Winona, MN · Open to Opportunities
James McCormick
Sales & Operations Leader
I've carried a quota, helped build a sales agency from 8 to 20, and coached new agents to a weekly number. Most recently, while the owners ran sales, I built the pricing, pipeline, and marketing behind 5x growth ($1M→$5M).
Sales Record
#6 of 112 nationally on personal + team production
American Income Life · December 2017
Led a team of 10 through two supervisors; trained about 45 agents in two years against a $4,000-a-week release bar
American Income Life
~$90K in new revenue against a $60K first-year quota
The Horton Group
Proposed and helped run Project Constellation, centralizing senior-living sales across buildings — Minneapolis pilot, national rollout six months later
Brookdale Senior Living
Set the pricing rules, estimate templates, and pipeline stages; marketing I ran took Garden Maintenance from ~$95K (2024) to ~$250K (2026)
ArborScape Inc.
Experience
Each role shaped how I think about growth.
ArborScape Inc.
Business Manager → Fractional CFO
Woodstock, VT · Remote
Scaled revenue 5x and grew team from 8 to 30 in 4 years
- Set the pricing rules, estimate templates, and pipeline stages behind 5x growth ($1M→$5M)
- Marketing I ran took Garden Maintenance from ~$95K (2024) to ~$250K (2026)
- Full P&L ownership across 8 service divisions, partnering daily with ownership
- Shipped 3 production apps; 10+ AI workflows across 6 functions
United Church Camps
Business Development Consultant
Remote
Led second-largest capital raise in org history — $850K
- $850K capital raise — 2nd largest in org history
- Managed the donor pipeline in Salesforce: segmentation and A/B-tested outreach
- Stepped in as acting Marketing Director mid-engagement
The Horton Group
Risk Advisor & Sales Executive
Waukesha, WI
Closed ~$90K and held 100% account retention in the pandemic year — selling B2B risk programs to CFOs at a top-50 broker
- ~$90K in new revenue against a $60K first-year quota; never lost a client
- Sold risk programs to CFOs and owners at a top-50 U.S. broker
- Studied the risk management playbooks of 30+ companies from the inside
American Income Life
Regional Sales Manager
Minneapolis, MN & Milwaukee, WI
One of four agents who built a new agency from 8 to 20, $1M+ first-year sales — 100% commission-based
- Ranked #6 of 112 nationally (December 2017)
- Led a team of 10 through two supervisors
- Trained about 45 agents in two years against a $4,000-a-week release bar
- 1 of 4 regional agents: built the new agency from 8 to 20 in the first year
Brookdale Senior Living
Market Sales Manager
Minneapolis, MN
Proposed a centralized sales model that went national in six months
- Promoted Sales Coordinator → Sales Manager → Market Sales Manager
- Sole salesperson for an assisted-living community, filling capacity with the executive director and RN
- Proposed and helped run Project Constellation — Minneapolis pilot, national rollout six months later
Three Ways I Add Value
Carry the number, then build the pipeline behind it.
- Ranked #6 of 112 nationally (December 2017)
- ~$90K in new revenue against a $60K first-year quota; never lost a client
- $850K capital raise — 2nd largest in org history
Train to a standard, then hold the standard.
- Led a team of 10 through two supervisors
- Trained about 45 agents in two years against a $4,000-a-week release bar
- Ran the full talent cycle weekly: job ads, interviews, hiring decisions, and training to release
Price it right, then measure it.
- Yearly repricing on market research across 8 divisions
- Marketing I ran took Garden Maintenance from ~$95K (2024) to ~$250K (2026)
- Stayed profitable through 5x growth — mid-40s gross margin, double-digit net
What I Build
Tools that turn a lead into a job.
Not side projects — three apps on one shared database, running a landscaping company's sales-to-operations flow. A customer conversation, spoken into a voice note in the driveway, becomes a scheduled job — first on the operations team's planning board, then the office's M365 calendars, then every crew's phone. Nothing retyped in between.
Client Compass
- Problem
- Sales ran through the owner — client details captured as voice notes in the truck died before they reached the office or the pipeline.
- Built
- Two apps in one. In the field: a voice-first intake PWA — ElevenLabs speech-to-text tuned with a custom landscaping dictionary — that turns a driveway voice note into a structured client record. In the office: a CRM holding every recording, upload, estimate, and pipeline stage. When a job hits "Won," it hands off to the dispatch board.
- Outcome
- Spoken note in the field to a verified, schedulable job at HQ — no paperwork in between.
Chaos Coordinator
- Problem
- Crew scheduling for 8 divisions lived on a whiteboard — conflicts, no capacity visibility, hours of weekly planning.
- Built
- A drag-and-drop dispatch engine — every crew, truck, and machine on a week-by-week timeline — with real-time conflict detection, capacity forecasting, and weather-aware field conditions, synced live to the conference-room TV. Won jobs arrive from the sales pipeline; approved schedules publish to the company's M365 calendar.
- Outcome
- Replaced the whiteboard, eliminated scheduling conflicts, cut planning from hours to minutes.
Crew Companion
- Problem
- Institutional knowledge — procedures, plant ID, job-site protocols — lived in veterans' heads and left with them.
- Built
- A bilingual (English/Spanish) offline-first PWA on every crew phone, built for gloved hands. Twice-daily syncs pull each crew's dispatch from the M365 schedule and the CRM — job, trucks, equipment, work description, due dates — alongside job sheets, safety protocols, and the handbook. Crews see the operational picture; the office layer adds budgets and full client detail.
- Outcome
- Searchable institutional knowledge from day one — and the morning dispatch in every pocket.
Education
DePaul University
Chicago, IL · 2008 – 2011
Economics and Philosophy coursework
Illinois Institute of Technology — AFROTC Detachment 195
Chicago, IL · 2008 – 2011
Aerospace Studies & Military Science (Minor) — ROTC Leadership Laboratories
Combat Rescue Officer Training — USAF Special Operations Command
What I'm Looking For
Targeting sales leadership roles — greater La Crosse, WI, or remote.
A sales team with a number to hit and room to grow — a new territory, a new line, or a team ready for its next level.
A sales leadership seat that carries a number — under a leader who'll coach me, challenge me, and grow me into the next level
High trust, high ownership — teams that move fast and love winning
Thanks for making it this far.
Let's Build Something Together
Targeting sales leadership roles in the greater La Crosse, WI area (or remote)
Winona, MN