James Kaikis

The B2B sales cycle is collapsing. I highlight how GTM Operators navigate the change. | GTMshift + SolutionExec | Co-Founded PreSales Collective (Acq. 2021)

Location n/a
SolutionExecex-Salesforceex-PreSales Academy

The B2B sales cycle is collapsing. Most GTM teams haven't caught up yet.

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I've spent the last decade operating inside this shift — across Sales, Solutions, and GTM leadership at companies like Salesforce and Showpad, then as a founder. In 2020 I co-founded PreSales Collective, which grew to 35,000+ members across four business lines before being acquired by Sylva in 2021. That experience — building a category-defining community from zero — shapes everything I believe about where GTM is heading. Now I run two things: GTMshift - research, interviews, and live events for GTM leaders navigating the AI shift. Engineering Tailwinds is our flagship event series bringing together revenue and engineering leaders redefining how B2B companies go to market. SolutionExec - the first executive private network built exclusively for Solutions leaders in B2B SaaS. Co-founded with Jeff Margolese, GVP of Global Solutions at ServiceNow. I cover: The collapse of the traditional B2B sales cycle → AI's role in redefining how companies sell and buy → Why Solutions and PreSales is the most strategically critical GTM function right now Active on LinkedIn, Substack, and in rooms that matter. If you lead revenue, solutions, or GTM at a B2B SaaS company - follow me. com | com

Career TimelineNOW → PAST

GTM Index

  1. GTMFUNDJOB
    1. Limited Partner
      4Y 9M
  2. SOLUTIONEXECJOB
    1. Co-Founder
      7M
  3. GTMSHIFTJOB
    1. Founder
      7Y 7M
  4. STAGE 2 CAPITALJOB
    1. Limited Partner, Stage 2 C…
      4Y 5M
  5. PAVILIONJOB
    1. CRO Functional Leader
      11M
  6. TESTBOXJOB
    1. Chief Revenue Officer (CRO)
      7M
    2. Head of GTM
      1Y 3M
  7. PRESALES ACADEMYJOB
    1. Co-Founder (Acquired, Nov…
      1Y 11M
  8. PRESALES COLLECTIVEJOB
    1. Host: The PreSales Podcast…
      3Y
    2. Co-Founder (Acquired, Nov…
      3Y 5M
  9. SYLVAJOB
    1. General Mgr (Post PSC Acqu…
      1Y 7M
  10. SALESFORCEJOB
    1. Dir, Solutions Eng
      0M
    2. Senior Mgr, Solutions Eng
      1Y 3M

Time in market 7Y 7MOpen 4Closed 9Stints 13

gtmindex.io/p/jameskaikis

  1. Job: Salesforce — Director, Solutions Engineering · 2021-02 – 2021-02
  2. Job: PreSales Academy — Co-Founder (Acquired, Nov 2021) · 2021-07 – 2023-06
  3. Job: TestBox — Chief Revenue Officer (CRO) · 2024-12 – 2025-07
  4. Job: TestBox — Head of Go-To-Market / Chief Solutions Officer · 2023-09 – 2024-12
  5. Job: GTMfund — Limited Partner · 2021-11 – present
  6. Job: SolutionExec — Co-Founder · 2026-01 – present
  7. Job: GTMshift — Founder · 2019-01 – present
  8. Job: PreSales Collective — Host: The PreSales Podcast (Acquired, Nov 2021) · 2020-06 – 2023-06
  9. Job: Pavilion — CRO Functional Leader · 2025-01 – 2025-12
  10. Job: Stage 2 Capital — Limited Partner, Stage 2 Capital Catalyst · 2022-03 – present
  11. Job: Salesforce — Senior Manager, Solutions Engineering · 2019-10 – 2021-01
  12. Job: Sylva — General Manager (Post PSC Acquisition) · 2021-11 – 2023-06
  13. Job: PreSales Collective — Co-Founder (Acquired, Nov 2021) · 2020-01 – 2023-06

Skills

SalesforceGo-to-Market StrategyRevenueSolutionsAI StrategyEvent PlanningCustomer EngagementCustomer ExperienceSales EnablementPublic RelationsCorporate EventsArtificial Intelligence (AI)EntrepreneurshipCustomer Lifecycle ManagementManagementLeadershipCustomer ServicePublic SpeakingStart-upsSaaSSales

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