Alpesh Patel

GTM Advisor | Helping Enterprise Software Companies Simplify and Scale Enterprise Sales Through Vertical Specialization and AI driven Strategy | Ex-Salesforce, DocuSign, H1 | Building Sales Engines That Scale

Location n/a
Outmarket AIex-Motorola Mobility (a Lenovo Company)ex-Rational Software

I advise founders and GTM leaders on how to scale from product-market fit to predictable enterprise growth.

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I specialize in helping Software and AI companies build vertical go-to-market motions, expand into regulated industries (Insurance, Financial Services, Healthcare, Life Sciences), and close enterprise-scale deals. Over the past 20 years, I’ve led GTM transformations across Salesforce, DocuSign, and H1. At Salesforce, I closed the largest deal in company history (2012) in P&C insurance and later led the Enterprise Insurance sales team. At DocuSign, I built the Enterprise Insurance business from the ground up and led Financial Services and Insurance verticals to over $250M in ARR. Today, I serve as a strategic advisor to high-growth SaaS and AI companies including ai and Simplify Healthcare, helping them define and scale their GTM systems for the enterprise era. I’m open to selective advisory opportunities where founders value practical GTM experience, enterprise selling discipline, and a customer-centric growth mindset.

Career TimelineNOW → PAST

GTM Index

  1. OUTMARKET AIJOB
    1. Chief Revenue Officer
      6M
    2. Advisor
      11M
  2. SIMPLIFY HEALTHCAREJOB
    1. Advisory Board Member
      1Y 4M
  3. H1JOB
    1. GTM advisor
      2M
    2. Chief Revenue Officer (CRO)
      8M
  4. DOCUSIGNJOB
    1. VP, Enterprise Strategic V…
      5Y 4M
    2. VP and General Mgr, Insura…
      2Y 6M
  5. SALESFORCEJOB
    1. Regional VP of Sales
      1Y 1M
    2. Account Executive
      2Y 6M
  6. IBMJOB
    1. Software Sales Mgr for IBM…
      2M
    2. Software Account Executive
      7Y 4M
  7. RATIONAL SOFTWAREJOB
    1. Software Sales Specialist
      2Y 8M
  8. GE MEDICAL SYSTEMSJOB
    1. Sr. Software Eng
      2Y 5M
  9. MOTOROLA MOBILITY (A LENOVO COMPANY)JOB
    1. Software Eng
      3Y

Time in market 32Y 5MOpen 3Closed 11Stints 14

gtmindex.io/p/gtmsimplified

  1. Job: Motorola Mobility (a Lenovo Company) — Software Engineer · 1994-03 – 1997-03
  2. Job: Rational Software — Software Sales Specialist · 2000-07 – 2003-03
  3. Job: H1 — Chief Revenue Officer (CRO) · 2022-11 – 2023-07
  4. Job: IBM — Software Sales Manager for IBM Cloud/Collaboration · 2010-07 – 2010-09
  5. Job: Salesforce — Account Executive · 2010-09 – 2013-03
  6. Job: GE Medical Systems — Sr. Software Engineer · 1997-10 – 2000-03
  7. Job: Outmarket AI — Advisor · 2025-09 – present
  8. Job: Docusign — Vice President and General Manager, Insurance · 2014-07 – 2017-01
  9. Job: H1 — GTM advisor · 2023-07 – 2023-09
  10. Job: Salesforce — Regional Vice President of Sales · 2013-05 – 2014-06
  11. Job: Simplify Healthcare — Advisory Board Member · 2025-04 – present
  12. Job: Outmarket AI — Chief Revenue Officer · 2026-02 – present
  13. Job: Docusign — Vice President, Enterprise Strategic Verticals · 2017-02 – 2022-06
  14. Job: IBM — Software Account Executive · 2003-03 – 2010-07

Skills

SalesforceSales ProcessesSoftware SalesContract NegotiationsEnterprise SoftwareCloud ComputingSales ProcessSales OperationsDemand GenerationSolution SellingSales PresentationsSoftware IndustryCRMStrategyManagementLeadershipSalesTeam LeadershipSaaSStrategic Planning

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