Press Releases

Espressive Raises $23M to Provide AI Service Management

Share this post:

Pat Calhoun, former SVP at ServiceNow, is Leading Espressive to Redefine How Employees Get Help—Significantly Increasing Employee Productivity and Satisfaction

Santa Clara, Calif., July 31, 2018 – Espressive, the pioneer in AI for enterprise service management, today announced it has raised $23 million. Investors include General Catalyst Partners and Wing Venture Capital. In addition to Pat Calhoun, Espressive CEO, the board of directors consists of Steve Herrod, Managing Director at General Catalyst, Gaurav Garg, founding partner of Wing Venture Capital, and independent board member Tony Zingale, former CEO of Mercury Interactive and Jive Software. Pat is a former SVP at ServiceNow and his first startup, Airespace, grew revenues to over $80M in two years before being sold to Cisco for $450M.

Espressive was founded on the belief that getting help at work shouldn’t be so hard. Employees should be able to easily get answers to questions and resolution to issues so they can focus on their jobs rather than locating and navigating the many different self-service experiences offered throughout the enterprise. While other vendors have focused on solving the problems faced by help desk analysts, Espressive has shifted the focus to the employee because you can’t have self-service if employees are not engaged. The company believes that delivering a consumer-like experience to the workplace will cause a paradigm shift that will have a significant impact on employee productivity and satisfaction overall. Espressive has been shipping product since October 2017 that is redefining how employees get help within the enterprise.

“As consumers, we’re exposed to artificial intelligence (AI) every day and it has made our lives immensely easier,” said Pat Calhoun, Espressive CEO. “Look at apps like Waze, Uber, and even Spotify. Why shouldn’t employees expect and receive that kind of experience in the workplace? Without a consumerized self-help experience, help desks are beset by routine, mundane tasks. As low level as they are, these requests have to be completed expeditiously so analysts and employees can return to productive work. Espressive is changing the paradigm by redefining how employees get help with a consumer-like AI-based service.”

“For years, CIOs have resorted to building their own ITSM tools which has worked for back office processes but has failed for employee self-service because portals don’t provide the answers that employees need in a way they can easily consume,” said Marina Levinson, founder of the CIO Advisory Group and a former CIO of NetApp and Palm. “The introduction of AI gives the promise of automating problem resolution with a better employee experience, however, the skills required to pull this off are very difficult for a CIO to find. With Espressive, CIOs are able to further AI initiatives without needing to hire the talent. Enterprises reduce MTTR, maximize employee adoption, improve employee net promoter scores, and move valuable budget dollars from answering repetitive questions to working on strategic initiatives. All of that has significant bottom line impact.”

While AI has improved self-service portals by incorporating chatbots to reduce the number of knowledge base articles presented to an employee who is seeking an answer, they are still dependent on knowledge base articles that are often technical, can be out of date, and might not even contain the answer the employee is seeking. According to Gartner, “Through 2020, 99% of artificial intelligence (AI) initiatives in IT service management (ITSM) will fail due to the lack of an established knowledge management (KM) foundation.”[1]

Espressive takes a different approach by eliminating the dependency on knowledge base articles for answers. The Espressive approach constantly learns through human interaction, making it increasingly simple for employees to get answers. The resulting experience reminds employees of the ease of consumer virtual assistants like Alexa and Google Home, and maximizes employee adoption while reducing help desk call volume.

“Espressive has built a solution that gives companies a significant AI-driven advantage with greater employee engagement and ultimately, higher overall productivity. Given Pat’s track record for making work tasks as simple as the most intuitive consumer tasks, Espressive is an extremely compelling investment for us at GC,” said Steve Herrod, Managing Director at General Catalyst.“

Espressive promises to transform employee self-help via an intuitive consumer like experience that delivers direct answers to questions and proactive engagement,” said Gaurav Garg, Founding Partner at Wing. “What inspired us during our diligence was how enthusiastic large enterprise customers were about leveraging Espressive’s product to accelerate internal digital transformation.”

About Espressive

Espressive, the pioneer in automating digital workplace assistance, and a 2022 Forrester New Wave Leader, redefines how employees get help by delivering exceptional employee experiences. Barista, the company’s virtual support agent (VSA), brings the ease of consumer virtual assistants, such as Amazon Alexa and Google Home, into the workplace. Barista automates resolution of employee questions, issues, and requests with personalized experiences that result in employee adoption of 80 to 85% and reduced help desk call volume of 50% to 70%. Espressive is backed by Insight Partners, General Catalyst, and Wing Venture Capital, and is headquartered in Santa Clara, California. Visit for more information.

Media Contact

Pam Njissang
Bhava Communications for Espressive

[1]Gartner, “Predicts 2018: IT Operations.” Terrence Cosgrove, Hank Marquis, Pankaj Prasa, Chris Matchett, Robert Naegle, Will Cappelli, Colin Fletcher, Kenneth Gonzalez, Rich Doheny. December 4, 2017.