Sr. Manager, RFP & Sales Intelligence

At HopSkipDrive, our goal is to create opportunity for all through mobility. 

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country. 

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are:

Our Growth Initiatives and Sales Intelligence teams manage expansion efforts and the RFP process, including COIs and sales support; examine, create, and submit transportation-related RFP responses. 

We are seeking a strategic, high-impact, detail-oriented Sr. Manager, RFP & Sales Intelligence to lead our proposal development and sales intelligence functions. This is a critical leadership role responsible for building, developing, and managing a winning RFP engine from initial discovery to final submission.

The ideal candidate is a seasoned RFP professional with a heavy emphasis on project management and strategic prioritization. You will thrive in a high-velocity environment, managing multiple complex workstreams simultaneously while serving as a key liaison for our cooperative purchasing partners and driving sales intelligence initiatives.

Key Responsibilities:

Strategic Leadership & Team Management

• Team Leadership: Provide direct oversight, mentorship, and management to the RFP team, consisting of three RFP analysts. Foster a culture of excellence, accountability, and continuous improvement.
• Strategic Roadmap. Develop a long-term strategic roadmap for the RFP function, maintaining a holistic view of the pipeline to proactively align all bids and submissions with the company's overarching business strategy and revenue targets.
• Bidding Strategy: Lead the development and execution of a comprehensive strategy for bids and contracts, ensuring alignment with company revenue goals and market opportunities.
• Process Architecture: Design and refine a standard end-to-end RFP process that facilitates smooth, efficient, and consistently high-quality submissions.

Project Management & RFP Execution

• Multitasking & Prioritization: Manage the end-to-end RFP lifecycle (receipt, review, analysis, and submission) for multiple concurrent proposals, often with rapid turnaround deadlines.
• Workstream Coordination: Successfully execute internal project management and proactive communication plans to keep cross-functional partners (Sales, SME, Finance, Legal) informed, engaged, and on track.
• Content Excellence: Establish and maintain a sophisticated RFP content repository (e.g., Loopio) to ensure information is consistent, accurate, and compelling.
• Quality Assurance: Ensure 100% compliance with all RFP requirements, tailored specifically to the prospective client’s needs, with zero errors or omissions.

Sales Intelligence & Partnerships

• Sales Intelligence: Own the RFP intelligence function to support strategic initiatives. Utilize procurement data platforms (e.g., GovSpend, Burbio) to identify trends, track competitor outcomes, and inform leadership of market shifts.
• Cooperative Purchasing: Act as the primary liaison and account manager for our cooperative purchasing partners, maximizing the value of these strategic relationships.

Who You Are:

• 8+ years of related experience in RFP/proposal management from opportunity through submittal (in K-12 education strongly preferred).
• Management experience with a proven ability to effectively develop and lead a team of 3+ people and meet stringent deadlines.
• Ability to shift focus to a player-coach, demonstrating excellent written and verbal communication skills; demonstrated persuasive writing, technical writing, and editing skills to support development of RFPs. 
• Attention to detail; ability to manage all proposal requirements with zero errors or omissions.
• Experience building a standard process that facilitates smooth, eff