William Mooney
San Rafael
Summary
Sales leader with 15+ years of experience building and scaling SaaS revenue organizations across SMB, Mid-Market, and Upmarket segments. Proven track record leading high-performing sales teams, improving operational rigor, and building repeatable revenue systems in high-growth SaaS environments. Experienced in scaling outbound motions, improving forecast accuracy, and driving accountability through pipeline math, inspection cadences, and structured coaching frameworks. Strong background in high-velocity SaaS sales environments with short sales cycles and PLG/inbound-driven revenue motions. Known for stabilizing underperforming teams, developing future leaders, and building sustainable high-performance cultures through operational discipline and behavior-based coaching.
Overview
18
18
years of professional experience
1
1
Certification
Work History
Director of Upmarket Sales
Time Doctor
01.2025 - Current
- Lead global upmarket sales organization within a large PLG and inbound-driven SaaS environment focused on operational rigor, forecasting discipline, and scalable sales execution.
- Operate within a high-velocity sales environment averaging 2–3 week sales cycles across SMB and upmarket customer segments
- Rolled out MEDDICC framework to improve qualification consistency, pipeline visibility, and forecasting accuracy
- Hired and managed a global team of sales professionals, improving onboarding structure and performance accountability
- Implemented enhanced forecasting processes and weekly pipeline inspection cadence to improve predictability and operational discipline
- Led adoption of AI-driven sales workflows, including ChatGPT-powered prospecting and enablement systems to improve seller productivity
- Standardized executive presentations using Gamma, improving sales communication quality and customer engagement
- Deployed AI-powered call coaching (Glyphic) at scale to improve rep execution consistency and coaching effectiveness
- Improved outbound targeting, activity inspection, and pipeline generation rigor across the organization
Director of Upmarket Sales
CARET Legal
01.2023 - 01.2024
- Led top-performing team and closed largest deals in company history (~$450K ACV)
- Transitioned organization to more structured, value-based sales methodology
- Improved deal inspection and forecast accountability across team
Vice President of Sales
OpenComp
01.2023 - 01.2023
- Scaled revenue from $200K to $1M+ TCV in under six months
- Built structured coaching framework improving win rates by 31% and reducing ramp time by 72%
- Managed performance across AE and SDR functions with clear KPI accountability
Director of Commercial Sales, West
Outreach
01.2022 - 01.2023
- President’s Club leader with top-performing commercial sales team
- Closed largest commercial segment deal in company history ($700K ARR / $3M TCV)
- Increased self-generated pipeline contribution to 30%+ through outbound focus and coaching discipline
Director of Enterprise Sales
Level Access
12.2020 - 02.2022
- Second-line sales leader responsible for upmarket sales organization and $13M annual quota.
- Supported major wins with organizations including Google, Amazon, Microsoft, CVS, and Disney
- Transitioned team to more proactive new-logo acquisition motion
- Implemented operational cadence and deal inspection framework to improve accountability and forecasting
Director of Sales & Customer Success
ClickTime
01.2018 - 12.2020
- Promoted into expanded leadership role overseeing Sales, Customer Success, and Support functions.
- Led cross-functional revenue team delivering 100%+ new business attainment and 97%+ NRR
- Improved NRR from 90% → 97% through lifecycle management and retention strategy
- Built and scaled Account Management function, including hiring systems, onboarding, compensation plans, and success metrics
- Maintained 97–100% CSAT while improving operational efficiency and expansion opportunities
- Partnered cross-functionally with Product and Marketing to reduce friction throughout buyer and customer journey
Director of Sales
ClickTime
06.2016 - 12.2017
- Led SMB-focused sales team in high-velocity SaaS sales environment
- Reduced sales cycle by 50% through improved process discipline and funnel optimization
- Improved outbound effectiveness and conversion rates through structured coaching and sales process refinement
- Partnered with Marketing to improve trial conversion and pipeline efficiency
VP of Sales
TrustYou
01.2015 - 01.2016
- Doubled revenue and significantly improved close rates and sales cycle efficiency
- Formerly Checkmate.io
Director of Sales
Cvent
01.2014 - 01.2015
- Achieved 175% of quota while increasing ASP by 17%
- Formerly Social Tables
Director of Sales
Groupon
01.2011 - 01.2014
- Led organization of ~50 sales professionals across multiple teams and product lines
- Delivered $3M+ in revenue through strategic sales execution and coaching
- Formerly LivingSocial
Director of Inside Sales
FiscalNote
01.2010 - 01.2011
- Built SDR training academy and performance management systems
- Increased outbound activity and appointment generation significantly
- Formerly Frontier Strategy Group
Enterprise Account Executive
Acquirent
01.2008 - 01.2010
- Achieved 157% quota attainment and earned 3x President’s Club honors
- Formerly Vorsight
Education
BA - Sociology
San Francisco State University
Skills
- SMB & Upmarket SaaS Leadership
- Forecasting Accuracy & Pipeline Inspection
- Outbound Sales Strategy & Coaching
- SPIN Selling & MEDDICC Methodologies
- Revenue Operations & Funnel Metrics
- Pipeline Math & Capacity Planning
- Team Performance Management
- Hiring, Ramp Programs & Coaching Systems
- CRM Hygiene & Operational Discipline
- AI-Driven Sales Productivity & Enablement
- Cross-Functional GTM Collaboration
- Strategic planning
Certification
- AI Management Certification — University of California, Berkeley
- GTM Leadership Accelerator — Pavilion
- Challenger Sale | SPIN Selling | Value Selling
- JBarrows (Fill the Funnel, Driving to Close)
- JOLT Effect Certified
- Salesloft & Chorus Admin Certified
ADDITIONAL EXPERIENCE
- Go-To-Market Advisor, ImpacTree (Seed-stage startup)
- NASM Certified Coach | F45 Training
- HOA President | Muir Terrace Community
- Youth Soccer Coach (3+ years)
Timeline
Director of Upmarket Sales
Time Doctor
01.2025 - Current
Director of Upmarket Sales
CARET Legal
01.2023 - 01.2024
Vice President of Sales
OpenComp
01.2023 - 01.2023
Director of Commercial Sales, West
Outreach
01.2022 - 01.2023
Director of Enterprise Sales
Level Access
12.2020 - 02.2022
Director of Sales & Customer Success
ClickTime
01.2018 - 12.2020
Director of Sales
ClickTime
06.2016 - 12.2017
VP of Sales
TrustYou
01.2015 - 01.2016
Director of Sales
Cvent
01.2014 - 01.2015
Director of Sales
Groupon
01.2011 - 01.2014
Director of Inside Sales
FiscalNote
01.2010 - 01.2011
Enterprise Account Executive
Acquirent
01.2008 - 01.2010
BA - Sociology
San Francisco State University