Table of Contents
Share this article
Learn from the brightest minds how to predictably and efficiently grow revenue.
Related Content
Why Sales Training Fails – And How AI is Fixing It with Ivy Holt, Head of Global Revenue Enablement at PagerDuty
In this episode of Revenue Insights, host Guy Rubin sits down with Ivy Holt, Head of Global Revenue Enablement at PagerDuty, to explore the evolving role of enablement in driving sales success. Ivy shares insights on the distinction between revenue operations and enablement, the challenges of measuring effectiveness, and the impact of AI and remote…
Why Remote-First Sales Leadership Actually Works, Raja Agrawal, VP of Sales at BrowserStack
In this episode of Revenue Insights, Adam Roberts is joined by Raja Agrawal, VP of Sales at BrowserStack, to discuss his journey from a rural Indian village to global sales leadership, the evolution of B2B buying behaviors, and strategies for managing a 100% remote global sales team. They also explore the impact of AI on…
Optimizing Sales Processes: Lauren Boynton of Qstream on SPICED Methodology
In this episode of Revenue Insights, host Guy is joined by Lauren Boynton, Vice President of Sales at Qstream, and they discuss SPICED sales methodology, customer retention and sales enablement. Together, they explore the fascinating journey of Lauren’s career from project management to sales leadership, the importance of customer success in driving revenue, and the…
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.
Subscribe to the Revenue Insights Podcast:
Recommended Episodes:
- You Can’t Sell to Someone Who Can’t Buy with Michael Dalley, CRO at Aerial Vantage
- From Inbound to Outbound: The Sago Sales Transformation with CRO Katharine Reagan
- Optimizing Sales Operations Success with Akira Mamizuka of LinkedIn
- Active Listening, Intent Data, and Events as Pipeline Game Changers with Leslie Venetz of The Sales-Led GTM Agency