BILL MOONEY
San Francisco
Summary
Accomplished SaaS sales leader with extensive expertise guiding high-performing Mid-Market and Enterprise teams in dynamic, high-growth environments. Proven ability to coach and inspire quota-carrying teams to exceed goals through structured sales methodologies, rigorous pipeline discipline, and crossfunctional collaboration. Passionate about empowering individuals to achieve career milestones and aligning go-to-market execution with organizational strategy. Experienced product evangelist for HubSpot's AI features.
Overview
17
17
years of professional experience
1
1
Certification
Work History
Director of Sales, Upmarket
Time Doctor
08.2024 - Current
- Achieved 105% to 1H quota; on pace for 90% Q3 attainment with a global team of 6 Mid-Market & Enterprise AEs.
- Increased win rate from 37% → 44% YoY and doubled ASP through coaching and deal strategy refinement.
- Implemented a formal AI sales enablement plan; served as HubSpot AI product evangelist and quoted in HubSpot product team webinar.
- Elevated pipeline quality by coaching reps on multi-stakeholder management, procurement navigation, and outbound prospecting discipline.
- Member of the Senior Leadership Team, collaborating with Product, Marketing, Customer Success, and RevOps.
- Recruited, hired, and trained Mid-Market & Enterprise AEs, fostering a transparent, collaborative, and performance-driven culture.
- Maintained forecast accuracy and applied analytics for pipeline inspection, territory planning, and KPI accountability.
- Designed and implemented formal sales coaching programs and individual development plans (IDPs) to advance team member careers.
Manager, Upmarket Sales
CARET Legal
09.2023 - 08.2024
- 103% to Team Quota, leading top-producing sales team.
- Co-sold the two largest deals in company history (~$450k TCV each).
- Increased ASP by 67% and consistently forecasted revenue within 10% accuracy.
- Implemented call coaching program via Chorus; drove 100% ramp quota attainment by new AEs.
- Led remote team of 4 Enterprise AEs & 1 SMB AE with $5.4M annual quota.
- Admin for Salesloft, driving inbound lead follow-up and outbound pipeline generation.
Director of Sales
OpenComp
01.2023 - 09.2023
- Scaled revenue from $200k → $1M+ TCV in six months.
- Built and scaled sales org to 8 AEs and 3 SDRs, transitioning from founder-led to PLG motion.
- Improved ramp time by 72% and win rates by 31% via coaching programs.
- Doubled ASP and increased trial conversion by 86%.
Director of Commercial Sales, West
Outreach
02.2022 - 01.2023
- President's Club recipient, led top-performing Commercial team at 115% quota attainment.
- Guided team to self-generate >30% of pipeline.
- Supported closing of largest Commercial deal in company history (~$700k ARR / $3M TCV).
Director of Enterprise Sales
Level Access
12.2020 - 02.2022
- Managed 10 New Logo Enterprise AEs with $13M annual quota.
- Promoted AE to Sales Manager role who achieved immediate quota success.
- Helped secure wins with major accounts: Google, Amazon, Disney, Microsoft, CVS, Wells Fargo.
Director of Sales & Customer Success
ClickTime
06.2016 - 12.2020
- Founding sales leader, built new business, renewals, CS, and support org.
- 101% Y19 new business, 103% Y20 new business while maintaining >97% NRR.
- Improved NRR from 90% → 97% in 1.5 years.
- Cut sales cycle in half through improved PLG inbound motion.
VP of Sales
Checkmate.io
09.2015 - 06.2016
- Doubled revenue in first quarter by re-engineering GTM strategy.
- Increased close rate 23% → 32% and shortened sales cycle 54 → 33 days.
- Managed 10 AEs and 8 SDRs.
Director of Sales
Social Tables
11.2014 - 09.2015
- Achieved 175% of sales target in 2014 and 100% in 2015.
- Raised ASP by 17% in one year.
- Standardized sales process, improving forecasting and stage consistency.
Director of Sales
LivingSocial Escapes
07.2011 - 11.2014
- Managed multiple teams across product lines, peaking at ~50 Sales Associates.
- Secured $3M in net revenue for Escapes business.
Director of Inside Sales
Frontier Strategy Group
07.2010 - 07.2011
- Created Sales Development Academy, training SDRs into successful AEs.
- Managed remote, international SDR team generating meetings with Fortune 500 executives.
Enterprise Account Executive
Vorsight
04.2008 - 07.2010
- 3-time President's Club winner.
- Sold and delivered SDR consultations to major enterprises (HP, AT&T, Verizon, BMC).
Education
AI for Management -
UC Berkeley - Online Learning
10-2025
BA - Sociology
San Francisco State University
Skills
- Sales Team Leadership
- Tactical Sales Coaching & Training
- Formal Coaching Program Implementation
- Individual Development Plans (IDPs)
- Talent Recruitment & Development
- Pipeline Generation Coaching (Inbound & Outbound)
- Radical Candor
- High Emotional Intelligence (EQ)
- Consultative / Value Selling
- Challenger Sale
- SPIN
- JOLT Effect
- MEDDIC
- Multi-Stakeholder Deal Management
- Forecasting & Territory Planning
- Contract & Procurement Negotiation
- HubSpot CRM (Power User, Product Evangelist)
- Salesforce
- Salesloft
- Outreach
- ZoomInfo
- LinkedIn Sales Navigator
- Chorus
- Gong
- Avoma
- ChatGPT
- Clay
- Data-Driven Decision Making
- KPI Management
- Pipeline Analytics
- GTM Strategy Development
- Cross-Functional Collaboration (Product, Marketing, CS, RevOps)
- Change Management & Process Improvement
- Transparent & Collaborative Leadership
- Adaptability in Fast-Growth Environments
- Motivating Teams Through Change
- Product Evangelism & Thought Leadership
Certification
- Value Selling
- Challenger Sale
- SPIN Selling
- JOLT Effect
- MEDDIC
- JBarrows Fill the Funnel
- Driving to Close
- Salesloft Admin
- Chorus Admin
- HubSpot CRM (Power User, Product Evangelist)
- Pavilion Go-To-Market Leadership Accelerator (8-week course)
Outside Of Work
- Go-To-Market Advisor, ImpacTree (seed-funded startup)
- HOA President
- Youth Soccer Coach (3+ years)
- NASM Group Fitness Certified
- Part-Time Coach at F45 San Rafael
- Former Peace Corps Volunteer (Fiji, 2006-2008)
Skills
Sales Team Leadership, Tactical Sales Coaching & Training, Formal Coaching Program Implementation, Individual Development Plans (IDPs), Talent Recruitment & Development, Pipeline Generation Coaching (Inbound & Outbound), Radical Candor, High Emotional Intelligence (EQ), Consultative / Value Selling, Challenger Sale, SPIN, JOLT Effect, MEDDIC, Multi-Stakeholder Deal Management, Forecasting & Territory Planning, Contract & Procurement Negotiation, HubSpot CRM (Power User, Product Evangelist), Salesforce, Salesloft, Outreach, ZoomInfo, LinkedIn Sales Navigator, Chorus, Gong, Avoma, LEM List, Clay, Data-Driven Decision Making, KPI Management, Pipeline Analytics, GTM Strategy Development, Cross-Functional Collaboration (Product, Marketing, CS, RevOps), Change Management & Process Improvement, Transparent & Collaborative Leadership, Adaptability in Fast-Growth Environments, Motivating Teams Through Change, Product Evangelism & Thought Leadership
Timeline
Director of Sales, Upmarket
Time Doctor
08.2024 - Current
Manager, Upmarket Sales
CARET Legal
09.2023 - 08.2024
Director of Sales
OpenComp
01.2023 - 09.2023
Director of Commercial Sales, West
Outreach
02.2022 - 01.2023
Director of Enterprise Sales
Level Access
12.2020 - 02.2022
Director of Sales & Customer Success
ClickTime
06.2016 - 12.2020
VP of Sales
Checkmate.io
09.2015 - 06.2016
Director of Sales
Social Tables
11.2014 - 09.2015
Director of Sales
LivingSocial Escapes
07.2011 - 11.2014
Director of Inside Sales
Frontier Strategy Group
07.2010 - 07.2011
Enterprise Account Executive
Vorsight
04.2008 - 07.2010
AI for Management -
UC Berkeley - Online Learning
BA - Sociology
San Francisco State University
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