GTM Systems Engineer - Fleetio

About Fleetio

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.

About the Role

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 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 Do

• 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, helping to construct 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).

Benefits

• Multiple health and dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• 4 weeks PTO (increases at year two)
• 12 company holidays + 2 floating holidays
• Paid parental leave (16 weeks birthing parent / 4 weeks non-birthing)
• FSA & HSA options
• Short-term (100% paid) and long-term disability
• Professional development funds & community service funds
• Wellbeing fund ($150 quarterly)
• Business expense stipend ($125 quarterly)
• Mac laptop + new hire equipment stipend