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
Fleetio is seeking a systems-driven, strategic operator to own and optimize the technology powering our outbound operations. This role sits at the intersection of Marketing, Business Development, Sales, and GTM Operations, ensuring that our tools, data, and workflows work seamlessly together to drive pipeline and revenue growth. You’ll be the connective tissue between strategy and execution, building for the future to ensure our tech stack enables (not hinders) our outbound teams. If you love turning messy systems into smooth, high-performing engines and can balance tactical execution with a strategic roadmap, this role is for you.
What you'll be doing:
- Own the outbound tech stack: Manage, optimize, and expand tools like Outreach, 6sense, LinkedIn Sales Navigator, and Clay. Ensure integrations are seamless and data flows correctly between systems.
- Enable precision targeting: Partner with Revenue Marketing, AE leadership, and SDR leadership to design account and contact targeting strategies that leverage buying signals, intent data, and firmographic filters.
- Drive efficiency through automation: Build, maintain, and refine automated workflows and agentic systems to reduce manual effort for outbound teams while increasing speed-to-prospect.
- Improve data quality and accessibility: Partner with the GTM Systems team to ensure account and contact data is accurate, deduplicated, and enriched across systems.
- Lead experimentation: Evaluate and pilot emerging AI-powered GTM technologies…or build them! Help build the business case for scaling successful tools.
- Be the outbound systems expert: Partner with enablement to train and support outbound teams on best practices for leveraging the tech stack to maximize results.
- Measure and optimize: Partner with Data Engineering to define and track outbound performance KPIs (e.g., sequence engagement, lead-to-opportunity conversion rates, tool adoption) and make iterative improvements.
- Collaborate cross-functionally: Work closely with Ops, Sales, Marketing, and Enablement to align technology capabilities with outbound strategy.
Qualifications
- 5+ years in GTM Operations, Marketing Operations, or Sales Operations — with hands-on ownership of outbound technology.
- Proven track record of implementing and optimizing outbound tech stacks in a B2B SaaS environment.
- Deep hands-on experience with GTM technology stacks, including:
- CRM systems (Salesforce, HubSpot)
- Sales engagement tools (Outreach, SalesLoft)
- AI-driven prospecting tools (Actively, Clay, ChatGPT API)
- Automation platforms (Zapier, Workato, Glean)
- Strong project management skills and ability to work cross-functionally.
- Comfortable with data hygiene, enrichment, and governance best practices.
- Analytical mindset with experience defining and improving KPIs tied to outbound performance.
- Preferred: Proficiency in SQL and at least one scripting language (Python, JavaScript)
- 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.
Skills Required
- 5+ years of experience in GTM Operations, Marketing Operations, or Sales Operations
- Hands-on ownership of outbound technology
- Experience implementing and optimizing outbound technology stacks in a B2B SaaS environment
- Experience with CRM systems such as Salesforce or HubSpot
- Experience with sales engagement tools such as Outreach or SalesLoft
- Experience with AI-driven prospecting tools such as Actively, Clay, or the ChatGPT API
- Experience with automation platforms such as Zapier, Workato, or Glean
- Strong project management and cross-functional collaboration skills
- Knowledge of data hygiene, enrichment, and governance best practices
- Experience defining and improving KPIs tied to outbound performance
- Proficiency in SQL
- Proficiency in at least one scripting language, such as Python or JavaScript
Fleetio Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Fleetio and has not been reviewed or approved by Fleetio.
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Healthcare Strength — Health coverage includes multiple medical and dental options with full employee-premium coverage, plus vision, HSA/FSA, and employer-paid short-term disability. Core health benefits are consistently presented as comprehensive across official listings.
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Leave & Time Off Breadth — Time off includes PTO that increases with tenure, company holidays, and floating holidays. Paid parental leave is offered for both birthing and non-birthing parents.
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Wellbeing & Lifestyle Benefits — Extras include quarterly wellbeing and business-expense stipends, professional development funds, community service support, and remote-work setup assistance. These perks augment the core package and are emphasized across employer materials.
Fleetio Insights
What We Do
Our software helps organizations around the world track, analyze and improve their fleet operations. We're passionate about making it easy to manage a fleet so our customers can spend more time focusing on their mission.
