Demand Jump

Christopher Day and Sean Swigman spent 18 months discussing a massive pain point in marketing before launching Demand Jump in February 2015. Swigman, who had been CMO at Overstock through its growth from $3M to $800M and IPO, saw firsthand that marketers were blind to their actual digital ecosystem. "The internet came along and everybody forgot about location, location, location," Day recalls. "Marketers today are measured on new customers and revenue, but they have no visibility into where to actually find qualified traffic." They discovered that 90% of the 5,000+ martech tools were either silo-based or retention-focused—nobody solved acquisition at scale.

After launching in February 2015, the team spent months testing their core thesis before building what they called "the world's first traffic cloud" starting in October 2016. They went to market with version 1.0 to beta customers in July 2016, then launched version 2.0 just two weeks before this interview. The platform takes a customer's actual data, overlays their competitive digital ecosystem, and analyzes all data across channels to show exactly where to focus to capture qualified traffic. Day raised $4M in capital from angel investors including Bill Godfrey (co-founder/CEO of Aprimo, which sold to Teradata), Tim Kopp (former CMO of Exact Target, which sold to Salesforce for $2.6B), and other martech veterans who understood the gap they were filling.

Demand Jump pursued high-touch enterprise sales with strategic positioning. Day says he'd "do anything to acquire a customer"—willing to meet prospects at midnight in a bar if needed. The strategy paid off: by interview time, they had 22 customers with an average annual contract value of $45,000 (though new contracts were running $150k–$200k). They retained 89% of customers annually on both a logo and revenue basis, with a three-month payback period on their ~$10k customer acquisition cost. Most customers (8 of 10) paid annually upfront, giving them immediate cash flow.

Enterprise direct sales to Fortune 500 marketing teams worked extremely well, but the high-touch model limited scale. In 2016, their first real revenue year, they hit $165k total revenue and $10k MRR by December. By interview (roughly August 2017), they'd scaled to $85k MRR (~$1M ARR), a near 8.5x increase in less than a year. However, they realized they were capturing only the highest-tier enterprises. Day acknowledged they'd spent only ~$5k on paid digital marketing and planned to dramatically increase this. They were about to launch a self-service "walk-up" freemium model starting at just $200/month (for up to 1M events) to capture mid-market, while keeping enterprise contracts as high as $500k annually. This two-tier strategy would unlock massive scale without abandoning their high-margin enterprise business.

Day was raising a Series A ($5M target at a $25M–$30M pre-money valuation) with multiple VCs expressing serious interest and no lead yet selected. He believed they'd grow into that valuation in 24 months or less. The team had grown to 17 people across data science/engineering (7), customer success (3), sales (3), marketing (2), and a newly hired CFO. Based in Indianapolis with one salesperson elsewhere, they were preparing for a national announcement and planning to scale paid marketing from $5k to $20k+ monthly while maintaining their 82% pure SaaS recurring revenue (with 1% one-time data fees and 17% subscription-based assurance services). Day's philosophy: relationships matter most, and he'd already sold two companies to Fortune 100 firms before age 40.