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Fractional CROs in Boston Making Things Happen in 2025
Boston Interim Chief Revenue Officers to Know
In the fast-moving world of growth-stage startups and mid-market companies, agility isn't just a competitive advantage—it's survival. Nowhere is that more evident than in the evolving world of revenue leadership. Enter the Fractional Chief Revenue Officer (CRO): part operator, part strategist, and all-in on helping companies scale without the full-time overhead. And in Boston—a region long known for its intellectual capital, innovation economy, and deep tech roots—these CROs are quietly making big things happen.
At Digital Reference, our goal is to demystify the often opaque world of independent executive talent. We’re curating the go-to lists of trusted professionals who are shaping how modern companies operate. In this edition, we’re highlighting a handpicked group of Fractional CROs operating in Boston. Each of these leaders brings a unique combination of sales leadership, go-to-market strategy, and operational know-how that makes them worth knowing.
Our Methodology
This list is the result of both direct research and on-the-ground conversations with founders, investors, and other fractional operators. We looked for professionals who:
- Have a strong presence in the Boston metro and New England area
- Are actively consulting or operating as fractional or interim CROs
- Have a demonstrated track record of success in revenue leadership roles
- Are accessible as independent operators or founders of small consultancies
This is not a list of every fractional CRO in Boston—instead, it’s a vetted snapshot of the people who we believe are doing meaningful work in this space, right now.
Let’s meet the Fractional CROs in Boston making things happen.
Terry Ladisheff
Terry Ladisheff is the founder of Sunrise Revenue, a boutique firm that partners with B2B companies to unlock scalable growth. With experience leading sales organizations in both startups and enterprise environments, Terry brings a hybrid approach to sales and marketing alignment. He’s known for bringing structure to chaos, helping early-stage and Series A companies build repeatable revenue motions. Based in the Greater Boston area, Terry is also a regular collaborator with GTM teams across sectors including SaaS, cybersecurity, and professional services.
If your team is feeling the growing pains of inconsistent pipeline or unclear sales strategy, Terry brings the frameworks and operational rigor to get you unstuck.
Christopher Simone
Christopher Simone is a versatile revenue leader who’s walked the path from sales rep to CRO. Now operating as a fractional executive, he works closely with founders and CEOs to align sales, marketing, and customer success under a single revenue umbrella. Christopher's approach is deeply collaborative—he embeds himself in leadership teams to diagnose and design growth strategies that fit.
He has particular depth in complex sales environments and industries like fintech and healthtech, where multiple stakeholders and long sales cycles are the norm. Boston-based and well-networked, Christopher is the kind of fractional CRO who thrives in hands-on, fast-changing environments.
Thomas Libby
Thomas Libby is a small business sales specialist with a long-standing reputation in the New England market. With decades of experience in both sales execution and team leadership, Thomas now focuses on helping small to mid-sized businesses build sales functions from the ground up. His consulting practice emphasizes training, systems, and accountability, making him a valuable partner for founders navigating the shift from founder-led sales to structured teams.
What sets Thomas apart is his deep understanding of sales psychology and coaching. For Boston-area companies looking to grow methodically without losing their customer-first ethos, Thomas brings the rare ability to teach and lead simultaneously.
Raffi Yardemian
With more than 20 years of sales and GTM experience, Raffi Yardemian has built his career at the intersection of strategy and execution. Now operating as a fractional CRO and sales consultant, Raffi helps companies design GTM models that are both scalable and customer-centric. He’s a go-to advisor for growth-stage teams that are ready to go from reactive to proactive in their revenue planning.
Raffi has worked across SaaS, services, and B2B verticals, and he’s especially adept at helping sales leaders gain clarity around forecasting, compensation, and team structure. Whether stepping in to lead during a CRO transition or advising a founder-led team, Raffi brings steadiness and structure to the table.
Mark Rubin
Mark Rubin is a revenue leader turned fractional executive with a passion for driving results through simplicity and focus. With over 25 years in sales and business development roles, Mark now works with CEOs and founders to install clear revenue strategies and KPIs that actually move the needle. He brings a wealth of experience from working with both startups and publicly traded companies, and his Boston roots keep him grounded in a no-nonsense, results-first mindset.
Mark is also a believer in cross-functional collaboration and often plays a role in aligning marketing, product, and customer success around unified goals. For teams struggling with siloed departments or inconsistent execution, Mark is the kind of operator who can build bridges and deliver outcomes.
Why Fractional CROs Matter Now
The rise of the fractional CRO is more than just a hiring trend. It’s a strategic shift in how companies think about growth leadership. Startups don’t always need a full-time CRO. What they need is the right kind of leadership at the right time. Fractional executives offer the flexibility to:
- Test new sales strategies without committing to long-term overhead
- Bring in seasoned expertise during times of transition
- Align internal teams around shared metrics and GTM priorities
As companies continue to navigate uncertainty, fractional leadership is becoming the modern operating model for early- to mid-stage organizations.
Looking for More?
Our editorial lens is built around one simple idea: help professionals make smarter decisions about who they work with and why. Whether you're a founder, a board member, or an operator trying to solve for revenue, this list is a place to start.
And if you're a Boston-based CRO or GTM advisor who thinks you belong on this list? Get in touch. We're always open to new conversations.
Digital Reference is your backstage pass to the evolving world of professional talent. We cover the rise of independent executives, fractional roles, and the future of work with clarity, curiosity, and a little bit of edge.
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