Jerrold Calloway
Jerrold Calloway

Senior B2B Sales Professional

Actively looking · Member since 4 Nov 2026
Location
Hudson, United States
Desired salary
85k–115k USD/yearly
Work preference
Remote Only / Full Time
Experience level
Senior

About

Professional summary

I am a results-driven Senior B2B sales professional with more than 16 years of experience winning net-new business, growing strategic accounts, and managing full-cycle consultative sales processes.

I specialize in selling SaaS, managed services, cloud, workflow automation, fintech, payment processing, managed print, and information security solutions. I translate operational and technology challenges into practical business strategies that improve efficiency, reduce costs, and drive measurable outcomes.

I build trusted relationships with C-suite executives, finance leaders, IT stakeholders, business owners, and strategic partners. My approach combines executive-level discovery, solution design, proposal development, contract negotiation, and coordinated implementation.

I am experienced with MEDDIC and Challenger sales methodologies and have a strong record of pipeline creation, forecasting, quota attainment, account retention, and complex multi-stakeholder sales cycles. I use Salesforce CRM to maintain disciplined opportunity management and forecast accuracy.

Throughout my career, I have exceeded quota, generated significant partner-sourced pipeline, and ranked among top-performing sales professionals. My background spans commercial technology, financial services, banking, benefits, compliance, and communications markets.

I bring a consultative, relationship-focused mindset, strong business development discipline, and experience partnering with technical, engineering, operations, and finance teams to deliver customer-focused solutions.

Notice period: 1 week

Skills

26 capabilities

Tech stack & tools

Working toolkit

Application Hosting

Development

Marketing and Sales Tools

Experience

Career history

Senior Technology Consultant DEX Imaging

Drive new business development and expand strategic accounts by selling enterprise technology, managed print, workflow automation, and secure infrastructure solutions.

Advise C-level executives, finance leaders, and IT stakeholders on operational challenges and technology strategies. Own the full sales lifecycle from prospecting and discovery through proposal development, contract negotiation, implementation, and coordination with engineering teams.

Account Executive Kyocera Document Solutions

Achieved 135% of annual sales quota through consultative, solution-based selling across the Tampa commercial market. Generated new business and developed executive-level relationships from cold outreach through close.

Sold workflow automation, document management, managed print, and SaaS solutions designed to reduce client operating costs. Built and forecasted pipeline through cold calling, networking, and referrals while partnering with finance, operations, and IT leaders on long-term technology investments.

Partner Account Manager Human Interest

Generated more than $850K in pipeline opportunities through partnerships with payroll providers, HR consultants, and benefits advisors.

Built strategic partner relationships to increase awareness and adoption of retirement plan solutions. Supported partner onboarding and education activities to strengthen engagement and referral activity.

Regional Director of Business Development, Southeast NextBranch

Developed new business relationships with banks and credit unions across the Southeast, selling ATM outsourcing, fintech, and branch technology solutions.

Partnered with executive leadership and operations teams to diagnose business challenges and deliver customized solutions. Represented the company at banking conferences and trade shows to build brand visibility and pipeline.

Security & Compliance Sales Consultant Shred-it

Sold information security and compliance solutions to commercial organizations throughout South Florida.

Conducted operational assessments, delivered customized security recommendations, and ranked among the region's top-performing sales consultants.

Employee Benefits Consultant FBMC Benefits Management

Consulted with employers and HR executives on employee benefits strategy, building long-term relationships with business owners and decision-makers.

Generated new business through referrals, networking, and strategic account development.

Business Development Executive Konica Minolta Business Solutions

Managed the complete consultative sales cycle for SaaS, cloud, managed services, workflow automation, and document management solutions across healthcare, education, legal, AEC, and professional-services markets.

Consistently exceeded sales quota while driving long-term account growth and retention. Partnered with technical teams to develop and deliver customized client solutions.

AVP, Small Business Consultant Bank of America Merchant Services

Sold merchant services and payment processing solutions to small and mid-sized businesses.

Managed and grew an existing client portfolio through consultative relationship management and business development.

Business Sales Consultant Comcast Business

Sold communications and technology services to business owners.

Consistently ranked among top sales performers through new business development and solution-based selling.

Logistics Specialist United States Marine Corps

Managed inventory, procurement, and logistics operations in a military environment.

Developed leadership, operational discipline, and problem-solving capabilities that supported a transition into civilian sales roles.

Education

Learning history

Columbia Southern University

Bachelor of Science, Business Administration

Bachelor of Science in Business Administration.

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