Transwest Services Sales Manager - Midwest - Milwaukee, WI

About the role

Our client is a fast-growing, nationally recognized organization delivering innovative technology-driven solutions to enterprise and mid-market clients across the United States. The company fosters a results-oriented culture built on collaboration, accountability, and entrepreneurial growth. This is a high-visibility role offering both individual performance and long-term leadership opportunity as the national program expands.

Key Responsibilities

• Develop and execute a comprehensive sales strategy for the Midwest territory (Illinois, Indiana, Iowa, Kansas (Central Time area), Michigan, Minnesota, Missouri, Ohio, Wisconsin).
• Serve as an individual contributor, managing the entire sales cycle from prospecting to close while meeting or exceeding quarterly and annual revenue targets.
• Lead and oversee the regional sales program, including pipeline development, forecasting, and territory expansion.
• Collaborate with fellow Sales Managers to align messaging, share market insights, and create unified national sales initiatives.
• Build and maintain strong, long-term relationships with clients, partners, and internal stakeholders.
• Identify new market opportunities and emerging trends within assigned territories.
• Provide input on competitive intelligence, customer feedback, and strategic account development.
• Represent the company professionally at client meetings, industry conferences, and networking events.

Qualifications

• Bachelors degree in Business, Marketing, Communications, or related field (MBA preferred but not required).
• 5+ years of legal sector B2B sales experience
• Demonstrated success in achieving or exceeding sales targets in regional or territory-based roles.
• Strong understanding of the Midwest legal market landscape
• Excellent written and verbal communication skills; ability to build rapport with executives and decision-makers.
• Proven ability to work independently in a remote environment while collaborating across geographically distributed teams.
• CRM proficiency (Salesforce, Hubspot or similar) and comfort with virtual selling tools and analytics platforms.
• Willingness to travel regionally (approximately 25-35%).

Compensation & Benefits

Competitive base salary plus performance-based incentive plan
Comprehensive benefits package
Professional development and advancement opportunities
Supportive, innovative, and collaborative remote-team environment

About K L McKinney

K L McKinney is a national recruiting and legal-technology talent advisory firm connecting top professionals with leading employers across the United States. This opportunity is being managed exclusively by K L McKinney on behalf of our confidential client.

Interested candidates may submit a resume and brief introduction to careers@klmckinney.com with the subject line: Transcription Sales Manager Midwest (Application)- K.L. McKinney
14090 Southwest Freeway, Suite 300
Sugar Land, TX 77478
Phone: 7132595872