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Boston, MA, USA

Jon R.

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.

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Jon R.

Work

Jon Rheaume | Revenue Architecture & Pipeline Systems

jonrheaume.com
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.

Experience

Jun 2025 — Present

Independent/Fractional

VP, Pipeline Generation & GTM Strategy

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.
Jul 2022 — Present
ClearCompany Talent Management Software

ClearCompany Talent Management Software

Vice President, Demand Generation & Account Development

Jul 2022 — Jun 2025
ClearCo

ClearCo

Vice President, Pipeline Generation & GTM Strategy

  • 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
Jan 2019 — Jul 2022
ClearCompany Talent Management Software

ClearCompany Talent Management Software

Director of Demand Generation

  • 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
Apr 2017 — Dec 2018
ClearCompany Talent Management Software

ClearCompany Talent Management Software

Manager, Demand Generation

  • 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
Jan 2016 — Apr 2017
ClearCompany Talent Management Software

ClearCompany Talent Management Software

Manager, Business Development

Jan 2014 — Oct 2014

Advera Health Analytics, Inc.

Business Development Manager

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

Jan 2014 — Dec 2015

Advera Health Analytics (acquired by TriNetX)

Senior Business Development Manager - Regional Team Lead

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

Jan 2012 — Dec 2013

SnapKnot

Director of Sales

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.
Jan 2011 — Dec 2012
ADP

ADP

District Manager - SBS

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

Jan 2010 — Dec 2011
PTC

PTC

Business Analyst

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

Feb 2006 — Jan 2010
State Street

State Street

Senior Associate

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