Associate Proposals Consultant

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 Team

The Strategic Response Management (SRM) function sits inside Solutions Consulting and partners with Sales to win the RFIs, RFPs, security questionnaires, and vendor assessments that stand between Fleetio and our largest deals. In the first twelve months since launch, SRM has helped drive a step change in RFx win rate, scale response support into enterprise-tier deals (think multi-million-dollar opportunities), and build a repeatable workflow powered by a custom internal AI agent grounded in Fleetio's own documentation. We treat formal responses as a revenue lever, not an administrative task.

About the Role

As an Associate Proposals Consultant, you will own the day-to-day drafting and coordination work for a growing book of RFx responses, working alongside the Proposals Consultant on the function's most strategic opportunities. You will write evaluator-ready answers, coordinate input from subject matter experts across Product, Security, Legal, and Customer Success, and help maintain the response library and workflow that makes the function scale. This is a strong fit for someone with two to three years of proposal management or writing experience who wants to grow within a function that is still being shaped and is directly tied to measurable revenue outcomes.

What You Will Do

• Leverage AI tools to d raft, edit, and submit RFI, RFP, and security questionnaire responses for commercial and public sector opportunities, following APMP-aligned best practices (Theme, Proof, Benefit).
• Partner with Account Executives and Account Managers from intake through submission to shape evaluator-facing messaging, identify discriminators, and keep responses on time.
• Coordinate with cross-functional subject matter experts in Product, Security, Legal, and Customer Success to validate technical, compliance, and contractual answers.
• Use Fleetio's internal response AI tools to generate first-pass answers grounded in approved source material, then edit for voice, clarity, and win themes.
• Track response outcomes (progression, win rate, closed-won ARR influenced) and surface trends that help the function and Sales leadership improve pursuit decisions.
• Contribute to continuous improvement of the SRM workflow, intake process, and tooling, including battle card integration, competitive framing, and documentation.
• Represent SRM in internal reviews, pursuit syncs, and enablement sessions with Sales.

What You Bring

• At least two years of hands-on experience managing or drafting RFx responses (RFIs, RFPs, security questionnaires, or vendor assessments) for commercial or public sector clients.
• Strong business writing skills: plain English, active voice, specific over generic, with the ability to turn technical input into evaluator-friendly answers.
• Experience coordinating input from cross-functional contributors under deadline pressure, managing multiple concurrent responses without dropping balls.
• A detail-first mindset: you catch question numbering, column mapping, submission formatting, and compliance requirements before submittal .
• Comfort working in a remote, collaborative environment with asynchronous communication, including Slack, Google Workspace, and shared documentation platforms.

Nice to Have

• Experience responding to RFx opportunities on behalf of a software or SaaS company, including familiarity with security questionnaires such as CAIQ, SIG, or SOC 2 artifacts.
• APMP certification at the Foundation, Practitioner, or Professional level.
• Working knowledge of public sector procurement workflows, cooperative contracts, and state and local government RFP formats.
• Familiarity with fleet management, telematics, maintenance software, or an adjacent operational B2B software category.
• Comfort with AI-assisted drafting tools and prompt-based content generation.

What Success Looks Like

• 30 days: Shipped the first set of responses end-to-end with coaching, learned the SRM intake and submission workflow, and met the core cross-functional partners.
• 60 days: Independently owning smaller RFIs and security questionnaires, contributing to library updates, and partnering directly with AEs on live deals.
• 90 days: L eading mid-sized RFPs end-to-end, measurably contributing to the function's win rate and progression rate, and proposing at least one workflow or content improvement.

Why Fleetio, Why Now

The SRM function is young enough that your fingerprints will be on the standards, the library, and the tooling, and mature enough that your work ties directly to tracked monthly revenue outcomes. If you want to grow inside a function where great response writing is treated as a competitive weapon, this is the seat.

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.