Chris Kinsella
Dover,United States
Summary
Revenue leader with 25+ years of experience scaling B2B SaaS from startup to PE exit. Contributed to 7 acquisitions as an executive, building teams that generated $100M+ in cumulative annual revenue. Expert in MEDDPICC and agentic AI strategy. 8-time Presidents Club honoree and United States Marine Corps veteran. Chief Strategy Officer and former VP of Sales with a track record of multi-million dollar growth. Guided teams through acquisitions by Vista Private Equity, Bain Capital, KKR, and Clear Lake Capital Group. Expert in scaling GTM teams and integrating AI into operations.
Pragmatic professional with solid experience in leadership roles. Adept at implementing strategic business plans, driving growth and improving operations. Skilled in financial management and stakeholder relations. Collaborative and dedicated to building and leading talented and motivated individuals.
Overview
1
1
Certification
18
18
years of professional experience
Work History
Chief Strategy Officer
Prostions / EZPZ Train / Robin Hood HR
01.2026 - Current
- Implemented agentic AI within internal processes to enhance strategic decision-making and operational effectiveness
- Defined corporate strategy aligned with long-term vision, leading annual and quarterly strategic planning across all business units
- Assessed competitive landscape and emerging trends to identify opportunities for growth, innovation, and differentiation
- Partnered with CEO and executive team to evaluate, prioritize, and approve key strategic initiatives and investments
- Prepared and delivered board-level materials articulating strategic choices, trade-offs, and performance against objectives
- Analyzed market trends and competitive landscape to inform strategic planning processes.
- Mentored senior leadership on strategic decision-making and risk management practices.
- Spearheaded process improvements that increased efficiency in project execution and resource allocation.
Founder & Fractional CRO
CHHK Consulting
08.2025 - Current
- Provided fractional Chief Revenue Officer support to three companies, shaping revenue strategy, go-to-market alignment, and commercial leadership
- Implemented AI governance and strategy across three client organizations, aligning AI initiatives with business objectives and risk frameworks
- Advised executive teams on organizational structure, talent requirements, and full customer lifecycle strategy to enable scalable revenue growth
- Refined value propositions, core messaging, and market positioning in partnership with founders and leadership teams
SVP of Sales & Customer Success
Learning.com
04.2024 - 09.2025
- Drove 21% increase in new business in FY24 through strategic sales leadership, go-to-market execution, and sales enablement initiatives
- Improved customer retention from 82% to 89% through a redesigned Customer Success strategy, increasing recurring revenue predictability
- Implemented POD model by client enrollment size and geography, improving coverage, focus, and service delivery
- Enforced MEDDPICC sales methodology to standardize qualification, improve forecast accuracy, and elevate team performance
- Executed Account-Based Marketing (ABM) campaigns to drive marketing–sales alignment and higher-quality pipeline generation
- Led cross-functional teams in implementing innovative solutions for customer engagement and retention.
- Developed and executed strategic sales initiatives to drive revenue growth and market expansion.
- Analyzed market trends and competitor strategies to inform product positioning and sales tactics.
Vice President of Sales
PowerSchool
11.2022 - 03.2024
- Generated $13.5M in new business through a mid-market hybrid sales model, expanding market coverage and revenue capacity
- Rolled out MEDDPICC sales framework, standardizing deal qualification and improving forecast consistency across the organization
- Integrated Clari and Tableau into sales operations, enabling data-driven forecasting, pipeline visibility, and performance reporting
- Served as key member of executive leadership team through successful acquisition by Bain Capital
- Mentored and trained sales teams to enhance performance and achieve targets.
- Established strong relationships with key stakeholders to support business development efforts.
- Oversaw implementation of CRM systems to streamline sales processes and improve efficiency.
SVP of Sales
Alchemer
09.2021 - 08.2022
- Achieved 17.3% increase in new business and improved gross retention from 83% to 91% through regionalized sales and retention teams
- Implemented MEDDPICC methodology and integrated DOMO for advanced business intelligence across the sales organization
- Served as executive team member through successful acquisition by KKR
- Drove revenue growth through implementation of targeted sales strategies and customer engagement programs.
- Led cross-functional teams to develop and execute strategic sales initiatives across multiple markets.
Vice President of Sales
Xactly Corporation
01.2020 - 09.2021
- Built national SaaS hybrid sales team generating $14M in new business and $75M in renewal business
- Named to Presidents Club FY2020; restructured sales team and introduced new forecasting tools and processes
Vice President of Sales
Dodge Data & Analytics
07.2016 - 01.2020
- Built national SaaS inside sales team driving $15M in new acquisitions and $55M in renewals
- Formed Strategic Sales Organization securing $7.8M in new business; amplified annual sales 23% in FY2017
- Executive team member through successful acquisition by Clear Lake Capital Group
Vice President of Sales
On Center Software
04.2015 - 07.2016
- Built global SaaS sales team driving $12.7M in new business and $16.1M in renewals
- Integrated Marketo for marketing automation; guided sales division through acquisition by Roper Technologies
VP of SMB Sales
GeoLearning / SumTotal Systems
01.2008 - 04.2015
- Handpicked by Vista Private Equity to build and scale a 35-member high-performing sales force
- Generated $18.5M in annual new business revenue; oversaw Client Success team securing $36.5M in renewals
- 8-time Presidents Club honoree; instrumental in company growth and acquisition by Charterhouse Private Equity
Education
Bachelor of Science -
Iowa State University
Ames, IA01-1996
Skills
- Revenue optimization
- MEDDPICC sales expertise
- Managing group interactions
- Sales pipeline management
- Specialized knowledge in agentic AI
- Customer success management
- CRM strategy development
- Experienced in marketing strategies
- Advanced forecasting methods
- Talent acquisition strategy
- Strategic relationship management
- Data-informed strategy development
- Process optimization
Timeline
Chief Strategy Officer
Prostions / EZPZ Train / Robin Hood HR
01.2026 - Current
Founder & Fractional CRO
CHHK Consulting
08.2025 - Current
SVP of Sales & Customer Success
Learning.com
04.2024 - 09.2025
Vice President of Sales
PowerSchool
11.2022 - 03.2024
SVP of Sales
Alchemer
09.2021 - 08.2022
Vice President of Sales
Xactly Corporation
01.2020 - 09.2021
Vice President of Sales
Dodge Data & Analytics
07.2016 - 01.2020
Vice President of Sales
On Center Software
04.2015 - 07.2016
VP of SMB Sales
GeoLearning / SumTotal Systems
01.2008 - 04.2015
Bachelor of Science -
Iowa State University
MILITARY
- Military Service
- United States Marine Corps
- Attained E-5 rank; served in Desert Shield/Desert Storm and Operation Restore Hope
- Awarded multiple service medals; Honorably Discharged