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
Work Experience
Chief Revenue Officer
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.
Chief Operating Officer, Cognizant Digital Business
Cognizant
- 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.
President, Cognizant Accelerator
Cognizant
- 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.
Chief of Staff
Cognizant
- 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.
Management Consultant
PwC
- 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).
Education
Master's Degree in Business Administration (MBA)
The Wharton School of the University of Pennsylvania - Philadelphia, PA, USA
Bachelor's Degree in Computer Science
Cornell University - Ithaca, NY, USA
Skills
Finance
Startup Funding, M&A (Buy-side), Pricing Strategy, Market Research, M&A (Sell-side), M&A Modeling, Venture Funding, Revenue Modeling, Due Diligence, Pricing, M&A Reporting, Cross-border M&A, M&A Earn-out Agreements, Mergers & Acquisitions (M&A), Profit & Loss (P&L), P&L Forecasting
Other
Strategy, Sales, Client Services, Clients, Client Success, Delivery, M&A Strategy, Startups, Lean Startups, Enterprise Startups, Information Systems, IT Services, Growth, Consulting, Startup Consulting, Startup Growth Strategy Development, Digital Services, Management Consulting, Executive Consulting, Business Consulting, Business Plan Consulting, Investment Consulting, IT Consulting, Sales Strategy, Sales Growth, Tech Sales, Chief Operations Officer (COO), Key Performance Indicators (KPIs), Go-to-market Strategy, Microsoft, Google, Slack, Marketing, Finance, Commission Planning, Sales Commission Structure, Human Resources (HR), Enterprise SaaS, SaaS, Software Sales, Software Engineering, Digital Marketing, Investor Relations, Information Security, Pricing, Growth Strategy, Engineering, Programming, Databases, Artificial Intelligence (AI), Legal, Penetration Testing, Financial Analysis, Innovation, Software Design, Managed Services, Mobile, Analytics, Internet of Things (IoT), Enterprise, Enterprise Software, Staffing, Staff Management & Development, Revenue Strategy, Client Management, Client Relations, Teams, Team Building, Team Mentoring, Team Leadership, Team Management, Team Development, Team Restructuring, Education, Educational Platform Design, Training, Training Content, Employee Training, Training Materials, Training Workshops, Due Diligence Consultant, M&A Due Diligence (Financial), M&A Due Diligence (Technology), Innovation Labs, Innovation Promotion, Innovation Strategy, Disruptive Innovation, Software Innovation, Innovation Management, Innovation Workshops, Early-stage Venture Capital, Business, Business to Business (B2B), Small & Medium-sized Enterprises (SME), Integration, Costs, Cost Cutting (Cost-out), Optimization, Process Optimization, Pricing Optimization, Profit Optimization, OrgChart, Organizational Design, Organization Building, Organization Assessment, IT Strategy, M&A Value Creation, P&L Management, P&L Analysis, P&L Responsibility
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