Docket: from idea to investment in 20 days 

Few people understand the timing of a B2B sales deal better than Arjun Pillai. He built an account-based marketing platform from scratch for his last employer, ZoomInfo, and he’s studied every stage of a sale, from prospecting to proposal, at other career stops. Now Arjun is on a mission to speed up the sales engineering phase of B2B deals with his gen-AI platform DocketAI, which today announced $15 million in Series A funding. 

The thesis behind Docket is simple: any questions an account executive might encounter during the sales process have likely been asked before, and you’re wasting time searching for them when the moments to close a deal are precious. Arjun lived inside this problem as the Chief Data Officer at ZoomInfo and previously at the two startups he founded, Profoundis (acquired by FullContact) and Insent.ai (acquired by ZoomInfo). 

Breaking the ice for a first meeting

I had long admired Arjun’s work, and when I reached out to him about attending a Foundation Capital event last July, I learned he left ZoomInfo two days prior to start his third company. He wasn’t looking for venture funding. Not only because he had the resources already, but also because he believed outside investors usually slow things down. Arjun told me later: “I have heard from investors quite frequently in my career, and my usual email back is a one-sentence no,” he says.  

I have heard from investors quite frequently in my career, and my usual email back is a one-sentence no.

Arjun Pillai, Cofounder and ceo of docket

I insisted on setting up a meeting, and Arjun said he was impressed by the candor and directness of our exchanges. On the Foundation Capital side, General Partner Ashu Garg and I were impressed by the clarity of Arjun’s vision. “There was alignment before we even got on the call,” Arjun says. “I knew already that we were not talking past each other.” 

The week after the initial brainstorm, Arjun took a trip to Bali that coincided with one of Ashu’s trips to India. The two met, talked for four hours in a park near Bangalore, and agreed to work together. Ashu recognized Arjun’s deep expertise in sales and marketing tech; he knew Arjun had management skills to boot. Arjun saw that Ashu had experienced the pain Docket solves during his time running operations at Microsoft. Within a month, Foundation Capital made a seed investment of $5M in Docket, one of the firm’s speediest funding processes to date. “The whole thing was done in 20 days,” says Arjun, “based on an idea that had been solidified four days before we all met.”

Assembling a team, on the double

Meanwhile, Arjun had seized on a few key openings that helped him assemble a team quickly. When he departed ZoomInfo, he was not planning to start a company right away. But last July, he realized his friend and the former co-founder of Profoundis, CTO Anoop Thomas Mathew, was receptive to starting a new venture. The duo quickly assembled a team of 10 experienced engineers, who knew each other well from their past work on a Web3 project.

With builders in place and funding secured, Arjun could focus on strategy: Docket would go after medium to complex enterprise sales motions, characterized by higher ACV (>$50K annually) and lengthy sales cycles. Arjun knew after years in the space that sales motions involved tedious back-and-forth exchanges on technical and product-related questions. Getting to the finish line might involve sales engineers, product managers, product marketers, customer success staff, security and compliance staff, or even professional services. In addition to increasing GTM costs, this back-and-forth also reduced close rates. His big idea: cut the cost of technical sales resources for large enterprises and reduce sales cycle time with an AI-powered virtual sales engineer. 

Docket had many well-funded competitors, including Glean, Highspot, and Seismic, with the latter two focused on sales enablement. But few companies narrowed their scope to sales engineers, an area that gives Docket a competitive advantage. Sales engineers, or SEs, tend to draw high salaries and are tough to recruit, hire, onboard, and retain. Docket’s virtual SE learns a product deeply, understands customer questions, and takes actionable steps to keep deals moving forward. This sets it apart from a product like Glean, which provides general information synthesis. Because you can ask Docket natural-language questions in a Slack channel, it acts like a know-it-all coworker, responding with up-to-the-minute information about your team’s products and services.

Years of hustle and humility pay off

The AI at Docket’s core means it absorbs knowledge from top-performing account executives, sales engineers, and subject matter experts, giving that information a confidence score, then sharing it with others. Over time, Docket tailors responses to specific sales protocols and organizational values. Docket was production-ready and being used by enterprise customers in November 2023, just three months after its launch. Its current client list includes Zoominfo, Demandbase, and Whatfix. Though his company is only a year old, Arjun sees a future in which Docket branches beyond sales engineering, leveraging a company’s collective wisdom in other areas. 

From our first conversations, I could tell that Arjun had both singular vision and tremendous hustle. His journey from running campus engineering conferences at a university in Kerala, India, to battling through a string of product failures with Profoundis demonstrated his resilience. Profoundis went on to become the first tech product company from the state of Kerala to be acquired by a U.S. firm. Despite these accomplishments, Arjun remains remarkably humble. Now his hustle and humility are paying off, as his third venture Docket takes off in the genAI sales space. Congratulations to the entire team.