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Logan Stillwell
B2B Sales Executive
Chicago,IL
Passion is the difference between mediocracy and excellence.
Work Preference
Work Type
Full TimeLocation Preference
RemoteHybridImportant To Me
Company CultureHealthcare benefitsWork from home optionCareer advancementSummary
Dynamic Senior Enterprise Sales Leader and three-time Founder with over 15 years of experience in scaling ventures and driving exceptional revenue growth. Proven track record of consistently exceeding gross profit targets by 150% to 300%, generating $150K to $300K in monthly gross profit, a 12% and above margin. Expert in navigating complex B2B sales cycles and developing high-value pipelines from lead generation to account management and post sale growth. Strong analysis skills, able to identify and capitalize on market opportunities and trends. Thrives within ambiguous environments, leveraging a founders mindset through experience, delivering innovative solutions that address critical operational scaling challenges for targeted mid-market to enterprise clients.
Overview
10
10
+ Years in Sales within Logistics & Supply Chain Solutions
2
2
Years of Founder/CEO within Health & Wellness
3
3
Businesses Founded & Scaled
15
15
Years in Full-Cycle B2B Sales (SMB to Enterprise)
Work History
Founder & Head of Sales
STILLWELL GREENS, LLC
Chicago, IL
09.2023 - 10.2025
- Built and scaled a hospitality and wellness startup from inception through successful merger.
- Revenue Growth: Built a $175K ARR run rate within 18 months, securing 60+ recurring B2B accounts.
- Full-Cycle Ownership: Directed outbound prospecting, discovery, pricing, and multi-level stakeholder negotiation.
- Strategic Optimization: Designed subscription models and pricing strategies that maximized Customer Lifetime Value (LTV).
- Scalability: Developed repeatable sales SOPs that ensured business continuity during the post-merger transition.
Director of Business Development (Enterprise Sales)
TRAFFIX USA, LLC
Chicago, IL
01.2019 - 03.2022
- Promoted to lead enterprise acquisition and strategic growth for national accounts.
- Elite Performance: Ranked Top 3 of 137 sales representatives for 5 consecutive years; generated $1.5M–$3M in annual GP.
- Enterprise Deal Velocity: Closed long-cycle B2B deals (9–15 months) by navigating complex executive environments.
- Pipeline Generation: Averaged 8–12 qualified discovery meetings weekly through disciplined outbound strategies.
- Leadership: Mentored and supported sales pods of 6–8 representatives, fostering a high-performance culture.
Director of National Accounts
TRAFFIX USA, LLC
Chicago, IL
08.2018 - 01.2019
- Retention & Expansion: Sourced and owned strategic national shipper relationships, driving portfolio stability.
- Operational Partnership: Collaborated with operations to mitigate service risk and protect the customer experience.
Senior Sales Executive
TRAFFIX USA, LLC
Chicago, IL
07.2017 - 08.2018
- Market Growth: Prospected and closed new logos across multiple verticals, repeatedly surpassing company quotas.
Sales & Operations
ATOMIC TRANSPORT, LLC
Chicago, IL
08.2010 - 06.2017
- Portfolio Management: Managed strategic B2B transportation programs with consistent retention and recurring revenue.
- Negotiation: Improved margins and service reliability through aggressive customer and carrier agreement negotiations.
Education
Bachelor of Arts - Sociology
08.2003 - 05.2007
Post-BA Business Coursework - Management, Accounting, Finance, Marketing, And Operations
08.2008 - 05.2009
- Continuing education in Post-BA Business Coursework. College-level Studies in Management, Accounting, Finance, Marketing, And Operations
Skills
- Full-Cycle B2B Sales
- Pipeline & Forecast Management
- Complex Deal Execution
- Long Sales Cycles
- MEDDICC
- Contract Negotiation
- CRM Management
- High-Volume Account Management
- Team leadership
- Strategic thinking
- Entrepreneurial and innovative
Software
Microsoft Teams
Microsoft Excel
Microsoft Word
Microsoft Power Point
Microsoft One Note
Microsoft Outlook
Salesforce CRM
HubSpot CRM
LinkedIN Sales Navigator
ZoomInfo
Timeline
Founder & Head of Sales - STILLWELL GREENS, LLC
09.2023 - 10.2025
Director of Business Development (Enterprise Sales) - TRAFFIX USA, LLC
01.2019 - 03.2022
Director of National Accounts - TRAFFIX USA, LLC
08.2018 - 01.2019
Senior Sales Executive - TRAFFIX USA, LLC
07.2017 - 08.2018
Sales & Operations - ATOMIC TRANSPORT, LLC
08.2010 - 06.2017
Northeastern Illinois University - Post-BA Business Coursework, Management, Accounting, Finance, Marketing, And Operations
08.2008 - 05.2009
University of Colorado Boulder - Bachelor of Arts, Sociology
08.2003 - 05.2007
Interests
Entrepreneurship, Sales and Business Growth - Founder Level
Mentoring, Training, and Team Leadership
Team Driven Success and Shared Wins
Ongoing Professional Development
Networking
Purpose Driven Brands and/or Services
Skiing & Mountaineering
Adrenaline Sports