Remote Outbound Supervisor Jobs
Remote outbound supervisor jobs are open across the U.S. at remote-first firms and distributed teams in sectors including financial services, insurance, telecommunications, and software. Employers hiring remote outbound supervisors right now include Oscilar, Bloomerang, and ServiceNow. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 58+ Remote Outbound Supervisor jobs
A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!
More about our team and company:
- Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg
- Our careers page: https://www.fleetio.com/careers
About the Role
Fleetio is seeking a high-impact Sales Development Manager (Outbound) to lead, coach, and scale a team of outbound SDRs. This leader will be responsible for driving pipeline generation, improving full-funnel stage progression, and instilling a culture of accountability and performance.
This is a hands-on leadership role for someone who thrives in fast-paced environments, understands outbound at a tactical level, and can translate activity into measurable business outcomes.
What You’ll Do
- Lead and scale a team of 8–10 outbound SDRs, driving consistent pipeline generation
- Develop and execute outbound strategy aligned to company growth targets
- Coach SDRs on:
- Prospecting fundamentals
- Messaging and objection handling
- Multi-threading and authority mapping Stage progression from meeting booked
- SQO
- Hold the team accountable to daily activity, quality standards, and conversion metrics
- Diagnose funnel bottlenecks quickly and implement actionable improvement plans
- Partner cross-functionally with Sales, Marketing, and RevOps to optimize performance
- Present team performance, pipeline health, and strategic insights to Senior Leadership
- Build a culture of ownership, resilience, and continuous improvement
What We’re Looking For
Leadership & Scaling Experience
- Proven experience scaling teams of 8–10 outbound SDRs
- Demonstrated ability to drive consistent attainment across a team
- High standards for performance and accountability
Seller DNA
- Prior experience as an SDR or AE preferred
- Deep understanding of outbound selling fundamentals
- Ability to coach from lived experience, not theory
Coaching & Funnel Expertise
- Exceptional ability to coach outbound prospecting
- Strong understanding of full-funnel stage progression Knows how to improve conversion from meeting SQO
- pipeline
Executive Presence
- Comfortable presenting business results and strategic plans in front of Senior Leadership
- Data-driven storyteller with clear communication skills
Operator Mindset
- Track record of making sound decisions in fast-paced environments
- Quickly diagnoses issues and builds structured action plans to fix them
- Balances urgency with long-term team development
What Success Looks Like
- Predictable outbound pipeline generation
- Improved conversion rates across funnel stages
- Strong team morale paired with high accountability
- Clear visibility and trust in reporting and forecasting
- A culture where performance is owned, coached, and elevated consistently
Requirements
- 2+ years of sales leadership experience, including leading a team of 6+ SDRs
- 2+ years of full sales cycle experience with proven success in a quota-carrying role in the Mid-Market or Enterprise space
- A track record of operational excellence and development
- Exposure to coaching methodologies and techniques to drive performance & growth
- Desire to build, combined with scrappiness and agility needed to scale an already robust SDR team
- Ability to travel to Fleetio HQ for meetings quarterly
- Level up if you know a thing or two about cars and engines
Benefits
- Multiple health/dental coverage options (100% coverage for employee, 50% for family)
- Vision insurance
- Incentive stock options
- 401(k) match of 4%
- PTO - 4 weeks (increases at year two!)
- 12 company holidays + 2 floating holidays
- Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
- FSA & HSA options
- Short and long term disability (short term 100% paid)
- Community service funds
- Professional development funds
- Wellbeing fund - $150 quarterly
- Business expense stipend - $125 quarterly
- Mac laptop + new hire equipment stipend
- Fully stocked kitchen with tons of drinks & snacks (BHM only)
- Remote working friendly since 2012 #LI-Remote
Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.
This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.
If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.
A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!
More about our team and company:
- Fleetio overview video: https://www.youtube.com/watch?v=YoXyXTFWbkg
- Our careers page: https://www.fleetio.com/careers
About the Role
Fleetio is seeking a high-impact Sales Development Manager (Outbound) to lead, coach, and scale a team of outbound SDRs. This leader will be responsible for driving pipeline generation, improving full-funnel stage progression, and instilling a culture of accountability and performance.
This is a hands-on leadership role for someone who thrives in fast-paced environments, understands outbound at a tactical level, and can translate activity into measurable business outcomes.
What You’ll Do
- Lead and scale a team of 8–10 outbound SDRs, driving consistent pipeline generation
- Develop and execute outbound strategy aligned to company growth targets
- Coach SDRs on:
- Prospecting fundamentals
- Messaging and objection handling
- Multi-threading and authority mapping Stage progression from meeting booked
- SQO
- Hold the team accountable to daily activity, quality standards, and conversion metrics
- Diagnose funnel bottlenecks quickly and implement actionable improvement plans
- Partner cross-functionally with Sales, Marketing, and RevOps to optimize performance
- Present team performance, pipeline health, and strategic insights to Senior Leadership
- Build a culture of ownership, resilience, and continuous improvement
What We’re Looking For
Leadership & Scaling Experience
- Proven experience scaling teams of 8–10 outbound SDRs
- Demonstrated ability to drive consistent attainment across a team
- High standards for performance and accountability
Seller DNA
- Prior experience as an SDR or AE preferred
- Deep understanding of outbound selling fundamentals
- Ability to coach from lived experience, not theory
Coaching & Funnel Expertise
- Exceptional ability to coach outbound prospecting
- Strong understanding of full-funnel stage progression Knows how to improve conversion from meeting SQO
- pipeline
Executive Presence
- Comfortable presenting business results and strategic plans in front of Senior Leadership
- Data-driven storyteller with clear communication skills
Operator Mindset
- Track record of making sound decisions in fast-paced environments
- Quickly diagnoses issues and builds structured action plans to fix them
- Balances urgency with long-term team development
What Success Looks Like
- Predictable outbound pipeline generation
- Improved conversion rates across funnel stages
- Strong team morale paired with high accountability
- Clear visibility and trust in reporting and forecasting
- A culture where performance is owned, coached, and elevated consistently
Requirements
- 2+ years of sales leadership experience, including leading a team of 6+ SDRs
- 2+ years of full sales cycle experience with proven success in a quota-carrying role in the Mid-Market or Enterprise space
- A track record of operational excellence and development
- Exposure to coaching methodologies and techniques to drive performance & growth
- Desire to build, combined with scrappiness and agility needed to scale an already robust SDR team
- Ability to travel to Fleetio HQ for meetings quarterly
- Level up if you know a thing or two about cars and engines
Benefits
- Multiple health/dental coverage options (100% coverage for employee, 50% for family)
- Vision insurance
- Incentive stock options
- 401(k) match of 4%
- PTO - 4 weeks (increases at year two!)
- 12 company holidays + 2 floating holidays
- Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
- FSA & HSA options
- Short and long term disability (short term 100% paid)
- Community service funds
- Professional development funds
- Wellbeing fund - $150 quarterly
- Business expense stipend - $125 quarterly
- Mac laptop + new hire equipment stipend
- Fully stocked kitchen with tons of drinks & snacks (BHM only)
- Remote working friendly since 2012 #LI-Remote
Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.
This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.
If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.
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Who's Hiring
Top Industries Hiring
- Technology & Software
- Waste Management & Environmental Services
What Employers Look For
The qualifications that appear most often in remote outbound supervisor jobs.
- 2 or more years of supervisory experience in a warehouse or distribution environment
- Proficiency with warehouse management systems such as SAP, Oracle, or Manhattan
- Demonstrated ability to manage outbound shipping workflows and meet daily throughput goals
- Strong knowledge of carrier pickup schedules, load planning, and dock management
- High school diploma or GED required, with associate or bachelor's degree often preferred
- OSHA safety compliance knowledge and forklift certification commonly required
Tips for Your Remote Outbound Supervisor Job Search
Apply early to remote roles that fit
Migrate Mate lists remote outbound supervisor openings from across the U.S. in one place, so you can find roles that match your background and apply directly without sorting through unrelated listings.
Show your remote management setup upfront
Remote employers want to know you can run outbound teams without an office. Call out the specific tools you use, such as dialers, CRM dashboards, and video coaching platforms, so hiring managers see your remote workflow immediately.
Prove you coach reps through written feedback
Remote outbound supervisors rely on written communication to develop reps who they rarely see on camera. Bring call notes, written coaching examples, or async feedback samples to your interview to demonstrate you can lead without being in the room.
Prepare for async interview rounds
Many remote-first companies use recorded video or written response screens before a live call. Practice delivering concise answers about your outbound metrics and team results on camera so your first impression lands even before you speak to a hiring manager.
Remote Outbound Supervisor Jobs: Frequently Asked Questions
How do I get a remote outbound supervisor job?
Target remote-first companies and distributed sales organizations that run outbound teams across multiple time zones, since those employers are most likely to hire supervisors who never come into an office. Remote hiring managers screen heavily for self-direction, clear written communication, and demonstrated ability to coach reps through video calls and async feedback. Candidates who show experience managing metrics, running virtual stand-ups, and holding remote reps accountable without in-person oversight stand out consistently.
Which companies hire remote outbound supervisors?
Employers currently hiring remote outbound supervisors include Oscilar, Bloomerang, and ServiceNow, per current remote listings on Migrate Mate as of November 2026. These tend to be remote-first firms, distributed SaaS companies, insurance carriers, and financial services organizations that run outbound sales or collections teams without a central office.
Can you get a remote outbound supervisor job with no experience?
Yes, but remote entry-level supervisor roles are harder to land because employers expect you to manage reps independently from day one, with no in-person safety net. Your best path is to move from a high-performing remote outbound rep role into a team lead position first, build a record of hitting metrics and helping peers, and show written communication skills that prove you can coach and document performance without walking to someone's desk.
Do you need a degree for remote outbound supervisor jobs?
Not always. Most remote employers weigh demonstrated outbound performance, measurable team results, and the ability to manage people through digital tools far more than a diploma. Candidates who can show a clear history of hitting outbound targets, coaching reps to quota, and running remote one-on-ones effectively often move ahead of degree holders who lack direct supervisory results.
Which industries hire the most remote outbound supervisors?
The sectors hiring the most remote outbound supervisors are Technology & Software and Waste Management & Environmental Services, based on current remote listings on Migrate Mate as of November 2026. These industries rely on distributed outbound teams to reach customers across the country, making remote supervision a natural fit for how they operate.
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