Strategic operations & Chief of Staff

Strategic operations for small teams who’d rather be building than firefighting.

I work alongside CEOs and leadership teams to create the structure, rhythms, and follow-through they need to grow with less chaos.

ThoughtfulOps is built for CEOs of early and maturing teams who have outgrown informal ways of working but do not yet need a full-time operations executive.

Ways to work together

Four ways I plug into a leadership team.

  1. 01

    Operational Diagnostic

    A clear-eyed look at how your company actually runs — priorities, ownership, workflows, tools, rhythms — and a prioritized roadmap for what to fix first.

  2. 02

    Operational Foundations

    Build the roles, decision rights, dashboards, documentation, and operating cadence a growing company needs to stop running on heroics.

  3. 03

    Strategic Initiative Leadership

    An experienced owner for the cross-functional work that matters most — launches, integrations, reorganizations, planning cycles, transformations.

  4. 04

    Fractional Strategic Operations Partner

    Ongoing senior operating support — Chief of Staff and Head of Operations work — for founders who need executive-level partnership without a full-time hire.

What clients say

"People think operations is about tools and rigid processes. It's really about understanding a company's culture and where they're going. That's exactly what I trust Maylen with."
Charles Gedeon · Co-Founder, District 3 Innovation Center & Pragmatics Studio
Maylen Cytryn, founder of ThoughtfulOps

Hi, I'm Maylen

A senior operator who works the way a great Chief of Staff does.

I'm the founder of ThoughtfulOps. I partner with CEOs and leadership teams as a fractional Chief of Staff and Head of Operations — owning cross-functional initiatives, building the operating systems a growing company needs, and giving founders back the space to actually lead.

You work directly with me: a senior operator who can sit close to the business, understand the moving pieces, and stay accountable for outcomes that cross teams and functions.

More about me →

Let's build a company that can grow without you in every meeting.

A 30-minute intro call. No pitch deck, no commitment. We'll talk through where the company is stuck and whether I'm the right person to help.

Book an intro call