Best Fractional Chief Sales Officers in Boston

Boston Fractional CSO Services & Fractional Chief Sales Officers

The Boston–Cambridge–Newton corridor has always punched above its weight when it comes to innovation, research, and disciplined growth. This is a region shaped by world-class universities, life sciences, enterprise technology, and B2B companies that value rigor as much as results. In Boston, revenue leadership isn’t flashy—it’s thoughtful, data-driven, and earned over time.

For companies across Massachusetts and southern New Hampshire, revenue growth is rarely about hype cycles. It’s about navigating long sales cycles, sophisticated buyers, regulated industries, and high expectations from investors and boards. That reality has made Fractional Chief Sales Officers (CSOs) an increasingly strategic choice—especially for organizations that need senior revenue leadership without over-committing too early.

At Digital Reference, we focus on how revenue leaders actually perform inside organizations—not just how they describe themselves. Our work is grounded in radical authenticity, verified leadership experience, and human context, helping companies make smarter decisions about who they trust to lead growth. 

This article introduces our curated list of Boston-area Fractional CSOs—a mix of firm-based leaders, solo consultants, and fractional executives who understand how revenue, people, and process intersect in one of the most intellectually demanding markets in the U.S.

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⚾ Our Methodology: How Digital Reference Curated This List of Boston’s Top Fractional Chief Sales Officers

This list was built through intentional research and qualitative evaluation, not sponsorships or automated scraping.

Our methodology includes:

• Deep analysis of LinkedIn career paths to understand progression, specialization, and leadership depth
• Review of websites and advisory offerings to identify real operating focus versus generic sales consulting
• Attention to how each leader discusses teams, enablement, and execution, not just revenue outcomes
• A strong preference for professionals actively serving the Boston–Cambridge–Newton market

We consistently prioritize fractional sales leaders who:

• Have led revenue in complex, credibility-driven environments
• Understand how sales leadership affects hiring, onboarding, and retention
• Communicate clearly with founders, boards, and non-sales stakeholders
• Align with Digital Reference’s belief that trust is built through transparency and proof

The professionals below are not ranked. Each brings a distinct revenue leadership style shaped by Boston’s emphasis on depth, discipline, and long-term value creation.

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🌟 Meet the Top Boston Fractional Chief Sales Officers

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🔵 Ray Ritter

Managing Director of Fractional Sales Leadership at King & Bishop

Ray Ritter brings a measured, enterprise-grade approach to fractional sales leadership that fits naturally within Boston’s business culture.

At King & Bishop, Ray operates at the intersection of talent, strategy, and execution—helping organizations strengthen sales leadership without sacrificing rigor. His background reflects extensive experience guiding revenue teams through complexity, change, and growth.

What distinguishes Ray’s work is his focus on leadership effectiveness, not just sales output.

Key characteristics include:

🔹 Designing sales leadership structures that scale with the business

🔹 Helping organizations align sales roles with real buyer behavior

🔹 Strong partnership with HR and executive leadership

🔹 Emphasis on accountability, clarity, and repeatability

Ray’s approach resonates with Boston organizations that value thoughtful growth over quick wins.

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🔵 Steve Osterman

Fractional CRO / CSO, The Sales Solutions Group LLC

Steve Osterman brings full-funnel revenue leadership to companies that need alignment across sales, marketing, and operations.

Through The Sales Solutions Group, Steve works with organizations navigating revenue complexity—often stepping in where growth has stalled or leadership gaps exist. His background reflects a strong command of both strategy and hands-on execution.

Steve’s work is particularly impactful in mid-market environments.

Notable strengths include:

🔹 Aligning sales strategy with operational reality

🔹 Helping leadership teams move from reactive to proactive growth

🔹 Establishing forecasting discipline and revenue visibility

🔹 Supporting sales leaders through change and scale

Steve’s leadership style fits Boston’s expectation for competence, preparation, and follow-through.

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🔵 Brian Fiske

Fractional CSO / CEO & Advisor, Fiske Biotech Consulting

Brian Fiske brings deep biotech and life sciences expertise to fractional sales leadership—a critical asset in the Boston-Cambridge ecosystem.

Through Fiske Biotech Consulting, Brian helps science-driven organizations translate innovation into commercial success. His background reflects years of working in regulated, technically complex environments where credibility and precision matter deeply.

Brian’s leadership stands out for its fluency in both science and sales.

Key aspects include:

🔹 Bridging technical teams and commercial strategy

🔹 Leading revenue efforts in regulated markets

🔹 Helping founders and scientists navigate go-to-market decisions

🔹 Building sales motions grounded in trust and evidence

Brian’s work is especially valuable in Boston’s biotech and medtech corridors.

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🔵 Annette Iafrate

Freelance Fractional / Interim VP, Partnerships & Channel Sales

Annette Iafrate brings partner-led growth expertise to fractional sales leadership.

Her work focuses on building and scaling channel strategies—an often underdeveloped but powerful lever for revenue growth. Annette’s background reflects deep experience managing alliances, partnerships, and indirect sales motions.

Key strengths include:

🔹 Designing partner ecosystems that actually perform

🔹 Aligning sales and partnerships under shared goals

🔹 Helping organizations avoid channel conflict

🔹 Supporting long-term, relationship-based revenue

Annette’s leadership is especially relevant for Boston companies expanding through alliances.

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🔵 Jess Toomey, MBA

Fractional Director of Sales at Clusivi

Jess Toomey brings a people-first, inclusive approach to fractional sales leadership.

At Clusivi, Jess focuses on building sales organizations that perform without burning people out. Her background reflects a strong emphasis on leadership development, communication, and culture.

Notable aspects of Jess’s work include:

🔹 Coaching sales managers to lead with empathy and clarity

🔹 Designing sales systems that support diverse teams

🔹 Aligning performance expectations with human sustainability

🔹 Supporting growth through trust and transparency

Jess’s approach resonates strongly in Boston’s values-driven organizations.

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🔵 Kelly Bottenfield

Fractional Sales Executive & Co-Founder at The Honey Pot Company

Kelly Bottenfield brings a founder-operator mindset to fractional sales leadership.

As a co-founder of The Honey Pot Company, Kelly understands revenue from the inside out—combining brand building, sales execution, and leadership responsibility. Her experience reflects real entrepreneurial accountability.

Key characteristics include:

🔹 Building sales strategies aligned with brand identity

🔹 Leading with authenticity and conviction

🔹 Helping organizations scale without losing their voice

🔹 Strong understanding of consumer and B2B crossover dynamics

Kelly’s leadership style adds depth to Boston’s revenue ecosystem.

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🔵 Ryan Sullivan

Fractional Sales Leader & Founder at Ratchet Ventures

Ryan Sullivan brings a modern, execution-focused approach to fractional sales leadership.

Through Ratchet Ventures, Ryan helps companies tighten their go-to-market motion and accelerate revenue without unnecessary complexity. His work often centers on momentum—turning strategy into measurable progress.

Defining strengths include:

🔹 Simplifying sales processes for faster execution

🔹 Helping teams focus on what actually moves revenue

🔹 Strong alignment with founders and operators

🔹 Clear communication that builds confidence

Ryan’s approach fits Boston’s bias toward clarity and action.

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Why Digital Reference Matters for Revenue Leadership in Boston

In a market like Boston, credibility compounds. Buyers are informed, leaders are scrutinized, and trust is earned through consistency—not claims.

Digital Reference exists to make professional credibility more transparent and human. We help organizations move beyond resumes and titles through structured references, real context, and tools designed to show how leaders actually operate.

👇 Continue exploring Digital Reference resources:

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

Boston companies don’t chase growth blindly—they build it carefully. We’re proud to support the fractional sales leaders helping organizations scale with discipline, integrity, and intention.