Chief of Staff

ABOUT OPSMILL OpsMill is building the next generation of infrastructure data management, focusing on helping automation teams unify data and scale automation reliably. Our platform empowers network, infrastructure, NetDevOps, and IT automation teams to manage infrastructure intent data more flexibly, predictably, and safely. As a commercial open‑source company, we are practitioners who understand the real‑world challenges of scaling infrastructure automation. We are remote‑first, serve sophisticated technical customers, and care deeply about clarity, execution, quality, and trust. THE ROLE We’re hiring a Chief of Staff to partner with the Founders (CEO and COO) and leadership team on OpsMill’s highest‑priority strategic and operational initiatives. This is an early-career, high-trajectory role for a sharp, structured thinker who wants to operate at the centre of a fast-scaling company and grow quickly into greater responsibility. This role reports to the CEO with a dotted line to the COO. In practice you will work daily with both founders and expect your time to be split across both. You’ll help turn priorities into plans, decisions into action, and cross‑functional work into tangible progress. You will not own functions but make the people who do become more effective. You will need to move fast, write clearly, know when to push and when to listen. This role will work closely with our Head of Company Operations, who owns the company’s financial, legal and people infrastructure. Your remit is the operating rhythm and strategic coordination layer, not the underlying machinery. What You’ll Be Doing: Operating Rhythm and Execution - Run and improve the operating cadence: leadership meetings, business reviews, planning forums, and follow‑through - ensuring momentum doesn’t stall between teams. - Own OKR discipline across the company: definition, alignment, tracking, review, and escalation; build lightweight systems that surface progress and risks early. - Drive quarterly/annual planning cycles; translate strategy into measurable priorities, sequencing, and execution plans; highlight gaps in ownership or org design. Strategic Support - Work with the founders on high‑priority strategic initiatives; structuring ambiguous goals into clear plans, milestones, owners and decision points. You will be doing a lot of the analytical and drafting work, the Founders will be providing the judgement and direction. - Prepare concise decision memos, briefings and research summaries; frame options, trade offs and risks clearly so decisions can be made quickly - Own special projects that do not fit neatly into a single function; step into the undefined spaces with speed, structure and follow-through. Board, Investor and Fundraising - Support board and investor processes; board prep and materials, meeting follow-ups and investors updates - Build and maintain the operational infrastructure of fundraising workstreams; data room management, investor update cadence, and overall process coordination. Whilst this will not be the mainstay of the role initially this will become significant when the time comes relevant Internal Communication & Culture - Support internal leadership communications and all-hands preparation; clarifying priorities, progress and major decisions to improve alignment without making noise - Help maintain a coherent, high-trust remote culture as the team scales from 25 to 40+ people across multiple time zones. Owning the rituals, rhythms and communications that keep the company aligned and energised. WHAT YOU BRING - 2+ years in Chief of Staff, strategy & operations, biz ops, founder associate, consulting, investing, or operational leadership in a high‑growth environment. - Demonstrated ability to structure ambiguous problems and drive execution across product, engineering, GTM, finance, and operations. - Excellent written and verbal communication; able to produce crisp briefs, memos, and executive‑ready materials. - Strong judgment and maturity—knowing when to push, when to facilitate, and when to operate behind the scenes. - Comfort partnering with founders and senior leaders on sensitive, high‑stakes topics; high trust, discretion, and reliability. - Ability to oscillate between strategic thinking and hands‑on execution; exceptional organization and follow‑through. - Business acumen with the ability to quickly grasp technical, product, operational, and commercial topics. - Thrives in a fast‑moving, remote‑first startup environment. NICE‑TO‑HAVES - Experience in B2B SaaS, enterprise software, infrastructure, developer tools, or open‑source companies. - Experience running OKRs, operating cadences, and planning cycles. - Exposure to investor relations, board processes, or fundraising. - Direct experience working with founders or senior executives. - Strong analytical and financial fluency; cross‑functional operator in a scaling startup.