Enterprise revenue & go-to-market

OffSec: Building an enterprise B2B business from practitioner adoption

When I joined Offensive Security following its private equity acquisition, it was primarily an online training business with approximately $12 million in annual sales. My mandate was to build the go-to-market organization, develop an enterprise B2B business, and expand internationally.

Establish the commercial foundation

I negotiated the Salesforce agreement and implemented the initial setup myself, then hired an administrator to support it. I hired and trained the first two sellers, joined their customer calls, and used their feedback to refine our understanding of the market.

Starting with two sellers gave us a way to compare performance and learn before expanding the team. Once they were consistently closing business, I added capacity, segmented the market, and introduced clearer account ownership.

Find the enterprise behind the practitioner

An important discovery shaped the sales approach: an individual training purchase often represented a much larger team. The practitioner could be part of an organization with broader cybersecurity responsibilities, a training budget, and a need to develop people consistently.

We used that insight to define ideal customers, understand buying motivations, sharpen the value proposition, and reach the people responsible for larger training programs.

At Deloitte, we identified teams behind individual purchases, engaged cybersecurity leadership, and developed a buying agreement to support broader training needs. With the U.S. Army, conversations expanded from training purchases into curriculum planning and how OffSec training and certifications could fit into internal development pathways.

Build distinct routes to market

As the business developed, I built inside sales, enterprise, and public-sector coverage, added prospecting support, and hired sales management and specialist leaders. Larger enterprise accounts and government opportunities required different expertise, buying-process knowledge, and account strategies.

I also worked with senior international stakeholders. In Saudi Arabia, that included senior government leadership and universities on a workforce-development initiative. Those discussions highlighted the need for foundational content that could help less experienced learners progress toward OffSec's advanced training and certifications.

I closed multimillion-dollar enterprise deals as we built the B2B business. The broader work was developing the coverage, partnerships, and delivery requirements that could support more complex customer programs.

Connect marketing, product, and sales

I worked closely with marketing on positioning, pricing, packaging, and how we explained the offer on the website. Much of the initial pricing stayed in place, while we developed volume-based buying options and adapted the commercial approach for organizational customers.

Customer conversations also surfaced product and delivery requirements: learning pathways, enterprise administration, reporting, and support for larger training programs. Connecting those requirements to commercial opportunities was an important part of the role.

Create operating discipline and develop the team

I established consistent definitions and a sales methodology with clear entry and exit criteria for each stage. We connected the process to Salesforce, forecasting, pipeline development, and lead qualification.

The work included training sellers, coaching through customer calls, and building the management structure as the team grew. The processes evolved as the company matured and the product portfolio expanded.

Manage the relationship beyond the first sale

Sales owned commercial renewal and expansion conversations, working with customer success on customer goals, engagement, and program health. We tracked renewal opportunities separately from new business, and I worked directly on renewal deals.

As the commercial model evolved, the work included improving sales-to-success handoffs and shaping practical buying terms for enterprise customers. These commercial processes connected the initial sale to the customer’s ongoing training needs.

Build for the next stage

My role combined strategy with hands-on execution: understand the customer, establish the commercial foundation, develop the first sellers, and add specialization as the business grows. The organization and its processes have to evolve together.