Interviewing for Character: First Job Question

Jason Eubanks on Building Oracel: Raising $30M in 28 Hours to Disrupt the $236B Go-To-Market Tooling Market with AI-Native Sales AutomationJason Eubanks, CEO and Co-founder of Oracel, discusses how the company raised $30 million in just 28 hours—oversubscribed at $40 million—by solving a critical problem in the go-to-market industry. With a $236 billion market opportunity and only a "desert of innovation" since the late 1990s, Aurasell is building an AI-native platform to intelligently automate sales workflows and consolidate the 12-15 fragmented tools that plague modern sales teams. Jason shares how his experience scaling revenue from $1M to $100M+ across five startups—including Twilio (IPO), Meraki (acquired by Cisco for $1.2B), and Harness—directly informed the founding vision of AurasellEpisode Timestamps- 00:00 - Introduction and Jason Eubanks joins the podcast- 00:26 - Why Oracel raised $30M in 28 hours despite initial $40M oversubscription- 01:24 - The "desert of innovation" in go-to-market tooling since the late 90s- 01:42 - History of CRM evolution from mainframe to cloud to niche products- 03:12 - Founding vision: One intelligent GTM sales platform to replace them all- 03:39 - How pain as a CRO across five startups led to Oracel's creation- 05:58 - The X-Ray productivity assessment revealing tool sprawl inefficiencies- 07:59 - Sellers spending 28% of time selling and 70% on manual tasks- 09:03 - First principles AI-native approach with whiteboards in the kitchen- 09:29 - Five key personas: SDR, seller, IC manager, executive, ops team- 12:18 - AI-native architecture: multimodal interface, lakehouse, and 10,000 agents- 14:39 - Unified data model importance for contextualized AI automation- 15:45 - Current hat wearing: product focus and 50% building go-to-market engine- 18:43 - Platform features and customer experience design philosophy- 19:05 - Three wow moments per persona as success metric- 20:39 - Onboarding experience: automatic territory building and customer choice- 21:40 - 10,000 agents discovering ICP, personas, and competitors automatically- 24:07 - Automated account research and value hypothesis creation- 25:34 - Outbound prospecting content generation with propensity scoring- 26:32 - Outbound sequencer integration and email platform plugins- 27:00 - AI voice dialer coming in three weeks with closed-loop automation- 28:47 - What's missing: deep marketing and customer success automation- 30:49 - Ideal customer profiles: startups and enterprises with tool sprawl- 31:30 - Solution for heavily customized legacy systems coming in December- 34:24 - Dynamic change detection layer solving technical debt- 36:23 - Jason's career arc from BMC Software through Harness- 37:09 - Why: helping go-to-market operators solve problems he experienced- 39:55 - Meraki's disruptive cloud-managed network architecture- 41:51 - Three constants: great product builders, important problems, massive markets- 43:22 - Intrinsic motivation as foundation for hiring and culture- 45:31 - Hiring from first job onward to assess character and values- 51:24 - Understanding why someone wanted to work at 14 years old- 53:21 - Importance of formative years for work ethic and intelligence- 55:46 - AI adoption culture: using own product and building agents internally- 56:36 - All employees use AI daily across PMs, engineers, and operations- 59:25 - Ask AI features: analytics dashboards, data enrichment, natural language-