Principal Product Operations Manager, Guild Education
Grow
$180-215k
Plus bonus and stock options
More information about location
Upskilling and education platform for America's workforce
Be an early applicant
Upskilling and education platform for America's workforce
1001+ employees
Be an early applicant
$180-215k
Plus bonus and stock options
More information about location
1001+ employees
Company mission
To unlock opportunity for America’s workforce through education and upskilling.
Role
Who you are
- Systems thinking and technical acumen. You design operational systems that scale and understand how changes ripple across teams and platforms. Credible in rooms with engineers and architects - you understand architecture trade-offs, data flows, service dependencies, and when to go deep vs. zoom out to cross-team sequencing
- AI-forward mindset. You have real opinions about where AI should and shouldn’t be applied in a product development lifecycle - and you’ve built or prototyped something with it. You don’t treat AI as a feature; you treat it as a lever
- Ownership, not coordination. You drive outcomes. You step into gaps rather than route around them. When something is unclear, you make it clear
- Executive communication. You distill operational and technical complexity for a VP without losing precision with an Engineering Director. You know what to escalate, what to absorb, and how to frame both
- 12+ years of experience in Product Operations,Technical Program Management, Product Management, or a related role on Product Teams
- Proven track record of designing and scaling product delivery systems across multiple teams or product areas
- Experience leading cross-functional product initiatives end-to-end with accountability for outcomes
- Hands-on experience designing or prototyping AI-assisted tools and workflows - not just familiarity with AI tools
- Strong analytical mindset - you define metrics, build dashboards, and use data to drive decisions, not just report on them
- Expertise with agile methodologies and associated tooling (Jira, Confluence, etc.)
- Experience operating autonomously at senior IC or staff level with demonstrated influence across engineering and product leadership
What the job involves
- Guild is hiring a Principal Product Operations Manager for our Grow product area. This is the most senior individual contributor Product Operations role at Guild
- This role sits at the intersection of product strategy, technical execution, and operational excellence - owning the systems, workflows, and delivery infrastructure that make Grow run, while leading high-impact strategic initiatives end-to-end alongside Engineering and Product leadership
- Lead high-impact, cross-functional product initiatives end-to-end - from aligning teams and clarifying technical trade-offs to driving execution and measuring outcomes
- Translate product strategy into concrete execution plans by working closely with Engineering leaders on architecture boundaries, dependencies, sequencing, and technical trade-offs
- Own launch and release readiness across all stakeholders: teams are informed, equipped, and ready before anything ships
- Develop and refine operational systems, tools, and AI-enabled workflows to enhance the efficiency of Product, Engineering, Design, and Data teams
- Conduct regular audits of Grow’s R&D processes to identify friction, map system dependencies, and drive scalable improvements with clear operational standards
- Build and maintain operational playbooks, escalation frameworks, and governance models
- Establish operating cadences for Grow, with a bias toward reducing coordination overhead and protecting time for high-value work
- Design and continuously evolve the end-to-end product delivery system for Grow - intake, prioritization, planning cadences, release readiness, and delivery standards
- Define and own delivery performance metrics and dashboards; use data to identify trends, diagnose systemic issues, and validate impact of improvements
- Identify where AI can be embedded across the product development lifecycle.Design and test AI-assisted workflows; validate impact before scaling broadly
- Model responsible, high-leverage AI use for the broader P&E org
- Assess tooling gaps, lead vendor conversations, and ensure tools are appropriate, integrated, and adopted across Grow
- Facilitate alignment across Product, Engineering, Design, Data, GTM, EPS, and Operations - ensuring priority clarity and seamless execution
- Establish feedback loop infrastructure so customer, partner, and operational signals reach the roadmap systematically
- Build communication norms and shared artifacts that scale across teams and reduce coordination overhead
Our take
The recruitment process can be the most costly element of a company's operation, with future-proof skillsets requirements resulting in the hiring of staff for niche tasks. Many existing employees of a company could have the potential to fill talent gaps and prevent the need for a new hire, but they often lack the training for such roles. Helping to solve this problem, Guild Education helps employers partner with nonprofit universities to train staff across a variety of subject matters, including high school completion programs, vocational opportunities, and enrollment in higher education.
As professional development is a strong employer benefit, Guild Education also pitches itself as a perk for employees, aiming to increase retention and worker satisfaction. By solving two major problems - a skills shortage and worker retention, it has gained large companies such as Chipotle, Target, Hilton and PepsiCo as corporate clients.
The platform has secured some serious funding too. And is using this funding to develop its healthcare and financial services learning modules and increase its offering to workers by exploring new ways to lower the barriers to learning, for instance through childcare solutions and financial wellness tools.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-5% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Jun 2022
$265m
SERIES F
Jun 2021
$150m
SERIES E
Total funding: $643.5m
Company benefits
- Equity stake in the company providing ownership and a path to future earnings (when we succeed, we all benefit)
- free one-on-one coaching with a certified financial planner, a platform with budgeting tools, investment and equity management center and many more financial resources through Origin (we believe financial literacy not only supports you personally, but also has a lasting impact in creating positive generational wealth practices)
- Employee Assistance Fund for unforeseen crises, disasters, and/or personal hardships and you need a little extra financial support (funded by the company and fellow Guilders to create a community of support)
- legal support and resources to navigate complicated situations like estate planning name changes, immigration, and more
- 401(k) plan with a range of diverse investment options and personalized retirement advice
- 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
- Multiple paths to meet educational and professional goals
- Fertility benefits built into all of our medical plans
- A $10,000 family planning fund to take care of costs that aren’t covered by the medical plans like adoption, surrogacy, and egg freezing expenses
- 12-20 weeks of paid leave and a ramp-up program for Guilders to ease back into work after an extended time away
- An additional 3 weeks of paid leave if you are going through the adoption, surrogacy, or foster process to use prior to your child's arrival/placement to prepare and attend necessary meeting
- Inclusive guidance and support as you go through your family planning journey through Cleo
- Our on-site childcare center, The Beehive, offering care for children 3 months-6 years of age for employees and their friends and family members located in Colorado
- Personalized 1:1 support for anyone on the parenthood journey with access to a network of clinicians, experts, and specialists through Cleo
- 80 hours of low cost ($2/hr) emergency backup care for times employees unexpectedly find themselves without primary care for the ones they are responsible for
- Dedicated support in finding background-checked care providers to assist with child care, elder care, and chronic care needs through Helpr
- The ability to bring an actively nursing child and companion on work related trips
- Inclusive, affordable medical and behavioral healthcare when you need it
- Open PTO is available so Guilders can rest, recharge, and bring their best selves to work
- 10 Holidays including a collective week off over the 4th of July plus 5 floating holidays for cultural and religious events you celebrate
- Our leave policies are there to support employees and offer 12 weeks of fully paid medical, non-birthing parent, and caregiving leave as of day one of employment while birthing parents receive 18-20 weeks of fully paid leave
- Once Guilders reach 4.5 years of service, they are eligible for a 5-week fully paid sabbatical leave
- Up to 10 days of bereavement leave
- Up to 10 days of jury duty
- 8 sick days
Company HQ
Central Business District, Denver, CO
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