Fractional Chief of Staff

Why this role exists We're a founder-led company running two business lines across four countries. Things get committed to in meetings and Slack threads — and then don't close unless the CEO personally chases them. That's a cadence problem, not a talent problem, and it's the problem you're here to solve. You will own the company's operating rhythm and drive decisions from made to done — across a senior leadership team you don't manage. When you're doing this well, follow-up becomes structural instead of the CEO's job. Fractional Chief of Staff Company : Workday consulting + AI/SaaS products company (~40 people, US HQ) Location : Remote, US-anchored hours; team spans US, India, Singapore, and Switzerland Commitment : ~2–3 hours/day (fractional), monthly retainer Reports to : Founder & CEO Start: 60–90 day trial → ongoing What you'll own Operating cadence. Design and run the weekly and monthly operating reviews: agenda, pre-reads, decisions logged, owners and dates assigned, progress tracked between meetings. Accountability tracking. Maintain a single source of truth for commitments across the leadership team. Know the status of every open loop and surface what's slipping before it's late. Follow-through, on the CEO's behalf. Chase progress with senior leaders — a revenue leader, a practice lead, a delivery lead, country heads — with the CEO's authority behind you, and without creating friction. Delivery is where commitments most often slip against client timelines, so keeping the delivery lead on track is a core part of the mandate. Meeting-to-action discipline. Turn leadership discussions into clear owners, deadlines, and next steps. Close the loop. CEO leverage. Prep the CEO for the week, flag what needs attention, and keep priorities visible so nothing important goes cold. Who you are You've been a Chief of Staff, COO-lite, or head of operations at a 30–150 person company, ideally distributed / multi-timezone. You've held peers and senior leaders accountable — people who report to the CEO, not to you — and made it feel like help, not policing. You're systems-native: you think in cadences, trackers, decision logs, and owner/date discipline, not vision decks. You're comfortable with the ambiguity and pace of a founder-led company, and you close loops without being asked twice. You can operate across US and Asia-Pacific hours enough to keep a four-country team in sync. ​ Nice to have Exposure to professional services and/or B2B SaaS operating models. Experience standing up operating rhythm in a company that was scaling through your stage. About AssistNow AssistNow is a fast-growing digital transformation company specializing in: Workday consulting and implementation AI-driven automation (including our flagship platform, Assistly ) IT and professional staffing services We serve clients across healthcare, higher education, financial services, and professional services . Our global presence spans North America, APAC, and India, with a growing portfolio of enterprise and mid-market clients. Our mission is to simplify, innovate, and transform businesses by combining deep domain expertise with the power of AI and modern ERP solutions. Why Join Us At AssistNow, you’ll join a high-impact team where innovation and learning are a daily way of life. We combine the agility of a startup with the stability of an established global company. You’ll work on meaningful projects, collaborate with experienced professionals, and contribute directly to our growth across Workday, AI, and tech staffing. We offer flexibility, ownership, and the chance to shape the future of enterprise transformation. Our Values Our core values ground us: Innovation – We embrace curiosity, challenge norms, and build more innovative solutions. Integrity – We do what’s right, not what’s easy. Ownership – We take initiative and deliver with accountability. Diversity & Inclusion – We thrive on different perspectives and inclusive collaboration. These values guide how we work, how we lead, and how we grow — together. Learning & Growth We invest in your future. At AssistNow, you’ll have access to: Sponsored certifications (e.g., Workday, AWS, AI/ML platforms) Leadership development and mentorship On-the-job learning across international markets and diverse projects We'll support your growth path, whether early in your career or looking to level up. Equal Opportunity & Inclusion AssistNow is proud to be an equal opportunity employer. We value diversity and are committed to building an inclusive workplace for everyone — regardless of background, identity, or ability. We do not discriminate based on race, religion, color, gender identity, sexual orientation, age, disability, or any other protected category.