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.

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.

Assist Now 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.

At Assist Now, 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 core values ground us:

• Innovation - We embrace curiosity, challenge norms, and build more innovative solutions.

• Integrity - We do…