Freelancer Hiring & Onboarding Workflow

We love working with freelancers because:

  • They can add additional capacity to our team so we can do bigger and more ambitious projects
  • They can add specialist skills that we don’t have in the core team
  • Working with freelancers gives us a chance to try out working together, which can lead to an in-house engagement eventually. Similarly, some in-house team members may want to shift to freelance sometimes, to fit their life goals better.
  • When we know lots of freelancers, we can refer clients within our freelancer network, and use our network to connect us with more freelancers and even clients. More friendships = better results.

Our goal is to have approximately 50% of our hours provided by freelancers. In recent years this has been closer to 20%. In order to reach our 50% goal, we have created an all-new workflow for 2023 which makes it easy for high-quality freelancers to get into our systems and be “pre-boarded” before there is an urgent need to use them. This allows them to be settled in to our systems and practices and ready to fulfill that need, rather than them having to scramble to get set up when something is urgent.

Our current frequent freelancer collaborators are some of the best in the industry. We hope that by having a streamlined, optimized methodology for how we work with freelancers, we can attract more folks like them, and create a robust freelancer pool that will help us achieve our growth goals.

As of 2023 we will start to only work with official Cantilever freelancers who are in our freelancer pool and working according to our standardized processes.

Freelancer Access

  • They are in our Slack as a multi-channel guest, with access to the #cantilever-communityand #freelancers channels.
    • If the person has their own Slack workspace, they can also be invited using Slack Connect to those specific channels.
  • They are in our Harvest as a Contractor. Their cost rate should be defined as their freelance rate.
  • They are in our Asana but with access only to specific projects – NOT the Cantilever Asana team.
  • They are in our Notion account as a member (not a guest). They have access to the “Cantilever Community” and “Freelancers” Teamspaces in Notion, but NOT the “Cantilever Team” Teamspace.
  • They are in our 1pass as a member (not a guest). They should have access to the “Cantilever Community” vault (which all members have), but NOT the “Cantilever Internal Team” vault.
  • They are in our Team Directory within the “Freelancers” tab. Only our team has access to the whole directory, but the freelancer themselves has access to their own entry.
  • They may need to have access to Figma, Zoom, GitLab, etc. as determined by their role. By default they should have only the access they specifically need for the projects/work they are doing.

For more information about how Freelancers are treated differently from our internal team, please review


Freelancer Management

Freelancers have a “manager” at Cantilever. By default this should be the head of their department:

  • For designers, it’s the .
  • For devs, it’s the
    Technical Director
  • For PMs/Strategists, it’s the
    Director of Production
  • For Ops staff, it’s the Director of Operations (Role is pending re-definition and hire – for now, it’s Ty)
  • For Biz Dev staff, it‘s the Director of Business Development (Role is pending re-definition and hire – for now, it’s Ty)

The manager may delegate this responsibility for specific freelancers to specific individuals on their team, by mutual consent.

Workflow Summary

(This workflow is also reflected in the standard task template format within the Freelancer Recruiting Pipeline Asana project)

  1. Freelancers apply on our website.
    1. If they are introduced to us by a mutual acquaintance, we should ask them to fill out the form anyway to kick off the process, and inform Ops of the reference so they know who the applicant is.
  2. Ops does a screen of the application.
    1. If the application is from a spammer, agency, or other non-qualified individual, block them.
    2. If the person is a real freelancer but obviously does not have skills we use at Cantilever or is not qualified to work with us yet, keep them in our database but send a polite rejection email.
    3. If the person is qualified and has skills we use at Cantilever, proceed to step 3.
    4. Note: Some freelancers may charge rates that are extremely high, and we may not have a profitable way to use them right now, but such freelancers are still worth interviewing and getting in our database, because we could use them in the future, or they could connect us with other good people.
  3. The relevant department head (Creative Director, Technical Director or Director of Delivery) does a portfolio/resume review to see if the person appears to have the chops to work here.
    1. If not, the department head should request that Ops send a polite rejection note. The person can remain in our database for the future.
    2. If so, the department head should inform Ops, and Ops should set up a 30 minute interview with an Ops representative and the relevant department head or someone they select to do the interview instead of them.
  4. The Ops representative and department head/representative should meet with the candidate and ask them about their history, working style, ability to work remotely, ability to meet deadlines, etc.
    1. If there are any red flags, they should be rejected. “If it’s not a hell yes, it‘s a hell no”. Ops should send a polite rejection letter and keep them in our database.
    2. If there are no red flags, proceed to step 5.
  5. Ops should conduct a reference and background check on the candidate.
    1. If there are any red flags, reject and send polite email.
    2. If there are no red flags, send a contract!
  6. Ops should send a form contract to the candidate using the Consulting Agreement template in Google Drive. The contract should be sent via Docusign.
    1. If the person has any feedback/requested changes to the agreement, Ops should handle according to their best judgment. When in doubt, feel free to ask the
      as a last resort.
    2. If the person signs, proceed to onboarding!
  7. Ops should onboard the candidate by creating a new Onboarding project in Asana (in the Cantilever workspace) and following the steps therein. This will get the person into all the systems mentioned above.
    1. This project will call for ops to set up meetings as appropriate to make sure the person is onboarded successfully.

Future Goals

Someday we would like to:

  • Build out our database such that freelancers can receive reviews from internal Cantilever team members, and can leave reviews for PMs and Strategists on our team
  • Allow freelancers to see the other freelancers in our database, so they can have a sense of where their pricing falls in the market