Sean Middleton, Finance Expert in New Canaan, CT, United States
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Sean Middleton

Verified Expert  in Finance

Management Consulting Expert

New Canaan, CT, United States
Toptal Member Since
July 14, 2023

Sean has driven $3 billion+ in new revenue by helping B2B technology leaders grow their businesses. He blends 20 years of experience as a PwC consultant, an operating executive (president) for Cognizant, and the chief revenue officer at Toptal to create and execute market-winning strategies. Working with startups and Fortune 500 companies, Sean has deep expertise in sales, operations, finance, M&A, and the PE/VC ecosystem. He has an MBA from Wharton and a BS in computer science from Cornell.

Career Highlights

Education Highlights

Master's Degree
The Wharton School of the University of Pennsylvania
Bachelor's Degree
Cornell University

Case Studies

Work Experience

Chief Revenue Officer

2020 - 2023
Toptal, LLC
  • Led strategy, sales, client services, service line practices, and delivery across global SMB and enterprise markets resulting in significant revenue growth.
  • Promoted a client-centric culture that prioritized long-term relationships by segmenting clients and restructuring territories to give reps more time with each client.
  • Fostered a consultative sales model that emphasized creating value by solving client problems over transactional staffing fulfillment.
  • Expanded the number of client-facing roles while unifying disparate groups under a common pursuit process emphasizing team-based selling.
  • Built a high-performing client team: set clear expectations, standardized metrics and reporting, provided robust coaching and training, and published career paths that enabled most roles to be filled through internal promotions.
  • Expanded offering portfolio: built a new organizational construct around practices, launched a management consulting category, and expanded depth in multiple technology services to respond to client demand.
  • Collaborated with other executive leaders, including marketing, talent operations, and product.
Focus areas: Strategy, Sales, Client Services, Clients, Client Success, Commission Planning, Sales Commission Structure, Delivery, Startups, Lean Startups, Enterprise, Enterprise Startups, Enterprise Software, Staffing, Staff Management & Development, IT Services, Digital Services, Software Engineering, Tech Sales, Sales Strategy, Sales Growth, Revenue Strategy, Revenue Modeling, Client Management, Client Relations, Teams, Team Building, Team Mentoring, Team Leadership, Team Management, Team Development, Team Restructuring, Analytics, Business Consulting, Business Plan Consulting, Consulting, Enterprise SaaS, Growth, Growth Strategy, Key Performance Indicators (KPIs), Go-to-market Strategy, Market Research

Chief Operating Officer, Cognizant Digital Business

2019 - 2020
  • Led finance, M&A, marketing, human resources, information technology, and facilities for Cognizant's $5 billion digital services division.
  • Doubled the top-line growth rate, reduced overhead cost by 25% to fuel investment, and improved employee morale over 12 months by installing rigorous, financially driven operating discipline.
  • Implemented a review and forecasting cadence with practice leaders to drive transparency and accountability and orient toward data-driven action.
  • Shifted sales toward repeatable solutions that improved value creation and pricing leverage. Built buyer/problem-focused positioning, sales training, and pricing/packaging guidelines to sell on value.
  • Resolved the stalled integrations of 11 companies to bring them back in line with business case targets by creating an M&A operations team and cadence.
  • Created a role-based career lattice that gave 40,000 associates a foundation for advancement and objective, ongoing performance management.
  • Implemented an annual planning process to build account-level revenue and profitability targets and zero-based overhead expenses.
Focus areas: M&A Strategy, M&A (Buy-side), Finance, Human Resources (HR), Sales, Strategy, IT Services, Mobile, Analytics, Artificial Intelligence (AI), Internet of Things (IoT), Software Engineering, Growth, Sales Growth, Growth Strategy, Sales Strategy, Enterprise, Enterprise Startups, M&A Modeling, Integration, Revenue Strategy, Costs, Cost Cutting, Optimization, Process Optimization, Pricing Optimization, Profit Optimization, Pricing, Pricing Consulting, OrgChart, Organizational Design, Organization Building, Organization Assessment, Chief Operations Officer (COO), Key Performance Indicators (KPIs), Go-to-market Strategy, Pricing Strategy

President, Cognizant Accelerator

2012 - 2020
  • Founded this CEO-reporting division and built a portfolio of startup businesses that generated $10 million to $1 billion in revenue and collectively contributed $1.5 billion+ in profitable annual revenue upon graduation.
  • Owned the entire P&L, including strategy, sales and marketing, product engineering and delivery, finance, M&A, operations, and human resources.
  • Created an incubation program that found and screened thousands of ideas each year, built business plans exploring their strategic and financial value, and funded cohorts of aspiring entrepreneurs to launch the most promising products.
  • Built a culture and a financial and operating model that protected, incented, and managed investments that had return horizons of 3+ years against a public company backdrop that prioritized quarterly and annual outlooks.
  • Promoted innovation that took advantage of Cognizant's strengths (e.g., client relationships, domain knowledge, and operating infrastructure) while remaining agile and independent.
  • Chaired Cognizant's investment committee, which allocated and monitored the performance of approximately $500 million.
Focus areas: Startups, Lean Startups, Enterprise Startups, Enterprise SaaS, SaaS, Software Sales, Software Engineering, Digital Marketing, IT Services, Client Services, Software Design, M&A Strategy, M&A (Buy-side), Venture Funding, Growth, Sales Growth, Growth Strategy, Strategy, IT Strategy, Sales Strategy, Revenue Strategy, M&A Reporting, M&A Value Creation, Cross-border M&A, M&A Due Diligence (Financial), M&A Modeling, M&A Earn-out Agreements, M&A Due Diligence (Technology), Mergers & Acquisitions (M&A), Finance, P&L Management, P&L Analysis, P&L Responsibility, Profit & Loss (P&L), P&L Forecasting, Innovation, Innovation Labs, Disruptive Innovation, Innovation Strategy, Innovation Management, Chief Operations Officer (COO), Key Performance Indicators (KPIs), Go-to-market Strategy, Pricing Strategy, Market Research

Chief of Staff

2010 - 2012
  • Built the Office of the CEO infrastructure as Cognizant more than doubled in size from $3.3 to $8.8 billion.
  • Created scale for the CEO by serving as a proxy, advisor, and head of operations, strategic projects, and transformation initiatives.
  • Monitored the performance of business units and the corporate function. Identified, investigated, resolved, and escalated problems.
  • Formalized and ran processes and meetings for quarterly earnings, the board of directors, and executive leadership; served as the primary interface with board members.
  • Led all CEO communications (including ghost and speechwriting) for internal and external stakeholders.
Focus areas: Strategy, Investor Relations, Finance, Marketing, Legal, IT Services, Client Services, Managed Services, Key Performance Indicators (KPIs), Go-to-market Strategy

Management Consultant

2003 - 2010
  • Served as a corporate strategy consultant for Fortune 1000 companies, covering commercial due diligence, market analysis, customer segmentation, pricing strategy, profitability analysis, and innovation strategy.
  • Led teams to analyze technology problems. Architected and delivered solutions to improve business performance and manage risk. Specialized in information security.
  • Ran operations for a startup business unit that grew organically by 35% year-over-year. Served as the lead partner's advisor and proxy and oversaw business performance reviews, budgeting, and investment allocation and reviews.
  • Progressed rapidly from the associate level to a director-level consulting leader by receiving promotions every two years (on average).
Focus areas: Information Security, Information Systems, Penetration Testing, Strategy, M&A Strategy, M&A (Sell-side), IT Services, Business Consulting, Clients, Client Services, Client Success, Enterprise, Key Performance Indicators (KPIs), Go-to-market Strategy, Pricing Strategy, Market Research
2007 - 2009

Master's Degree in Business Administration (MBA)

The Wharton School of the University of Pennsylvania - Philadelphia, PA, USA

1999 - 2003

Bachelor's Degree in Computer Science

Cornell University - Ithaca, NY, USA

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