ROBERT CALABRESE

Enterprise Sales Leader | Strategic Partnership Executive | GTM Strategist
Stamford, US.

About

A highly accomplished Enterprise SaaS Sales Executive with 15+ years of experience driving significant revenue growth, strategic partnerships, and market expansion within cybersecurity, SASE, SSE, and AI-powered infrastructure. Proven leader in full-cycle sales execution, consistently exceeding quotas and closing multi-million dollar deals by leveraging deep expertise in partner-led GTM strategies, cross-functional collaboration, and executive alignment with Fortune 500 CIOs, CISOs, and CTOs. Adept at applying MEDDPICC and value-based selling to align complex technologies with critical business objectives and deliver transformational outcomes.

Work

Plixer
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VICE PRESIDENT OF GLOBAL SALES

Summary

Led global enterprise sales and strategic technology partnerships as a quota-carrying player-coach for Plixer's network observability platform across hybrid multi-cloud environments.

Highlights

Drove significant business growth by embedding MEDDPICC rigor, achieving a 17% YoY revenue increase, reducing customer churn by 28%, and improving Net Revenue Retention (NRR) from 87% to 104%.

Designed and executed a full-funnel Go-to-Market (GTM) strategy that expanded market adoption across financial services and other highly regulated industries.

Launched and scaled a global partner enablement program, fostering joint innovation and aligning strategic technology partnerships with product roadmap evolution.

Led cross-functional account teams, including Solutions Architects and Product Management, to develop long-term account strategies and deliver transformational outcomes for global financial services clients.

Orchestrated executive Quarterly Business Reviews (QBRs) and internal stakeholder Monthly Business Reviews (MBRs) to ensure strategic alignment with top-tier partners and key customers.

ExtraHop Networks
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MAJOR ACCOUNT EXECUTIVE

Summary

Managed strategic enterprise relationships and expanded adoption of Network Detection and Response (NDR) solutions across highly regulated industries, including financial services.

Highlights

Exceeded annual quota by 116%, closing $1.9M in revenue in 2022 and earning President's Club recognition; achieved top-performer honors in Q1 2023 by booking $1.2M (66% of annual target) in a single quarter.

Acted as a trusted strategic advisor to CIOs, CISOs, and business unit stakeholders, guiding complex account planning and fostering internal influence efforts.

Negotiated multi-year, enterprise-wide agreements, integrating NDR solutions into clients' broader digital transformation and cloud migration initiatives.

Led account mapping and stakeholder alignment initiatives, driving quarterly review cadences that surfaced upsell and cross-sell opportunities across distributed teams.

Imperva
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NAMED ACCOUNT MANAGER

Summary

Reignited growth within a dormant SLED and enterprise territory by repositioning Imperva's platform within partner ecosystems and customer transformation initiatives.

Highlights

Delivered a 4.5x pipeline increase and secured $1M in bookings by strategically aligning technology solutions with client compliance and risk management goals.

Activated comprehensive stakeholder engagement plans and formal Quarterly Business Review (QBR) cadences, integrating partner-delivered messaging with Imperva's security roadmap.

Collaborated cross-functionally with Marketing, Channel, and Product teams to successfully relaunch the brand in key regions, leading to the formation of a new dedicated SLED team across multiple U.S. territories.

LogRhythm, Inc.
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REGIONAL SALES MANAGER

Summary

Built new market presence for SIEM and security analytics in the Northeast by establishing a partner-led Go-to-Market (GTM) model in a competitive, greenfield territory.

Highlights

Generated $4.8M in pipeline within nine months and closed $2M in Annual Recurring Revenue (ARR), onboarding 10 new enterprise clients and earning President's Club honors.

Successfully displaced entrenched competitors through value-based positioning, establishing a strong foothold in a greenfield territory.

Executed comprehensive stakeholder mapping and coordinated multi-touch engagement strategies across procurement, security, and risk functions.

Orchestrated internal and partner teams to align on customer sourcing strategies, legal negotiations, and deployment frameworks, accelerating deal closure and streamlining adoption.

Akamai, Inc.
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ENTERPRISE ACCOUNT EXECUTIVE

Summary

Drove Zero Trust and cloud security adoption across Fortune 500 accounts during critical digital transformation cycles.

Highlights

Closed $1.9M in Annual Recurring Revenue (ARR) and successfully uncovered hidden cross-sell potential through strategic executive alignment and long-term roadmap planning.

Led strategic, multi-threaded sales efforts, effectively targeting and engaging senior technology decision-makers, including CISOs, CTOs, and CIOs within Fortune 500 accounts.

Co-developed scalable solution roadmaps with key partners like KPMG, Accenture, IBM, and AT&T, driving long-term growth initiatives.

Facilitated robust internal collaboration across product, sales, and channel teams to support co-innovation initiatives and influence overall partner strategy.

Smartling, Inc.
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ENTERPRISE ACCOUNT EXECUTIVE

Summary

Accelerated SaaS adoption for localization and content automation solutions through aggressive new business development and consultative selling strategies.

Highlights

Consistently ranked as a top-performing sales executive, achieving 110% to 150% of quota between 2015 and 2017, and reaching 56% of annual quota in Q1 2018.

Acquired 55 new enterprise accounts and increased average deal size by 38% by strategically aligning product functionality with key customer goals.

Maintained 90% forecast accuracy through disciplined pipeline governance and structured sales cadences, ensuring reliable revenue forecasting.

Led comprehensive account expansion initiatives through proactive stakeholder management, Quarterly Business Review (QBR) planning, and post-sale enablement.

Education

Berkeley College

B.B.A.

Business Management

Grade: Phi Theta Kappa, National Honors Society, President's List, Dean's List

Certificates

Life, Health, & Accident Insurance License
MEDDPICC
Sandler Sales Training
The Challenger Sale
Force Management; Command of the Message
Value Selling
CoachMEdia
Series 3, 7, 63, & 65

Skills

Sales Methodologies

Net New Logo Acquisition, Full-Cycle Enterprise Sales, MEDDPICC, Value-Based Selling, Solution Selling, Complex Deal Negotiations, Pipeline Growth & Forecasting, Enterprise Pipeline Development, Territory Expansion.

Strategic Sales & Partnerships

Strategic Account Development, GTM Strategy Development & Execution, Channel & Partner Ecosystem Strategy, Executive Relationship Management (CIO/CTO/CISO), Go-To-Market Strategy Execution.

Technical & Industry Expertise

Zero Trust Architecture, Cloud Security, Digital Transformation, Cybersecurity, SASE, SSE, AI-powered Infrastructure, Network Observability, NDR Solutions, SIEM, Security Analytics.

CRM & Sales Tools

Salesforce.