Alex Wakefield

About

I architect and scale revenue engines for high-growth tech companies. Former Dropbox GTM strategist with an engineering foundation, startup-founder grit, and deep enterprise RevOps experience. Today I’m building the next-gen revenue system at Tremendous, the platform that lets organizations pay anyone, anywhere—in seconds. My focus: turning messy GTMs into clean, AI-driven feedback loops that fuel predictable growth. Advisor to B2B startups on GTM transformation. Off the clock, come find me enjoying a slice of paradise under the Encinitas sun.

Company history

1. 
   DropboxSales Development, Enterprise 2017-05 – 2017-11 · 6 mo
2. 
   TremendousDirector of Revenue OperationsRevOps2025-06 – present · 1y 2mo
3. 
   AmplemarketHead of GTM Engineering (Scale Rev. | Solutions Eng. | RevOps)Head of GTM Engineering2023-11 – 2025-06 · 1y 7mo
4. 
   GoodyRevOps ConsultantRevOps2021-10 – 2022-06 · 8 mo
5. 
   AmplemarketHead of Revenue Strategy & Operations2022-03 – 2023-11 · 1y 8mo
6. 
   DropboxSales Strategy, Global Sr. Analyst2018-05 – 2020-01 · 1y 8mo
7. 
   DropboxCustomer Success, Growth Manager2017-11 – 2018-05 · 6 mo
8. 
   DropboxHead of Sales Strategy, AMER2020-01 – 2021-05 · 1y 4mo
9. 
   National InstrumentsLabVIEW Student Ambassador2015-08 – 2016-05 · 9 mo
10. 
    National InstrumentsEngineering Leadership Program Intern2015-05 – 2015-08 · 3 mo
11. 
    LoomRevOps AdvisorRevOps2023 – 2023 · 0 mo
12. 
    OpalRevOps AdvisorRevOps2023 – 2023 · 0 mo
13. 
    National InstrumentsApplications Engineer2016-08 – 2017-02 · 6 mo
14. P
    Parking Grid TechnologiesCoFounder & COO2015-05 – 2016-10 · 1y 5mo
15. 
    MakerSightsDirector, Sales Strategy & Operations2021-05 – 2022-02 · 9 mo
16. 
    National InstrumentsSales Engineer2017-02 – 2017-05 · 3 mo

Skills

No playbooks indexed for this profile yet.