Our COMPANY

Accelerating Your Success by Redefining How Employees
Get Help

The Pioneer in AI, Automating Enterprise-Ready Digital Workplace Assistance

By applying the perfect blend of digital experience, intelligence, and automation, Espressive helps organizations redefine how employees get help at work.

We were founded on the belief that getting help at work shouldn’t be so hard. While others focused on solving the search problem, we focused on automating what service desk agents do every day. Most employees are not technical enough to self-diagnose or even fully describe their issues — which is why traditional portals fail and employees call the service desk in the first place.

The innovative Espressive Barista platform takes on the role of a service desk agent, bringing the best of human experience with the best of artificial intelligence. Barista engages with employees to understand their issues and gain clarity so that the best possible resolution can be delivered. That’s how we achieve the highest resolution rates in the industry, saving costs while boosting employee experience, productivity, and satisfaction starting day one — guaranteed.

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Our Leadership Team

Pat Calhoun

Pat Calhoun

Chief Executive Officer

Pat is a visionary leader with an intense focus on user experience and customer adoption. He has founded two companies – Airespace and Espressive. As CEO at Espressive, Pat is set to transform the enterprise self-service experience to a consumer-like approach that drives employee adoption and significantly reduces help desk calls. Espressive has helped companies like Dexcom, SurveyMonkey, and Guardant Health achieve high ticket deflection, containing costs while improving workforce productivity.

Most recently, Pat served as senior vice president of product at ServiceNow where he was responsible for ServiceNow applications. Prior to that, he was general manager of the McAfee network security business. Pat’s first startup, Airespace, grew revenues to over $80M in two years before being sold to Cisco for $450M. After the acquisition, Pat served as both CTO for the Cisco $14B switching, routing, wireless, and security access business and GM of the Cisco identity business. Pat holds 35 patents and has been published in more than 16 publications.

Robert Mally

Robert Mally

Chief Financial Officer

Robert has over 25 years of experience supporting and enabling the growth of enterprise software companies at all stages. He received his BA from the University of Maryland, College Park and his MBA from Carnegie Mellon University. Over the years, Robert has held senior financial and operational leadership roles at both publicly and privately held companies including Bertelsmann, Disney, Business Objects/SAP, Intuit, and Druva. Prior to joining the Espressive team, he served as CFO of Palerra, a venture capital backed cloud security company acquired by Oracle.

Keno Helmi

Keno Helmi

Chief Revenue Officer

Keno is an industry veteran with over 25 years of experience in the Enterprise Software Space. He has led Sales organizations at both publicly traded and startup companies spanning the likes of Parametric Technology Corporation, Amdocs, Opsware, Hewlett Packard Software, Digby, Duetto, Platform9, and Pegasus. Prior to his career in high tech, Keno was an Economics Professor with a concentration in pricing optimization. In his spare time Keno enjoys hiking, cooking, college football, and time with his four daughters. He is based in Austin, Texas.

Prashant Luthra

Prashant Luthra

Chief Technology Officer

Prashant is a seasoned technology leader passionate about developing intelligent enterprise platforms with 20+ years of product development experience spanning HR, CRM, and ITSM domains. Prior to joining Espressive, Prashant was VP Engineering at Freshworks leading their Digital CX initiatives that included their Freshchat, Freshbots, and Freddy AI data platforms. Before that, Prashant was Co-founder and CTO of AnsweriQ, building AI-powered solutions for Customer Service. AnsweriQ was acquired by Freshworks in 2020.

Prashant holds a Masters in Computer Science from University of Kentucky and lives in Seattle, Washington.

Fran Fernandez

Fran Fernandez

Chief Product Officer

Fran is the Espressive “Batman” of product. His mission involves blending consumer design principles with the best artificial intelligence (AI) technologies to create exceptional self-help experiences that employees love and enterprises profit from.

Fran has a wealth of enterprise service management experience spanning a 20-year period of time, including companies such as ServiceNow, BMC Software, and CA. He was the first product manager hired at ServiceNow, and so he is intimately familiar with the IT service management (ITSM) market including key enterprise pain points. Immediately prior to Espressive, Fran was director of product management at BigPanda where he helped organizations process a storm of data into meaningful inputs that they could react to.

Fran graduated from UC Berkeley and is an avid mountain biker and coffee drinker.

Alex Yupanqui

Alex Yupanqui

Chief Customer Success Officer

Under Alex’s leadership, the Customer Success team at Espressive is focused on making sure each and every customer truly finds success with Espressive. Prior to joining our company, Alex was an early employee at ServiceNow where he held various leadership roles in the Solutions Consulting organization and was charged with building the pre-sales leadership team while supporting a rapidly growing business. In all roles, Alex consistently partnered with sales, marketing, and product teams to ensure outstanding prospect and client experiences. Before ServiceNow, Alex held senior solution architect and sales engineering positions with Hewlett Packard, BDNA Corporation, and Mercury Interactive.

Alex graduated from UC Davis with a degree in Computer Engineering. In addition to a successful sales and technical career, he is also active in promoting diversification in technology. Today, he holds several board positions in organizations and non-profits that help promote STEM (science, technology, engineering, and math) for Latinos in the local community.

Gaby Flores

Gaby Flores

Chief People Officer

Gaby is a passionate Human Resources professional with more than 7 years of experience in the industry. She has held HR roles in both the corporate and startup world, helping businesses achieve their goals and objectives while working to give employees the best possible experience. She enjoys turning independent work groups into multi-cultural, cross-functional teams.

Gaby has also focused her professional career on attracting and developing top talent and has held management positions in that field. A psychologist by profession, she also holds a Masters in Business and Talent Administration. She lives in Guadalajara, Mexico.

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The Team That
Makes It Happen


Our team of Espressionists includes some of the most talented designers and technologists in AI today. We hire the data scientists so that you don’t have to. Our employees are driven by your success and inspired by making a difference.

Our Board of Directors

Pat Calhoun

Pat Calhoun

Pat is a visionary leader with an intense focus on user experience and customer adoption. He has founded two companies – Airespace and Espressive. As CEO at Espressive, Pat is set to transform the enterprise self-service experience to a consumer-like approach that drives employee adoption and significantly reduces help desk calls. Espressive has helped companies like Dexcom, SurveyMonkey, and Guardant Health achieve high ticket deflection, containing costs while improving workforce productivity.

Most recently, Pat served as senior vice president of product at ServiceNow where he was responsible for ServiceNow applications. Prior to that, he was general manager of the McAfee network security business. Pat’s first startup, Airespace, grew revenues to over $80M in two years before being sold to Cisco for $450M. After the acquisition, Pat served as both CTO for the Cisco $14B switching, routing, wireless, and security access business and GM of the Cisco identity business. Pat holds 35 patents and has been published in more than 16 publications.

Gaurav Garg

Gaurav Garg

Gaurav Garg is a Founding Partner of Wing. Gaurav is a board member at several private technology companies, including Cohesity, Shape Security, and Instart Logic. He incubated and helped build FireEye (IPO 2013), Ruckus Wireless (IPO 2012), and Jasper (Acquired 2016) into significant businesses, serving as a board member at each for more than ten years. Gaurav has served on the boards of several other companies, including some that staged successful exits via IPOs or acquisitions such as NetScaler (Acquired 2005) and MobileIron (IPO 2014). He also worked extensively with, and co-sponsored investments in, Aruba (IPO 2007) and RingCentral (IPO 2013).

Gaurav was a partner at Sequoia Capital from 2001 to 2010, and a Special Limited Partner at the firm from 2010 to 2012. Prior to joining Sequoia, he founded Redback Networks in 1996 (IPO 1999), and served as a board member and Senior Vice President of Product Management. Prior to Redback Networks, he held various engineering positions at SynOptics and Bay Networks.

Gaurav holds a BS and MS in Electrical Engineering and a BS in Computer Science, all from Washington University in St. Louis.

Max Rimpel

Max Rimpel

Having grown up in a small village in Germany, I have a deep appreciation for entrepreneurship. To this day, I believe it’s the most powerful mechanism to bring about positive change. My drive “to see the world” ultimately led me to high school in the U.S., university in Berlin, advanced degrees in Paris and Madrid, internships in Japan and Brazil, stints at intergovernmental institutions and equity market research in the U.S. I was intrigued how technology changed our lives and began my tech career at Google in London.

I transitioned into venture capital, joining Index Ventures, just as Europe became a fertile ground for ambitious founders. At General Catalyst, I continue to focus on B2B investment opportunities, now across both New York and Europe, which are the two ecosystems I’m most bullish about. Away from work, I love any sport involving a racquet or paddle, am a passionate piano player of limited ability and support organizations that take on big challenges, such as Human Rights Watch and Black Girls CODE.

Tony Zingale

Tony Zingale

Tony currently serves as an independent outside Director on the Boards of SaaS cloud software companies Carbon Black, Espressive, Percolate, Reflektive and Dynamic Signal, as well as coaching several first time CEOs at privately held high growth software companies.

Tony has 37+ years of experience building profitable, high growth, enterprise software companies. He most recently served as the Executive Chairman of Jive Software where he also served as CEO for 5 years. Jive was the pioneer of the social collaboration and communication software market that he led through its $185M IPO and growth to over $200M in revenue. Prior to Jive, he was the CEO of Mercury Interactive, the worldwide leader of Business Technology Optimization (BTO) solutions. Tony successfully grew Mercury to over $1B in annual sales and then engineered the $5B merger with Hewlett Packard which was completed at the end of 2006. Prior to Mercury, he was the CEO of Clarify, the original CRM company, grew it to over $300M in revenue and then engineered its $2.1B acquisition in 2000.

Tony holds a Bachelor of Science degree in electrical and computer engineering and a Bachelor of Arts degree in business administration from the University of Cincinnati. He is a member of the University of Cincinnati Foundation’s Board of Trustees.

Jeff Horing

Jeff Horing

Jeff Horing has been a co-founder and managing director at Insight Partners since 1995. Under his leadership, Insight has become a premier venture capital and private equity firm with over $20 billion of assets under management. Jeff’s areas of focus include data, analytics, mobile, and infrastructure and SaaS software in Europe, North America, and Israel.

Jeff has invested in more than 30 companies, notably Alteryx (AYX), AirWatch (acquired by VMware), Shutterstock (SSTK), TeamViewer (acquired by Permira), WIX (WIX), Greenfield Online (SRVY, later acquired by Microsoft).

Prior to founding Insight, Jeff worked at Warburg Pincus and Goldman Sachs. Jeff graduated from M.I.T. and the University of Pennsylvania.

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