Guild · 6 days ago
Chief of Staff to the CPTO
United States
Full-time
Remote
Senior Level
$185K/yr - $215K/yrGuild is a leading talent development company focused on connecting employees to real-world learning and career support. They are seeking a Chief of Staff to the CPTO to enhance the Product & Technology organization by improving decision quality and speed, ensuring strategic alignment, and tackling complex cross-organizational challenges.
Career PlanningEdTechEducation
Responsibilities
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
Qualification
Required
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
Preferred
Technical and operational depth (not just product strategy)
Experience in a scaling, multi-product environment
A calm head when things get hectic
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
Company
Guild
Guild is a learning platform that offers classes, programs, and degrees for working adults.
Founded in 2015
1001-5000 employees
Funding
Current Stage
Late StageTotal Funding
$643.17MKey Investors
Wellington ManagementGeneral CatalystFelicis
2022-06-02Series F· $264.67M
2021-06-02Series E· $150M
2019-11-13Series D· $157M
Leadership Team
Bijal Shah
Chief Executive Officer
Jessica Rusin
Chief Technology Officer
Recent News
2026-01-16
felicis.com
2025-12-30
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