Rob S

Owner & Principal

Consulting • Freelance

Feb 2026 - Present • 5 mos

Founded an independent consultancy providing director-level proposal strategy, bid desk operations, and deal desk commercials on a fractional and project basis to Series B/C SaaS companies in GovTech, HealthTech, and Public Safety. • Manages concurrent, multi-volume RFP responses end-to-end for clients: bid qualification and PWIN scoring, compliance matrices, SME coordination, pricing strategy, and on-time submission through procurement portals (Ariba, SAM.gov, state/SLED portals). • Delivers compliance-heavy responses spanning FedRAMP, SOC 2, CJIS, and security questionnaires/DDQs, bridging the gap between proposal writing and security/legal review. • Overhauls and maintains RFP content libraries in Loopio and Responsive, paired with sales team enablement training that lets sellers self-serve customized proposals. • Provides flat-fee emergency RFP turnarounds (7–10 days) and recurring retainer engagements with defined project-slot capacity, SOWs, and US-friendly MSAs.

Senior Manager, Revenue Operations

Tech Comm Tools • Full time

May 2024 - Feb 2026 • 1 yr 9 mos

Led RevOps and sales enablement strategy post-acquisition, aligning sellers from both companies on an updated Data Lifecycle, Proposal Process, Presentation Process, and Collateral Organization. • Launched Equiti University onboarding and enablement program, reducing time-to-productivity and increasing sales rep engagement by 25% through SOPs, training modules, and a company knowledge hub. • Responded to 2 RFPs and 3 questionnaires per month, aligning with all applicable Subject Matter Experts (SMEs) and improving win rate by 20%. • Collaborated with the Data and Analytics Lead to automate Salesforce billing and sales process requirements, contributing to cleaner data, reduced manual effort, and more accurate forecasting and performance tracking. • Rolled out a full Sales Presentation process, saving an average of 3 hours of administrative burden for all SMEs assigned to each presentation. • Implemented a process for all Sellers and Account Managers to manage Enterprise Opportunities.

Deal Desk Manager

Tech Cloud • Full time

Aug 2022 - May 2024 • 1 yr 9 mos

Owned the end-to-end deal desk and procurement lifecycle, supporting sales and legal/compliance teams by standardizing RFPs, streamlining contracting, and aligning operations to support risk-aware, scalable SaaS revenue growth. • Managed $10+ million in RFPs and due diligence requests, improving submission speed by 20% through the industry leading RFP response tool Loopio. • Implemented DocuSign CLM to streamline contract workflows, improving time to close renewals by 3 days with automated approvals integrated within Salesforce. • Developed and maintained an RFP library of 2,000+ entries, boosting auto-response accuracy and cutting manually filled answers by 25%. • Coordinated with 10+ internal stakeholders and external partners to manage opportunity documentation, reducing administrative backlog and improving internal response time for active pursuits by 20%. • Created playbooks in Confluence for all sellers and subject matter experts to navigate key sales processes.