Chief of Staff to the CPTO

Denver, CO - USA

Monthly Salary: Not Disclosed

Posted on: 16 hours ago

Vacancies: 1 Vacancy

Job Summary

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 weve identified consistent expectations for all of Guilds 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 whats 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 Guilds trajectory technical bets and strategic tradeoffs.

What youve likely accomplished in your career thus far:

Youve been a strategic force multiplier for an executive whether in a Chief of Staff role or as a senior product leader
Youve built and run or materially improved a product operating system
Youve owned the most complex multi-team initiatives and turned them into streamlined operations
Youve acted as a pressure valve for leadership pro-actively absorbing chaos and fixing before escalation
Youve 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 - youre 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 $00 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.

Guild is Americas leading talent development company partnering with the countrys most innovative employers including Chipotle Target Walgreens JPMorgan Chase Hilton PepsiCo Tyson and more to build the talent needed for today and a resilient workforce for tomorrow. Guild helps employers identify develop and mobilize internal talent enabling workers to gain skills for in-demand roles and helping companies stay agile. By connecting employees to real-world learning coaching and career support and providing companies with actionable talent insights Guild transforms overlooked talent into high-impact contributors and positions companies for long-term sustainable growth. For more information visit.

Guild is female-founded and a certified B Corp. The company has been named to the TIME100 Most Influential Companies of 2022 list CNBC Disruptor50 list three years in a row Inc. Best Led Companies list Fast Co. World Changing Ideas list and the B Lab Best for the World list among many others.

Guild is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you have a disability or special need that requires accommodation please let your recruiter know. We currently offer the following benefits:

Access to low-cost high-quality health care options through Collective Heath 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

PRIVACY NOTICE

I understand that I am applying for employment with Guild and am being asked to provide information in connection with my application. I further understand that Guild gathers this information through a third-party service provider and that Guild may use other service providers to assist in the application process. Guild may share my information with such third-party service providers in connection with my application and for the start of employment.

I understand and agree to Guilds use of my information in accordance with Guilds and for applicants that are residents of the State of California Guilds Applicant Privacy Notice and California Notice at Collection.

Required Experience:

Senior IC

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

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The Opportunity

Overview

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 whats 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 Guilds trajectory technical bets and strategic tradeoffs.

What youve likely accomplished in your career thus far:

Youve been a strategic force multiplier for an executive whether in a Chief of Staff role or as a senior product leader
Youve built and run or materially improved a product operating system
Youve owned the most complex multi-team initiatives and turned them into streamlined operations
Youve acted as a pressure valve for leadership pro-actively absorbing chaos and fixing before escalation
Youve 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 - youre 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

Posting Date: 1/17/26

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

Access to low-cost high-quality health care options through Collective Heath 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