TN Visa Head Of Customer Success Jobs
Head of Customer Success roles qualify for TN visa sponsorship under the USMCA's Management Consultant category when the position involves strategic client retention, team leadership, and measurable business outcomes. Canadian citizens can apply at the border or a U.S. consulate without a cap; Mexican citizens are subject to a 5,500 annual allocation.
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Get Access To All JobsINTRODUCTION
Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself—Dropbox is ready for you.
TEAM DESCRIPTION
The Dropbox Sales and Channel Team brings the power of enlightened work to organizations worldwide. We develop relationships that transform how companies collaborate and stories that shape how they see Dropbox. We don’t just sell products—we create partnerships that help companies leverage Dropbox Business to ignite new ways of working. From crafting sales strategies to analyzing business performance, we work with senior leaders to develop insights, identify opportunities, and do the planning and execution necessary to drive growth. If you're excited about creating partnerships inside the organization and out, join the Sales team. Areas of work include Sales Enablement, Sales Analytics, Customer Success, Account Management, Business Development, Channel Partnerships, Enterprise Sales, and Sales Operations.
ROLE DESCRIPTION
As the Head of Sales Ops and Analytics at Dropbox, you will lead the strategy, operating model, and team responsible for scaling a data-driven, efficient, and predictable go-to-market engine. This leader sits at the center of sales execution, partnering across Sales, Finance, Strategy, Marketing, Product, Customer Success, and Engineering to translate business priorities into durable systems, trusted metrics, streamlined processes, and actionable insights. You will play a central role in sales planning, forecasting support, territory and account planning, pipeline visibility, seller productivity, and business performance analytics. You will also help shape the data and systems foundation that powers revenue execution, ensuring leaders and frontline teams can make faster, better decisions with confidence. This is a highly visible leadership role for someone who enjoys building high-performing teams, simplifying complexity, and driving cross-functional outcomes. You will have the opportunity to influence senior leadership decisions, modernize critical GTM workflows, and create measurable impact on seller efficiency and business performance.
Responsibilities
- Lead the Sales Operations and Analytics function, including strategy, organizational design, prioritization, and operating rhythms for the team.
- Own the sales operating backbone across planning, forecasting support, territory and account planning, pipeline visibility, reporting, and productivity measurement.
- Build and evolve the authoritative sales data foundation, including standardized metric definitions, trusted reporting tables, governance, SLAs, and cross-functional alignment.
- Partner across Sales, Finance, Strategy, Marketing, Product, Customer Success, and Engineering to design scalable processes, systems, dashboards, and insights that improve execution and decision-making.
- Drive automation and workflow improvements across core seller motions including account planning, quoting and approvals, outbound routing, and related revenue workflows.
- Establish a high-bar analytics practice that delivers actionable insights embedded in seller and leadership workflows.
- Hire, coach, and develop senior operations and analytics leaders while building a culture of rigor, urgency, and business impact.
REQUIREMENTS
- 15+ years of experience in sales operations, revenue operations, business operations, analytics, or closely related go-to-market leadership functions.
- 7+ years of people leadership experience, including leading senior managers and building high-performing, cross-functional teams.
- Deep experience with sales planning, forecasting, pipeline management, performance reporting, and operational cadence design in a complex B2B go-to-market environment.
- Proven track record of partnering effectively with executive stakeholders across Sales, Finance, Strategy, Product, and Engineering.
- Strong analytical and systems thinking, with experience building trusted metrics, data governance practices, and scalable reporting foundations.
- Experience driving process redesign and workflow automation across CRM, forecasting, quoting, or seller productivity workflows.
- Excellent communication and executive influence skills, including the ability to turn ambiguous business needs into clear operating plans and measurable outcomes.
PREFERRED QUALIFICATIONS
- Experience leading both Sales Operations and Analytics under a single organizational umbrella.
- Experience supporting enterprise or multi-segment sales organizations with complex planning, forecasting, and renewal motions.
- Familiarity with modern GTM tooling and data ecosystems, including CRM, forecasting, engagement, and analytics platforms.
- Experience embedding AI-driven signals, predictive insights, or automation into go-to-market workflows.
- MBA or other advanced degree in business, analytics, economics, or a related field.
COMPENSATION
US Zone 1
This role is not available in Zone 1
US Zone 2
$251,700—$340,500 USD
US Zone 3
$223,700—$302,700 USD
The range(s) listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change. Please note, OTE are for sales roles only. Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs). Dropbox takes a number of factors into account when determining individual starting pay, including job and level they are hired into, location/metropolitan area, skillset, and peer compensation. We target most new hire offers between the minimum up to the middle of the range. Dropbox uses the zip code of an employee’s remote work location to determine which metropolitan pay range we use. Current US Zone locations are as follows:
- US Zone 1: San Francisco metro, New York City metro, or Seattle metro
- US Zone 2: California (outside SF metro), Colorado, Connecticut (outside NYC metro), Delaware, Illinois (Chicago metro), Indiana (Chicago metro), Maryland, Massachusetts, Michigan (Chicago metro), New Hampshire, New Jersey (outside NYC metro), New York (outside NYC metro), Oregon, Pennsylvania (D.C. metro), Pennsylvania (outside NYC or DC metro), Texas (Austin metro), Virginia (DC metro), Washington (outside Seattle metro), Washington DC metro, West Virginia (DC metro), Wisconsin (Chicago metro)
- US Zone 3: All other US locations
BENEFITS
Dropbox is committed to investing in the holistic health and wellbeing of all Dropboxers and their families. Our benefits and perks programs include, but are not limited to:
- Competitive medical, dental, and vision coverage
- 401(k) plan with a generous company match and immediate vesting
- Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more, allowing you time to unplug, unwind, and refresh
- Income Protection Plans: Life and disability insurance
- Business Travel Protection: Travel medical and accident insurance
- Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food and groceries, and much more
- Parental benefits including: Parental Leave, Child and Adult Care, Day Care FSA, Fertility Benefits, Adoption and Surrogacy Support, and Lactation Support
- Access to over 10,000 global co-working spaces through Gable, making it easy to book flexible workspaces for collaboration or individual work
- Quarterly Cell phone and internet allowance
- Mental health and wellness benefits
- Disability and neurodivergence support benefits
Additional benefit details are available upon request. Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI philosophy.
Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.
INTRODUCTION
Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself—Dropbox is ready for you.
TEAM DESCRIPTION
The Dropbox Sales and Channel Team brings the power of enlightened work to organizations worldwide. We develop relationships that transform how companies collaborate and stories that shape how they see Dropbox. We don’t just sell products—we create partnerships that help companies leverage Dropbox Business to ignite new ways of working. From crafting sales strategies to analyzing business performance, we work with senior leaders to develop insights, identify opportunities, and do the planning and execution necessary to drive growth. If you're excited about creating partnerships inside the organization and out, join the Sales team. Areas of work include Sales Enablement, Sales Analytics, Customer Success, Account Management, Business Development, Channel Partnerships, Enterprise Sales, and Sales Operations.
ROLE DESCRIPTION
As the Head of Sales Ops and Analytics at Dropbox, you will lead the strategy, operating model, and team responsible for scaling a data-driven, efficient, and predictable go-to-market engine. This leader sits at the center of sales execution, partnering across Sales, Finance, Strategy, Marketing, Product, Customer Success, and Engineering to translate business priorities into durable systems, trusted metrics, streamlined processes, and actionable insights. You will play a central role in sales planning, forecasting support, territory and account planning, pipeline visibility, seller productivity, and business performance analytics. You will also help shape the data and systems foundation that powers revenue execution, ensuring leaders and frontline teams can make faster, better decisions with confidence. This is a highly visible leadership role for someone who enjoys building high-performing teams, simplifying complexity, and driving cross-functional outcomes. You will have the opportunity to influence senior leadership decisions, modernize critical GTM workflows, and create measurable impact on seller efficiency and business performance.
Responsibilities
- Lead the Sales Operations and Analytics function, including strategy, organizational design, prioritization, and operating rhythms for the team.
- Own the sales operating backbone across planning, forecasting support, territory and account planning, pipeline visibility, reporting, and productivity measurement.
- Build and evolve the authoritative sales data foundation, including standardized metric definitions, trusted reporting tables, governance, SLAs, and cross-functional alignment.
- Partner across Sales, Finance, Strategy, Marketing, Product, Customer Success, and Engineering to design scalable processes, systems, dashboards, and insights that improve execution and decision-making.
- Drive automation and workflow improvements across core seller motions including account planning, quoting and approvals, outbound routing, and related revenue workflows.
- Establish a high-bar analytics practice that delivers actionable insights embedded in seller and leadership workflows.
- Hire, coach, and develop senior operations and analytics leaders while building a culture of rigor, urgency, and business impact.
REQUIREMENTS
- 15+ years of experience in sales operations, revenue operations, business operations, analytics, or closely related go-to-market leadership functions.
- 7+ years of people leadership experience, including leading senior managers and building high-performing, cross-functional teams.
- Deep experience with sales planning, forecasting, pipeline management, performance reporting, and operational cadence design in a complex B2B go-to-market environment.
- Proven track record of partnering effectively with executive stakeholders across Sales, Finance, Strategy, Product, and Engineering.
- Strong analytical and systems thinking, with experience building trusted metrics, data governance practices, and scalable reporting foundations.
- Experience driving process redesign and workflow automation across CRM, forecasting, quoting, or seller productivity workflows.
- Excellent communication and executive influence skills, including the ability to turn ambiguous business needs into clear operating plans and measurable outcomes.
PREFERRED QUALIFICATIONS
- Experience leading both Sales Operations and Analytics under a single organizational umbrella.
- Experience supporting enterprise or multi-segment sales organizations with complex planning, forecasting, and renewal motions.
- Familiarity with modern GTM tooling and data ecosystems, including CRM, forecasting, engagement, and analytics platforms.
- Experience embedding AI-driven signals, predictive insights, or automation into go-to-market workflows.
- MBA or other advanced degree in business, analytics, economics, or a related field.
COMPENSATION
US Zone 1
This role is not available in Zone 1
US Zone 2
$251,700—$340,500 USD
US Zone 3
$223,700—$302,700 USD
The range(s) listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change. Please note, OTE are for sales roles only. Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs). Dropbox takes a number of factors into account when determining individual starting pay, including job and level they are hired into, location/metropolitan area, skillset, and peer compensation. We target most new hire offers between the minimum up to the middle of the range. Dropbox uses the zip code of an employee’s remote work location to determine which metropolitan pay range we use. Current US Zone locations are as follows:
- US Zone 1: San Francisco metro, New York City metro, or Seattle metro
- US Zone 2: California (outside SF metro), Colorado, Connecticut (outside NYC metro), Delaware, Illinois (Chicago metro), Indiana (Chicago metro), Maryland, Massachusetts, Michigan (Chicago metro), New Hampshire, New Jersey (outside NYC metro), New York (outside NYC metro), Oregon, Pennsylvania (D.C. metro), Pennsylvania (outside NYC or DC metro), Texas (Austin metro), Virginia (DC metro), Washington (outside Seattle metro), Washington DC metro, West Virginia (DC metro), Wisconsin (Chicago metro)
- US Zone 3: All other US locations
BENEFITS
Dropbox is committed to investing in the holistic health and wellbeing of all Dropboxers and their families. Our benefits and perks programs include, but are not limited to:
- Competitive medical, dental, and vision coverage
- 401(k) plan with a generous company match and immediate vesting
- Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more, allowing you time to unplug, unwind, and refresh
- Income Protection Plans: Life and disability insurance
- Business Travel Protection: Travel medical and accident insurance
- Perks Allowance to be used on what matters most to you, whether that’s wellness, learning and development, food and groceries, and much more
- Parental benefits including: Parental Leave, Child and Adult Care, Day Care FSA, Fertility Benefits, Adoption and Surrogacy Support, and Lactation Support
- Access to over 10,000 global co-working spaces through Gable, making it easy to book flexible workspaces for collaboration or individual work
- Quarterly Cell phone and internet allowance
- Mental health and wellness benefits
- Disability and neurodivergence support benefits
Additional benefit details are available upon request. Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI philosophy.
Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.
See all 59+ Head Of Customer Success jobs
Sign up for free to unlock all listings, filter by visa type, and get alerts for new Head Of Customer Success roles.
Get Access To All JobsTips for Finding TN Visa Sponsorship as a Head Of Customer Success
Frame your credentials around Management Consultant criteria
TN approval hinges on the Management Consultant category, not a customer success job title. Your resume and support letter must emphasize analytical methodology, organizational recommendations, and measurable client outcomes rather than day-to-day account management tasks.
Target employers experienced with visa sponsorship
SaaS companies and enterprise software firms with recent visa filings are far more likely to understand work visa sponsorship processes. By identifying employers with a track record of sponsoring work visas, you can focus your applications on companies experienced with the paperwork and requirements involved in hiring international talent.
Secure a detailed employer support letter before crossing the border
Canadians can get TN status at a port of entry, but a vague offer letter is the most common reason for a secondary inspection. The letter must describe your specific duties, your degree's relevance, and the temporary nature of the engagement.
Use Migrate Mate to find sponsoring employers efficiently
Searching broadly wastes time if employers haven't sponsored TN workers before. Migrate Mate filters Head of Customer Success listings by verified sponsorship history, so you're applying to companies already equipped to file on your behalf.
Clarify TN scope if your role spans product and success functions
Hybrid titles like VP of Customer Experience that blend product feedback loops with retention strategy can create category ambiguity at adjudication. Work with your employer to scope the offer letter duties narrowly within management consulting functions.
Understand the difference between Canadian and Mexican TN procedures
Mexican citizens must obtain a TN visa stamp at a U.S. consulate before entry and cannot self-petition at the border like Canadians. Factor in consular appointment wait times and the 5,500 annual cap when planning your start date with an employer.
Head Of Customer Success jobs are hiring across the US. Find yours.
Find Head Of Customer Success JobsHead Of Customer Success TN Visa: Frequently Asked Questions
Does a Head of Customer Success role qualify for a TN visa?
It can qualify under the Management Consultant category, but the job duties must align with that classification. Roles centered on strategic client retention analysis, cross-functional recommendations, and measurable business improvement map well. Positions that are primarily account management or support escalation coordination are harder to justify under USMCA's category definitions.
How does TN compare to H-1B for a Head of Customer Success position?
TN has no lottery, no annual cap for Canadians, and no lengthy USCIS petition wait for port-of-entry applicants. H-1B requires winning a lottery and waiting months for adjudication. The tradeoff is that TN is strictly nonimmigrant with no dual intent, while H-1B allows you to pursue a green card simultaneously.
What documents does my employer need to provide for TN sponsorship?
Your employer must supply a signed offer letter on company letterhead specifying your job title, a detailed description of consulting-oriented duties, your start date, the temporary nature of the role, and your qualifications. For Canadian applicants at a port of entry, this letter is your primary filing document alongside your degree credential.
Where can I find Head of Customer Success jobs that offer TN visa sponsorship?
Most general job boards don't filter by TN sponsorship willingness, which means you spend significant time on employers who won't or can't file. Migrate Mate is built specifically for USMCA professionals and lets you search Head of Customer Success listings by verified sponsorship history, saving the back-and-forth of asking each employer individually.
Can I renew my TN status indefinitely in a Head of Customer Success role?
TN status is granted in three-year increments with no statutory limit on renewals, provided your role continues to meet the Management Consultant criteria and remains temporary in nature. USCIS can scrutinize repeat renewals for evidence of indefinite intent, so your employer should document the ongoing project-based or consultative scope of your work at each renewal.
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