Enterprise revenue & go-to-market

Go-to-market strategy: Making the choices that growth requires

My experience centers on technology businesses below $100 million in revenue, where customer demand, the commercial model, and the sales organization are still evolving. Go-to-market strategy connects the market we choose to the way we reach customers and the resources required to serve them.

Start with the customer and the evidence

I look at who is buying, what prompted the purchase, the problem they need to solve, and who else is involved. Early sellers and customer conversations help test those assumptions before we commit more resources.

At OffSec, individual practitioner purchases often pointed to larger teams. That insight helped us develop an enterprise B2B sales approach around organizational training needs.

Choose the sales approach for each market

An enterprise account, a government buyer, and an education partner can need different conversations, contracts, sales expertise, and delivery support. Geography adds further choices around local knowledge, direct coverage, and partners.

The strategy needs to be specific about which segments to pursue, how to reach them, and what we will defer until the business can support it.

Make the commercial offer work

I work closely with marketing on positioning, pricing, and packaging. The offer needs to make sense to the customer and support the way the team sells.

Enterprise buying also introduces practical questions: volume, contract terms, purchasing authority, license administration, and how customers add more training over time. These decisions connect sales to product, finance, and customer success.

Build the organization in stages

I stay close to the work early: setting up systems, hiring sellers, joining calls, and coaching. As we learn what works, I add capacity, account segmentation, prospecting support, management, and specialist coverage.

At OffSec, this developed into distinct enterprise, public-sector, and partner approaches. The goal is to build the capabilities the next stage requires, with evidence informing the investment.

Connect the sale to delivery and customer growth

The sales approach must account for what happens after the contract is signed. Customer goals, onboarding, engagement, renewal, and expansion require clear ownership and effective handoffs.

At OffSec, sales owned commercial renewals and expansion, working with customer success on program health and customer value. That relationship was part of building the commercial operation, even while the broader subscription model was still developing.

Use the operating system to learn

Shared definitions, qualification standards, stage criteria, CRM, and forecasting help the team understand what is working. I use that evidence to revisit market choices, resource allocation, and the sales approach as the business evolves.