
Episode #10: Kevin O’Brien of GreatHorn
02/19/20 • 21 min
Episode Summary:
Matt and Rob visit Kevin O’Brien, CEO and Co-Founder of GreatHorn, to discuss Kevin’s 20 year history as part of early teams within the cloud security space - most notably with CloudLock (Cisco), Conjur (CyberArk), and @stake (Symantec). Be sure to tune in to learn more about Kevin's journey, how he's drawn on his past experiences in his current role, and what they don't tell you about being a CEO.
Uncovered in this episode:
- What previous job roles helped prepare Kevin the most for being a CEO
- What patterns to look out for when starting a company in a new space and the signals that point to potential success as well as warning signs that point to potential failure
- Kevin's thoughts on hiring and building teams at every stage of growth
- The realities (and sometimes the not-so-glamorous side) of startup life
List of resources mentioned and suggested reading in episode
- GreatHorn website: https://www.greathorn.com/
About Kevin:
Currently CEO and co-founder of email security company GreatHorn, Kevin O’Brien is a frequent speaker, commentator, and author that advises customers and the public on data security and privacy issues. With 20 years of deep cybersecurity expertise, most notably with CloudLock (Cisco), Conjur (CyberArk), and @stake (Symantec), Kevin also serves as co-chair for the Mass Technology Leadership Council’s cybersecurity group.
Outside of security, Kevin is a lifelong martial artist, avid skier, and amateur sailor.
About GreatHorn:
Global 2000 companies use GreatHorn to reduce the inherent and pervasive risk associated with the everyday use of email. GreatHorn’s multi-staged approach to email security automatically combines data science, machine learning techniques, and technical analysis with human context to protect organizations before, during, and after a phishing attack.
By treating email security as a risk management function, customers can not only detect and remove more attacks but also warn users in real-time of potential threats and provide response teams with the tools to limit exposure and minimize risk. As a result, GreatHorn Email Security safeguards cloud email from advanced threats such as business email compromise, impersonations, credential theft, account takeover, and other phishing attacks.
Episode Summary:
Matt and Rob visit Kevin O’Brien, CEO and Co-Founder of GreatHorn, to discuss Kevin’s 20 year history as part of early teams within the cloud security space - most notably with CloudLock (Cisco), Conjur (CyberArk), and @stake (Symantec). Be sure to tune in to learn more about Kevin's journey, how he's drawn on his past experiences in his current role, and what they don't tell you about being a CEO.
Uncovered in this episode:
- What previous job roles helped prepare Kevin the most for being a CEO
- What patterns to look out for when starting a company in a new space and the signals that point to potential success as well as warning signs that point to potential failure
- Kevin's thoughts on hiring and building teams at every stage of growth
- The realities (and sometimes the not-so-glamorous side) of startup life
List of resources mentioned and suggested reading in episode
- GreatHorn website: https://www.greathorn.com/
About Kevin:
Currently CEO and co-founder of email security company GreatHorn, Kevin O’Brien is a frequent speaker, commentator, and author that advises customers and the public on data security and privacy issues. With 20 years of deep cybersecurity expertise, most notably with CloudLock (Cisco), Conjur (CyberArk), and @stake (Symantec), Kevin also serves as co-chair for the Mass Technology Leadership Council’s cybersecurity group.
Outside of security, Kevin is a lifelong martial artist, avid skier, and amateur sailor.
About GreatHorn:
Global 2000 companies use GreatHorn to reduce the inherent and pervasive risk associated with the everyday use of email. GreatHorn’s multi-staged approach to email security automatically combines data science, machine learning techniques, and technical analysis with human context to protect organizations before, during, and after a phishing attack.
By treating email security as a risk management function, customers can not only detect and remove more attacks but also warn users in real-time of potential threats and provide response teams with the tools to limit exposure and minimize risk. As a result, GreatHorn Email Security safeguards cloud email from advanced threats such as business email compromise, impersonations, credential theft, account takeover, and other phishing attacks.
Previous Episode

Episode #1: Paul English and Mike Volpe of Lola.com
Episode Summary:
Our Boston founders series kicks off with guests Paul English, Cofounder and CTO of Lola.com and Mike Volpe, CEO of Lola.com. Hosts Rob May and Matt Hayes visit Lola’s headquarters in Boston to learn more about the founding of Lola (Paul’s 5th company to date), and how Mike and Paul's different work styles provide a well-balanced leadership approach.
Uncovered in this episode:
- Fun facts most people don't know about Paul and Mike
- Why Paul English transitioned from CEO to CTO and how they made it a smooth and successful transition for the Lola team
- Hiring at Lola.com; making it fun to come to work; and building a culture around collaboration and learning
- Why vulnerability is important to discuss and how implementing one simple practice has helped both Paul and Mike drive stronger managerial relationships
List of resources mentioned in episode:
- Hiring Religion by Paul English: http://paulenglish.com/hiring.html
- Learn more on Lola: http://www.lola.com
About Mike Volpe:
Mike Volpe is the CEO at Lola.com, the corporate travel SaaS platform that helps companies stop wasting time and start saving money on their business travel program. He has been asked to speak at numerous conferences on sales, marketing and growth, as well as people operations, leadership, hiring and culture and is a strong advocate for building great teams with a wide range of talent.
Previously Mike was CMO at Cybereason, a cybersecurity SaaS company, where he helped the company increase its sales pipeline by 650% in a single year and grow revenue by five times during his tenure. He was also part of the founding team at HubSpot, where he spent eight years growing the company from five people to over 1,000 employees, $175m in revenue, and a successful IPO.
Mike is well-known and active in the Boston SaaS and startup communities as a member of the board of directors of Validity and Privy, and as an angel investor in more than 30 startups. He holds an MBA from the MIT Sloan School of Management and a BA from Bowdoin College. Check him out on Twitter, LinkedIn, and Instagram.
About Paul English:
Paul English is the CTO and co-founder of Lola.com, where he oversees product strategy, definition, design, and development, working closely with customers to make sure that Lola’s newest features are well received by users, and that they become “must haves” not “nice to have”. He also makes sure Lola’s products are innovative, fast, and beautiful with the objective of completely shattering the soul-sucking experience today’s business travelers must endure when planning travel.
Paul was previously the CTO and co-founder of Kayak (took public then sold to Priceline), and he also co-founded GetHuman (ongoing), Boston Light (sold to Intuit), and Intermute (sold to Trend Micro). Separately, Paul is an investor in dozens of startups, and he sits on six nonprofit boards. You can read more about Paul at PaulEnglish.com.
Next Episode

Miniseries - Episode 1: Navigating Covid-19 as an Entrepreneur
In Episode 1 of our Covid-19 miniseries, Matt Hayes and Rob May discuss the impact that the Coronavirus is having on the venture capital and entrepreneurial landscapes, and the new normal that we can expect moving forward. Topics covered include:
- Advice for entrepreneurs on cash management, financial planning, and supply chain vulnerabilities
- Why early-stage companies may be impacted in a different way than growth companies
- What entrepreneurs can expect going into future funding rounds
- How PJC is thinking about investing in new opportunities
- The industries to keep an eye out for as an investor
The Uncovered Podcast - Episode #10: Kevin O’Brien of GreatHorn
Transcript
Welcome to the uncovered podcast where we take a deeper look into the ideas of companies and entrepreneurs that are creating the future and uncover the stories you haven't heard. Uncovered is presented by PJC and early stage venture capital firm committed to supporting the next generation of entrepreneurs.
Matt HayesWe're back with another episode of the uncovered podcast. I'm here with my cohost Rob and w
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