Best Fractional Chief Sales Officers in Chicago

Chicago Fractional CSO Services & Fractional Chief Sales Officers

Chicago has always been a city that knows how to sell. From the industrial corridors that once powered the Midwest to today’s fast-moving SaaS firms, professional services companies, and private-equity-backed growth plays, the Chicago–Naperville–Elgin metro area thrives on execution, accountability, and results. It’s a region where leadership isn’t theoretical—it’s operational.

In this market, sales leadership and Human Resources are inseparable. HR teams are being asked to hire faster, scale smarter, retain high-impact sellers, and justify leadership investments with real outcomes. That’s why more Chicago organizations are turning to Fractional Chief Sales Officers (CSOs)—experienced revenue leaders who step in without the long-term risk of a full-time executive hire.

At Digital Reference, we spend a lot of time inside this intersection of sales, leadership, and HR credibility. We evaluate not just resumes, but how leaders actually operate, how teams experience them, and how their impact shows up over time. 

This article introduces our curated list of Chicago-area Fractional CSOs—freelancers, solo operators, and firm-based leaders—who consistently demonstrate substance over buzzwords and who understand how revenue strategy connects to people, process, and culture.

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🌇 Our Methodology: How This List of Chicago Fractional Chief Sales Officers

This is not a directory scrape or a pay-to-play roundup.

Our team conducted extensive qualitative research across the Chicago region, including:

• Deep reviews of LinkedIn leadership narratives, career arcs, and consistency of focus
• Analysis of company positioning and messaging on each consultant’s website
• Evaluation of how each leader talks about people, enablement, and accountability—not just pipeline and quotas
• Alignment with HR realities, including hiring, onboarding, performance management, and change adoption

We prioritize leaders who:

• Have actually carried a bag, built teams, and lived inside revenue pressure
• Speak clearly about process, coaching, and systems, not vague motivation
• Understand how sales performance impacts hiring decisions, employer brand, and retention
• Operate in or serve the Chicago–Naperville–Elgin (IL-IN-WI) metro area

The professionals below are not ranked. Each brings a distinct approach to fractional sales leadership—and each shows up differently for HR partners and executive teams.

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🌟 Meet Chicago's Best Fractional Chief Sales Officers

🟣 Anthony Hegarty

CEO and Founder, The Sales Velocity Improvement Group

Anthony Hegarty brings a systems-first mindset to fractional sales leadership—one that resonates strongly with HR teams who are tired of heroic individual sellers and ready for repeatable performance.

As Founder of The Sales Velocity Improvement Group, Anthony focuses on the mechanics that actually drive revenue velocity: clarity of roles, consistency of execution, and leadership discipline. His background reflects decades of experience inside complex sales environments where growth stalls not because of talent shortages, but because of misaligned incentives and unclear expectations.

What stands out in Anthony’s work is his insistence that sales improvement is organizational, not personal. That framing matters enormously for HR leaders tasked with scaling teams responsibly.

Key characteristics and contributions include:

🔹 Deep expertise in diagnosing sales execution gaps rather than surface-level KPI misses

🔹 A strong emphasis on leadership accountability, helping CEOs and VPs understand their role in revenue outcomes

🔹 Practical frameworks that translate directly into better hiring profiles and onboarding paths

🔹 A coaching-oriented approach that supports managers—not just frontline reps

Anthony’s Chicago roots show up in his pragmatism. There’s no fluff, no hype—just a clear belief that when sales leadership is structured correctly, HR teams spend less time firefighting and more time building sustainable growth engines.

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🟣 Tim Rockwell

Founder, Rockwell Growth Strategies

Tim Rockwell operates at the intersection of strategy, execution, and enablement, which makes his work especially relevant for organizations undergoing revenue transformation without wanting cultural chaos.

As the founder of Rockwell Growth Strategies, Tim positions himself not as a temporary fixer, but as a growth partner—someone who helps companies establish the rhythms and disciplines they’ll rely on long after a fractional engagement ends.

From an HR perspective, Tim’s work stands out because of how intentionally he integrates people development into revenue planning.

Notable elements of Tim’s approach:

🔹 Focus on sustainable growth systems, not quarter-to-quarter heroics

🔹 Clear articulation of sales roles, competencies, and career paths, aiding HR workforce planning

🔹 Emphasis on coaching managers to become multipliers, reducing over-dependence on individual reps

🔹 Strong alignment between revenue goals and talent strategy, minimizing mis-hires

Tim’s leadership style reflects Chicago’s blend of ambition and practicality. He understands that growth can’t come at the expense of culture—and that HR leaders need sales executives who respect the human side of scale.

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🟣 Calvin Steinhoff

Fractional Chief Sales Officer & VP of Sales, GDS Link

Calvin “Cal” Steinhoff brings a global revenue lens to the Chicago market, shaped by experience leading sales across regions, industries, and growth stages.

In his role with GDS Link, Cal operates as both strategist and operator—balancing executive-level planning with hands-on leadership. His background reflects a deep understanding of how sales infrastructure must adapt as organizations mature, especially when international expansion or complex buyer journeys are involved.

For HR leaders, Cal’s work is particularly valuable in moments of organizational transition.

Defining aspects of Cal’s leadership include:

🔹 Experience aligning North American sales strategy with global business objectives

🔹 Clear frameworks for role clarity and performance expectations, reducing internal friction

🔹 Strong emphasis on leadership communication during periods of change

🔹 Ability to translate executive strategy into frontline execution

Cal’s presence as a fractional CSO helps Chicago organizations bridge the gap between ambition and readiness—ensuring teams are built, supported, and led with intention.

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🟣 Mark Crompton

Fractional Sales Leader, Sales Xceleration

Mark Crompton exemplifies the operator-advisor hybrid that many mid-market Chicago companies need but struggle to find.

As part of Sales Xceleration, Mark brings a proven methodology paired with real-world leadership experience. His work often centers on organizations that have outgrown founder-led sales but aren’t ready—or willing—to gamble on a full-time executive hire.

From an HR standpoint, Mark’s engagements tend to stabilize environments that feel chaotic.

Key strengths include:

🔹 Building repeatable sales processes that reduce reliance on tribal knowledge

🔹 Partnering with HR to define sales competencies and performance standards

🔹 Coaching sales leaders through mindset shifts required for scale

🔹 Helping organizations professionalize without losing momentum

Mark’s Chicago sensibility shows up in his straightforward communication and respect for time—traits that resonate deeply with HR and executive stakeholders alike.

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🟣 Matt Balducci

Fractional VP of Sales, 11th Hour Consulting

Matt Balducci’s work at 11th Hour Consulting reflects a deep understanding of what happens when companies wait too long to invest in sales leadership—and how to recover without burning teams out.

Matt often steps into high-pressure, high-expectation environments, where growth goals are aggressive and internal alignment is fragile. His approach balances urgency with empathy, making him a valuable partner for HR leaders navigating morale, turnover, or rapid hiring.

Distinctive elements of Matt’s leadership include:

🔹 Calm, structured leadership during periods of revenue stress

🔹 Focus on sales enablement as a retention strategy, not just a performance tool

🔹 Clear communication that helps reduce anxiety across sales and HR teams

🔹 Practical execution plans that create early wins and rebuild confidence

Matt’s Chicago-area experience lends him credibility with teams who value honesty and follow-through over flashy promises.

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🟣 Mike Lindert, MBA, CSL

Fractional VP of Sales, Sales Xceleration®

Mike Lindert brings an analytically grounded, credibility-driven approach to fractional sales leadership.

With advanced credentials and deep experience inside Sales Xceleration®, Mike is known for helping organizations replace guesswork with data-informed decision-making. His work often intersects closely with HR functions responsible for performance management and leadership development.

Highlights of Mike’s approach:

🔹 Strong emphasis on metrics that matter, not vanity dashboards

🔹 Alignment of compensation, incentives, and behavior

🔹 Clear frameworks for evaluating sales talent objectively

🔹 Support for HR leaders seeking defensible, transparent performance criteria

Mike’s style appeals to Chicago organizations that value rigor, accountability, and professionalism.

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🟣 David Hughes

Fractional Vice President

David Hughes brings a steady, people-first leadership presence to fractional sales engagements.

While his title may be succinct, his impact is anything but. David often works with organizations that need leadership maturity—helping teams move from reactive selling to intentional growth.

Key characteristics include:

🔹 Strong coaching orientation for frontline managers

🔹 Emphasis on communication clarity and expectation setting

🔹 Respect for organizational culture during periods of change

🔹 Practical leadership that HR teams can support and scale

David’s work reflects a belief that sales performance improves when people feel supported, understood, and challenged appropriately.

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🟣 Amy Shulman

Fractional Sales Leadership, Shulman Consulting

Amy Shulman brings a consultative, insight-driven approach to fractional sales leadership that aligns naturally with HR priorities.

Through Shulman Consulting, Amy focuses on helping organizations refine not just how they sell—but how they think about value, relationships, and long-term growth.

Notable aspects of Amy’s work include:

🔹 Strong alignment between sales messaging and employer brand

🔹 Thoughtful coaching that builds confidence and capability

🔹 Focus on collaboration across sales, marketing, and HR

🔹 Emphasis on ethical, relationship-based selling

Amy’s leadership style resonates in Chicago’s professional services and B2B ecosystems, where trust and reputation matter deeply.

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🟣 Michael Elliott

Fractional Sales Leader, Revenue Innovation

Michael Elliott’s work at Revenue Innovation reflects a passion for modernizing how sales teams operate—without losing the human element.

Michael often partners with organizations ready to rethink outdated sales models and embrace innovation grounded in real behavior change.

Key contributions include:

🔹 Reframing sales challenges as organizational challenges

🔹 Helping HR teams support adoption of new tools and processes

🔹 Strong emphasis on enablement, not enforcement

🔹 Clear communication that helps teams buy into change

Michael’s approach fits well with Chicago companies navigating modernization while protecting culture.

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Why Digital Reference Fits Into This Conversation

Across all of these leaders, one theme is consistent: credibility matters. HR teams, executives, and boards want more than polished resumes—they want proof of impact, transparency of leadership style, and insight into how people actually show up.

That’s where Digital Reference comes in.

We help organizations and consultants alike move beyond static credentials through:

• Structured, shareable professional references
• Video-based context that reveals leadership style
• Tools that support radical authenticity and trust

If you’re exploring fractional sales leadership—or building credibility as one—our platform exists to support smarter, more human decisions. You can learn more about our philosophy on the Digital Reference or dive deeper into:

• Best Fractional CROs in Chicago
• Sales & Business Development Consultants in Chicago to Watch
• Best Fractional Sales Directors & Fractional VPs of Sales

Chicago’s business community deserves leadership that’s proven, transparent, and human. We’re proud to support that standard—and to spotlight the fractional CSOs helping shape the region’s future.