Chief of Staff to the CPTO

At Guild, we believe talent is everywhere and that opportunity should be too. We continue to have our home and headquarters in Denver, but we have embraced a distributed model of working to reach the best talent in the United States. While some roles may require proximity to our Denver office, roles based outside of our Denver office can sit in any of the following 32 states: AZ, CA, CO, CT, FL, GA, ID, IL, IN, KS, MA, MD, ME, MI, MN, MO, NC, NH, NJ, NV, NY, OH, OK, OR, PA, SC, TN, TX, UT, VA, WA, WI and Washington D.C. Please only apply if you are able to live and work full-time in one of the states listed above. State locations and specifics are subject to change as our hiring requirements shift. 

If you are an Internal Candidate, please apply via our Internal Job Board. 

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To thrive as a company and meet our impact goals, we must cultivate a culture of high-performance. We know managers are often the single-largest driver of employee satisfaction and growth, and our talent is our biggest asset. Because of that, we’ve identified consistent expectations for all of Guild’s people managers — helping you know what to expect from your experience here.

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The Opportunity

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 streamli