Summary
Overview
Work History
Education
Skills
Accomplishments
Timeline
Generic

Justin Squezello

Raleigh,NC

Summary

Accomplished leader with a robust background in revenue operations and strategic planning. Recognized for implementing data-driven initiatives that enhance operational efficiency and drive predictable and scalable revenue growth.

Overview

19
19
years of professional experience

Work History

SVP Revenue Operations

Medallia
05.2024 - 08.2025
  • Evaluated current systems and processes to identify opportunities for streamlining operations.
  • Built and executed on bookings targets, top/down bookings models, territory carves, quotas, comp plans, and communication cascade in the first 60 days. Year-end actuals were within 5% of target.
  • Built GTM Operations Center of Excellence (CoE) inclusive of standing up teams from scratch (e.g. Strategy & Planning and Analytics), redefining existing scope (e.g. GTM Tools & Programs), and refining roles/responsibilities and levelling (e.g. Deal Desk, Variable Comp) which provided clarity of responsibilities and developmental paths resulting in doubling Employee Engagement scores.
  • Established and optimized a recurring forecasting cadence that ultimately resulted in the business repeatedly hitting or exceeding its forecast.
  • Partnered with sales leadership to optimize variable compensation plans, and established a skills and performance framework with accompanying reporting that clarified performance measures for sellers giving front line leadership unprecedented telemetry to performance manage their teams.
  • Advocated and drove a data driven program to re-segment all customer accounts and sales territories resulting in year over year growth in pipeline generation and reducing SFDC account records from 80k to 12k.
  • Established GTM Rules of Engagement documentation, and accompanying optimization process, which served as a playbook for all GTM teams across the customer value lifecycle resulting in nearly doubling the beginning of quarter pipeline at a proposal or negotiation stage.

Sr. Director, Strategy & Operations

Twilio
01.2021 - 01.2024
  • Built and optimized a global business operations team across Product, R&D, and GTM to support Twilio's Contact Center software business.
  • Championed change management efforts to facilitate smooth transitions during restructuring.
  • Formalized operating rhythms, documented rules of engagement, and playbooks across the customer value lifecycle to support rapid growth.
  • Formalized models and forecasting processes to consistently and reliably forecast bookings that had otherwise been unpredictable.
  • Drove sales playbooks that clarified all GTM teams' roles and responsibilities, and clarified enter/exit criteria across all stages of the customer value lifecycle.
  • Built and maintained the Product/R&D Plan of Record (i.e., single source of truth) and related mechanisms to track quantifiable results across R&D (OKRs, metrics across the product lifecycle, product roadmap decomposition, etc.), which led to unprecedented visibility into roadmap delivery and ultimately a greater than 30% reduction in scope changes and more than 2 months of acceleration in schedule delivery.
  • Collaborated with executive leadership team to develop long-term objectives that would drive success.

Vice President - Revenue Operations

Pipedrive
01.2018 - 01.2020
  • Built GTM operations teams inclusive of strategy and planning, business analysis, data engineering, and program management from inception across the US, EU, and UK locations.
  • Instrumented variable compensation plans and recurring operating rhythms across all GTM teams, which resulted in doubling top-line revenue.
  • Built consistently accurate and reliable models across the customer value lifecycle, from marketing to sales to customer adoption/deployments to customer retention/expansion, which were leveraged heavily for GTM strategy and product roadmap planning.
  • Established granular campaign tracking of marketing acquisition by lead source, leading to a 20% growth in new customer ARR from paid acquisition channels, while driving down cost per acquisition by 25%.
  • Partnered with the CRO and CFO to formalize and track all variable compensation plans and performance.
  • Oversaw budget planning to align resources with business objectives and priorities.

COO

Suzie
New York, NY
01.2015 - 01.2017
  • Oversaw daily operations to ensure efficiency across all departments.
  • Lead efforts to optimize pricing and packaging, resulting in a 20% increase in average contract value.
  • Rebuilt variable compensation plans to align sales and customer success with aligned incentives across the customer lifecycle.
  • Formalized playbooks to support customer lifecycle management from first touch MQL to renewal, resulting in accelerated sales velocity, cutting quote to close in half, reducing time to customer onboard in half, and improving customer retention by 25%.
  • Established relational forecasting models and KPI reporting mechanisms across Marketing, Sales, and Customer Success.
  • Streamlined billing and collections processes, which resulted in accelerating cash flow.
  • Participated in development of new products, services through collaboration with marketing, R&D teams.
  • Presented quarterly progress updates at board meetings outlining successes achieved since last report.

Vice President - Finance & Revenue Operations

IAC/Interactive Corp.
New York, NY
01.2007 - 01.2015
  • Identified and executed on acquisition synergies of About.com, which increased operating margin by 30% year-over-year within 6 months post-acquisition close.
  • Led and executed a revived GTM plan and organizational design for About.com, which resulted in a 70% increase in revenue and a 40% favorable EBITDA, in lieu of a 40% higher headcount two years post-acquisition.
  • Lead acquisition integration of GTM and back-office tools (e.g., ERP migration from Great Plains to Oracle, SFDC migration, GL chart of accounts).
  • Executed an audit of the quote-to-cash process, leading to accelerated billings, collections, and a shored-up month-end close process from 3 weeks to 2 days.
  • Optimized forecasting variances from greater than 20% to consistently less than 5%.
  • I built the Financial Planning and Accounting teams from the ground up for the Pronto.com BU.
  • Supported the international GTM expansion of Pronto.com into the UK, EU, and APAC, resulting in scaling revenue from $100MM to $200MM.
  • Executed ERP and CRM system migrations, which expedited monthly close from 3 weeks to 2 days, expedited billing and cash collections, and erased massive forecasting and accrual variances.
  • Implemented processes to support capitalizing R&D wages, which resulted in substantive relief to the P/L.
  • Lead the organizational restructuring of the Ask.com Business Unit.
  • Lead the financial and GTM restructuring of IAC Advertising and Evite.com, which resulted in sequential revenue growth for the first time in years, margin expansion, and a turnaround to profitability in less than one year, resulting in a $200M divestiture.
  • Restructured and simplified compensation plans, which drove clarity and alignment to incentives and business outcomes.
  • Successfully executed complicated billing, order management, and ad server migration simultaneously. Workflow controls and system efficiencies accelerated cash collections from 120 days to 45 days, and reduced operating expenses by 40%.

Education

Bachelor of Arts - ADVERTISING, Psychology

MARIST COLLEGE
Poughkeepise, NY

Executive Education - Mergers & Acquisitions

THE WHARTON SCHOOL - UNIVERSITY OF PENNSYLVANIA
Philadelphia, PA

Skills

  • Strategic planning
  • Operational excellence
  • Revenue forecasting
  • Compensation planning
  • Business process optimization
  • Data analysis
  • Team leadership
  • Change management
  • Cross-functional collaboration
  • Mergers and acquisitions

Accomplishments

  • Recipient of 2024 Top 100 Revenue Operations Leaders, a recognition published annually by the @themodernsale and @collectivei.

Timeline

SVP Revenue Operations

Medallia
05.2024 - 08.2025

Sr. Director, Strategy & Operations

Twilio
01.2021 - 01.2024

Vice President - Revenue Operations

Pipedrive
01.2018 - 01.2020

COO

Suzie
01.2015 - 01.2017

Vice President - Finance & Revenue Operations

IAC/Interactive Corp.
01.2007 - 01.2015

Bachelor of Arts - ADVERTISING, Psychology

MARIST COLLEGE

Executive Education - Mergers & Acquisitions

THE WHARTON SCHOOL - UNIVERSITY OF PENNSYLVANIA

Similar Profiles

CREATE PROFILE