Jeff Bailey

Chief Revenue Officer at Pinwheel
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Contact Information
us****@****om
(386) 825-5501
Location
Denver, Colorado, United States, US

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5.0

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Chelsea Doran (she/her)

Jeff is the first Chief Revenue Officer I’ve had who 100 percent of the time was willing to roll up his sleeves and get

Lee Cush

I can't recommend Jeff highly enough as a leader. HIs approach strikes the right combination of very thoughtful strategy, collaboration & support while maintaining the balance required to challenge his team to accomplish disproportionate growth. He is an empathic servant leader, he sees the big picture and can lead and rally change in dynamic and volatile environments. He has the depth and competency to be detail oriented to execute complex plans, he hires great teams and nurtures a growth culture. Teams thrive working for him!

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Experience

    • United States
    • Software Development
    • 1 - 100 Employee
    • Chief Revenue Officer
      • Aug 2023 - Present

      Pinwheel is $500M Series B fintech startup on a mission to build the fourth credit bureau. We have the largest coverage, highest conversion, and most accurate real-time data on consumer income and employment because we connect directly into payroll & HR systems. With the ability to both read and write into payroll systems, our killer use cases include switching direct deposits, verifying income in real-time, and enabling new products like earned wage access with up-to-date shifts data. Our customers include the biggest fintechs (Block, Cash App, Credit Karma, etc) and the biggest traditional banks (4 of the top 10) as well as 200+ other financial services companies. We've raised $77M to date from top investors like Coatue, GGV, First Round, A16z, AMEX and more. Show less

    • United States
    • Software Development
    • 700 & Above Employee
    • Chief Revenue Officer
      • Mar 2020 - Apr 2023

      Payscale empowers people and employers with fresh, transparent, and validated salary data, easy-to-use software, and services to get pay right under any market conditions. We are $220M in ARR with 750 employees in the US, UK and Manila. I came to Payscale to rearchitect and lead all revenue functions including Sales, Channels, CS, & Operations. In 2022, to continue scaling growth, my role was divided in half as we brought in a Chief Customer Officer. I am currently responsible for Global Sales, Channels, supporting functions, and our Manila based shared services center; this ,current team is 300 people. When I arrived at Payscale, the company was not growing and not profitable, we improved EBITDA to ~30% and increased growth to 20%. Achievements include: • Grew company from $80M in 2020, to $220M in 2022 - Net new sales growth $10.6M in 2020 to $40.1M in 2022 • Exceeded YoY annual revenue targets of 2020, 2021, and 2022, as well as 10 of 12 quarters • Inherited a business where 75% of sales was SMB and transformed to 75% enterprise in 2022 - Transformed the revenue organization by replacing 85% of the team - Increased bookings per AE by more than 4X - Sales efficiency improved from 50% in Q1 2020 to 80% in Q1 2023 • Improved customer retention rates from 75% to 90% • Integrated three acquisitions - one $40M and two smaller ones • Implemented a new sales process, tools, enablement, value consulting and solution consulting • Expanded business from N. America only, into the UK to cover European business • Built Manila Center for Tech Support, Services, Customer Success, Collections and SDRs to drive cost savings and a better customer experience • Built a Channel team to partner with leading compensation services companies including Mercer, Aon, Deloitte and Korn Ferry • Received 2022 award from our investors for top 3 performing revenue teams out of their entire portfolio Show less

  • ServiceSource
    • Denver, CO
    • SVP Global Sales
      • Jan 2008 - Feb 2020

      ServiceSource is the leader in Customer Lifecycle Management. The solutions include the people, process, platform and pay-for-performance model to provide a fully managed service for Inside Sales, Customer Success and Recurring Revenue Management. Grew from $30M to $240M recurring revenue business. Developed existing and net new accounts, current bookings quota of $50M ACV. Track record of closing large, complex deals with companies ranging from $1 – 100B in revenue, such as Cisco, Microsoft, Red Hat, Symantec and Dropbox. Managed sales team, account management, solution design and inside sales. Utilized well-developed communication and presentation skills for communicating at the CXO level. Mastery of enterprise sales planning, customer development, territory management, solution targeting, and market segmentation. Drove innovation of all solutions in collaboration with Marketing and Managed Services Delivery Show less

    • United States
    • Financial Services
    • 700 & Above Employee
    • VP of Sales
      • Mar 2004 - Jan 2008

      Xign was a Procure to Pay / Payments company acquired by JPMorgan in May of 2007. Grew from $0 ARR pre-product / pre-revenue to $30M ARR. I was responsible for Sales at Xign, which consisted of enterprise outside salespeople, business development reps and solution design resources. Xign offered the premier global settlement network for enterprise businesses - with Xign, the Fortune 500 could process and pay electronic invoices in days, not weeks or months, in order to streamline operations, improve cash management and optimize working capital. Show less

    • United States
    • IT Services and IT Consulting
    • 700 & Above Employee
    • Senior District Manager
      • Mar 2002 - Feb 2004

      Western Region Sales Manager focused on the high tech vertical. Closed enterprise CRM deals at companies such as Network Associates and Intel. Western Region Sales Manager focused on the high tech vertical. Closed enterprise CRM deals at companies such as Network Associates and Intel.

    • United States
    • Financial Services
    • 700 & Above Employee
    • Director of Sales
      • Sep 2000 - Mar 2002

      First sales professional at Xign, selling the first 6 customers and performed as the top salesperson. Left in February 2002, but returned to the company in March of 2004 and led the outside sales team in North America through the acquisition of JPMorgan in 2007. First sales professional at Xign, selling the first 6 customers and performed as the top salesperson. Left in February 2002, but returned to the company in March of 2004 and led the outside sales team in North America through the acquisition of JPMorgan in 2007.

    • VP Sales Western Region
      • Jul 1999 - Sep 2000

      Annunicio was an early leader in the eCRM space. Responsible for the Western Region Sales team of 10 people which was personally built from the ground up, becoming a considerable business of over $10M in annual recurring revenue. Annunicio was an early leader in the eCRM space. Responsible for the Western Region Sales team of 10 people which was personally built from the ground up, becoming a considerable business of over $10M in annual recurring revenue.

    • United States
    • Financial Services
    • 1 - 100 Employee
    • Sales Manager
      • Sep 1993 - Jul 1999

      Managed the Western Region and was a top performer of the Public Sector Sales team working with customers such as State of Montana, City of Seattle, and the City & County of San Francisco. He was among the top 5 performers in the world out of hundreds of sales professionals, closing a single customer worth $29M in software and services. Managed the Western Region and was a top performer of the Public Sector Sales team working with customers such as State of Montana, City of Seattle, and the City & County of San Francisco. He was among the top 5 performers in the world out of hundreds of sales professionals, closing a single customer worth $29M in software and services.

Education

  • UCLA
    BA, Economics
  • San Marin High School

Community

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