Frequently asked questions

Getting started

Why should I use Sidekick instead of hiring someone part-time?

Finding a great assistant is hard work. Sidekick makes it easy to get started with an experienced and vetted assistant right away, with little long-term commitment. On top of that, we train our sidekick’s with industry best practices so you don’t have to, and give you access to workflows and tips from our community to kick start your collaboration. Finally, the tools we build help you and your sidekick save time every day, making it more efficient to work with Sidekick than anyone else.

I just signed up. What's next?

Welcome! Complete a matching survey so we can learn more about your expectations and preferences. Once we know more about you, we’ll find the best Sidekick to fit your needs and introduce them to you during our onboarding call. You can start sending projects to your Sidekick right after the call.

Can I interview my Sidekick?

Our goal is to make it as fast and easy for you to get you started. That’s why we pick the best Sidekick for you based on the information we gathered from your matching survey. We take into account the tasks you need help with, the Sidekick‘s experience, timezone, and personality. Wrong matches rarely happen, but when they do, we’ll find you a new Sidekick asap and transition all your projects to them.

What factors do you consider when matching me with a Sidekick?

Sidekick goal is to foster long-term working relationships between executives and executive assistants, so we have a thorough matching process in place. We match Sidekick’s based on location, task expertise, industry fit, and shared working style preferences. We do not tolerate discrimination in our matching process, and will not make matches based on race, religion, disability, sexual orientation, sex, gender identity, age, or any other characteristics protected under law.

Where is Sidekick available?

We currently have Sidekick’s in the United States, Canada, and France and are accepting clients in these countries.

About our assistants

What is a Sidekick?

Sidekick’s are all college-educated executive assistants, based in the United States and France. They have at least 5 years experience working as assistants for busy CEOs and C-level executives. Once you’re matched with your Sidekick, they will be the only person you work with: they’ll get to know you, your company, and your team and learn to be proactive about your needs.

What tasks can my Sidekick help with?

Sidekick’s can help with calendar management, scheduling, inbox help, travel, meeting preparation and follow-ups, contact management, project management, administrative tasks, expenses, invoices, onboarding new employees, recruiting process, data entry, research projects, personal projects…and more!

What tasks can't my Sidekick help with?

Sidekick cannot help with any physical errands (though we can help find someone to run them), or tasks that require a specific expertise (legal, advanced accounting, graphic design…).

When is my Sidekick available?

Sidekick’s work standard business hours, Monday through Friday, and are not required or expected to work on weekends or after 6 p.m. You can send new tasks anytime — if sent after hours, your Sidekick will have a look as soon as they’re back. During business hours, you will always get an answer to your messages in less than 2 hours.

About our app

How do I communicate with my sidekick?

We have a desktop app, a Gmail extension, and an iOS app to help you communicate seamlessly with your sidekick and track projects. On top of that, we’ll help you give your sidekick access to the tools you already use: Slack, Asana, Trello, … And of course, you can always email or call your sidekick.

Why do you only accept people who have a Google Suite or Outlook account?

We are a small team building tools for both our clients and our sidekick’s, on desktop and mobile. Unfortunately, this means that we’ve had to make tough choices on where to begin. We recently expanded our app to include Outlook users from previously only accepting Gsuite at login. Our mobile app is currently only on iOS, and we have plans to expand to Android in the future, but it is not required to use our service.

How do you protect client privacy and data?

Every sidekick we hire signs an NDA before they are matched with an executive. The NDA covers all data they receive from third-parties while working with Sidekick. This measure protects not only Sidekick‘s data, but any and all information our executives share with our Sidekick assistants while working with us, regardless of which clients they’re working with or who provides the information to them.

When executives are onboarded to Sidekick, we either ask them to add their sidekick to their existing password manager, or we guide them through creating a free and secure 1Password vault through Sidekick that is shared between them and their new assistant. This ensures all shared, sensitive information is protected.

We also recommend our clients interact with their assistant through our Sidekick mobile app, desktop app, or Chrome extension. The data passed through these communication tools are always encrypted—both at rest and in transit.


How does billing work?

Our plans start at just 10 hours per calendar month for $499. After your first month, you can choose to upgrade to another pricing plan that works best for your needs. Each plan includes a set number of hours to be used every calendar month, for any hours your Sidekick works beyond the included hours, you will be billed at the hourly rate according to your plan. As you upgrade to a higher tier plan the cost per hour reduces further.

The first week of every new month your credit card gets charged for the plan plus any additional hours used in the previous calendar month. Some plans allow you to receive an invoice and pay it online.

Can Sidekick support a team?

Yes, Sidekick can support multiple individuals in one organization or team. We offer Plans for Teams to bundle hours for even greater benefits and lower costs per hour.

While we cannot guarantee that you and your teammates will have the same Sidekick due to availability and compatibility, we do our best to have as few Sidekick’s working across your team as possible. Our Sidekick’s go through a rigorous vetting and selection process, so you can expect a consistent level of service and excellent collaboration.

The primary user of your Sidekick for Teams plan will have the ability to add and remove team members and set a maximum number of hours for their teammates, in addition to deciding whether personal tasks are allowed or not. If you have any other questions, please feel free to schedule some time to speak with our team.

Vetting and selection process

How do you source your assistants?

We receive thousands of applications to become a Sidekick assistant per week. While the majority of assistants apply directly through the job board on our website, many of our prospective sidekick’s are referred by our trusted current assistants and executive community. Among the tens of thousands of applications we receive, just 0.3% become Sidekick assistants.

What is your candidate vetting process?

Our team only considers applications from candidates who have been executive assistants for 2+ years and have proven experience working remotely and with top executives. We then begin an extensive interview process that lasts a minimum of two weeks. During the interview process, candidates must:

In addition, our team performs reference calls and speaks with the assistants’ former employers. Verified background checks are also required for every assistant we hire. We use a thorough background checking platform called Checkr to safely verify identity and confirm the individual’s employment history.

How do you evaluate candidates for experience and professionalism?

During each part of the interview process detailed above, our team evaluates candidates across five key competencies that we have identified as critical indicators to success.

How do you ensure successful matching between an assistant and executive?

Before an assistant can be matched with an executive, they must complete a week-long onboarding process. During this time period they review all of our guidelines and policies and meet with current, experienced sidekick’s. New assistants also take a personality assessment, which is one of the data points we use during matching.

When matching clients and assistants, we take into account the following attributes: – Cities and timezones – Assistant experience working with different executives and industries – Executive experience working with assistants – Difficulty level of anticipated tasks, balance of personal vs professional support – Executive style of organization and communication – Common interests and pet peeves

Once an assistant has completed their onboarding, they are matched with only one or two executives to begin with, so that they have time to ramp up. Each seasoned Sidekick assistant supports 3 to 4 executives on average.

How do you ensure ongoing success with the assistants after they are onboarded and matched?

All Sidekick assistants are monitored by our team on an ongoing basis. They participate in regular coaching sessions and attend community webinars on new productivity methods, tips for working remotely, and ways to anticipate an executives’ needs. We collect candid feedback from our executives that we are able to effectively translate and deliver to our assistants. This feedback loop enables our sidekick’s to work on and adjust their performance to best meet their executives’ needs. If an assistant does not provide satisfactory work to more than one executive, we take all necessary measures to ensure long-term satisfaction of our executive clients, such as coaching or matching the executive with a new sidekick.