CPT Principal Jobs
Principal roles sit at the intersection of educational leadership and administrative management, making them a strong CPT fit for graduate students in education policy, leadership, or administration programs. Your DSO must document how the role integrates directly into your degree coursework before CPT authorization is granted.
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Get Access To All JobsAbout Gusto
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 400,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.
About The Role
Are you looking for an opportunity to transform a business? Gusto is looking for a strategic, customer-focused leader to leverage customer feedback and operational key metrics to develop actionable insights and strategies that shape our product and service, and positively impact customer love. Working with the Product, Engineering, Design and Customer Experience teams, you will be expected to tackle both highly strategic and deeply operational initiatives to deliver value for customers and Gusto. You’ll be customer-obsessed, business-minded, strategic, detail-oriented, and highly creative. In this role, you'll help stand up the operational and service foundation for a new Gusto product, using both deep human judgment and emerging AI tools to move faster and make better decisions. If this sounds exciting to you, we’d love to connect!
About The Team
The Benefits Product Operations team at Gusto is made up of committed, creative, collaborative people who care deeply about our mission to enable Benefits for all small and mid-sized businesses and their employees. We’re a highly cross-functional team focused on ensuring our product and service are co-designed and co-developed along the product lifecycle to deliver a best in class customer experience; Gusto is listening to, synthesizing and acting on customer and front-line team feedback; and that cross-functional teams are collaborating and swimming together to build the best version of Gusto for our customers.
Here’s What You’ll Do Day-to-day
- Shape and support product development and its integration into service strategy for existing customers across the product lifecycle, in collaboration with Engineering, Design, Product Management, and Customer Experience teams.
- Understand our product and end-to-end service experience and organizations in intimate detail, including internal and external pain points and feedback. Collaborate to ensure customer support considerations are integrated into broader company decisions.
- Lead and partner on product launches between Product Management and Customer Experience (CX) teams to ensure readiness and deliver insights post-launch to ensure a positive experience for customers and internal teams.
- Provide business insights and recommendations based on quantitative and qualitative data to influence strategy and operational design in both product and service roadmaps.
- Identify and drive cross-functional initiatives that will deliver value for customers and Gusto. Help develop and communicate a clear roadmap for enhancing service capabilities and experiences.
- Hypothesis-driven problem solving to drive our business.
- Contribute to advancing the Product Operations craft at Gusto and build AI fluency within the team:
- Model how to use AI tools to accelerate service design, insight synthesis, and agent-driven operational workflows.
- Identify and build AI-assisted operational workflows, including agents, to accelerate VoC synthesis, launch readiness monitoring, and cross-functional signal aggregation.
- Use AI tools to prototype service solutions and surface requirements faster, compressing the feedback loop between customer signal and product/service response — before full engineering investment.
Here’s What We're Looking For
- 10+ years of relevant work experience at growing startups in operating roles (i.e., biz ops/strategy roles, product operations, project/program management, and/or consulting):
- Experience scaling service strategy alongside growing SaaS products, including incubating products, building and managing product betas, and/or integrating new products into a scalable best-in-class service model.
- Highly adaptable and resilient to changes in business needs or requirements, with the ability to navigate challenges and make decisions even when information is incomplete.
- Demonstrated self-starter and organized problem-solver. Self-sufficient, resourceful, and bias for action towards continuous improvement.
- Experienced with managing a variety of cross-functional stakeholders on complex strategic initiatives, including influencing senior leaders in Product or Customer Experience orgs.
- Strong data literacy and results-orientation, with the ability to identify the right questions, interpret quantitative and qualitative signals, and translate findings into decisions — including comfort using AI-assisted tools for analysis and synthesis.
- Excellent written and verbal communication skills, with the ability to effectively communicate complex subjects to both technical and non-technical audiences.
- Demonstrated AI fluency in an operational and product context — comfort using AI tools to synthesize qualitative data, identify automation opportunities in service workflows, and building or directing AI agents to reduce manual operational lift:
- Experience prototyping with AI (e.g., Claude, Cursor, Codex or similar) is a plus.
- Experience with service design and/or service blueprinting.
- Experience working in the healthcare or benefits space (PEO, health insurance, etc.) is a plus; candidates with new product incubation experience in any complex regulated space are strongly encouraged to apply.
Compensation
- Our cash compensation amount for this role is $148,000/yr to $182,000/yr in Denver, and $167,000/yr to $217,000/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.
Location
Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
About Gusto
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 400,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.
About The Role
Are you looking for an opportunity to transform a business? Gusto is looking for a strategic, customer-focused leader to leverage customer feedback and operational key metrics to develop actionable insights and strategies that shape our product and service, and positively impact customer love. Working with the Product, Engineering, Design and Customer Experience teams, you will be expected to tackle both highly strategic and deeply operational initiatives to deliver value for customers and Gusto. You’ll be customer-obsessed, business-minded, strategic, detail-oriented, and highly creative. In this role, you'll help stand up the operational and service foundation for a new Gusto product, using both deep human judgment and emerging AI tools to move faster and make better decisions. If this sounds exciting to you, we’d love to connect!
About The Team
The Benefits Product Operations team at Gusto is made up of committed, creative, collaborative people who care deeply about our mission to enable Benefits for all small and mid-sized businesses and their employees. We’re a highly cross-functional team focused on ensuring our product and service are co-designed and co-developed along the product lifecycle to deliver a best in class customer experience; Gusto is listening to, synthesizing and acting on customer and front-line team feedback; and that cross-functional teams are collaborating and swimming together to build the best version of Gusto for our customers.
Here’s What You’ll Do Day-to-day
- Shape and support product development and its integration into service strategy for existing customers across the product lifecycle, in collaboration with Engineering, Design, Product Management, and Customer Experience teams.
- Understand our product and end-to-end service experience and organizations in intimate detail, including internal and external pain points and feedback. Collaborate to ensure customer support considerations are integrated into broader company decisions.
- Lead and partner on product launches between Product Management and Customer Experience (CX) teams to ensure readiness and deliver insights post-launch to ensure a positive experience for customers and internal teams.
- Provide business insights and recommendations based on quantitative and qualitative data to influence strategy and operational design in both product and service roadmaps.
- Identify and drive cross-functional initiatives that will deliver value for customers and Gusto. Help develop and communicate a clear roadmap for enhancing service capabilities and experiences.
- Hypothesis-driven problem solving to drive our business.
- Contribute to advancing the Product Operations craft at Gusto and build AI fluency within the team:
- Model how to use AI tools to accelerate service design, insight synthesis, and agent-driven operational workflows.
- Identify and build AI-assisted operational workflows, including agents, to accelerate VoC synthesis, launch readiness monitoring, and cross-functional signal aggregation.
- Use AI tools to prototype service solutions and surface requirements faster, compressing the feedback loop between customer signal and product/service response — before full engineering investment.
Here’s What We're Looking For
- 10+ years of relevant work experience at growing startups in operating roles (i.e., biz ops/strategy roles, product operations, project/program management, and/or consulting):
- Experience scaling service strategy alongside growing SaaS products, including incubating products, building and managing product betas, and/or integrating new products into a scalable best-in-class service model.
- Highly adaptable and resilient to changes in business needs or requirements, with the ability to navigate challenges and make decisions even when information is incomplete.
- Demonstrated self-starter and organized problem-solver. Self-sufficient, resourceful, and bias for action towards continuous improvement.
- Experienced with managing a variety of cross-functional stakeholders on complex strategic initiatives, including influencing senior leaders in Product or Customer Experience orgs.
- Strong data literacy and results-orientation, with the ability to identify the right questions, interpret quantitative and qualitative signals, and translate findings into decisions — including comfort using AI-assisted tools for analysis and synthesis.
- Excellent written and verbal communication skills, with the ability to effectively communicate complex subjects to both technical and non-technical audiences.
- Demonstrated AI fluency in an operational and product context — comfort using AI tools to synthesize qualitative data, identify automation opportunities in service workflows, and building or directing AI agents to reduce manual operational lift:
- Experience prototyping with AI (e.g., Claude, Cursor, Codex or similar) is a plus.
- Experience with service design and/or service blueprinting.
- Experience working in the healthcare or benefits space (PEO, health insurance, etc.) is a plus; candidates with new product incubation experience in any complex regulated space are strongly encouraged to apply.
Compensation
- Our cash compensation amount for this role is $148,000/yr to $182,000/yr in Denver, and $167,000/yr to $217,000/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.
Location
Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.
Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
See all CPT Principal Jobs
Sign up for free to unlock all listings, filter by visa type, and get alerts for new CPT Principal Jobs.
Get Access To All JobsPrincipal CPT: Frequently Asked Questions
Does a Principal role qualify for CPT authorization?
Yes, if your degree program explicitly covers educational leadership, school administration, or policy and the Principal duties connect to those learning outcomes. Your DSO evaluates whether the role is an integral part of your curriculum, not simply related to your field. A strong job description that references instructional leadership, staff management, and community engagement typically satisfies that standard for students in education or organizational leadership programs.
Can I work as a Principal on CPT before finishing my degree?
CPT authorization is available at any point during your F-1 program, including before graduation, as long as the practical training is a required or elective component of your curriculum. Many education leadership programs build administrative internships or residencies directly into the degree plan, which makes early CPT approval straightforward. Confirm with your DSO that the role is listed or approvable under your program's training requirements.
What documentation does my employer need to hire me on CPT?
Your employer needs your current I-20 with the CPT authorization endorsement listing the specific employer, start date, and whether the authorization is part-time or full-time. Most school districts also require a copy of your F-1 visa stamp and I-94 arrival record to complete onboarding. Some districts run E-Verify, which processes F-1 CPT students without issue when your I-20 reflects the correct authorization dates.
How do I find Principal jobs where employers understand CPT?
Search Migrate Mate for Principal openings filtered by employers with international hiring experience. Districts and charter networks that have previously employed international students are significantly less likely to withdraw offers after learning you're on CPT. Reaching out through your program's alumni network to connect with working principals who navigated CPT at similar districts is also an effective way to identify receptive employers.
Does CPT as a Principal affect my H-1B eligibility later?
CPT itself does not affect H-1B visa eligibility. The concern arises if you accumulate 12 or more months of full-time CPT, which eliminates your OPT eligibility entirely, including the STEM OPT extension. Without OPT, you lose the additional post-graduation work authorization window that many F-1 students use while waiting for H-1B selection. If the Principal role is full-time, track your cumulative CPT hours carefully with your DSO before committing.