Chief of Staff to the CPTO

Overview

Guild is hiring a Chief of Staff to the CPTO in order to make the Product & Technology organization faster, clearer, and more impactful. You will operate as a senior product leader and executive partner - shaping decisions, running the product operating system, and ensuring that strategy turns into outcomes.

This role is about leverage, and you will be expected to improve the quality and speed of decisions, surface misalignment early, and take personal ownership of the thorniest problems.

Why Might You Want To Do This?

• You thrive at the intersection of product strategy, product delivery, and operational excellence - and you dream of aligning all three to enable an organization to outperform
• You take pride in enabling and lifting others, especially through uncertainty and ambiguity
• You live in the realm of data and outcomes, and wake up at night having seen around a corner to identify an obstacle that lies ahead
• You want to see your judgement shaping executive decisions and the trajectory of an entire organization

What you will be responsible and accountable for:

Your overarching objective is to increase the quality and speed of decisions across the Product and Technology organization. Success will look like:

• The CPTO is spending time on fewer, but better structured decisions
• The organization is operating with explicit shared context - early detection of misalignment
• An operating system or rhythm of business setup that produces high signal and minimal noise - fewer meetings and better outcomes
• The hard cross-org and cross-Guild problems are being solved, rather than the easy or convenient ones - you will personally own these and chase them down until addressed
• Portfolio level tradeoffs are explicit and intentional at all times
• The executive team and board have a clear grasp of the reality in the org - with consistent credibility

What you might do to achieve this:

• Anticipate and identify decisions before they bubble up to the CPTO
• Downgrade decisions that do not need to be escalated - but ensure that the CPTO retains clarity and understanding on what’s happening
• Ensure clear framing with options, recommendations, and risks where they do
• Maintain and communicate a clear and coherent narrative for strategy, priorities, and tradeoffs
• Actively seek out divergence, unaired disagreement, or shadow priorities, and surface them for intervention
• Establish and evolve forums such that they are clearly focused on articulating 
• Whether we are working on the right things,
• How we are progressing against measures of success,
• What risks are at play,
• And what decisions need to be made
• Ensure a decision → action → outcome path is always established and followed, and eliminate anything that deviates from this.
• Shape the narratives and artifacts that communicate Guild's trajectory, technical bets, and strategic tradeoffs.

What you’ve likely accomplished in your career thus far:

• You’ve been a strategic force multiplier for an executive, whether in a Chief of Staff role or as a senior product leader
• You’ve built and run, or materially improved a product operating system
• You’ve owned the most complex multi-team initiatives and turned them into streamlined operations
• You’ve acted as a pressure valve for leadership, pro-actively absorbing chaos and fixing before escalation
• You’ve operated with sustained exposure to executive and board level discussions, shaping narratives that may have been beyond your official remit

What you will unequivocally bring to the table:

• Deep Product DNA - you’re a product leader at heart, thinking in systems, and grounded in your customer and market in everything that you do. You know when to go hard, and when to cut clean.
• Data fluency with outcome-centricity - you know why leading indicators matter, you can challenge metrics, and you can use the data to build strong narratives or eliminate weak ones
• Ability to operate at different altitudes - you can prepare a board narrative and go deep with a PM on a thorny problem with the same level of comfort
• AI fluency - you can actively engage and push as Guild embraces being AI-native in both our product and operation
• Exceptional communication - you routinely distill complexity into simple clarity. You understand different audiences and can speak to all to create alignment
• Bias to action - you measure success by value delivered and are happy to make difficult decisions with imperfect information in pursuit of that

What the strongest candidates will also have:

• Technical and operational depth (not just product strategy)
• Experience in a scaling, multi-product environment
• A calm head when things get hectic

We are committed to equal pay for equal work and believe in compensation transparency. All salary ranges are standardized nationwide and will not vary by region. This role offers a competitive total compensation package, including a base salary of $185,000-215,000 , variable compensation, and stock options. Compensation offered will be based on a combination of factors such as experience, competencies, and internal equity.

Posting Date: 1/17/26

*This role will stay open for a minimum of 3 days.