Outreach is looking for a Lead Proposal Manager to own the day-to-day execution of security questionnaires (DDQs, SIG, CAIQ, VSAQ, etc.) and other formal buyer requests; the large majority of this role's workload; along with RFPs and RFIs that our Go-To-Market and deal teams need to win business. This is an individual contributor role, and you will be the person deal teams trust to turn a complex, multi-stakeholder ask into a clear, compliant, on-time, and compelling response. This role sits within Solution Consulting and will report to the VP of Solution Consulting.
You'll work cross-functionally with Security, Privacy, Product & Engineering (PDE), Legal, and Sales to gather accurate answers, keep response content current, and manage the proposal process from intake to submission. This role is weighted heavily toward compliance and security questionnaires (roughly 85% of workload), with RFP/RFI support making up the remainder — so deep comfort with security and compliance frameworks is essential for success. You'll also help evaluate and recommend tooling (e.g., RFx management platforms) that make the broader response process faster and more scalable as deal volume grows.
Location: Ideal location is based in Seattle or Atlanta near in office teams. We are open to remote within the U.S.
Your Daily Adventures Will Include
Own end-to-end execution of security questionnaires (DDQs, SIG, CAIQ, etc.), RFPs, RFIs, and other buyer-issued requests, from intake through final submission
Manage a high-volume queue of inbound security questionnaires across multiple formats/frameworks (SIG Lite/Core, CAIQ, VSAQ, custom vendor risk assessments) and prioritize by deal urgency and SLA
Partner with Account Executives and Solution Consultants to understand deal context, timelines, and win themes, and translate those into a proposal plan with clear ownership and deadlines
Coordinate cross-functional subject-matter input from Security, PDE, Legal, Customer Success, and other functions, and know when to escalate versus resolve directly
Maintain the company’s Trust Center and assist team (when needed) to ensure timely delivery to prospects/customers
Maintain and continuously improve a repository of approved content, templates, and reusable answers so responses get faster and more consistent over time
Manage questionnaire portals/platforms (e.g., OneTrust, Whistic, vendor-specific portals) in addition to RFx tools
Review responses for compliance with solicitation requirements, accuracy, clarity, and consistency of voice before submission
Track proposal status, volume, and turnaround time, and flag capacity or process risks to stakeholders early
Identify opportunities to streamline the response process, including evaluating and helping implement supporting tools and platforms
Support post-submission follow-up, including clarification requests and revisions
Our Vision of You
4+ years of experience in proposal management, bid management, deal desk, or a similar cross-functional coordination role, ideally in B2B SaaS
Working familiarity with common frameworks referenced in questionnaires: SOC 2, ISO 27001/27701, GDPR, CCPA, NIST, and increasingly AI governance frameworks (e.g., ISO 42001)
A track record of independently managing multiple concurrent proposals against firm deadlines without dropping quality or compliance
An AI first mindset; actively using AI in your workflows and continue to push how to streamline content, response process and scalability using AI
Strong written communication skills; you can take technical or security-related input from subject-matter experts and turn it into clear, buyer-ready language
Comfort coordinating across functions (Security, Product, Engineering, Legal, Sales) without formal authority over any of them
Comfort with high question-volume, fast-turnaround work (some DDQs run 200+ questions with short SLAs), as distinct from the longer-cycle, narrative-heavy nature of RFPs
Excellent organizational skills and close attention to detail, especially around compliance requirements and version control
Experience building or maintaining a proposal content library, playbook, or knowledge base
A proactive, ownership-driven approach: you flag risks before they become blockers and look for process improvements without being asked
Nice to Have
Experience with RFx management or proposal automation platforms (e.g., Responsive, Loopio, RFPIO)
Familiarity with security and compliance frameworks commonly referenced in questionnaires (SOC 2, ISO 27001, GDPR)
Experience supporting enterprise deal cycles
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
