Jon Rheaume

Boston, MA, USA

Driving Revenue Growth through Strategic Pipeline Innovation

With a proven track record of scaling ARR from $10M to $90M, I specialize in transforming pipeline generation and GTM systems to achieve substantial revenue impact. My expertise lies in leveraging AI and innovative sales strategies to enhance SDR and outbound efforts, resulting in over $400M in pipeline influence. Passionate about data-driven decision-making and solution selling, I thrive on building robust sales processes that empower teams and drive business development in the B2B and enterprise software sectors.

Jon Rheaume

Work

  • Jon Rheaume | Revenue Architecture & Pipeline Systems

    Jon Rheaume | Revenue Architecture & Pipeline Systems

    Built and scaled pipeline engines that supported growth from $10M to $90M ARR across 38 consecutive quarters.

    My work focuses on the operating math behind revenue: how pipeline is created, when it converts, and whether the plan is actually achievable given capacity and timing.

    Led SDR and outbound systems from zero to 40+ reps, reduced ramp time from 90 to 30 days, and improved lead-to-opportunity conversion from 24% to 48%.

    Today I work on pipeline architecture, GTM systems, and AI-assisted prospecting models that improve coverage, execution, and forecast reliability.

    https://www.jonrheaume.com

Experience

  • Independent/Fractional

    VP, Pipeline Generation & GTM Strategy

    Jun 2025 - Present

    Independent/Fractional offers consultancy services focused on enhancing pipeline generation and revenue architecture for B2B SaaS companies.

    • Successfully rebuilt outbound pipeline systems leading to improved SDR performance.
    • Aligned sales and marketing functions to consistently improve pipeline creation.
    • Introduced AI-driven prospecting to expand account coverage and enhance efficiency in execution.
  • ClearCompany Talent Management Software

    ClearCompany Talent Management Software

    Vice President, Demand Generation & Account Development

    Jul 2022 - Present

  • ClearCo

    ClearCo

    Vice President, Pipeline Generation & GTM Strategy

    Jul 2022 - Jun 2025

    • Led the development and scaling of outbound pipeline generation into a consistent, repeatable source of pipeline (~$20M annually, 500+ SQOs/year)
    • Scaled inbound-sourced pipeline from ~$4M to ~$35M (~1,500 SQOs/year) annually by redesigning qualification, routing, and conversion into sales-ready opportunities
    • Led SDR strategy, organizational design, and hiring, evolving the function toward coverage-based execution and consistent pipeline creation
    • Developed account targeting and segmentation frameworks to improve outbound efficiency and expand qualified pipeline coverage
    • Aligned sales, marketing, and operations around shared pipeline metrics, improving visibility into pipeline creation, conversion, and coverage against plan
    • Introduced AI-assisted prospecting approaches to expand account coverage and improve SDR productivity within pipeline generation workflows
  • ClearCompany Talent Management Software

    ClearCompany Talent Management Software

    Director of Demand Generation

    Jan 2019 - Jul 2022

    • Supported the development of outbound and SDR-led pipeline generation, contributing to growth in overall pipeline coverage
    • Partnered with sales and marketing to improve lead qualification, routing, and conversion into sales-ready opportunities
    • Helped establish early processes for pipeline tracking, performance measurement, and cross-functional alignment
  • ClearCompany Talent Management Software

    ClearCompany Talent Management Software

    Manager, Demand Generation

    Apr 2017 - Dec 2018

    • Managed SDR and inbound qualification efforts, supporting pipeline creation across inbound and outbound channels
    • Contributed to outbound prospecting initiatives and account targeting approaches to expand pipeline coverage
    • Worked cross-functionally to improve lead flow, routing, and early-stage conversion into qualified opportunities
  • ClearCompany Talent Management Software

    ClearCompany Talent Management Software

    Manager, Business Development

    Jan 2016 - Apr 2017

  • Advera Health Analytics, Inc.

    Business Development Manager

    Jan 2014 - Oct 2014

    Advera Health Analytics focuses on enhancing patient safety and healthcare cost efficiency using data-driven insights.

  • Advera Health Analytics (acquired by TriNetX)

    Senior Business Development Manager - Regional Team Lead

    Jan 2014 - Dec 2015

    Advera Health Analytics improves patient safety and reduces healthcare costs through real-world outcomes data analysis.

  • SnapKnot

    Director of Sales

    Jan 2012 - Dec 2013

    SnapKnot connects engaged couples with photographers through a comprehensive search platform based on location, budget, and style.

    • Expanded SnapKnot's brand partnerships leading to an increase in customer base via marketing opportunities.
    • Implemented strategic marketing initiatives that improved brand visibility and engagement within the target market.
  • ADP

    ADP

    District Manager - SBS

    Jan 2011 - Dec 2012

    ADP provides comprehensive HR management solutions and services globally, including payroll, compliance, and benefits administration.

  • PTC

    PTC

    Business Analyst

    Jan 2010 - Dec 2011

    PTC is a leader in Product Lifecycle Management software, helping enterprises streamline product development and enhance service operations.

  • State Street

    State Street

    Senior Associate

    Feb 2006 - Jan 2010

    State Street offers financial services to institutional investors, including investment management and trading.

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