Professional Services
Technology, Information and Media
Financial Services
Holding Companies
Active

Michael Fleishman

CEO / CRO

About Me

Michael Fleishman is a senior CEO and CRO-level operator with 25+ years of experience driving growth, turnarounds, and transformation across SaaS, FinTech, Generative AI, Cloud, and professional services organizations. He has scaled businesses from $10M to $2B+ in revenue, led global teams of 3,000+, and delivered measurable outcomes for public companies, PE-backed firms, and global enterprises — often stepping in during periods of inflection, complexity, or change. Michael has deep experience leading revenue transformation, go-to-market redesign, operational restructuring, and post-acquisition integration (20+ acquisitions). As CEO of Mastech InfoTrellis, he drove double-digit EBITDA expansion and launched AI-enabled data and analytics services. At Cognizant, he ran a $2.3B digital transformation portfolio spanning banking, data, and cloud services. Today, Michael partners with founders, CEOs, boards, and investors in interim, advisory, and project-based roles — helping companies accelerate revenue, professionalize execution, build leadership teams, and apply AI and automation pragmatically to improve performance. His style combines hands-on execution with executive-level judgment, making him particularly effective in high-stakes, time-bound engagements where clarity, speed, and outcomes matter.

Jurisdiction

United States

Experience

Seniority LevelC-Suite
Years of Experience20+ years
Current StatusActive
CEOMastech Infotrellis
2022 - 2024

• Led a $100M P&L and 1,000+ global employees for a NYSE-listed data modernization and engineering company. • Repositioned the business toward higher-margin Data, GenAI, and Agentic AI solutions, shifting both GTM and delivery models. • Drove EBITDA expansion from 11% to 23% through pricing discipline, delivery modernization, and operating-model changes. • Rebuilt the go-to-market organization, improving client retention from 82% to 98% and strengthening enterprise pipeline quality. • Launched AI-enabled offerings and deepened strategic partnerships with AWS, Azure, and GCP. • Upgraded leadership structure, operating cadence, and accountability across sales, delivery, and operations.

Head of Data & Analytics Banking Financial Services (BFS) North AmericaCognizant
2021 - 2022

• Owned a $2.3B Data, AI, and Cloud portfolio serving Tier-1 banking and financial services clients. • Led 3,200+ global team members across sales, delivery, and engineering in a highly regulated enterprise environment. • Drove double-digit growth while modernizing analytics and AI operating models across large financial institutions. • Operationalized GenAI and Agentic AI adoption, introducing accelerators that improved delivery velocity and solution reuse. • Expanded hyperscaler partnerships and joint solutions, increasing enterprise adoption across banking clients. • Worked directly with C-suite stakeholders to align GTM strategy, operating cadence, and transformation outcomes.

Independent Executive AdvisorIndependent Executive Advisor
2024 - Present

• Advised CEOs, CROs, and PE/VC operating partners on enterprise Digital, GenAI, and Agentic AI transformation, aligning AI strategy directly to revenue growth, operating efficiency, and margin expansion. • Led AI-first GTM and operating-model redesigns, embedding GenAI and agentic workflows across sales execution, RevOps, service delivery, and customer expansion motions. • Designed and executed Agentic AI use cases (revenue intelligence, deal support, pipeline governance, delivery automation, IT and MSP modernization) moving clients from experimentation to production. • Diagnosed and resolved growth and execution bottlenecks through time-bound executive engagements, delivering measurable improvements in ARR growth, forecast accuracy, productivity, and retention. • Partnered with leadership teams to modernize digital architectures, integrating AI, automation, and cloud platforms into scalable, secure, and compliant operating environments. • Supported pricing, packaging, and monetization transformation informed by AI-driven insights, ICP segmentation, and usage-based expansion strategies. • Served as interim executive leadership (CRO / GM / CEO coverage), stabilizing organizations during transition while introducing AI-enabled cadence, metrics, and decision systems. • Led commercial and technical AI diligence for PE and VC firms, assessing AI readiness, data maturity, operating-model gaps, and value-creation opportunities pre- and post-acquisition. • Advised on next-generation MSP and IT modernization strategies, including agentic automation, security, compliance, and AI-driven service orchestration.

Chief Revenue OfficerIgnite Technologies (ESW Capital)
2016 - 2021

• Scaled revenue 917% ($60M → $550M) through a combination of acquisitions, platform monetization, and disciplined commercial execution. • Built and led global sales, pre-sales, and customer success teams from 5 to 60+, establishing repeatable enterprise GTM motions. • Led commercial due diligence on 60+ acquisitions, evaluating revenue quality, pricing models, customer concentration, and expansion potential. • Implemented standardized commercial and monetization frameworks across a multi-product portfolio, improving pricing discipline, renewals, and cross-sell performance. • Unified packaging and GTM strategy across acquired products, accelerating cross-product expansion and share-of-wallet growth. • Partnered closely with PE ownership on growth strategy, forecasting, and operating cadence across a highly acquisitive platform.

Global VP Sales, Cybersecurity & Service ManagementUnisys
2014 - 2016

• Led a 200+ person global sales organization, driving enterprise software and services growth across security and service management portfolios. • Grew annual revenue 28% to $960M+, expanding footprint within large global accounts and regulated enterprises. • Commercialized cybersecurity and SaaS offerings, positioning them effectively within long-cycle, multi-stakeholder enterprise buying environments. • Strengthened large-account pursuit discipline, improving qualification, deal governance, and executive-level sales execution across regions. • Managed complex global deal cycles, partnering with delivery, product, and operations teams to ensure execution alignment and deal success.

VP Sales, North AmericaVirtusa
2012 - 2014

• Scaled the North America business from $75M to $225M, driving growth across enterprise accounts and strategic verticals. • Launched and scaled Application Managed Services (AMS) and cloud transformation offerings, expanding recurring revenue and deal size. • Strengthened solutioning governance and deal qualification, improving win rates and execution consistency across the region. • Built and led regional sales and delivery leadership, aligning GTM strategy with execution and client outcomes. • Partnered with clients on digital transformation initiatives, positioning Virtusa as a strategic services partner rather than staff augmentation.

Head of North America & Chief Revenue OfficerCyient
2010 - 2012

• Owned full P&L responsibility for North America, scaling revenue 421% to $236M across strategic enterprise accounts. • Built and executed the regional GTM model, strengthening sales execution, account expansion, and pipeline discipline. • Drove share-of-wallet growth within key clients through improved account planning and cross-service expansion. • Led organizational scale across sales, delivery, and operations to support rapid growth without degrading execution quality. • Partnered closely with global leadership to align regional growth strategy with broader corporate objectives.

Senior Sales Leadership RolesIBM
1997 - 2010

• Led large, complex portfolios up to $1.7B across software, hardware, and services, supporting enterprise and public-sector clients. • Managed and scaled global teams of 400+, operating across sales, delivery, and client engagement functions. • Played a senior role in multi-year modernization programs as IBM transitioned toward software- and services-led growth models. • Worked closely with executive stakeholders to align go-to-market strategy, delivery execution, and client transformation outcomes. • Gained deep exposure to regulated enterprise environments, long sales cycles, and large-scale technology transformation initiatives.

Education

Degree of Aerospace EngineeringBoston University
1990 - 1994
Masters of Management & TechnologyRensselaer Polytechnic Institute
1997 - 1999

Skills

Core skills1
Languages1

Skills

• Executive Leadership (CEO & CRO Roles) • Generative AI & Digital Transformation Strategy • SaaS & Cloud Go-to-Market Leadership • Private Equity Growth & Value Creation • M&A Strategy & Post-Acquisition Integration • Enterprise & Hyperscaler Partnerships (AWS, Azure, GCP) • Professional Services & IT Consulting Growth • P&L Oversight up to $2.3B • Global Sales & Revenue Operations (North America, EMEA, APAC) • Building High-Performance Executive Teams

Languages

English

Services