Hack the Box

Hack the Box increased contract value by 50%

Better conversations, bigger results

Tom Fernandez has been with the company for four years, initially tasked with leading the APJ team before taking on the Chief Revenue Officer role at the start of 2025. The business was already doing very well, but Tom knew they could do better. 

In particular, Tom was looking at four key metrics: 

• Annual contract value (ACV)
• Pipeline
• Deal velocity
• Multi-year engagement rates

To improve those, Hack The Box needed to consistently move upmarket and sell at a more strategic level. Rather than simply adding more leads to the top of the funnel, they needed to work more on the quality and robustness of those opportunities as they progressed through the sales cycle. 

That meant improving qualification. For example, the team was already using elements of MEDDPICC as a qualification framework, but adoption and skill execution were inconsistent. Despite performing very well, conversations sometimes remained transactional when they could have been transformative.

Will Demars, VP of Sales for the Americas, saw the same pattern from the field. “We were really strong on the product and the content,” says Will. “But we weren’t doing enough to translate technical value into business value that would be relevant to economic buyers.”

Ensuring that their people were enabled to meet the market’s demands was one of Tom’s top priorities for the year. Just as they helped clients learn new cybersecurity skills, Hack The Box now needed to equip their various revenue teams with the right consultative skills. 

It all kept coming back to conversation. “We solve board-level problems,” Tom says. “We just weren’t necessarily talking about them that way.” By being able to talk the prospect’s language, by educating and bringing new and thought-provoking insights to the table, the team could find and solve problems that matter.

Expertise from experience

Hack The Box wanted a sales enablement team with the expertise to help them build out their approach, refine it, and then continue growing. They went to market to see what options were out there, from large legacy training organisations to smaller boutique businesses. 

After careful consideration, Hack The Box chose Flow State as its sales enablement partner.

Tom was already aware of Flow State from shared connections who’d previously worked with Flow State. He also enjoyed their LinkedIn content. “I’ve been a bit of a fan for a few years now. We have a very similar philosophy,” he explains. While sales might have a bad reputation for some, he appreciated Flow State’s more buyer-centric approach.

Above all, Tom valued Raff and Aaron’s real-world sales experience. “It was just great to have two individuals who, first and foremost, understand how buyers actually buy and renew. There are a lot of ‘sales enablers’ who don’t have that background.” 

Before the engagement officially started, Aaron and Raff had already begun working with Tom to fully understand what he was trying to achieve. By discussing the current issues and challenges Hack The Box was experiencing, Flow State was able to align its curriculum and approach to those particular problems.

Together, they decided on the key objectives:

• Improve the team’s ability to close higher-value deals
• Create a cleaner, more robust pipeline through better deal qualification
• Tie the business’s value to strategic goals for their prospects and customers
• Create a coaching framework for managers and reps around opportunities, pipeline and revenue outcomes

Once they’d agreed on what the engagement would look like, Flow State and Hack The Box formally began the partnership.

Teach the competency, coach for the competency

Flow State rolled out a full-scale sales transformation program, with weekly sessions and workshops carried out over six months – something that Will particularly appreciated. “With some other sales enablement programs, you do an intensive day or two, and then everyone goes back to normal,” he says. 

The longer cadence meant Aaron and Raff got to understand the personalities in the room, the realities in the field and the pressures the team was under. Consequently, Flow State was able to continually train, coach, reinforce and evidence use of learnt skills out in the field. This hands-on approach was vital in highlighting role model behaviours and milestones that enabled revenue teams to go on a transformative journey.

Hack The Box is a global company, so sessions mainly took place online. However, Aaron and Raff also flew out to Athens to deliver in-person sessions on a couple of occasions, where they were part of the company’s annual sales kick-off and global retreat.

The first few phases were carried out with the management team. “A training program’s success really lies in a business’s leaders,” says Tom. “If they’re not bought in, the likelihood of the program working drops to zero. They’re the ones who have to internalise and then deliver at the end of the day, during the program and then afterwards too.”

Those early sessions focused primarily on helping managers become better teachers and coaches. “The program is really about how we teach, then how we instill,” says Tom. “Teach the competency, then coach for the competency.” 

From there, the sessions were expanded to cover all the revenue teams – from BDRs and Renewals to Sales Engineering and Customer Success – with different modules tailored for the different roles. Rather than simply delivering content, they were able to spark discussions while drawing on Hack The Box’s own leaders’ experience.

Rather than confining learning to workshops and role plays, the team applied what they were learning in live deals, then brought those experiences back into the next session. “There’s often resistance to role play,” says Will. “It can feel artificial. But this wasn’t just theory. We were trying it in real opportunities, then coming back and talking about what worked and what didn’t.”

Speaking the same sales language

A key part of the engagement was helping the teams develop a common sales language with MEDDPICC. Flow State worked with the team to apply the framework in live opportunities and build it into their day-to-day qualification and deal execution process.

Additionally, they improved their customer handover process between teams and were able to frame sales conversations around the business case. Internal collaboration across the various customer-facing teams improved as they worked together to provide a more seamless customer experience. 

As the team put what they were learning about MEDDPICC into practice, they were able to qualify pipeline significantly better, gain access to more senior stakeholders and solve top-level business problems. People were now more comfortable talking about those board-level issues and constructively challenging buyers where appropriate. This meant that, as well as closing more multi-year deals with new clients,  Hack The Box was also able to expand within some of its existing clients.

Hack The Box updated its CRM and sales documentation in parallel with the training, so that what reps were learning in sessions matched exactly how they were working. When reps could see how MEDDPICC improved their processes and strengthened customer conversations, the framework felt less like a tick-box exercise and more like a powerful tool.

“That was a real turning point for the organisation,” says Tom. “As people started to adopt what they were learning, they became confident asking these harder questions. Because of that, we’re able to articulate and solve problems that we’re then presenting back to the prospect and progress up the value chain.”

For Will’s team in the Americas, the business case was their “Aha” moment. “We spent weeks on it,” he says. “Teaching, coaching, reinforcing, using real examples.”

That shift in quality didn’t go unnoticed by customers. Through a dedicated Slack channel where the team shared field examples, reps began reporting that prospects were complimenting the level of detail and preparation they were bringing to conversations, specifically noting that competitors they were evaluating weren’t operating at the same level.

The impact showed up in how deals were run. As a result of Flow State’s recommendations regarding pipeline management, any opportunity over $50,000 now includes a co-created business case presented back to the customer. Reps are equipping buyers with something they can use internally to justify the decision at senior levels.

Finding another gear

Hack The Box started the year with a clear set of commercial priorities shaping its next phase of growth: 

• Workforce development and enablement
• Offering additional functionality to fuel expansion within existing accounts
• Doubling down on proven territories and growth markets
• Continuing to pioneer AI in the cybersecurity upskilling market.

Flow State played a crucial role within that workforce capability pillar, helping embed MEDDPICC into day-to-day execution and raising the standard of qualification, problem discovery and business case development across the revenue team.

With those initiatives working in parallel, the commercial indicators began to move. All of the identified key metrics improved, with contract value increasing by 50% and pipeline growing by 40%.

Will saw deal sizes in the Americas go up significantly, in some cases doubling. ARR in the region grew around 40% year over year, and attainment rose from roughly 95% the previous year to approximately 115%. The team was closing more six- and seven-figure deals. 

However, for Tom, the biggest win lies in how his team now runs sales conversations. Frontline leaders and sellers feel better equipped to operate in a modern, consultative environment. They’re more deliberate in how they guide prospects through complex decisions, particularly in the final third of a deal where risk and hesitation tend to surface.

Where buyers might previously have stalled, worried about getting the decision wrong, the team is now more comfortable supporting them through that uncertainty. “We’ve seen deeper engagement from our customers, and following the process has allowed us to move up the hierarchy within an organisation and get larger deal values,” says Tom. “We’ve found another gear.”

“We didn’t just do something that got stamped in time,” adds Will. “We set up foundations that will continue to snowball. As a sales leader, there’s so much I can build off those fundamentals.”

A sales organisation that’s on the march

When asked what he would say to another CRO considering Flow State, Tom doesn’t hesitate.

“Do it.”

For Tom, the success of any sales enablement program starts at the top. Are leaders backing their revenue teams? Are managers holding sellers accountable? Are the behaviours being reinforced in real deals?

If the answer is yes, the results follow.

“Flow State has a good finger on the pulse of what selling is really like today,” adds Will. “They understand the difference between theory and what actually happens in the field.”

“I can’t speak highly enough of Aaron and Raff,” says Tom. “If you’re looking to build a modern workforce, you can’t do better than introducing Flow State into your business. We’re on the march, and thanks to Flow State, we’ll get there quicker.”

With a shared methodology, embedded systems and leaders reinforcing the behaviours in the field, Hack The Box has improved sales performance and built the infrastructure to sustain it.

The outcome