Susan Whittemore
Pepperell
Summary
Accomplished VP of Revenue Operations with over 15 years of experience in Revenue, GTM, and Sales Operations. Expertise in optimizing operations for maximum efficiency, providing data-driven insights for strategic decision-making, and aligning operations with executive goals. Proven track record in leading large-scale teams in hyper-growth environments, driving growth in organizations with revenues from $5M to $400M ARR. Skilled in GTM tooling, Sales Methodologies, and Change Management, ensuring robust continuity and fostering a culture of innovation. With a broad-based experience and thirst for learning, this new chapter of operations includes a continuous learning mindset, incorporating AI into our processes, and further driving efficiency and reducing friction through the buyers' and customers' journey.
Overview
29
29
years of professional experience
1
1
Certification
Work History
VP, Revenue Operations
tax.com, the software division of Ryan LLC
Boston
04.2024 - Current
- Identified and Led integration of GTM stack (ZoomInfo, Outreach, LinkedIn Sales Navigator) and established first enterprise deployment of Gong for enhanced pipeline visibility.
- Delivered over 600+ Salesforce enhancements through a shared service to ensure accurate data capture and process enablement across Sales, Marketing, Customer Success, Finance, and Executive Leadership.
- Championed an accelerated contractor engagement to establish value messaging across our four product domains and 17 products, focused on differentiators, outcomes we solve, and defended by customer proof points—all within two months.
- Implemented scalable pre- and post-sales controls, reducing time to invoice from 17 days to 24 hours, reducing lumpy revenue, and accelerating cash receivables.
- Established the first enterprise operating cadence, and annual and monthly reports for comprehensive funnel and contribution model visibility across various metrics.
- Designed and launched inaugural software commission plans for Sales and Customer Success, shifting revenue mix from 70% expansion to 70% new logo.
- Increased average sales price by 63% from 2024 to 2025 through targeted compensation strategies.
- Optimized operational efficiency by implementing robust internal control procedures to streamline processes.
- Enhanced executive reporting capabilities, providing transparency into key performance indicators, and defendable bookings reporting.
GTM and Revenue Operations Executive Advisor
QFlow.ai
Boston
06.2023 - 04.2024
- Advised QFlow.ai's initial product development, ensuring agile execution and strategic alignment with emerging market demands.
- Crafted targeted ICP and Buyer Persona strategies, boosting lead generation, engagement, and introductions by leverage market insights and my community of networks.
- Refined investor deck and strategic positioning, enhancing QFlow.ai's market promise narrative, facilitating pivotal iterations to captivate funding prospects.
Head of Revenue Operations
Teampay
New York
11.2021 - 04.2023
- Tech Stack Optimization: Streamlined GTM tech stack, aligning with processes for a 30% reduction in execution friction and vendor costs.
- Data Integrity & Metrics Definition: Ensured data accuracy across teams, establishing a reliable data 'source of truth' and defining key SaaS metrics, enhancing sales productivity measurably.
- Internal Controls & Efficiency: Implemented control procedures for pre- and post-sales, increasing operational efficiency, reducing errors by 30%, and boosting customer success team productivity by 25%.
- Resource Assessment & Support: Conducted strategic resource assessments, ensuring successful project execution and full operational transparency across cross-functional teams.
- Leadership Collaboration & Insight: Partnered with go-to-market and C-suite leaders, delivering quantitative support through dashboards, process audits, and analyses, revealing real-time insights on funnel conversions and impacting annual planning by improving pipeline predictions by 20%.
VP, GTM Operations
Starburst Data
Boston
10.2020 - 06.2021
- Unified Operations Team Efficiency: Designed a unified team of Sales, Marketing, and Customer Success operators, enhancing organizational efficiency by 25%, and elevating customer satisfaction and retention by 20%.
- Revamped GTM Tech Stack: Redesigned the GTM tech stack to support new process definitions, achieving end-to-end funnel measurement and enhancing funnel visibility by 30%, significantly improving alignment between marketing and sales.
- Optimized Sales Recruitment for Hypergrowth: Standardized hiring criteria and practices using PXT Select, reducing hiring time by 50%, ensuring team cohesion and retention, including an expansion into the EMEA market.
- Strategic Forecasting Enhancement: Implemented a scalable forecast model and MEDDICC from ICs to second-line management, including forecast coaching sessions.
Sr. Director, Sales Operations
Silk
Needham
04.2019 - 10.2020
- SaaS Transition Architect: Orchestrated the company's evolution from hardware to software, driving operational overhaul, GTM strategy innovation, commission plans, and financial model transformation, catalyzing revenue growth.
- Sales Empowerment Champion: Led the integration of Force Management, managing core workshops, content, and training from executive to field levels, culminating in a successful rollout at the SKO. Completed the Command of the Message Train the Trainer program.
- Marketing Funnel Innovator: Transformed the marketing funnel, realizing a 40% pipeline growth and a 25% uplift in revenue by refining lead scoring, nurturing processes, and data-driven territory planning.
- Sales Transformation Leader: Spearheaded a pivotal transition, achieving 100% adoption of Command of the Message and MEDDICC, transforming traditional hardware sellers into adept Enterprise SaaS sellers. Orchestrated a comprehensive shift from commission models to robust enablement strategies, ensuring seamless adoption and proficiency in cutting-edge sales methodologies.
VP, Sales Operations
Perfecto Mobile Inc
Burlington
11.2014 - 06.2019
- Revenue Growth & Team Expansion: Drove ARR from $13M to $75M in four years and expanded the operations team from one Salesforce administrator to a robust team of 16, encompassing renewals, SDRs, and Sales Enablement.
- Methodology Integration & Performance Building: Seamlessly integrated MEDDICC & Value-Based CoM Selling, aligning systems and processes to consistently maximize and measure sales performance and revenue outcomes.
- Strategic Planning & Compensation Management: Developed a comprehensive GTM strategy and managed adaptive compensation plans, ensuring sales team motivation and performance were aligned with company growth targets.
- Corporate Culture & Operational Cadence: Orchestrated world-class corporate events and maintained a rigorous KPI-driven operational cadence, significantly contributing to team morale, collaboration, and sustained success during hypergrowth.
- Finance Collaboration & Deal Desk Efficiency: Fostered a strong partnership with the finance team, managing a highly responsive deal desk with a commitment to 24-hour SLAs for active negotiations, 48-hour SLAs for month & quarter-end closures, and a 5-day post-close commission SLA in collaboration with finance.
Sr. Director, Sales Operations
Rocket Software
Waltham
06.2011 - 11.2014
- Brand Integration Excellence: Seamlessly merged 15 legacy brands into a cohesive Rocket sales framework, spurring operational efficiency, boosting cross-sell revenue, and unifying to one identity.
- CRM & Marketing Automation Integration: Led the strategic design and rollout of an integrated Salesforce CRM and Marketo system, uniting 15 business units and reinforcing the sales infrastructure for enhanced CEO oversight.
- Lead-to-Order Optimization: Implemented a comprehensive lead-to-order framework, integrating lead management, CPQ, and forecasting tools, driving sales performance & providing key insights for ELT.
- Event Management: Orchestrated annual and quarterly sales meetings, managing program design, content, logistics, and execution, ensuring impactful and cohesive sales team engagements.
Sr. Executive Support and Project Manager
NOVELL
Waltham
12.2000 - 06.2011
- Onboarding & Productivity Transformation: Spearheaded the launch of a global onboarding portal, elevating productivity and engagement by 50%, and playing a critical role in a GTM transformation that increased operating profit by 13% over two years.
- M&A Efficiency & Workforce Strategy: Co-authored the M&A Playbook, markedly improving integration efficiency, and provided strategic consultation on retention, skill development, and performance, significantly boosting workforce engagement.
- Organizational Transition & Sales Administration: Led a smooth organizational transition from SilverStream to Novell, ensuring continuity and efficiency in sales administration during critical growth phases.
Account Manager - Sr. Associate
DELOITTE & TOUCHE
Boston
06.1997 - 05.2000
- CRM Development & Innovation: Pioneered the development and launch of AtlasTax CRM, the first of its kind for the division, revolutionizing tax management and setting a new standard for operational efficiency.
- Portfolio Management Excellence: Expertly managed a substantial book of business exceeding $25M in client tax liabilities, ensuring rigorous nationwide compliance and maintaining the highest standards of tax liability management.
- Leadership & Client Retention Mastery: As East Region Consultant, I led client advocacy and AtlasTax integration efforts, securing a 100% client retention rate post-acquisition through seamless transitions and dedicated service.
Education
MBA - Finance
Southern New Hampshire University
06.2012
Bachelors of Science - Business Management
Northeastern University
04.2008
Skills
- Revenue operations strategy
- Data analysis and insights
- Operational efficiency
- Change management
- Cross-functional collaboration
- Process improvement
- Revenue cycle management
- Operations management
- Competitor analysis
- Sales operations efficiency
- Force management transformation
- MEDDICC implementation
- Systems thinking and design
- AI-driven go-to-market optimization
- Customer journey mapping
- Onboarding process development
- Data-driven decision making
- Forecasting processes
Certification
Building AI Literacy 2025
GTM Architecture 2025
AI in GTM - 2024, 2025
Revenue Growth Architecture - 2021, 2024
Enterprise CRO School - 2023
Product Led Sales - 2023
Revenue Operations Advanced - 2022
Enterprise GTM - 2022
InsightSquared Revenue Ops - 2018
OpFocus Salesforce Admin - 2013
Certified Firewalker Instructor - 2024
CCO School - 2022
CMO School - 2022
Coaching for High Performance - 2022
CRO School - 2021
MassTLC Board-Ready Bootcamp - 2019
SSCA, Inc Leadership Process: Motivating Achievement - 2018
Prosci Change Management Practitioner - 2014
Everything DiSC Practitioner - 2023
PXT Select Practitioner - 2021
Predictive Index Practitioner - 2013
GTM Architecture 2025
AI in GTM - 2024, 2025
Revenue Growth Architecture - 2021, 2024
Enterprise CRO School - 2023
Product Led Sales - 2023
Revenue Operations Advanced - 2022
Enterprise GTM - 2022
InsightSquared Revenue Ops - 2018
OpFocus Salesforce Admin - 2013
Certified Firewalker Instructor - 2024
CCO School - 2022
CMO School - 2022
Coaching for High Performance - 2022
CRO School - 2021
MassTLC Board-Ready Bootcamp - 2019
SSCA, Inc Leadership Process: Motivating Achievement - 2018
Prosci Change Management Practitioner - 2014
Everything DiSC Practitioner - 2023
PXT Select Practitioner - 2021
Predictive Index Practitioner - 2013
References
- Keith Butler, President and CRO, Observe, Inc., 781-640-4428
- Sam Jacobs, CEO, Pavilion, 917-701-0358
- Sabba Nazhand, VP, Sales, Chegg Skills, 917-238-1708
- Chris Healey, Regional Sales Director, Snowflake, 617-470-2070
- Jim Parker, CEO, Velocity Consulting Group, 801-319-4291
Volunteer Experience
- Board of Directors, YMCA of Greater Nashua, 04/01/21, Present
- Finance Committee Member, YMCA of Greater Nashua, 11/01/20, Present
- Pavilion Envoy and Ambassador, COO Community, Boston Co-Chapter Leader 11/01/20, Present
Timeline
VP, Revenue Operations
tax.com, the software division of Ryan LLC
04.2024 - Current
GTM and Revenue Operations Executive Advisor
QFlow.ai
06.2023 - 04.2024
Head of Revenue Operations
Teampay
11.2021 - 04.2023
VP, GTM Operations
Starburst Data
10.2020 - 06.2021
Sr. Director, Sales Operations
Silk
04.2019 - 10.2020
VP, Sales Operations
Perfecto Mobile Inc
11.2014 - 06.2019
Sr. Director, Sales Operations
Rocket Software
06.2011 - 11.2014
Sr. Executive Support and Project Manager
NOVELL
12.2000 - 06.2011
Account Manager - Sr. Associate
DELOITTE & TOUCHE
06.1997 - 05.2000
MBA - Finance
Southern New Hampshire University
Bachelors of Science - Business Management
Northeastern University