Lead Project Manager


The Lead Project Manager acts as the PM for our most intense and intricate projects. Since these projects are so involved, they often delegate work to other project managers to handle all the requirements of the work. The Lead PM should expect to be involved in around five substantial projects at any given time, with light involvement in many others, often in an advisory capacity.

The Lead Project Manager also acts as manager for our other PMs. They work with the CEO to define standards and practices for how our project management should be done, reacting to results from our projects. When we are recruiting new PMs, the Lead Project Manager helps the CEO understand the requirements for the role and review candidates.

As of Q3 2021, we use a PM model where each project has a principal "DRI" who is accountable for the outcomes of the project. The Lead Project Manager would act as the DRI for many of the projects they are involved in. However, we are working on a change under which a separate "strategist" would be the DRI for each project. This job description assumes that this change will take effect. As of Q4 2021, our expectation is that the Lead PM will not usually act as DRI on projects. This does not mean they will not be pivotal – they are going to be one of the most important figures on any project they will be involved in. It just means that they do not hold the ultimate accountability for the outcomes of the project for the company. They will hold accountability for executing the vision of the Strategist/DRI accurately.

While the Lead Project Manager does not need to be a designer or developer, they need to know the web and be passionate about it. This is a great role for an seasoned PM with experience working professionally as a designer or developer. The Lead Project Manager does not need to know the intricacies of the code but they should know general web architecture and understand how websites work. The Lead Project Manager does not necessarily need to figure out the solution to technical or design problems, but they must be able to articulate the problem clearly, steer our team towards a solution, explain that solution to a client, and take action on it.

Like all Cantilever staff, the Lead Project Manager must be passionate about our mission: to use “Digital Hospitality” to provide an incredible experience for the users who use our sites, and to meet our clients’ business requirements.

Key Responsibilities


Cantilever uses a project onboarding methodology called a Diagnostic. This is a paid mini-project in which we seek to absorb the project requirements fully and to craft a detailed, rock-solid plan.

  • Consult with teams performing diagnostics to provide reliable perspective and insight about the plans being proposed to the team
  • Help strategists write accurate project estimates. Review existing estimates and timelines critically and provide feedback. Solicit insight from designers and developers and synthesize that into thoughts for the strategist.

Project Management

  • Manage critical and intense projects according to our methodology. Be a dependable, insightful, proactive PM.
    • Follow and absorb all internal and external communication. Provide clear, actionable instructions for designers and developers based on client feedback and requests. Be the expert on our status and plan for the project.
    • Understand and absorb the strategist’s vision for the project and how things should be done. Translate that understanding into clear action items for all parties involved. Follow up and make sure things get done or moved to someone else.
    • Help maintain the project documentation.
    • Maintain an appropriate staffing plan for the project, taking into account other existing commitments and potential new work. Work with the CEO and other project managers to ensure that your projects have a staffing plan that is realistic and fits in with the organization’s general direction.
    • Maintain a clear, consistent line of communication with clients, including weekly updates, status meetings, and so on. Ensure that all meetings have clear notes, action items, transcript, etc.
    • Manage legal paperwork and invoices related to projects in a timely and accurate fashion

Other Responsibilities

  • Act as manager & mentor for other project managers
  • Help CEO when they are recruiting new project managers
  • Solicit reviews from satisfied clients


  • At least five years experience specifically running website or web application projects (Not just general PM experience)
  • Prior experience as a web designer, dev, or other artisanal role (or substantial off-the-job training in these fields)
  • Inherent passion for the web. Strong opinions about what makes for a good user experience. Deep knowledge of web technologies.
  • Incredible level of personal organization. Fantastic deadline and commitment management.
  • Collaborative, team-first attitude
  • Excellent written and verbal communication skills (for both internal and external communication).
  • Comfort with digital project management tools like Basecamp
  • Experience successfully working full-time remote.

Career Ladder Notes

This person should be at least in the mid/high ⭐️⭐️ tier of each item on the PM career ladder.


  • This person’s projects should be complete with at least a 50% profit margin. This means that if we take in $1 in project fees from the client we should be spending at most $0.50 on labor and vendors.
  • At least 90% of this person’s projects should be delivered on time, disregarding delays due to clients.
  • This person’s new clients should come back for a second project at least 50% of the time.
    • Maintenance work is considered "coming back".