My journey into the world of data began at a time when big enterprises were waking up to the promise of ‘big data’. At the same time, cloud providers like AWS, Google and Microsoft were making huge investments in database solutions and the open-source community was gaining serious traction. Among the movement’s icons was Hadoop, a distributed storage and processing framework with a yellow elephant for a logo –
named after a toy belonging to co-founder Doug Cutting’s son.
Open-source software had existed since the ‘70s, but it wasn’t until the mid-‘90s that it went mainstream with Linux. In 2008, Yahoo released Hadoop to the market and by 2012 it became an Apache project, paving the way for a wave of data tools that would dominate tech for the next decade. During that time, selling open-source software felt like living in the Wild West. I joined Hortonworks in 2013, right after Hadoop went public. It was a time of huge opportunity – but also of chaos.
One of my earliest gigs was a roadshow with a couple of partners, pitching Hadoop to the oil and gas sector. We hit Stavanger, Aberdeen, Rome and Bahrain, targeting engineers and data teams. The message was simple: companies were drowning in data and legacy systems couldn’t handle it. Hadoop made storing data free and we supported it with something new and strange: ‘the cloud’.
The first pitch in Stavanger was a total disaster. Not because the tech failed or the market wasn’t there. The problem was simpler: people weren’t ready. The oil and gas sector was cautious and risk averse. And that’s why learning to sell to strangers is so critical – because problems alone don’t create opportunities.
People do. And unless we understand their fears, doubts and motivations, we have no shot.
The next stop was Aberdeen and I was dreading it. I’d spent the flight from Norway wondering how I could inject energy into the pitch – or at least not walk off stage in defeat. Then, in true cinematic fashion, the plane skidded off the runway in high winds. No one was hurt, but I couldn’t help thinking: maybe this was a sign.
We made the event and I made a decision – I would go first. I knew the other vendor presentations would be dry, so I wanted the floor before the boredom set in. I opened with a question: ‘Who’s heard of Hadoop?’ One hand went up. ‘Anyone seen this elephant before?’ Same hand.
I paused. Half the room smiled. I leant into it, showing slides of other open-source mascots – more smiles, then some laughs. I’d spoken to enough engineers in Norway to know what they were thinking: This is risky. Why would I bet my job on this? They weren’t worried about the tech. They were worried about themselves.
So that’s all I talked about: them. The risk to their careers. The fear of adopting something new. But then I showed what success could look like. How they could future-proof their roles. I wasn’t selling Hadoop. I was telling their story.
And by doing that – by speaking to their doubts and standing in their shoes – I gave them a reason to trust me. I turned scepticism into curiosity. I got them to laugh. I left the stage with conversations, not contracts – but that was a win. I wasn’t trying to close. I was trying to connect.
Creativity for Startups
Creative flexibility and problem solving tend to flourish most in startup cultures: when the focus is on the first wave of an addressable market and teams have latitude to innovate. But divergent thinking isn’t just for startups – it can be infused into any organisation. Yes, you still need a solid sales process framework. But you also need sales professionals and leaders who know how to bend the process to the people, not force the people into a rigid process.
At Hortonworks we were fortunate – at least for a time – to blend strong personalities, diverse experience and creative sales leadership. The software sales world is hyper competitive, with new entrants emerging weekly. Only a handful of top sales professionals position themselves with products that have enough market potential to go public. Many variables lead to success: product market fit, marketing, sales, timing, people, culture, leadership. Early stage businesses succeed more on probabilities than certainties; very few ever hit $100 m, fewer still IPO.
In our early years at Hortonworks we ‘cracked the code’. We had people who could think creatively, a sales process that supported rather than restricted and a leadership team willing to let us shape our own styles. We entered into competition with our primary rival, Cloudera, and for three years we led the opensource bigdata market. We weren’t perfect – but we were fast, creative and adaptive.
One of the biggest challenges we encountered was personality mismatch – selling to strangers who were engineers, Clevel buyers, technologists. We had to ‘level up’ and mirror their styles, manage their doubts, take risks. The success wasn’t from the product alone; it was from the environment that let us use our creativity rather than being locked into a fixed sales script.
As a sales leader, I believe every organisation needs a robust sales enablement strategy. But I also believe even more strongly that sales leaders must tailor the process to the people, not force people to conform to the process. Otherwise you kill creativity, you kill adaptability and you lose when you’re selling to strangers in unpredictable terrain.
The Best of Both Worlds
Many organisations focus exclusively on traditional sales methods and ignore the cognitive styles that drive innovation.
This is a mistake.
Convergent Thinking
Convergent thinking narrows possibilities to a single correct solution. It brings structure, logic and focus. It suits sales processes (frameworks like MEDDICC) because it helps you drive to a defined outcome. Key aspects of this style of thinking include:
- Single solution
- Logical and analytical
- Defined problem structure
- Objective outcome
Divergent Thinking
Divergent thinking generates a broad variety of possible ideas and paths. It’s exploratory, creative and unconventional – exactly what you need when you’re selling something unusual or to a stranger. Key aspects of this style of thinking include:
- Producing many ideas
- Exploring possibilities
- Cognitive flexibility
- Encouraging originality and collaboration
Bringing Them Together
Yes, you can combine divergent thinking with a convergent sales methodology. When you:
- maintain a robust foundation (process, structure).
- empower your team to be flexible and creative when engaging different buyers and unique situations.
- reduce personality mismatch because you allow styles to adapt.
- foster a more empathetic, human-centric engagement.
I’m convinced that adopting a dual approach helps elevate the entire organisation: sales, product, marketing, all working together. Ultimately it creates deeper trust, better relationships with buyers and stronger outcomes.
How Ethicly Supports Divergent + Convergent Thinking
The Ethicly platform is designed to bridge the gap between structure and creativity in modern sales. By scoring and reviewing engagements, it gives teams the data-driven feedback needed to refine convergent processes while also offering real-time prompts and empathetic guidance to encourage more human, adaptive interactions.
Whether your salespeople are following a structured framework like MEDDIC or improvising in complex, high-stakes conversations with strangers, Ethicly helps to:
- Reinforce ethical behaviour and trust-building language
- Provide suggested prompts based on context, to support empathetic engagement
- Track predictability, reliability and transparency across interactions
- Highlight when reps deviate from or align with best practices without punishing creative thinking
In this way, Ethicly empowers organisations to benefit from the best of both worlds: rigorous sales discipline paired with the freedom to be flexible, human and innovative when it matters most.