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Chuck B.

Chuck B.

Fractional VP of RevOps | Salesforce & HubSpot | 10X ARR for Startups

I’ve taken a B2B startup from 6 wins a month to 34, grown ARR by 10X in 12 months, and hit 197% of quota by rebuilding the revenue engine from the CRM up. I do it again for every client I take on. I’m a fractional VP of Revenue Operations. I’ve carried a quota, led sales and marketing teams, and sat on executive committees. So when I work with your CRM, I’m building for revenue. **The Problem I Solve** Most companies don’t have a CRM problem. They have a revenue problem caused by messy data. Your reps are working around the system instead of in it. Your forecasts are BS. Marketing and sales blame each other because there’s no shared source of truth. Leadership can’t make confident decisions because the data is unreliable. I fix this. Quickly and cleanly. **What I Deliver** *CRM Architecture & Rebuilds (Salesforce & HubSpot)* Full instance audits, object redesign, pipeline modeling, lifecycle mapping, lead routing, forecasting models, and permissioning *Migrations & Integrations* Salesforce to HubSpot (and vice versa), CPQ transitions, tool consolidation, clean data imports with historical mapping. I connect your CRM to everything via native integrations, Zapier, Make, or n8n. *Go-to-Market Execution* Cold email infrastructure (DMARC, SPF, domain warming, inbox rotation), outbound sequence builds, multi-channel cadences, ICP targeting with Apollo and Clay, and conference/event strategy. I’ve managed 20+ sending inboxes and scaled outreach from 1K to 10K emails per week. *Fractional RevOps Leadership* I act as your Head of RevOps or Sales Ops. I partner with your CEO, CRO, or VP Sales to own the RevOps roadmap: KPIs, dashboards, accountability, comp structures, and quarterly planning. I deliver meaningful wins in the first 30 days. *AI & Automation* AI-powered lead scoring, predictive pricing optimization, automated carrier onboarding, and workflow automation that eliminates manual data entry. I build practical AI solutions that integrate directly into your CRM and daily workflow. **Results That Matter** - BoomPay: 10X ARR in 12 months. Took monthly wins from 6 to 34. Moved annual contract adoption from 42% to 99%. Generated 1,200% conference ROI. - CaaStle: Hit 197% of quota. Built outbound engine with 5% reply rates. Rebuilt Salesforce and stood up an India-based sales team. - Applico: Closed enterprise deals ($500K–2M). Scaled outreach from 1K to 10K emails/week. Built association and advisor channel strategy. - Rubicon Global: Drove 303% YOY net revenue growth across 57 new markets. Cut ML pricing algorithm error rate from 30% to 15%, increasing usage by 450%. - GreenSky: 400% growth in outbound activity. Completed full sales restructure (4 new units, 5 comp plans, telephony overhaul). 75% reduction in rep time per application via Salesforce custom objects. **Who I Work With** *Best fit:* • 15–200 employee B2B companies • Seed to Series C, or strong bootstrapped teams • Salesforce or HubSpot users (or migrating between them) • Growing revenue but feeling operational drag • Need a senior operator, not a junior admin or offshore dev shop I’m US-based (Pacific time), senior-only, and I send every client a personalized Loom video before we ever get on a call. No templates. No yes-men. Just a revenue operator who’s been in your seat.

🇺🇸Bend, United States$200/hr90% JSS3.00 (1)Since Sep 2018

Earnings and projects

MRR
$3.6k

Last 6 months ÷ 6

World#9,349 / 412k
🇺🇸Country#2,733 / 62.1k
Revenue, last 30 days
$0

Last 6 months: $22k

Total earnings
$62k

Billed in all: $65k

World#63,493 / 412k
🇺🇸Country#11,915 / 62.1k
Per project
$31k

$11k in the last 6 months

World#2,705 / 412k
🇺🇸Country#593 / 62.1k
Projects, last 6 months
2
0% fixed100% hourly
World#88,918 / 412k
🇺🇸Country#11,762 / 62.1k
Projects in all
2
0% fixed100% hourly
World#328,886 / 412k
🇺🇸Country#47,959 / 62.1k

Earnings, last 30 days

$65.1kNothing earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$64k$65k$66k$67kOct 8Oct 23Nov 7

Skill rankings: Top 2% in Management Skills

Ranked by MRR among everyone on Upwork with the skill.

  1. #12Sales Leadership456 freelancers · 🇺🇸 #5Top 3%
  2. #14Sales Enablement248 freelancers · 🇺🇸 #10Top 6%
  3. #30Revenue Management523 freelancers · 🇺🇸 #12Top 6%
  4. #41Go-to-Market Strategy820 freelancers · 🇺🇸 #18Top 5%
  5. #55Sales Operations1,136 freelancers · 🇺🇸 #21Top 5%
  6. #61Marketing Operations & Workflow1,406 freelancers · 🇺🇸 #28Top 4%
  7. #71Data Migration1,443 freelancers · 🇺🇸 #27Top 5%
  8. #105Salesforce CRM3,059 freelancers · 🇺🇸 #44Top 3%