Lessons in Scaling Cybersecurity Sales with Dean Hickman-Smith, CRO at HackerOne

This week on the Revenue Insights Podcast, Guy Rubin, CEO of Ebsta, speaks with Dean Hickman-Smith, Chief Revenue Officer at HackerOne, on Scaling Cybersecurity Sales.

In this episode, Guy and Dean explore the evolution of sales leadership, the power of community in B2B sales, and how AI is transforming sales enablement and performance.

Dean Hickman-Smith is the Chief Revenue Officer at HackerOne, where he leads a global team helping organizations find and fix critical vulnerabilities through ethical hacking. With over 20 years of experience scaling InfoSec and identity companies through every phase of growth from startup to IPO, Dean has held leadership positions at companies including Netscreen, Proofpoint, and AeroHive. At HackerOne, he oversees a team of 70+ sellers globally, managing the world’s largest network of ethical hackers with over 2 million people on their platform.

• Dean Hickman-Smith on LinkedIn
• HackerOne website
• Guy Rubin on LinkedIn
• Ebsta Revenue Insights Newsletter 

Time Stamps:

• 00:00 – Introduction
• 01:43 – Early career and entering cybersecurity
• 03:26 – Journey through tech startups
• 05:38 – Current team structure and global expansion
• 09:22 – Partner strategy and ecosystem
• 14:24 – Building community and events
• 20:25 – Sales qualification methodology
• 24:20 – AI implementation in sales
• 28:02 – Sales performance metrics
• 34:57 – Focus on relationship building
• 39:21 – Closing thoughts and contact information

Highlights of Lessons in Scaling Cybersecurity Sales

The Power of Community in Sales

Dean emphasizes the importance of building community through events and networking. HackerOne has developed “Community One,” which brings together customers, prospects, and ethical hackers in casual environments. These events allow natural conversations and relationship-building without traditional selling pressures. As Dean notes, “No one’s really selling in this world anymore. You’re advising, you’re putting content out, people are doing their own research. You’ve got to tap into that motion much more than 10, 15, 20 years ago.”

Partner-Led Growth Strategy

HackerOne is actively expanding its partner ecosystem, recognizing the efficiency of indirect selling motions. Dean highlights that partners bring credibility, local language support, and streamlined contract processes. The company is investing heavily in partner support, including marketing and enablement resources, to build a robust channel program that enhances their direct sales efforts.

AI and Sales Enablement

The team is leveraging AI for research, pre-call analysis, and post-event analysis, though Dean acknowledges they’re still early in their AI journey. They’ve recently launched “Hi,” an AI-powered collation, benchmarking, and recommendations engine. The focus is on using AI to improve targeting efficiency and enable better coaching, with Dean drawing an interesting parallel to how AI assists pilots in aviation.

Sales Training Evolution

Dean emphasizes the importance of effective preparation and training, particularly in today’s virtual environment. HackerOne has revamped their enablement approach to be more modular and bite-sized, allowing sales team members to learn at their own pace. They’ve also created virtual sales floors through Slack to facilitate peer learning and best practice sharing.

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