James A. O'Sullivan

#1 Sales Hero

Greater Chicago Area

About

I believe that 99% of people are 99% good. Bookmark Apollo.io/academy for a good time. Creating content for beginners, founders, business owners, people new to Apollo.io & sales vets looking for an edge.

Experience

  • Apollo Academy Sales Expert at Apollo.io
    Nov 2023 - Present · 2 yrs 9 mos

    The best sales trainings and content @ www.apollo.io/academy Bookmark for a good time.

  • Leadership Network at Entrepreneur Media
    Sep 2020 - Sep 2024 · 4 yrs 1 mo

    Can anyone even remember what life was like before my Entrepreneur.com webinar "The Winners and Losers of Covid-19"? [Highest audience retention of any Entrepreneur Mag webinar ever.]

  • VP of Sales (GTM) at Teamflow
    Apr 2021 - Mar 2023 · 2 yrs

    +Development of outbound GTM playbook: Building process and infrastructure from an ecomm-only starting point, while selling to both our inbound leads and outbound generated opportunities +Sold 63% of net new logos (2022), covering every viable bucket (SMB, MM, Enterprise, EDU and Gov) and covering every continent +Increased avg deal size by 138% (2022) +Created Enterprise-Tier paid pilot program that improved our large customer average run rate by 580% +Handled sales, negotiation and procurement for F500 customers [6 net new sold in 2022]\ TIME Magazine featured us as a "Top Invention of 2021" - check out the article here: https://time.com/collection/best-inventions-2021/6113096/teamflow/

  • Vice President of Sales at Assemble
    Jul 2020 - Apr 2021 · 10 mos

    Brought in by existing investors (Studio.VC, Entrepreneur Media) and leadership to build out sales and pivot the product toward a scalable, sustainable model. Participated in fundraising efforts to close Seed round; brought on largest investor to close out the round and improve capital position of company. Leveraged experience from CareerBuilder and Uber Works in partnering with the Leadership and Product teams to pivot the organization toward a 2-way marketplace - building the first "Fractional Talent" engine and creating differentiation against entrenched competitors. Increased NRR by 82% and improved margins on new customers by 40%

  • Senior Manager, Uber Works [GTM] at Uber
    Apr 2019 - Jul 2020 · 1 yr 4 mos

    A "wizard", as termed by founder and CEO. +Brought in first seven-figure ($XM) deals for company +Handled sale, negotiation and onboarding of largest accounts +Zero biller accounts sold to $50M+ARR (had to stop selling, company hit capacity limits of current tech and HC) +NRR of 320% by month 9 (compared to pre-existing 43% NRR) +Increased ARR from $500K/yr to ~$25M/yr within first 12 months +Was credited with saving company and getting Uber Works full funding to move out of stealth +Increased pricing and margins by 55%+ ["First Uber startup to launch at-scale profitable."] GTM and Sales Strategy for incubator company and (stealth) pilot. Hired to fix sales; develop GTM and sustainable revenue base in order to graduate incubator, achieve public launch and multi-market expansion. Created a sales process that resulted in dramatically improved metrics (margin, top line, churn, acquisition pace, utilization rate, MOM existing client trend). Created scalable and sustainable sales process that graduated Uber Works from incubator and got initial funding for launch into 3 markets. [Uber response to COVID crisis resulted in all internal start-ups being shut down, and any business unit not materially contributing to profitability was to be shut-down or sold.]