Jake RandallBook 30 Minutes

Technology Investor and Strategist

Jake Randall

I invest in and study enterprise technology at Sapphire Ventures, working across strategy, research, and capital markets. Before Sapphire, I evaluated software acquisitions at Tritium Partners and advised investors and corporate leaders at EY-Parthenon and Monitor Deloitte.

Current WorkEnterprise AI, software, data-center infrastructure, fintech, and public markets.

View ExperienceRead Essays
Jake Randall outdoors.
Austin, Texas

01 / Do

Experience

I have worked on acquisitions, portfolio strategy, pricing, AI adoption, data-center power, and commercial diligence.

The work has ranged from building investment and valuation models to interviewing customers, mapping markets, and advising management teams on growth and operating decisions.

01

Investment Analysis

Commercial diligence, investment theses, financial modeling, valuation, and investment-committee materials.

02

Company Strategy

Pricing, monetization, market entry, go-to-market planning, portfolio KPIs, and M&A screening.

03

Market Research

Market sizing, competitive analysis, capital markets, enterprise software, and data-center infrastructure.

04

Applied AI

Workflow design, use-case prioritization, product assessment, valuation tools, procurement, and adoption.

Selected Project Experience

Client Names Withheld

Sapphire Ventures

Senior Associate, Strategy, Research & Capital Markets

Nov 2025 - Present

Thematic research, portfolio analysis, strategic projects, and capital-markets work for a $10B+ venture firm.

01

Pricing & Monetization

Advised the CEO of an AI commerce platform on monetizing new products. Built a pricing model and recommended a premium subscription plus outcome-based fees, informing the adopted architecture.

02

Public Portfolio Strategy

Analyzed a $100M-$150M public-equity portfolio using filings, research, and scenario analysis. Recommended a holding strategy that preserved exposure through near-term appreciation and established a path toward a blended ~3.0x gross return.

03

Data-Center Power Thesis

Mapped power constraints, market structure, and investment opportunities across the AI data-center ecosystem. The work informed investor discussions and CEO evaluation of a bespoke investment vehicle.

04

LP Engagement

Led AI investment-workflow teach-ins for Fortune 500 and institutional executives.

05

Capital Markets & Thought Leadership

Co-authored monthly market memos, an annual capital-markets report, and related analysis distributed to more than 2,000 founders and investors.

Tritium Partners

Investment Associate

Jun 2024 - Oct 2025

Acquisition analysis and portfolio work for a $1.5B private equity firm investing in high-growth technology businesses.

01

Talent-Intelligence Acquisition

Built financial, retention, LTV/CAC, and valuation models for a $100M+ acquisition. The analysis supported investment-committee approval and the transaction closed.

02

Vertical SaaS & Embedded Payments

Evaluated more than 20 payments providers to design a vertical SaaS roll-up strategy. The work produced an executed LOI and advanced discussions with additional acquisition targets.

03

Portfolio Oversight

Served as Board Observer across five portfolio companies, leading KPI monitoring and advising executives on M&A, forecasting, growth, and profitability.

04

AI Valuation Tool

Built an automated tool that interpreted target-company inputs and benchmarked valuation against public and private market data.

05

AI Procurement & Adoption

Led sourcing, negotiation, and firm-wide rollout of an AI market-intelligence platform under a ~$100K annual contract.

EY-Parthenon

Senior Associate, Private Equity

Aug 2022 - May 2024

Commercial diligence and corporate strategy for private equity and corporate clients.

01

$300B+ Pharmaceutical Company

Prioritized generative-AI use cases and a product-quality reporting roadmap. The selected initiatives were expected to produce approximately $50M in annual savings.

02

B2B SaaS Company In Buy-Side Diligence

Interviewed customers and modeled recession-driven seat changes to test the effect of weaker enterprise spending. The work found that software spending in the relevant vertical was counter-cyclical.

03

Oilfield Services Company In Commercial Diligence

Quantified a 15% gross-profit drag from product and geographic mix and SG&A/R&D inefficiencies. The analysis supported an activist thesis targeting approximately $4B of equity value.

04

Manufacturing Company In Buy-Side Diligence

Analyzed revenue by customer, region, and end market to test whether historical growth was defensible. The work identified attractive semiconductor and pharmaceutical exposure but flagged semiconductor cyclicality as a material risk.

05

Utility Company Expanding EV Charging

Consolidated commercial fleet data to size the fleet-management opportunity and identify priority customer segments for a utility's EV-charging division.

Monitor Deloitte

Strategy Consultant

Nov 2020 - Jun 2022

Growth and transaction strategy across software, financial services, shared services, and real estate.

01

Financial Services Organization Evaluating Growth Markets

Benchmarked consumer-finance markets across size, growth, competition, and right to win. Financial data and insights tied to savings products ranked as the strongest investment opportunity.

02

Investors Evaluating Movie-Production Real Estate

Combined historical investment and demand data into a geographic supply-demand forecast for movie-production real estate. The analysis identified London and Atlanta as attractive entry markets.

03

Enterprise Software Company Building An Acquisition Strategy

Screened and ranked 30 software acquisition targets with $100M to $500M in revenue. The prioritized list formed the basis of management's acquisition strategy.

Earlier Experience

2017 - 2019

Cisco Systems

Summer Intern / 2019

Global enterprise software and networking company.

SVB Capital

Summer Intern / 2018

Venture-capital platform investing in funds and companies.

Playground Global

Summer Intern / 2017

Early-stage venture firm investing in deep technology.

Civic & Community Work

Austin, Texas
City of AustinCity of Austin

Economic Prosperity Commission

Develop policy recommendations for City Council. Current work includes an assessment of AI's potential labor impact and analysis supporting a responsible, long-term funding model for Austin Parks and Recreation through a bond.

Big Brothers Big Sisters of Central Texas

Big Brothers Big Sisters of Central Texas

Mentor a young person with a focus on life skills, confidence, and academic success.

Selected Clients

Alphabetical / Independent of Project Work

02 / Write

Essays

Enterprise AI, markets, institutions, and the social effects of technology.

Enterprise AI

Intelligence Is Not Enough

Anthropic's enterprise lead rests more on product design than on a lasting model advantage.

Institutions & Society

Spiritual Pollution

Mass shootings erode trust and public participation long after the immediate violence. Any serious response must address both violent intent and access to weapons.

AI & Education

Convergence 2: Socrates vs. Mao

AI could expand access to individual instruction or make personalized control easier. Openness and accountability will decide which version wins.

Technology & Human Connection

Convergence 1: Michelangelo, HAL-9000, a Burning Monk, and Run Clubs

AI cannot replace the parts of human expression rooted in mortality and lived experience. Digital products can also help rebuild the real-world communities earlier products weakened.

I also co-author monthly market memos, an annual capital-markets report, and related analysis distributed to more than 2,000 founders and investors.

03 / Read

Books

Books I return to, recommend, or am still working through.

Non-Fiction

  1. 01IncertoNassim Nicholas Taleb
  2. 02The Rational OptimistMatt Ridley
  3. 03FactfulnessHans Rosling, Ola Rosling, and Anna Rosling Rönnlund
  4. 04The Almanack of Naval RavikantEric Jorgenson
  5. 05The Anthology of BalajiEric Jorgenson
  6. 06The Network StateBalaji Srinivasan
  7. 07Steve JobsWalter Isaacson
  8. 08Elon MuskWalter Isaacson
  9. 09The Rise of Theodore RooseveltEdmund Morris
  10. 10EssaysMichel de Montaigne
  11. 11Complexity: A Guided TourMelanie Mitchell
  12. 12Artificial Intelligence: A Guide for Thinking HumansMelanie Mitchell
  13. 13Capitalism in AmericaAlan Greenspan and Adrian Wooldridge
  14. 14The Selfish GeneRichard Dawkins
  15. 15SapiensYuval Noah Harari
  16. 16On ChinaHenry Kissinger
  17. 17BreakneckDan Wang
  18. 18Poor Charlie's AlmanackCharles T. Munger
  19. 19Wanting: The Power of Mimetic Desire in Everyday LifeLuke Burgis
  20. 20The Psychology of MoneyMorgan Housel
  21. 21Zero to OnePeter Thiel with Blake Masters
  22. 22MeditationsMarcus Aurelius
  23. 23Thinking, Fast and SlowDaniel Kahneman

Fiction

  1. 24Dune SeriesFrank HerbertRead Through Dune Messiah
  2. 25The Sun Also RisesErnest Hemingway
  3. 26A Farewell to ArmsErnest Hemingway
  4. 27Hyperion CantosDan SimmonsFinished
  5. 28Red Rising SeriesPierce BrownReading Iron Gold
  6. 29A Song of Ice and FireGeorge R. R. MartinRead Through A Clash of Kings
  7. 30All the Light We Cannot SeeAnthony Doerr
  8. 31A Gentleman in MoscowAmor Towles
  9. 32The HobbitJ. R. R. Tolkien
  10. 33The Lord of the RingsJ. R. R. Tolkien
  11. 34Any Human HeartWilliam Boyd
  12. 351984George Orwell
  13. 36Brave New WorldAldous Huxley