Rob Crumpler

San Francisco12.3k followers

Gravity AI

ex-Altrooz

ex-Microsoft

I’m a multi-time startup CEO, CFO, and CRO with a track record of building companies from zero to one – and scaling them to meaningful revenue in highly disruptive markets, including Mobile, Big Data, SaaS, and now
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I’ve scaled businesses from $0 to $10M+ ARR multiple times in under two years and built the first profitable division at Microsoft/MSN, growing it from $0 to $180M in ARR in under 24 months. My experience spans fundraising, P&L ownership, go-to-market strategy, product-led growth, and operational execution – with a consistent focus on building high-performing teams that deliver measurable customer Over the past three decades, I’ve operated through every major technology and economic inflection point – Y2K, the dot-com collapse, 9/11, the 2008 financial crisis, COVID, and now the AI transformation. Each shift reinforced a core belief: technology changes rapidly, but customer needs – resilience, clarity, growth, and actionable insight – remain Today, my focus is on AI-driven companies that turn data into a durable competitive advantage. I specialize in:• Building and leading executive teams in high-growth environments• Driving revenue from early traction to scaled ARR• Structuring and raising venture capital• Designing product-led and ecosystem-driven growth models• Translating emerging technology into valuable customer impactI believe great AI companies are built at the intersection of technical innovation, operational discipline, and customer empathy. Behind every metric is a customer depending on the outcome – and behind every strategy is a team that must execute with speed, focus, and If you’re building or investing in the next generation of AI-native companies, let’s connect.

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GTM Index

GRAVITY AIJOB
1. Head of GTM & Partnerships
  5M
ALTROOZJOB
1. Founder & CEO
  13Y 4M
ADKNOWLEDGEJOB
1. Executive Leader
  1Y 2M
MARKETWIRED (NOW NOTIFIED)JOB
1. Executive Leader
  1Y
BUZZLOGICJOB
1. Co-Founder & CEO
  5Y 7M
MICROSOFTJOB
1. BD Mgr | MSN
  6Y 8M
INTUITJOB
1. BD Mgr
  1Y 9M
ON THE GO SOFTWAREJOB
1. Founder, CEO
  6Y 1M

Job: Altrooz — Founder & CEO | Mobile Ad-Tech Startup · 2012-11 – 2026-03 — Founded and scaled a high-growth mobile advertising platform, reaching profitability within 8 months and surpassing $10M in ARR within 24 months. Built a performance-driven digital media acquisition engine serving major brands and gaming advertisers, delivering an average of 4M/year high-value mobile app users across global campaigns. Designed and launched two proprietary mobile applications that generated first-party behavioral data for a machine learning–powered data management platform (DMP), enabling advanced audience cohort segmentation and materially improving ROAS for enterprise clients. Led customer acquisition and account growth for marquee brands including Microsoft, Amazon, Star…
Job: Microsoft — Business Development Manager | MSN · 1997-11 – 2004-07 — Designed and executed MSN’s first scalable ad-supported monetization model, driving $50M in revenue in year one and accelerating to $180M in ARR by year two (3.6x YoY growth), establishing the first profitable business unit within Microsoft/MSN ahead of CarPoint. Led go-to-market strategy, enterprise partnerships, and channel expansion across the financial services vertical, unlocking high-LTV distribution relationships and recurring licensing revenue. Co-created a wealth management platform for RIAs, securing strategic integration and channel partnership with Advent Software that materially expanded distribution across wealth management providers, increased enterprise adoption, and strengt…
Job: Adknowledge — Executive Leader | Ad-Tech Company (Turnaround) · 2011-08 – 2012-10 — Following Facebook's launch of its own virtual currency and removal of SuperRewards, I led company-wide expansion into new growth markets, repositioning the SuperRewards virtual currency platform within the MMO gaming ecosystem and launching a new mobile performance ad network. Scaled revenue from $12M to $20M+ ARR within 12 months (67% YoY growth) through strategic repositioning, product-market alignment, and GTM execution. Built and reorganized the senior leadership team, integrating core AORs across product, sales, marketing, and operations to drive executional alignment and operating leverage. Incubated and launched a 0-to-1 mobile ad network that reached $3M ARR within six months, est…
Job: BuzzLogic — Co-Founder & CEO | Brand Monitoring & Social Advertising Company · 2005-01 – 2010-08 — Co-founded and scaled a category-defining brand monitoring and social media advertising platform based on natural language processing (NLP), raising $20M in venture capital and surpassing $10M in ARR within 24 months. Built the organization from the ground up – recruiting exceptional cross-functional talent across product, engineering, sales, and marketing – and implementing a balanced scorecard framework that defined OKRs, enforced accountability, and institutionalized execution velocity as a competitive advantage. Iterated and commercialized innovative, creative ad products that powered 40% of overall go-to-market activity, accelerating customer acquisition and expanding enterprise deal…
Job: Intuit — Business Development Manager | Internet Strategy Team · 1996-02 – 1997-11 — Designed and executed MSN’s first scalable ad-supported monetization model, driving $50M in revenue in year one and accelerating to $180M in ARR by year two (3.6x YoY growth), establishing the first profitable business unit within Microsoft/MSN ahead of CarPoint. Led go-to-market strategy, enterprise partnerships, and channel expansion across the financial services vertical, unlocking high-LTV distribution relationships and recurring licensing revenue. Co-created a wealth management platform for RIAs, securing strategic integration and channel partnership with Advent Software that materially expanded distribution across wealth management providers, increased enterprise adoption, and strengt…
Job: Marketwired (now Notified) — Executive Leader | Brand Monitoring & Public Relations Company · 2010-08 – 2011-08 — Led strategic product partnerships that secured and integrated direct access to the Twitter Firehose through collaboration with Twitter and Gnip. Negotiated commercial and technical agreements enabling real-time ingestion of the full Twitter data stream into the Marketwire platform, positioning the company at the forefront of social media intelligence and enterprise-grade analytics. Drove cross-functional execution across product, engineering, and BD teams to operationalize large-scale data infrastructure and unlock new revenue opportunities in media monitoring and social analytics.
Job: On The Go Software — Founder, CEO | SMB & Enterprise Financial Software Company · 1990-01 – 1996-02 — Led development and commercialization of enterprise workflow software for corporate expense management, pioneering automated financial reporting for mid-market and enterprise customers. Scaled customer base to 3,600+ SMB and Fortune 500 clients, including Johnson & Johnson, Baxter, and Procter & Gamble, driving rapid market adoption. Successfully positioned the company for acquisition by Intuit (NASDAQ: INTU) in 1996.
Job: Gravity AI — Head of GTM & Partnerships | AI-Native Advertising Startup · 2026-03 – present — AI-Native Advertising
School: University of California, Los Angeles — Bachelor of Arts - BA, Economics

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New Market ExpansionSales StrategyAdvertisingRevenue GenerationUnstructured DataSQLCloud ApplicationsLean StartupEnterprise SoftwareBusiness InnovationDue DiligenceBig DataCustomer EngagementMentoringBusiness-to-Business (B2B)StrategyTeam LeadershipPython (Programming Language)Amazon Web Services (AWS)Customer Segmentation Strategy

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Rob Crumpler

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