Skip to content
BackNov 7
Kathleen R.

Kathleen R.

Remote Executive & Operations Support | Inbox, Calendar & Async System

I help founders and senior leaders reduce mental load by quietly running the systems that keep their days moving. With 9+ years of executive support experience in remote and hybrid environments, I specialize in inbox and calendar management, priority filtering, multi-time-zone scheduling, and operational coordination. My work style is calm, proactive, and outcome-focused — I don’t require constant supervision to deliver consistent results. After transitioning into self-employment and managing my own operations, I developed a deeper understanding of founder pressure, time sensitivity, and decision fatigue. I now intentionally support leaders part-time so they can focus on growth while I handle the operational flow behind the scenes. What I Can Support: - Executive inbox organization & priority filtering - Calendar management & conflict prevention - Meeting coordination & follow-up tracking - Travel scheduling & documentation prep - Light operations & administrative systems - Data entry & records management How I Work: - Async-first and independent - Clear communication & structured workflows - High discretion with sensitive information - Focused on outcomes, not clock-watching - I’m best suited for part-time or ongoing support roles where reliability, clarity, and calm execution matter. If you're looking to offload mental bandwidth and regain focus, I’d be happy to support you.

🇨🇦Toronto, Canada$45/hr60% JSS5.00 (1)Since Jan 2023

Earnings and projects

MRR
$1.9k

Last 6 months ÷ 6

World#24,256 / 412k
🇨🇦Country#488 / 7,133
Revenue, last 30 days
$2.5k

Last 6 months: $11k

World#16,457 / 412k
🇨🇦Country#370 / 7,133
Total earnings
$11k

Billed in all: $13k

World#185,062 / 412k
🇨🇦Country#3,313 / 7,133
Per project
$5.7k

$5.7k in the last 6 months

World#30,124 / 412k
🇨🇦Country#502 / 7,133
Projects, last 6 months
2

Across 3 contracts

33% fixed67% hourly
World#88,918 / 412k
🇨🇦Country#1,341 / 7,133
Projects in all
2

Across 3 contracts

33% fixed67% hourly
World#328,886 / 412k
🇨🇦Country#5,740 / 7,133

Earnings, last 30 days

$12.9k+$2.5k earned in the last 30 daysBilled in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$10k$12k$14kOct 8Oct 23Nov 7

Skill rankings: Top 4% in Data Entry

Ranked by MRR among everyone on Upwork with the skill.

  1. #90Travel Planning1,777 freelancers · 🇨🇦 #3Top 5%
  2. #130File Management2,593 freelancers · 🇨🇦 #1Top 5%
  3. #214Calendar Management4,894 freelancers · 🇨🇦 #5Top 4%
  4. #320Executive Support5,288 freelancers · 🇨🇦 #6Top 6%
  5. #333Google Workspace6,041 freelancers · 🇨🇦 #12Top 6%
  6. #388Scheduling6,335 freelancers · 🇨🇦 #4Top 6%
  7. #754Microsoft Office15,119 freelancers · 🇨🇦 #20Top 5%
  8. #864Email Communication14,123 freelancers · 🇨🇦 #10Top 6%