05 — FAQ
Common questions about working with a fractional Chief of Staff. If you're evaluating whether this kind of role fits your company, these answers should cover most of what you need before a first call.
Depends on the week. Usually: untangle whatever's eating leadership time, build the systems that should already exist, run the project nobody has time to own. I'm the person who walks in, figures out what's broken, and ships the fix.
Consultants write the deck and leave. I stay long enough to make the change stick. I also do the work, not just the recommendation; if your onboarding is broken, I rewrite it, not write a report telling you to rewrite it.
US or Israeli founders, usually 5-30 people. That size is the sweet spot because there's real building to do; the systems aren't in place yet, and the founder has more ideas than the company has bandwidth to act on. I've worked across consumer goods, real estate tech, B2B SaaS, nonprofits, and consulting firms. I lived in Israel for nearly a decade and worked through the Supersonic Ads acquisition by ironSource; I understand how Israeli companies actually run and where the friction shows up when they expand into the US.
Yes. That's most of what I'm there for. Being a founder is lonely; most of the people around you can't fully see what you're building, and even fewer will tell you when they think you're wrong. I'll tell you. I'll also go on the journey with you; the pushback isn't from outside the work, it's from inside it. If you want a Chief of Staff who only executes, I'm probably not the right one.
Depends on hours and engagement type. I work monthly retainers, project-based, or hourly. Most engagements land between 10-20 hours a week. We figure out the right structure on the call.
Usually within a week or two. I take 1-2 new clients per quarter; if I'm full, I'll tell you on the first call and connect you to someone good.
I'm in Brooklyn. I'll come to your office in NYC for kickoff and key meetings. Day-to-day work is remote. If you need someone in-seat full-time, you need a full-time Chief of Staff, not a fractional one.
Both, and they're harder to separate than they used to be. I build the prompt libraries and workflows that turn individual AI hacks into team practice. If your team is already shipping with Claude or Cursor, I work at that speed. I'm also a Section Leader for Stanford's Code in Place, so I stay current on what's actually useful versus what's hype.
We figure that out on the first call. Onboarding takes real time on both sides; a wrong fit wastes your time and means I don't get the sustained relationship I'm trying to build. If I'm not the right person, I'll say so on the first call and point you toward someone who is. The whole model breaks if I take work I shouldn't.
Anything that needs a full-time, in-seat employee. Anything where leadership wants a report instead of changes. Anything where the real problem is co-founder conflict; that's a coach's job, not mine.
I also don't work with founders who are unkind to their teams. I've seen what it costs a company when the top of the org chart treats people badly, and I'm not interested in cleaning up the operational damage of that pattern. Founders I work with are demanding and direct; that's good. Founders who burn through their team are a different thing.
I keep client names off the site because most of my work is sensitive (HR, finance, strategic pivots). I'll share specifics on the call once we know we're a fit.
Recent engagements include an early-stage AI sales ops company, a national nonprofit with 12+ branches, and Stanford's Code in Place teaching program. One recent engagement closed when the founder took a lucrative full-time role for the financial stability; founders make the right call for their own life, and a good Chief of Staff celebrates that.
That's what the first call is for. 25 minutes, no pitch.
SHAYNA MOLIVER · Fractional Chief of Staff for founders · Operations, strategy, AI workflows · MIT-trained, NYC-based · shayna@moliver.tech