Lead Strategist


To build and maintain successful, long-term client relationships by working with clients to understand their needs and leading amazing projects that meet those needs.


In our system, the Strategist is in charge of outlining what problems we should be solving, why, and by when. The team is responsible for solving those problems. The Project Manager pulls the strings to ensure that this is happening effectively and efficiently, and must be swift to make changes when not.

The Strategist is the "Directly Responsible Individual" for their clients and projects. The buck stops with them when it comes to their clients. Therefore, they get to decide how they want to manage their client relationships. Most of the time the Strategist will delegate a lot of the nuts-and-bolts work of a project. However, the Strategist is ultimately accountable for that work getting done properly, and sometimes may need to hop in and make things happen themselves.

The Lead Strategist is a high-level Strategist who is in charge of large accounts and complex projects. This role is designed for a company partner.


  • Set realistic and reasonable outcome goals for each project they lead. Meet those goals at least 75% of the time.
  • Achieve a minimum 50% average profit margin each quarter across all projects led.
    • 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.
  • Minimize client attrition to at most 25% in a year.
    • This means losing at most one out of every four clients you start with each year.

Key Competencies

Note our global values here:
Mission, Values and Beliefs
These are a specific lens on those values, for this particular role.
  • Deep passion for Digital Hospitality
  • The instinct to act empathetically towards users, clients, and peers
  • Deep understanding of the web and web technologies and how different project approaches will affect cost, timeline, and effectiveness
  • Ability to meet new people and present the company and our values to them in a friendly and effective way
  • Flexibility to deal with different toolkits, circumstances, client styles, and project types
  • Courage to make the tough calls and push for excellence
  • Discernment to understand when a solution meets the requirements and when not
  • Imagination to come up with unorthodox solutions
  • Intuition about how the market will react to solutions we provide
  • Solid reliability and follow-through
  • Rolodex of industry relationships

Key Responsibilities – Possibilities...


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. When a new client wants to do a diagnostic, we will select a Strategist for the account based on fit and availability. When chosen, the Strategist is the DRI of the Diagnostic process, commonly working with a project manager to facilitate the logistics.

  • Lead the Diagnostic to establish the client’s core needs, circumstances, and constraints
  • Brainstorm and envision technical solutions – or ascertain that solutions are not available.
  • Clarify these solutions for the client, get feedback, and work towards a final project plan.
  • Codify the plan in clear documentation. Work with the PM to ensure that the plan is viable.
  • Finalize the project plan document, present it to the client, work through revisions, and work towards signature of a final SOW.


  • Act as the lead account manager for several large clients.
  • When new needs and requests come through for those clients...
    • Analyze the request and ensure that the problem is clear
    • Brainstorm solution ideas with the team
    • Consolidate the best possible plans and share them with the client
    • Act on feedback and negotiate the final solution, cost, timeline, etc.
    • Work towards a final SOW with the PM
  • For ongoing clients, manage the backlog of issues on a regular basis. Ensure that the right priorities are being targeted and in an effective way. Often this will be in a client’s own project management tools.
  • Keep an eye on everything happening within one’s projects. Ensure that we are meeting expectations, timelines, and budgets. If not, identify the problem and make adjustments.
  • Report back to the client regularly on our status, priorities, and activities, with the help of the PM.

Project/Product Management – Possible?

  • 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 analysis of project problems and challenges. Translate somewhat fuzzy input into clear action items for all parties involved. Follow up and make sure things get done.
    • Ensure that project documentation is maintained accurately. Absorb it fully.
    • Maintain an appropriate staffing plan for the project, taking into account other existing commitments and potential new work. Work with the Head of Production 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
    • Solicit reviews from satisfied clients

Maybe some development from time to time? Or experimentation/prototyping?

Career Ladder Notes

This person will be compensated according to the Executive pay tier. We don‘t have a career ladder for executives yet, but need one. This person can be either at the low end of that ladder or the middle.