About this role.
Fleetio is hiring an Outbound Sales Development Representative to generate and qualify Mid-Market pipeline for its fleet-management SaaS platform. The role centers on cold calling, email and social outreach, prospect research, CRM management, and booking meetings and demos for Account Executives. Candidates need at least one year of outbound sales experience, resilience, coachability, attention to detail, and strong self-motivation; SaaS and familiarity with Salesforce, Outreach, ZoomInfo, and LinkedIn Sales Navigator are preferred. This is a remote-friendly U.S. role with a clear development path toward Lead SDR or Account Executive positions.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
5/5Autonomy Level
4/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I begin by researching the company, fleet profile, likely operational challenges, and relevant stakeholders. I build a concise, personalized multichannel sequence across email, phone, and LinkedIn, then track engagement in the CRM and adjust messaging based on response patterns.
I treat rejection as data rather than a personal outcome. In a prior outreach effort, I reviewed call recordings and objection trends, refined my opening and value proposition, and maintained a consistent activity cadence until conversion improved.
I would confirm the prospect's role, fleet-related workflow or pain point, current solution, business impact, decision process, and timing. I would document these details clearly in Salesforce so the Account Executive has context for a productive discovery conversation.
I update records immediately after meaningful interactions, use standardized fields and notes, and verify contact information during research. I also regularly review my pipeline for duplicates, stale records, and next-step gaps.
Fleetio addresses a practical operational need for organizations that manage vehicles and equipment, which makes the value proposition tangible. I am also motivated by the opportunity to develop in a high-growth SaaS environment while contributing directly to qualified pipeline and ARR growth.
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
As an Outbound Sales Development Representative (SDR), you make the first impression! You’ll use ZoomInfo, LinkedIn Sales Navigator, Outreach, and Salesforce to identify, engage and qualify prospective customers. You’ll also partner with our Account Executives by creating a pipeline of opportunities for them to close, schedule meetings, shadow demos, etc.
If you’re highly motivated, not afraid to make a cold call, and are looking to break into the fast-paced world of software sales, this could be the position for you!
Who you are
You’re a driven, results-oriented sales professional who thrives in a fast-paced environment and is motivated by uncapped earning potential. You’re excited by the opportunity to work with fascinating customers and prospects across a wide range of industries—because nearly every organization that operates a fleet is a potential Fleetio customer. You’ll be responsible for sourcing and identify, engage and qualify prospective customers to drive ARR growth. You’re eager to join a team of “A” players who are passionate, supportive, and committed to success. Whether you’re working remotely from anywhere in the U.S. or from our HQ in Birmingham, AL, you’ll find a collaborative, customer-centric culture where your contributions matter and your success is celebrated.
Your impact
- You will manage outbound lead generation for our Mid-Market territory by researching and contacting (cold calling, emailing, social, etc.) prospective customers to understand their business needs and educate them on how Fleetio can help them achieve their goals
- Actively source new leads and develop detailed lead profiles in our CRM (Salesforce)
- Qualify prospect accounts and schedule meetings and demos with our Account Executives
- Assist in other strategic efforts to create qualified sales opportunities for Fleetio
- Develop and refine skills that will contribute to your success as an Outbound SDR and will be transferable to other opportunities as you grow (i.e., Lead SDR, Account Executive, etc.)
Your experience
- 1+ years of experience in Outbound sales, preferably as an SDR or AE
- Self-motivated with an outstanding work ethic
- Coachable & Eager to Learn
- Team Player
- Resilient, fearless, and persistent
- Problem solver with strong attention to detail
- SaaS experience is preferred but not required
- Bonus points if you have experience with the Fleetio tech stack (Salesforce, Outreach, ZoomInfo, LinkedIn Sales Navigator, Slack)
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.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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