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John M.
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John M.

Competitive Intelligence & Win/Loss Analysis for B2B SaaS

🔍 Enterprise SaaS Competitive Intelligence & Market Analysis Expert | 30+ Years in Global Software Leadership Most early-stage and growth SaaS companies lose winnable deals without ever knowing why. CRM notes are incomplete. Sales team feedback is biased. And while AI can generate reports, it can’t uncover what buyers actually say behind closed doors. That’s where I come in. I specialize in Win/Loss Analysis, Competitive Intelligence, and Secret Shopping for B2B SaaS. With 30+ years as a VP of Marketing, Product, and Business Development in enterprise software, I bring executive-level insight into why deals are won or lost, and how you can fix GTM gaps before they cost millions. My services include: Win/Loss Buyer Interviews — confidential conversations with buyers who chose you (or a competitor). AI can’t do this. Competitive Secret Shopping — I sit through your competitors’ demos to uncover how they pitch, price, and position. Board-Ready Insights — polished, data-backed reports your investors and leadership team can trust. Clients hire me when they need more than a generic “AI landscape report.” They hire me when they want actionable intelligence that changes outcomes this quarter. Recent Projects: Win/Loss analysis for a PE-backed SaaS firm → identified GTM gaps that increased close rates by 18%. Competitive demo shopping for a seed-stage SaaS startup → revealed key feature gaps to prioritize in roadmap. Market-entry audit for a European SaaS → reframed positioning and accelerated U.S. pipeline development. If you want reports you could get from ChatGPT, I’m not the right fit. If you want real buyer intelligence that improves close rates, retention, and valuation, let’s talk.

🇨🇷Tilaran, Costa Rica$45/hr100% JSS4.98 (16)Since Sep 2018

Earnings and projects

MRR
$91

Last 6 months ÷ 6

World#137,383 / 412k
🇨🇷Country#158 / 515
Revenue, last 30 days
$0

Last 6 months: $544

Total earnings
$72k

Billed in all: $73k

World#54,962 / 412k
🇨🇷Country#90 / 515
Per project
$1.7k

$544 in the last 6 months

World#86,195 / 412k
🇨🇷Country#163 / 515
Projects, last 6 months
1
100% fixed0% hourly
World#128,092 / 412k
🇨🇷Country#127 / 515
Projects in all
42
88% fixed12% hourly
World#72,392 / 412k
🇨🇷Country#35 / 515

Earnings, last 30 days

$72.7kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$71k$72k$73k$74kOct 8Oct 23Nov 7

Skill rankings: Top 23% in Blog Writing

Ranked by MRR among everyone on Upwork with the skill.

  1. #8Post-Merger Integration31 freelancers · 🇨🇷 #1Top 26%
  2. #150Strategic Plan632 freelancers · 🇨🇷 #1Top 24%
  3. #180Mergers & Acquisitions485 freelancers · 🇨🇷 #1Top 37%
  4. #203Product Marketing661 freelancers · 🇨🇷 #1Top 31%
  5. #225Competitor Research507 freelancers · 🇨🇷 #1Top 44%
  6. #434Sales Strategy1,043 freelancers · 🇨🇷 #2Top 42%
  7. #528Competitive Analysis1,472 freelancers · 🇨🇷 #1Top 36%
  8. #738Business Writing2,455 freelancers · 🇨🇷 #1Top 30%