Remote Regional VP Sales Jobs
Remote Regional VP Sales jobs are open across the U.S. at remote-first companies and distributed sales organizations in sectors like technology, healthcare, and financial services. Employers hiring remotely right now include Fidelity Investments, Protective, and Map Retirement. See the openings below and apply to the ones that match your experience.
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Omada Health is on a mission to bend the curve of chronic disease.
Job overview:
Omada Health is on a mission to inspire and enable people everywhere to live free of chronic disease. Employers are a critical part of that mission, sponsoring access to Omada's programs for their employees.
With 29 peer-reviewed publications demonstrating clinical and economic outcomes and a pay-for-performance business model, Omada is looking for a Regional Vice President, Enterprise Sales to grow our impact with the nation's largest self-insured employers.
This is an individual contributor role focused only on new-logo acquisition. You will own a territory of named enterprise prospects, typically employers with 10,000 or more covered lives, and be responsible for turning those accounts into Omada customers. Success requires a disciplined, account-based approach to prospecting, the patience and rigor to manage 6–12 month sales cycles, and full ownership of pipeline development. You will work closely with national and regional benefits consultants, health plans, and PBM partners while taking responsibility for creating opportunities—not relying solely on inbound interest, RFPs, or partner referrals.
Just as important, you are a skilled solution-based seller who leads with discovery rather than a product pitch. You build relationships across large, multi-layered organizations, uncover the business problems that matter to executive leaders, and understand how each employer makes decisions before recommending a solution. You translate those insights into a compelling, financially grounded business case that can withstand scrutiny from Benefits, HR, Finance, Procurement, and consultant advisors.
The ideal candidate combines drive and tenacity with strategic thinking, executive presence, sound judgment, and integrity. They are comfortable orchestrating complex enterprise buying processes, engaging C-suite and senior leaders, and sustaining momentum across long cycles with many stakeholders. They care deeply about their craft, their customers, and the relationships they build across the healthcare ecosystem.
This position reports to the National VP and works collaboratively across Omada's sales organization and cross-functional teams.
What You'll Do
Create and Develop Enterprise Pipeline:
- Own new-logo business development for a territory of named enterprise prospects, typically self-insured employers with 10,000+ covered lives.
- Build and execute a multi-year territory plan that prioritizes target accounts based on fit, timing, benefits strategy, and buying triggers such as consultant reviews, plan renewals, and vendor consolidation.
- Develop account-level plans for priority prospects that map the organizational structure, key stakeholders, influencers, consultant relationships, and incumbent vendors.
- Run a consistent, account-based prospecting cadence through executive outreach, benefits consultant relationships, and health plan and PBM partnerships.
- Engage multiple stakeholders within each account to build early relationships, often well before a formal buying process begins.
- Sustain pipeline-building activity across your named accounts while managing active, long-cycle opportunities toward closure.
- Evaluate what is working, adapt your approach, and find new paths into accounts when initial efforts do not produce results.
Lead Discovery and Solve Executive-Level Problems:
- Lead thorough, multi-threaded discovery to understand each employer's benefits strategy, workforce health priorities, cost drivers, point-solution landscape, and desired outcomes.
- Move beyond surface-level requests to uncover underlying needs, quantify the impact of existing challenges, and identify the compelling reasons an enterprise would act.
- Identify economic buyers, champions, decision criteria, decision process, and paper process early, and validate them throughout the cycle.
- Develop tailored recommendations that connect Omada's multi-condition platform to the customer's specific needs, existing vendor ecosystem, and health plan or PBM arrangements.
- Build a credible, data-driven business case, including ROI and cost-of-inaction analysis, and present it effectively to senior leaders across Benefits, Total Rewards, HR, and Finance.
Orchestrate Complex Enterprise Deals:
- Own the full new-business sales cycle, from prospecting and qualification through consultant-led evaluations, RFPs, finalist presentations, contracting, and close.
- Build and maintain mutual action plans with customers that define milestones, owners, and timelines across 6–12 month cycles.
- Navigate enterprise buying processes that include procurement, legal, security and privacy review, data-sharing requirements, and health plan or PBM coordination.
- Lead an internal deal team that may include solutions consultants, clinical and analytics experts, legal, implementation, and executive sponsors.
- Partner with national and regional benefits consultants on account strategy, RFP responses, and finalist positioning.
- Lead complex negotiations on pricing, performance guarantees, and contract terms in partnership with Deal Desk and Legal.
- Ensure a clean handoff to Account Management and Client Success after close so new customers launch successfully.
- Take accountability for pipeline development, sales execution, and quota achievement.
Maintain Accurate Sales Forecasting:
- Maintain an accurate, up-to-date forecast grounded in customer engagement, confirmed next steps, and a clear understanding of each enterprise buying process.
- Critically assess opportunity stage, close timing, and likelihood to close using evidence from discovery and deal progression—not optimism alone.
- Apply a structured qualification framework, such as MEDDPICC, to inspect deals consistently over long cycles.
- Proactively identify and communicate deal risks, stalled opportunities, and changes in timing, along with a plan to address them.
- Keep CRM records current, including account plans, stakeholder maps, decision criteria, approval processes, and outstanding milestones.
- Participate in regular pipeline and forecast reviews, clearly articulating what must happen for each opportunity to close and taking accountability for forecast accuracy.
What You'll Bring:
- 5+ years of experience selling health and/or benefits solutions to large self-insured employers, including a track record of closing enterprise deals with organizations of 10,000+ employees or covered lives.
- Demonstrated success winning new logos through proactive, account-based prospecting and sustained development of a named-account territory.
- Experience managing long, complex sales cycles of 6–12 months or more with multiple stakeholders, formal evaluations, and RFPs.
- Strong discovery skills, including the ability to uncover underlying business problems, quantify their impact, and understand the implications of leaving challenges unresolved.
- Proven solution-based selling skills, with the ability to build a tailored, financially grounded business case for executive audiences.
- Executive presence and experience engaging C-suite and senior leaders in Benefits, Total Rewards, HR, and Finance.
- Established relationships with, and experience working alongside, national and regional benefits consulting firms.
- Experience collaborating with health plan and PBM account teams in large employer accounts.
- Experience negotiating enterprise contracts, including pricing, performance guarantees, and procurement and legal terms.
- Experience using a structured qualification methodology (such as MEDDPICC) to manage pipeline and forecast accurately.
- A consistent record of quota achievement and clear ownership of results.
- Strong presentation, communication, and listening skills.
- The self-direction to manage a named-account territory independently, prioritize effectively, and maintain momentum over long cycles.
- Resilience when faced with rejection, stalled opportunities, or difficult sales cycles—and the judgment to adapt your approach.
- Experience working in an emerging-growth company.
- Bachelor's degree.
Location and Travel:
- Candidates must reside in the midwestern United States; Illinois is preferred.
- Ability to work Central Time business hours and support customers and partners across Central and Eastern time zones.
- Willingness to travel approximately 25%–50% of the time within the territory, including onsite executive meetings, finalist presentations, and consultant meetings.
Benefits:
- Competitive salary with generous annual cash bonus
- Equity grants
- Employee stock purchasing plan (ESPP)
- Remote first work from home culture
- Flexible Time Off to help you rest, recharge, and connect with loved ones
- Generous parental leave
- Health, dental, and vision insurance (and above market employer contributions)
- 401k retirement savings plan
- Lifestyle Spending Account (LSA)
- Mental Health Support Solutions
- ...and more!
It takes a village to change health care. As we build together toward our mission, we strive to embody the following values in our day-to-day work. We hope these hold meaning for you as well as you consider Omada!
- Cultivate Trust. We listen closely and we operate with kindness. We provide respectful and candid feedback to each other.
- Seek Context. We ask to understand and we build connections. We do our research up front to move faster down the road.
- Act Boldly. We innovate daily to solve problems, improve processes, and find new opportunities for our members and customers.
- Deliver Results. We reward impact above output. We set a high bar, we're not afraid to fail, and we take pride in our work.
- Succeed Together. We prioritize Omada's progress above team or individual. We have fun as we get stuff done, and we celebrate together.
- Remember Why We're Here. We push through the challenges of changing health care because we know the destination is worth it.
About Omada Health: Omada Health (Nasdaq: OMDA) is reverse engineering the way healthcare is delivered in America, putting the space between doctor visits–where health is won or lost–at the center of care. Today's healthcare system poorly serves chronic conditions that require ongoing support outside of the exam room, like obesity, diabetes, hypertension, cholesterol, and musculoskeletal conditions. Omada's virtual-first model combines human-led care teams, connected devices, and AI-enabled technology to deliver personalized care at scale, including support for GLP-1 therapy. Omada has served more than two million members since launch across 2,000+ employers, health plans, pharmacy benefit managers, and health systems. Learn more at omadahealth.com.
Omada is thrilled to share that we've been certified as a Great Place to Work! Please click here for more information.
We carefully hire the best talent we can find, which means actively seeking diversity of beliefs, backgrounds, education, and ways of thinking. We strive to build an inclusive culture where differences are celebrated and leveraged to inform better design and business decisions. Omada is proud to be an equal opportunity workplace and affirmative action employer. We are committed to equal opportunity regardless of race, color, religion, sex, gender identity, national origin, ancestry, citizenship, age, physical or mental disability, legally protected medical condition, family care status, military or veteran status, marital status, domestic partner status, sexual orientation, or any other basis protected by local, state, or federal laws. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
Below is a summary of salary ranges for this role*. These ranges represent a good faith estimate of the minimum and maximum base salary for the position in that zone at the time of posting. Please refer to this resource for detail on zone designations.
Zone 1: $304,680 - $345,850
Zone 2: $297,520 - $336,900
Zone 3: $283,200 - $319,000
Please note that zones may be updated as market data changes but we will honor the range applicable to your zone (which is determined by your location) as of your application date.
- Range is indicative of On Target Earnings (OTE) and includes both base pay and commission at 100% achievement of established targets. Base salary is approximately 51% - 60% of total compensation range. This role is also eligible for equity grants. The actual offer, including the compensation package, is determined based on multiple factors, such as the candidate's skills and experience, and other business considerations.
Please click here for more information on our Candidate Privacy Notice.
Omada Health is on a mission to bend the curve of chronic disease.
Job overview:
Omada Health is on a mission to inspire and enable people everywhere to live free of chronic disease. Employers are a critical part of that mission, sponsoring access to Omada's programs for their employees.
With 29 peer-reviewed publications demonstrating clinical and economic outcomes and a pay-for-performance business model, Omada is looking for a Regional Vice President, Enterprise Sales to grow our impact with the nation's largest self-insured employers.
This is an individual contributor role focused only on new-logo acquisition. You will own a territory of named enterprise prospects, typically employers with 10,000 or more covered lives, and be responsible for turning those accounts into Omada customers. Success requires a disciplined, account-based approach to prospecting, the patience and rigor to manage 6–12 month sales cycles, and full ownership of pipeline development. You will work closely with national and regional benefits consultants, health plans, and PBM partners while taking responsibility for creating opportunities—not relying solely on inbound interest, RFPs, or partner referrals.
Just as important, you are a skilled solution-based seller who leads with discovery rather than a product pitch. You build relationships across large, multi-layered organizations, uncover the business problems that matter to executive leaders, and understand how each employer makes decisions before recommending a solution. You translate those insights into a compelling, financially grounded business case that can withstand scrutiny from Benefits, HR, Finance, Procurement, and consultant advisors.
The ideal candidate combines drive and tenacity with strategic thinking, executive presence, sound judgment, and integrity. They are comfortable orchestrating complex enterprise buying processes, engaging C-suite and senior leaders, and sustaining momentum across long cycles with many stakeholders. They care deeply about their craft, their customers, and the relationships they build across the healthcare ecosystem.
This position reports to the National VP and works collaboratively across Omada's sales organization and cross-functional teams.
What You'll Do
Create and Develop Enterprise Pipeline:
- Own new-logo business development for a territory of named enterprise prospects, typically self-insured employers with 10,000+ covered lives.
- Build and execute a multi-year territory plan that prioritizes target accounts based on fit, timing, benefits strategy, and buying triggers such as consultant reviews, plan renewals, and vendor consolidation.
- Develop account-level plans for priority prospects that map the organizational structure, key stakeholders, influencers, consultant relationships, and incumbent vendors.
- Run a consistent, account-based prospecting cadence through executive outreach, benefits consultant relationships, and health plan and PBM partnerships.
- Engage multiple stakeholders within each account to build early relationships, often well before a formal buying process begins.
- Sustain pipeline-building activity across your named accounts while managing active, long-cycle opportunities toward closure.
- Evaluate what is working, adapt your approach, and find new paths into accounts when initial efforts do not produce results.
Lead Discovery and Solve Executive-Level Problems:
- Lead thorough, multi-threaded discovery to understand each employer's benefits strategy, workforce health priorities, cost drivers, point-solution landscape, and desired outcomes.
- Move beyond surface-level requests to uncover underlying needs, quantify the impact of existing challenges, and identify the compelling reasons an enterprise would act.
- Identify economic buyers, champions, decision criteria, decision process, and paper process early, and validate them throughout the cycle.
- Develop tailored recommendations that connect Omada's multi-condition platform to the customer's specific needs, existing vendor ecosystem, and health plan or PBM arrangements.
- Build a credible, data-driven business case, including ROI and cost-of-inaction analysis, and present it effectively to senior leaders across Benefits, Total Rewards, HR, and Finance.
Orchestrate Complex Enterprise Deals:
- Own the full new-business sales cycle, from prospecting and qualification through consultant-led evaluations, RFPs, finalist presentations, contracting, and close.
- Build and maintain mutual action plans with customers that define milestones, owners, and timelines across 6–12 month cycles.
- Navigate enterprise buying processes that include procurement, legal, security and privacy review, data-sharing requirements, and health plan or PBM coordination.
- Lead an internal deal team that may include solutions consultants, clinical and analytics experts, legal, implementation, and executive sponsors.
- Partner with national and regional benefits consultants on account strategy, RFP responses, and finalist positioning.
- Lead complex negotiations on pricing, performance guarantees, and contract terms in partnership with Deal Desk and Legal.
- Ensure a clean handoff to Account Management and Client Success after close so new customers launch successfully.
- Take accountability for pipeline development, sales execution, and quota achievement.
Maintain Accurate Sales Forecasting:
- Maintain an accurate, up-to-date forecast grounded in customer engagement, confirmed next steps, and a clear understanding of each enterprise buying process.
- Critically assess opportunity stage, close timing, and likelihood to close using evidence from discovery and deal progression—not optimism alone.
- Apply a structured qualification framework, such as MEDDPICC, to inspect deals consistently over long cycles.
- Proactively identify and communicate deal risks, stalled opportunities, and changes in timing, along with a plan to address them.
- Keep CRM records current, including account plans, stakeholder maps, decision criteria, approval processes, and outstanding milestones.
- Participate in regular pipeline and forecast reviews, clearly articulating what must happen for each opportunity to close and taking accountability for forecast accuracy.
What You'll Bring:
- 5+ years of experience selling health and/or benefits solutions to large self-insured employers, including a track record of closing enterprise deals with organizations of 10,000+ employees or covered lives.
- Demonstrated success winning new logos through proactive, account-based prospecting and sustained development of a named-account territory.
- Experience managing long, complex sales cycles of 6–12 months or more with multiple stakeholders, formal evaluations, and RFPs.
- Strong discovery skills, including the ability to uncover underlying business problems, quantify their impact, and understand the implications of leaving challenges unresolved.
- Proven solution-based selling skills, with the ability to build a tailored, financially grounded business case for executive audiences.
- Executive presence and experience engaging C-suite and senior leaders in Benefits, Total Rewards, HR, and Finance.
- Established relationships with, and experience working alongside, national and regional benefits consulting firms.
- Experience collaborating with health plan and PBM account teams in large employer accounts.
- Experience negotiating enterprise contracts, including pricing, performance guarantees, and procurement and legal terms.
- Experience using a structured qualification methodology (such as MEDDPICC) to manage pipeline and forecast accurately.
- A consistent record of quota achievement and clear ownership of results.
- Strong presentation, communication, and listening skills.
- The self-direction to manage a named-account territory independently, prioritize effectively, and maintain momentum over long cycles.
- Resilience when faced with rejection, stalled opportunities, or difficult sales cycles—and the judgment to adapt your approach.
- Experience working in an emerging-growth company.
- Bachelor's degree.
Location and Travel:
- Candidates must reside in the midwestern United States; Illinois is preferred.
- Ability to work Central Time business hours and support customers and partners across Central and Eastern time zones.
- Willingness to travel approximately 25%–50% of the time within the territory, including onsite executive meetings, finalist presentations, and consultant meetings.
Benefits:
- Competitive salary with generous annual cash bonus
- Equity grants
- Employee stock purchasing plan (ESPP)
- Remote first work from home culture
- Flexible Time Off to help you rest, recharge, and connect with loved ones
- Generous parental leave
- Health, dental, and vision insurance (and above market employer contributions)
- 401k retirement savings plan
- Lifestyle Spending Account (LSA)
- Mental Health Support Solutions
- ...and more!
It takes a village to change health care. As we build together toward our mission, we strive to embody the following values in our day-to-day work. We hope these hold meaning for you as well as you consider Omada!
- Cultivate Trust. We listen closely and we operate with kindness. We provide respectful and candid feedback to each other.
- Seek Context. We ask to understand and we build connections. We do our research up front to move faster down the road.
- Act Boldly. We innovate daily to solve problems, improve processes, and find new opportunities for our members and customers.
- Deliver Results. We reward impact above output. We set a high bar, we're not afraid to fail, and we take pride in our work.
- Succeed Together. We prioritize Omada's progress above team or individual. We have fun as we get stuff done, and we celebrate together.
- Remember Why We're Here. We push through the challenges of changing health care because we know the destination is worth it.
About Omada Health: Omada Health (Nasdaq: OMDA) is reverse engineering the way healthcare is delivered in America, putting the space between doctor visits–where health is won or lost–at the center of care. Today's healthcare system poorly serves chronic conditions that require ongoing support outside of the exam room, like obesity, diabetes, hypertension, cholesterol, and musculoskeletal conditions. Omada's virtual-first model combines human-led care teams, connected devices, and AI-enabled technology to deliver personalized care at scale, including support for GLP-1 therapy. Omada has served more than two million members since launch across 2,000+ employers, health plans, pharmacy benefit managers, and health systems. Learn more at omadahealth.com.
Omada is thrilled to share that we've been certified as a Great Place to Work! Please click here for more information.
We carefully hire the best talent we can find, which means actively seeking diversity of beliefs, backgrounds, education, and ways of thinking. We strive to build an inclusive culture where differences are celebrated and leveraged to inform better design and business decisions. Omada is proud to be an equal opportunity workplace and affirmative action employer. We are committed to equal opportunity regardless of race, color, religion, sex, gender identity, national origin, ancestry, citizenship, age, physical or mental disability, legally protected medical condition, family care status, military or veteran status, marital status, domestic partner status, sexual orientation, or any other basis protected by local, state, or federal laws. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
Below is a summary of salary ranges for this role*. These ranges represent a good faith estimate of the minimum and maximum base salary for the position in that zone at the time of posting. Please refer to this resource for detail on zone designations.
Zone 1: $304,680 - $345,850
Zone 2: $297,520 - $336,900
Zone 3: $283,200 - $319,000
Please note that zones may be updated as market data changes but we will honor the range applicable to your zone (which is determined by your location) as of your application date.
- Range is indicative of On Target Earnings (OTE) and includes both base pay and commission at 100% achievement of established targets. Base salary is approximately 51% - 60% of total compensation range. This role is also eligible for equity grants. The actual offer, including the compensation package, is determined based on multiple factors, such as the candidate's skills and experience, and other business considerations.
Please click here for more information on our Candidate Privacy Notice.
See All 60 Remote Regional VP Sales Jobs
Find roles that match your experience and apply in just a few clicks.
Find Remote Regional VP Sales JobsRemote Regional VP Sales Job Market
Who's Hiring
Top Industries Hiring
- Healthcare & Medical Services
- Insurance
- Food & Beverage
- Medical Devices
- Technology & Software
What Employers Look For
The qualifications that appear most often in remote regional VP sales jobs.
- 7 or more years of B2B sales experience with at least 3 years in a management role
- Demonstrated ability to build and lead a regional sales team toward quota
- Proficiency with CRM platforms such as Salesforce or HubSpot for pipeline management
- Experience developing territory plans and go-to-market strategies from scratch
- Strong executive presence with the ability to present to C-suite buyers
- Bachelor's degree in business, marketing, or a related field
Tips for Your Remote Regional VP Sales Job Search
Demonstrate async leadership in your application
Remote regional vp sales employers want evidence you can coach, align, and hold a distributed team accountable without walking the floor. Reference specific examples of async pipeline reviews, written deal coaching, or remote QBR formats you've run successfully.
Highlight CRM and remote sales stack fluency
Name the tools you've used to manage a remote territory, whether Salesforce, HubSpot, Gong, or similar platforms. Remote hiring managers want to know you can run forecasting, rep activity tracking, and deal inspection entirely through software.
Apply early to remote roles that fit
Migrate Mate lists remote regional vp sales openings from companies across the U.S. in one place, so you can find roles that match your territory experience and apply directly without sorting through unrelated postings.
Prepare for a multi-stage remote interview process
Remote regional VP interviews often include a video panel with cross-functional leaders, a territory plan presentation, and an async written exercise. Practice delivering a 30-60-90 day remote ramp plan on video before your first screen.
Remote Regional VP Sales Jobs: Frequently Asked Questions
How do I get a remote regional vp sales job?
Landing a remote regional vp sales role means showing you can lead distributed teams and drive revenue without in-person oversight. Remote employers screen heavily for self-direction, crisp written communication, and experience managing sales pipelines asynchronously. Candidates who can point to measurable results across a dispersed territory, and who demonstrate comfort with video-based coaching and CRM-driven accountability, stand out consistently.
Which companies hire remote regional vp saless?
Remote regional vp sales roles are posted by Fidelity Investments, Protective, and Map Retirement and others right now, based on current remote listings on Migrate Mate as of November 2026. The companies hiring most consistently are remote-first technology firms, healthcare platforms, and financial services companies that run distributed sales teams across multiple time zones.
Can you get a remote regional vp sales job with no experience?
Yes, but remote regional vp sales roles at this level are competitive, and hiring managers expect demonstrated leadership without the scaffolding of a physical office. Entry paths include moving up from a remote senior account executive or regional manager role, where you've already proven independent pipeline ownership. Showing quantified results, strong CRM proficiency, and experience mentoring junior remote reps can open the door even without a formal VP title.
Do you need a degree for remote regional vp sales jobs?
Not always. Remote employers hiring at the regional VP level weigh revenue performance, leadership scope, and territory growth far more heavily than academic credentials. A consistent record of hitting or exceeding quota, experience building remote teams, and fluency with modern sales tools often matter more than a specific degree field when hiring decisions are made.
Which industries hire the most remote regional vp saless?
The sectors hiring the most remote regional vp saless are Healthcare & Medical Services, Insurance, and Food & Beverage, based on current remote listings on Migrate Mate as of November 2026. These industries rely on distributed sales teams covering large geographies, making the regional VP role a natural fit for fully remote structures.
See All 60 Remote Regional VP Sales Jobs
Find roles that match your experience and apply in just a few clicks.
Find Remote Regional VP Sales Jobs