Chief of Staff to the CPTO

Guild

1d • $185,000 - $215,000

About The Position

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.
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

Requirements

• 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
• 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

Nice To Haves

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

Responsibilities

• Increase the quality and speed of decisions across the Product and Technology organization.
• 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
• 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.

Benefits

• Access to low-cost, high-quality health care options through Collective Health and Kaiser (due to coverage limitations, Kaiser is currently only available in CA & CO)
• Access to a 401k to help save for the future
• Vacation policy to rest and recharge
• 8 days of fully-paid sick leave, to take the time to heal and or recover
• Family-friendly benefits, including 12 weeks of parental leave for non-birthing parents and 18-20 weeks for birthing parents; 4-week ramp-up period for when employees return from a leave of 6 weeks or more; as well as employer-paid short-term and long-term disability, employer-sponsored life insurance, fertility and caregiving benefits.
• Well-rounded wellness benefits including free and low cost mental health resources and financial wellbeing support services
• Education benefits and tuition assistance to help your future development and growth

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed