Chief of Staff

Do you have excellent project management, operational skills, and knowledge of software engineering coding? Learn more about our Chief of Staff role.

Chief of Staff

$ 100k/Year   Flexible   Long-term
Good fit for: Chief of Staff, Software Development Manager

Would you like the opportunity to shadow the COO from a multimillion-dollar SaaS company? Do you have a managerial aspiration? Are you organized and capable of using your software engineering and project management skills to take immediate action to operationalize the executive strategy on a weekly basis? Then this job is for you.

As Software Development Manager performing the Chief of Staff role - you will have the critical responsibility of prioritizing and triaging requests from top executives each week to ensure commitments are met. You will be planning, coordinating, and executing global engineering programs.

“Working with very smart people from all around the world is fantastic, they bring their creativity and ideas, and new solutions get started. I'm proud of being part of it.”
-Luca V, VP of Inside Sales
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Crossover recruits and builds world class high performing teams to power the fastest growing portfolio of software products in the world. No other company provides the training and the opportunities to test yourself on the depth and diversity of projects that we do. All roles are location independent so you are guaranteed to work with the best in the world. Challenge yourself. Be part of the change.

As Software Development Manager performing the Chief of Staff role - you will meet daily with the COO group to prioritize and organize requests. You will take their vision to plan and execute business initiatives including software engineering projects. You will liaise with internal and external stakeholders to lead and support the global engineering program executives.

You will interact with cross functional teams to ensure commitments and deadlines from COO group are met. Your goal will be to offload and handle as many of executive projects as possible.

 This is not an administrative assistant role. You will be part of the COOs Chief of Staff team, you will start your way in a Bootcamp for managers, learning our WSPro skills and our company culture, you will graduate with the highest standards of our internal management methodologies and will be ready to join our product teams to fix and boost productivity.

You will be solving complex problems, and managing cross-functional groups to have a deep understanding of engineering.

To excel in this position, you will be a self-motivated individual that possess expert task management and operational skills, have extreme attention to detail, and thrive in a fast-paced virtual environment.


A hiring event is a scheduled online event where all our relevant testing relating to a role is conducted on the same day. Submissions received during the event are graded the following week, and successful candidates notified if they have progressed to the next round which is an online interview with a Hiring Manager.


Each week - you will:

Drive the COO’s vision within functional groups to operationalize the executive strategy

Prioritize and triages requests from the global organization

Able to proactively navigate complex organizations to find solutions for requests

Meet daily for a half hour with Group COO to ensure his commitments are met

Able to elicit required decisions to ensure your commitments are met

Create dashboards and provide deep dive analysis on key metrics that allows identification of any risk or deviation that prevents achievement of COO’s goals


The ideal Software Development Manager candidate for the Chief of Staff role comply the following requirements:

Computer Sciences Bachelor Degree or Higher

Management Experience within an International or Multinational Software Company

2+ years of experience in coding for software development

2+ years of experience in Project Management across cross-functional teams with the expertise to lead complex strategic and engineering operational initiatives

Must be organized with the ability to manage a vast number of projects simultaneously to ensure that COO’s office never misses sensitive deadlines

Excellent English, written and oral communication, presentation and facilitation skills

Comfort in a rapidly changing environment and able to work virtually and with cross-functional teams

Problem-solving and adaptability skills

A strong sense of urgency and results orientation to deliver on a weekly basis


In this role, you will learn how to set goals and operate at a weekly pace. The opportunity is to shadow the COO of a group with thousands of people within 75 companies marketing more than 100 software products. Our organization acquires one new software company per week, making us one of the fastest growing private equity businesses in the world. For someone interested in software M&A, this is a great place for practical experience.


Relevant Files and Links

The Chief of Staff is a strategic role in the organization. You will acquire a learning experience that prepares you for your next steps in software development by learning what it takes to manage a group of Saas companies.

The following videos take a look at the book “Consiglieri – Leading from the Shadows” where the strategic role of Chief of Staff is conducted.


and Answers

  • What does a typical day look like for the Chief of Staff?

    As Chief of Staff, you will liaise with internal and external stakeholders to lead and support global engineering programs, executive communication and customer relationship management. Your goal will be to offload and handle independently as many of these requests as possible, ensuring that commitments and deadlines are never missed across the dozens of wide-varying tasks.

  • Can you give some example metrics/deliverables for the job of chief of staff?

    In this role, you will learn how to set goals and operate at a weekly pace. You will be measured using the same metrics that you will learn to set for the different teams you will be working with, and provided to you by the COO. For instance, your efficiency to prioritize the multiple tasks and projects to follow up, and successfully achieve our COO’s commitments.

    As this is not an administrative role, you will need to be able to create dashboards for project follow up and success, as well as be capable of building reports among different technical projects.

  • Who does the chief of staff report to directly?

    This position reports directly to the COO organization.

  • Is this a technical or administrative role?

    This is not an administrative assistant role. You will be expected to solve complex problems, manage the execution of projects across functional groups and have a deep understanding of engineering. For example, your first assignment will be to deep dive into the docker based development environment platform called “devspaces” and prepare a business value delivery report.