age, disability, marital or veteran status, sexual orientation, or any other legally protected status. #J-18808-Ljbffr