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

Barrington, Illinois, United States9.6k followers

Outmarket AI

ex-H1

ex-DocuSign

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.

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GTM Index

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

Job: Outmarket AI — Chief Revenue Officer · 2026-02 – present · 6 mo — Chief Revenue Officer at Outmarket.ai Outmarket is building the intelligence layer for commercial insurance brokers. Commercial agencies (P&C and EB) operate in fragmented workflows — PDFs, emails, carrier portals, AMS systems, and institutional knowledge sitting in producers’ heads. We turn that chaos into structured insight that helps brokers move faster, make better decisions, and protect margin. We currently support 250+ agencies across the U.S., including several of the top 100 brokers. The demand is real. The opportunity is large. My mandate is to build a disciplined, repeatable revenue engine that scales. That includes: • Establishing high-velocity, structured sales execution • Tig…
Job: Outmarket AI — Advisor · 2025-09 – present · 11 mo — Providing strategic guidance on go-to-market and sales strategy, including org design, processes, pricing, customer acquisition, and mentorship for the leadership team. Supporting strategic planning, investor preparation, and high-value customer engagements.
Job: Simplify Healthcare — Advisory Board Member · 2025-04 – present · 1y 4mo — Simplify Healthcare powers connected benefits and provider journeys on a foundation of clean and rich product, benefits, and provider data across the Payer ecosystem through our end-to-end platform Simplify Health Cloud™. We are the Payer Platform that enables core payer administrative systems such as Claims Processing to be more fully integrated with product, benefits, and provider capabilities. The benefits? Better automation, faster product, benefits, and provider changes, greatly improved accuracy and regulatory compliance, and more transparent provider servicing all on a modern cloud platform.
Job: H1 — GTM advisor · 2023-07 – 2023-09 · 2 mo
Job: H1 — Chief Revenue Officer (CRO) · 2022-11 – 2023-07 · 8 mo — Alpesh leads the commercial team for H1
Job: DocuSign — Vice President, Enterprise Strategic Verticals · 2017-02 – 2022-06 · 5y 4mo — Alpesh is the Vice President for Enterprise Verticals at DocuSign. He leads DocuSign’s Go-to-Market strategy and execution for our Enterprise Financial Services, Insurance, Healthcare and Life Sciences, Telco, Media and Utilities customers. Alpesh also built DocuSign’s Enterprise Corporate Sales team for North America and led Enterprise wide Growth initiative (e.g. Value Engineering, Salesforce partnership, Big deal program). DocuSign helps businesses of all sizes easily and securely sign, send, and manage documents in the cloud with unmatched availability and legal enforceability. Its Digital Transaction Management platform keeps processes 100% digital from start to finish, accelerating…
Job: DocuSign — Vice President and General Manager, Insurance · 2014-07 – 2017-01 · 2y 6mo — Alpesh is the Vice President and General Manager for Insurance Industry at DocuSign. He drives DocuSign’s Go-to-Market strategy and execution for our Enterprise Insurance customers. In addition to leading sales team, he leads teams to execute on Industry Solutions, ISV alliances, Industry Marketing and Customer Success. In the past 2 years, under Alpesh's leadership Insurance has become the fastest growing vertical business for DocuSign. * 177% revenue attainment, with 600% Y2Y growth, against FY16 budget * 142% revenue attainment against FY15 budget DocuSign helps businesses of all sizes easily and securely sign, send, and manage documents in the cloud with unmatched availability and l…
Job: Salesforce — Regional Vice President of Sales · 2013-05 – 2014-06 · 1y 1mo — Job description: The Regional Vice President of Sales is fully responsible for developing and managing a team Senior Account Executives to generate revenue and achieve individual, team and organizational quotas. Contributes to Field sales strategy. Accomplishments: #2 Worldwide Regional Vice President - FY 14 (190% achievement against the budget) 52% Y2Y growth in one of the top 3 highest revenue generating territory of last FY 4 Strategic multi-year agreements in various industries (BPO, Bank, Healthcare provider, CPG) Rebuilt a team with onboarding 3 (out of 7) new Account Executives
Job: Salesforce — Account Executive · 2010-09 – 2013-03 · 2y 6mo — Lead a cross-functional team to drive customer success and generate new revenue for Salesforce.com. Accomplishments: Accomplishments: • #1 Worldwide Account Executive FY 2013 • #1 Worldwide Account Executive - FY 2012 • Led team of 100+ employees in closing key new customer win for $100M+
Job: IBM — Software Sales Manager for IBM Cloud/Collaboration · 2010-07 – 2010-09 · 2 mo — Lead a team of 13 direct software sales executives in the Midwest region to grow IBM Cloud and Collaboration business.
Job: IBM — Software Account Executive · 2003-03 – 2010-07 · 7y 4mo — Build strategic relationship with named accounts to grow IBM Software Revenue and Customer Satisfaction. Lead IBM Software team in account planning, demand generation and sales execution. Lead pricing and contract negotiations for large/complex Enterprise Software deals.
Job: Rational Software — Software Sales Specialist · 2000-07 – 2003-03 · 2y 8mo
Job: GE Medical Systems — Sr. Software Engineer · 1997-10 – 2000-03 · 2y 5mo
Job: Motorola Mobility — Software Engineer · 1994-03 – 1997-03 · 3y
School: University of Chicago — MBA, Strategy, Finance
School: Illinois Institute of Technology — MS, Computer Science
School: Gujarat University — Bachelor, Engineering

Skills

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

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Alpesh Patel

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