Oliver (Ollie) Stewart

A hands-on experienced Customer Success and GTM leader across 9 start-ups and scale-ups in the USA, UK and NZ. Success in building an FT500 portfolio from scratch and building the team, platforms and processes required to retain and grow this. Worked and advised series A-C scale-ups, right through to pre-seed start-ups. Experience in Customer Success, Sales, Partnerships, Solutions Consultancy and Marketing.

  • Built from scratch and scaled a $26M portfolio of FT500 Brands, with a 23-person global Customer Success team (CSMs, Support, Education and Premium Services) with an average upsell of 24% and an average team tenure of 5 years

  • Direct experience across 9 startups and scale-ups in the USA, UK and New Zealand

  • Coached 45+ Aotearoa startups and scale-ups as an ‘Expert in Residence at the Ministry of Awesome in Ōtautahi, helping them to:

  • Define their ICP, create customer personas, and design high-impact customer journeys to laser-focus their limited resources on the highest-value focus areas.

  • Decrease their time-to-value for onboarding customers, measuring and communicating the ROI of their products.

  • Build and execute GTM strategies.

  • Solutions Architect expertise (AKA Sales Engineer, Solutions Consultant): I’ve focused on reducing the sales cycle, increasing prospect confidence through proof-of-value sprints that showcase rapid ROI, delivering outcomes and measurable ROI, building sales and CS collateral, and coaching teams on value selling, writing impactful proposals.

  • Customer marketing: Skilled in creating new marketing channels for companies, focused on capturing and communicating ROI to drive expansion opportunities, support renewals and drive referrals

  • Building systems processes, assembling tech stacks, and producing high-quality collateral

Focus

  • Designing and building your customer journey to increase customer acquisition, improve time to value, and increase renewals, expansions and advocacy.

  • Reduce sales cycles and increase deal size through, Proof of value sprints, ROI modeling, proposals and coaching.

  • Customer marketing: Skilled in creating new marketing channels for companies, focused on capturing and communicating ROI to drive expansion opportunities, support renewals and drive referrals

  • Building systems processes, assembling tech stacks, and producing high-quality collateral.