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Casey S.
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Casey S.

Contracts, Proposals & Workflow Automation | DBA

I take messy contracting and operations and make them run. 775+ contract actions across a $1.4B+ portfolio, median cycle time cut from 58 days to 6, on-time completion lifted from 32% to 80%, and the automation built in-house rather than recommended. Three things I do, and they compound: CONTRACT OPERATIONS & GOVERNANCE MSAs, SOWs, amendments, renewals, BAAs, and the system that runs them. I design the governance underneath the documents: risk determination frameworks, delegation-of-authority tiering, escalation registers, and contracting manuals. Across roughly 2,000 active agreements I cut median cycle time on my own book from 45 days to 13, and instituted a weekly open-book review that moved the team from 32% on-time to 80% and median cycle time from 58 days to 6. PROPOSALS & RFPs, BOTH SIDES OF THE TABLE I have written proposals and I have scored them. 8+ enterprise RFPs led end to end, from scope authorship through evaluation, intent-to-award, incumbent transition, and public records response. On the response side: solicitation review, compliance matrices, win themes, technical and past-performance narratives, and submission QC, including a $350M federal pipeline built from zero that converted to $25M+ in awards. Knowing how evaluators score is why my responses answer what is actually being graded. WORKFLOW AUTOMATION & AI I build it, I do not just scope it. Microsoft 365 Copilot agents that review agreements term by term against standard positions and produce risk determination sheets. A Claude API integration running in production. Salesforce architecture with form routing, bidirectional sync, and automated multi-stage assessment workflows. Power BI and Power Apps for the reporting layer underneath. WHO I WORK BEST WITH Organizations with more agreements than process. Firms entering regulated or public-sector markets. Nonprofits that need real infrastructure instead of spreadsheets. Anyone who needs a playbook, fallback positions, and the workflow to run them, built once and built properly. CREDENTIALS Doctor of Business Administration (Florida International University). MBA and MS Business Analytics (University of Miami). MA Intelligence Operations. MS Finance in progress. Former US Army officer, Field Artillery and Military Intelligence, two company commands, Afghanistan. I am not an attorney and do not provide legal advice. I do commercial and federal contract work: drafting, review against standard positions, risk triage, and negotiation support. Send me the agreement, the solicitation, or the process that keeps breaking, and I will tell you in one pass what I would do with it. Contract management, contract lifecycle management, CLM, contract drafting, contract review, contract negotiation, MSA, SOW, BAA, redlining, contract playbook, proposal writing, RFP response, RFQ, IFB, capability statement, compliance matrix, past performance, government contracting, GovCon, SAM.gov, procurement, strategic sourcing, vendor management, third-party risk, workflow automation, business process automation, Microsoft Copilot, Copilot Studio, Salesforce, Power Automate, Power BI, SOP development, operations consulting.

🇺🇸Miami, United States$150/hr100% JSSSince Dec 2021

Earnings and projects

MRR
$900

Last 6 months ÷ 6

World#52,838 / 412k
🇺🇸Country#8,605 / 62.1k
Revenue, last 30 days
$0

Last 6 months: $5.4k

Total earnings
$33k

Billed in all: $35k

World#104,647 / 412k
🇺🇸Country#18,150 / 62.1k
Per project
$16k

$5.4k in the last 6 months

World#8,199 / 412k
🇺🇸Country#1,452 / 62.1k
Projects, last 6 months
1
0% fixed100% hourly
World#128,092 / 412k
🇺🇸Country#16,472 / 62.1k
Projects in all
2
0% fixed100% hourly
World#328,886 / 412k
🇺🇸Country#47,959 / 62.1k

Earnings, last 30 days

$34.6kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$34.0k$34.5k$35.0k$35.5kOct 8Oct 23Nov 7

Skill rankings: Top 10% in Technical Writing

Ranked by MRR among everyone on Upwork with the skill.

  1. #43Government Procurement208 freelancers · 🇺🇸 #17Top 21%
  2. #44Request for Proposal235 freelancers · 🇺🇸 #13Top 19%
  3. #72Business Proposal Writing637 freelancers · 🇺🇸 #21Top 11%
  4. #113Grant Writing1,019 freelancers · 🇺🇸 #72Top 11%
  5. #116Contract Management593 freelancers · 🇺🇸 #34Top 20%
  6. #124Proposal Writing936 freelancers · 🇺🇸 #46Top 13%
  7. #144Contract Negotiation953 freelancers · 🇺🇸 #44Top 15%
  8. #174Procurement991 freelancers · 🇺🇸 #18Top 18%