Sales & Business Development Consultants in Chicago to Watch
Sales and Business Development Consultants in Chicago to Watch for in 2025
Chicago Business Development & Sales Consultants to Know in 2025
Chicago has always been a powerhouse for innovation and industry, from logistics and manufacturing to finance, tech, and healthcare. In 2025, the city’s business community continues to evolve, powered by sales and business development leaders who help organizations reach new heights.
These professionals aren’t just generating leads—they’re building revenue engines, optimizing go-to-market strategies, and making growth sustainable. Whether they’re coaching executives, modernizing sales systems, or unlocking new market opportunities, they’re shaping how Chicago does business.
How We Built This List - Sales Consulting Services
At Digital Reference, we specialize in recognizing the professionals who build organizations from the inside out. For this Chicago edition, we evaluated consultants using criteria that balance both outcomes and ethos:
📍 Chicago-based or regionally active
📈 Track record of client impact and business growth
🧠 Alignment with modern sales practices (data-driven strategy, enablement, storytelling)
🗣 Visibility in the ecosystem—whether through leadership, education, or community
Featured Sales and Business Development Consultants in Chicago
Rich Cruz
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Rich Cruz is President and Management Consultant of Greater Chicago Consulting, a firm dedicated to equipping small and mid-sized businesses with sales training, digital strategy, and organizational development services designed to fuel both cultural and commercial success. Rich doesn’t just deliver tactics—he brings heart, structure, and an Organizational Development practitioner's lens to every engagement.
Drawing on over two decades of experience across organizational change, marketing, learning and development, and leadership coaching, Rich helps clients reimagine how they grow—from the inside out. His work is especially valuable to companies seeking transformation that lasts: culturally grounded, people-first, and strategically sharp.
💠 Signature Strengths
📊 Digital marketing meets sales strategy
📈 Lead generation and follow-through
🧠 Training for small sales teams
📘 Localized growth and visibility
Rich’s Approach, in His Own Words
What's your typical approach to client engagements?
"Be curious. Be humble. Be prepared."
Rich enters each engagement with a mindset of partnership and exploration. He focuses on identifying root causes—not just symptoms—through interviews, assessments, and collaborative discovery.
What type of clients are the best fit for you?
"Manufacturers under 500 employees, commercial construction companies, and professional services."
Rich thrives in operationally complex environments where growth depends on clear systems, aligned teams, and adaptable leadership.
What are your specialties or professional superpowers?
"OD, Change Leadership, Organizational Effectiveness Analysis, L&D, and Marketing."
He’s a rare blend of strategist and facilitator—equally comfortable designing a sales enablement plan or leading a workshop on organizational harmony.
What else should your clients know about you? What are your professional values? What motivates you professionally? What's your personality type?
"In addition to being an OD practitioner, I am a cartoonist, drum circle facilitator, and harmonica player. My values: Integrity, Honesty, Organizational Harmony, Making Change Our Friend, Psychological Safety, and Human Centricity. Motivations: my family, keeping people employed, keeping small and medium businesses thriving, and building communities. Personality type: Deliverer, Philomath, Empathizer, Problem Solver from High5; Restorative, Individualization, Empathy, Responsibility, and Developer from Gallup; High S and some C for DISC; INFJ from MBTI."
Why Choose Rich Cruz?
🔧 Systemic Solutions for Real Growth – Rich understands that performance issues often stem from structural or cultural misalignment. His OD-informed approach helps fix problems at the root.
📚 Cross-Functional Expertise – He blends organizational development, change leadership, and marketing strategy to offer clients holistic, lasting support.
🎯 Tailored for SMBs – Rich knows the pressures small and mid-sized businesses face and delivers practical, scalable solutions tailored to their needs.
🌱 People-First Philosophy – Whether he’s building out training programs or facilitating strategy sessions, Rich puts psychological safety, integrity, and human-centricity at the core of his work.
🎨 Creative and Empathic Leadership – His background in the arts and his deep empathy allow him to connect with clients on both strategic and personal levels.
Doug Dvorak
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Doug Dvorak is a globally recognized sales strategist, keynote speaker, and the founder of SalesCoach, a Chicago-based sales training organization that works with Fortune 1000 companies, startups, and professional associations worldwide. With over 25 years of experience, Doug has trained and motivated thousands of sales professionals, helping them sharpen their skills, increase pipeline efficiency, and close deals with confidence.
His speaking engagements blend actionable insight with high-energy delivery, earning him recognition from organizations like IBM, Marriott, and Nationwide. Doug customizes every program to align with a company’s sales culture, ensuring that training isn’t just informative, but transformative.
In addition to speaking and consulting, Doug has authored multiple books on sales, leadership, and professional development. His work combines theory and practice in a way that resonates with both new reps and seasoned sales leaders.
💠 Signature Strengths
🎤 High-impact keynote speaking & workshops
📈 Data-driven sales performance improvement
📘 Custom sales curriculum & content development
🧠 Executive sales coaching & team enablement
📊 Proven frameworks for pipeline growth & conversion
Dana (Toscano) Harder
Dana Harder is a partner at Indep Consulting, where she helps B2B organizations with go-to-market execution, sales enablement, and marketing alignment. Her ability to drive clarity and execution makes her a favorite among high-growth teams.
💠 Signature Strengths
🧩 Demand generation & GTM strategy
📘 Sales and marketing alignment
📈 Fractional sales & CMO leadership
🛠️ RevOps and pipeline strategy
Bernard Deir
As the founder of MB Consulting, Bernard Deir works with executives and founders to improve their sales operations and leadership development. His tactical mindset helps businesses go from scattered to strategic.
💠 Signature Strengths
📊 Sales management systems
📈 Operational consulting for SMBs
🧠 Strategic leadership development
📘 Business process improvement
Edmund Hodges
Founder of Edzecutive IQ, Edmund Hodges blends leadership coaching with business development strategy for entrepreneurs and early-stage companies. His work centers on mindset, clarity, and measurable action.
💠 Signature Strengths
🧠 Executive coaching
📘 Business growth strategy
🎯 Sales leadership training
💬 Clarity and accountability coaching
Lindsay Miller
At Reverie, Lindsay Miller supports creative entrepreneurs and founders in building systems for growth. She’s known for her blend of strategic thinking and sales system design that works for mission-driven brands.
💠 Signature Strengths
📈 Creative business sales strategy
📘 Founder-focused system design
🧩 Lead generation strategy
🛠️ Sales consulting for personal brands
Tasharia D. (Shar) Gardner
Tasharia Gardner is the Principal at Gardner & Gardner Consulting, where she focuses on business operations, team performance, and development strategy. Her holistic approach combines HR, sales, and leadership development into one seamless system.
💠 Signature Strengths
📘 Team performance and optimization
📈 Business growth strategy
🧠 Sales development and enablement
🛠️ Fractional COO consulting
Anthony DeRosa
As a partner at Platinum DB Consulting, Anthony DeRosa brings technical and operational experience to sales organizations. He helps teams transform their Salesforce infrastructure into a sales growth machine.
💠 Signature Strengths
📊 Salesforce optimization
📈 CRM-enabled revenue growth
🧠 Technical sales operations
🛠️ Process automation for scaling
Timothy Miller
Timothy Miller is the CEO of BDA, Inc., a business development agency that offers full-service consulting for organizations seeking to expand their reach. He works with startups, nonprofits, and legacy businesses looking to modernize their growth strategy.
💠 Signature Strengths
🧭 Business development consulting
📘 Strategic partnership development
📈 Growth enablement planning
💬 B2B sales strategy
David Winner
David Winner is the founder of DLW Consulting, where he provides high-level business development advisory services, especially for SaaS, real estate, and professional service firms. He brings deep operational insight to every engagement.
💠 Signature Strengths
🧠 B2B growth strategy
📘 Sales funnel design and automation
📈 Advisory for revenue scaling
🛠️ Strategic operations and enablement
Conclusion
Chicago’s business development leaders are building more than pipelines—they’re building momentum. From solopreneurs to legacy firms, these professionals are helping Chicago companies stay competitive in 2025 by aligning systems, strategy, and sales.
Where Business Grows, Talent Leads
At Digital Reference, we believe in spotlighting the operators who get results—whether they’re coaching founders or restructuring sales teams. The consultants listed here aren’t just growing revenue—they’re building capability, confidence, and sustainable scale.
Whether you’re launching a SaaS startup in River North, expanding a healthcare org in the Loop, or scaling a logistics firm in Naperville—these are the experts helping you make it happen.
A Note from Digital Reference
We’re building a new kind of professional network—one that rewards results, not just résumés. If you're a founder looking for traction, a team leader needing structure, or a consultant shaping growth from the ground up—we see you.
Want to recommend someone for this list? Get in touch.
Want to be part of this conversation? You’re already in the right place.
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Written by the Digital Reference editorial team. We exist to bring transparency to the world of fractional and independent talent.
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