Lennie Monteiro – How talking to a chatbot led to an award win

04 March 2024

In Summary...


Lennie Monteiro is a sales leader with decades of experience in sales enablement. He was considering studying an MBA, but instead chose to study for Consalia’s sales-specific master’s programme.

For his master’s dissertation, Lennie chose to write on how organisations can use AI ethically.

Introduction : Who is Lennie Monteiro?

Lennie Monteiro is a seasoned Sales Performance Director at Sysco Corp's Canadian subsidiary, a $76B global leader in selling food and non-food products. With a rich background in both sales and sales enablement, Lennie embarked on a unique academic journey, opting for Consalia's MSc in Professional Practice in Leading Sales Transformation programme over the traditional MBA route.

For his final master’s thesis, Lennie chose an innovative subject: Artificial Intelligence (AI). However, his interest extended beyond the practical aspects of this emerging technology. Instead, Lennie decided to delve into the ethical considerations surrounding the use of AI in organisations with a special lens on AI-Guided Selling.

Burning question : Talking to an AI salesperson without realising it

Lennie's interest in AI was piqued by two incidents. Firstly, Lennie signed up for a webinar on a new piece of sales tech, always hoping to find the next big thing. After the session, he found himself exchanging emails with Alexis, a persistent but helpful salesperson.

Time went on and Alexis continued to check in every once in a while to see if Lennie was interested. Eventually, impressed by her persistence and personalised messages, he sent her an email apologising for the delay in responding and asking to set up a call. This is when Alexis said he should speak to her manager named Leo.

Lennie was puzzled. Why would Alexis, after spending so much time and effort trying to speak to him, suddenly hand his account off to someone else? Was she not a salesperson herself? When he spoke to Leo, he finally discovered the truth:

Alexis was an AI chatbot!

Lennie became upset, feeling that he had been taken for a ride and that this was not an ethical way to deal with clients. Nevertheless, he describes it as his “eureka moment” where he realised just how powerful AI was becoming. After all, he hadn’t just corresponded with a chatbot without realising it – he had actually apologised to it!

The second incident occured when his organisation began to use a piece of AI-powered sales enablement software called SalesChoice. Lennie thought that the software was good, however, a sales director at the organisation was continually questioning its effectiveness.

“How do we know this is producing accurate results? Should we really be giving carte blanche to this system and trusting whatever it puts out?”

These probing queries ignited a fervent curiosity within Lennie's mind. They beckoned him to ponder deeply: How can we trust one piece of software over another? What assurances do organisations have that suppliers of AI solutions have upheld ethical standards?

Lennie decided to raise these points with Dr Cindy Gordon, the CEO of SalesChoice. It was Dr. Gordon who suggested that he could explore this topic in his master’s dissertation. Serving as a mentor, Dr. Gordon guided Lennie on his journey to understand the ethics of AI.

The Solution : Building an ethical framework for AI

Lennie quickly learned that there are two types of AI: “transparent” and “black box”. With transparent AI the source code is known, and users can understand the processes that led to specific outputs.

With black box AI on the other hand the inputs and outputs may be known, but the internal workings of the system remain a mystery to the user, who has no idea how it produced certain results. Furthermore, even the creators of the black box AI may not understand how it produced those results, as machine learning can swiftly develop systems too complicated for humans to understand.

Lennie came to the realisation that for sales teams, as well as organisations at large, to ethically leverage AI, they needed to establish an ethical framework for AI governance at the highest levels of leadership. This imperative initiative demanded proactive involvement from the board of directors and C-suite executives.

He used Dr Gordon’s framework from SalesChoice as a foundation, which outlined seven ethical principles to be considered when using AI in an organisation:

      1. Governance
      2. Process
      3. Technology
      4. People
      5. Data & Privacy
      6. Transparency
      7. Sustainability

Subsequently, he delved into researching the ethical frameworks adopted by countries (UK, Canada, USA, China), intergovernmental organisations, (European Union, World Economic Forum, OECD, The G20) multinational technology companies (IBM, Google, SAP, Baidu), non-profit organisations (Aequitas, AI Now Institute, International Committee of the Red Cross, Women Leading in AI), and global consulting firms (PricewaterhouseCoopers, Ernst & Young, McKinsey, Deloitte).

He found satisfaction in realising that the majority of these frameworks shared common ground, yet many still exhibited deficiencies in addressing one or more of the seven principles, particularly in the realm of sustainability.

Lennie leveraged his comprehensive research in his master’s dissertation to formulate a recommendation for his organisation to develop its own ethical AI framework. Additionally, he made three sales-specific recommendations:

      1. Sales leaders should enhance their understanding of AI. Coupled with the adoption of transparent AI, this will foster increased trust and confidence in AI outputs.
      2. Sales enablement teams need skilled resources in data science, capable of designing and advancing their current AI models. These models need ongoing refinement to uphold accuracy and mitigate data drift.
      3. An AI Governance cross-functional strategy team should be tasked with crafting a robust AI sales enablement journey roadmap.

The Results : Embracing AI with confidence

Lennie earned a well-deserved, highest distinction grade for his master’s project. His AI research, coupled with his growth as a sales leader during the rest of the programme, resulted in a significant impact on his company. By the conclusion of his tenure at the organisation, he oversaw a team of nearly 200 sales professionals, in addition to managing the entire Corporate Sales Communications and Sales Rewards & Recognition Portfolio.

Lennie's newfound expertise in AI propelled his organisation towards a data-driven culture, leveraging predictive analytics for prioritising opportunities and conducting data analysis for territory planning.

Some of the highlights of Lennie’s achievements include:

  • Launching a virtual selling training program for the entire sales team, fostering digital transformation and driving over $2 billion in annual sales.
  • Establishing a win/loss framework that offered a data-driven approach to the sales cycle, identifying key opportunities.
  • Forming a Sales Content Council and implementing a new CMS, resulting in an impressive 85% increase in sales team productivity.
  • Spearheading the development and deployment of an AI platform equipped with predictive and prescriptive analytics tools for real-time identification of prioritised sales opportunities.
  • Utilising said platform to construct unique AI models for each client, elevating win-rates from 36.12% to 43.46%.

We were so blown away by Lennie’s performance both during and after his master’s that, in 2022 our judges awarded him the Peter Critten Award with special commendation for cultural shift.

Conclusion : A master’s can be a catalyst for company-wide digital transformation

Lennie's success underscores the significance of embracing an ethical AI framework, revealing that it not only aligns with ethical standards but also enhances performance. Such a framework not only guarantees the selection of appropriate AI tools for an organisation but also boosts employee confidence in their utilisation.

Lennie recognised that the framework must not merely be built and then archived indefinitely, never to be looked at again. It requires endorsement at the highest levels of the organisation. Without that shortcuts may be taken, and employees may not receive adequate training to uphold the values outlined in the framework.

Lennie’s MSc in Professional Practice in Leading Sales Transformation not only enhanced his abilities as a sales leader, but also provided him with the opportunity to delve into a new domain of expertise and apply that knowledge within his organisation. The combination of the two resulted in a substantial ripple effect throughout his entire company, demonstrating how sales education for one individual can have a far-reaching impact.

Is your company ready for AI?

Organisations need to prepare for the legal and ethical minefield of AI. If you'd like support from Lennie and Consalia to build your own AI governance policies please click here to register your interest.