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Rhesa Lessey

Founder at Things TT

Port of Spain, Trinidad and Tobago

Top 25 Thought Leaders in CRM | Customer Journeys | Marketing Technology | Leadership

Rhesa Lessey Points
Academic 155
Author 3
Influencer 26
Speaker 4
Entrepreneur 6
Total 194

Points based upon Thinkers360 patent-pending algorithm.

Thought Leader Profile

Portfolio Mix

Company Information

Company Type: Service Provider
Minimum Project Size: $1,000+
Average Hourly Rate: $100-$149
Number of Employees: 1-10
Company Founded Date: Undisclosed

Areas of Expertise

AI 30.01
AI Ethics 30.21
Analytics 33.54
Business Strategy 30.61
CRM 30.58
Customer Loyalty 30.54
Design Thinking 30.80
Digital Disruption 30.48
Digital Transformation 30.03
Emerging Technology
Future of Work 30.16
Leadership 30.83
Management 31.04
Marketing 32.28
Personal Branding
Public Relations 31.77
Retail 30.24
Social 34.26

Industry Experience

Furniture
Retail
Telecommunications

Publications & Experience

11 Academic Certifications
Meta Certified Media Measurement Specialist
Meta
September 17, 2024
Meta Certified Media Measurement Specialists are experts in interpreting measurement results and applying relevant next steps, including formulating hypotheses, evaluating measurement methods, designing successful tests, interpreting results and implementing appropriate actions based on those results.

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Tags: Analytics, Marketing

Meta Certified Digital Marketing Associate
Meta
September 06, 2024
The Meta Certified Digital Marketing Associate credential is awarded to entry-level digital marketers who have foundational proficiency in the skills, tools, advertising policies and best practices required to buy ads on the Facebook App, Instagram and Messenger.

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Tags: Management, Marketing, Social

Meta Certified Discovery Commerce Specialist
Meta
January 14, 2023
Meta Discovery Commerce Specialists are experts at using Meta to generate demand, by bringing together the tools needed to help a business grow. These skills will help deliver personalized experiences, expressive creative formats, frictionless purchases, and impactful measurement.

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Tags: Design Thinking, Marketing, Social

Meta Certified Media Buying Professional
Meta
January 14, 2023
Meta Certification is a credentialing program for digital advertising professionals who demonstrate advanced proficiency in Meta marketing. The Meta Certified Media Buying Professional credential is awarded to digital advertising professionals who are proficient in the skills, tools, advertising policies and best practices required to buy ads on the Facebook app, Instagram and Messenger.

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Tags: Analytics, Marketing, Social

Meta Certified Creative Strategy Professional
Meta
October 01, 2022
Meta Certification is a credentialing program for digital advertising professionals who demonstrate foundational knowledge and best practices in Meta marketing solutions. The Meta Certified Creative Strategy Professional credential is awarded to digital advertising professionals who demonstrate proficiency in developing effective mobile creative strategy and creative briefs.

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Tags: Design Thinking, Marketing, Social

Google Analytics Individual Qualification
Google
July 20, 2022

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Tags: Analytics, Marketing

Reputation Management in the Digital World
Curtin University
December 01, 2017
This course examines how businesses can effectively manage their reputation, stakeholder relationships, and communications strategy in an increasingly complex digital world. Key areas include online reputation management, crisis communications, brand trust, media relations, and navigating the evolving influence of digital and social platforms.

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Tags: Leadership, Marketing, Public Relations

AdWords and Analytics: Remarketing
Google
November 01, 2017

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Tags: Analytics, Marketing

Marketing Foundations: Influencer Marketing
Linkedin Learning formally Lynda
August 01, 2017
Studied how strategic influencer partnerships can accelerate brand trust, customer acquisition, and business growth through authentic audience engagement and measurable marketing outcomes.

Credential ID 5868766B50924886890628882B55FE45

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Tags: Analytics, Customer Loyalty, Marketing

Digital Branding and Engagement
Curtin University
October 31, 2016
This course examines how organizations build brand equity, customer trust, and long-term competitive advantage through digital channels, content ecosystems, customer engagement, and experience design. It focuses on aligning brand strategy with evolving consumer behaviors to drive sustainable growth, loyalty, and business value in a digital-first world.

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Tags: Future of Work, Marketing, Public Relations

Social Media Marketing: Social CRM
Linkedin Learning formally Lynda
June 01, 2016
Studied the integration of social media and customer relationship management, including online reputation management, customer engagement strategies, social listening, community management, digital communications, and the use of customer insights to build stronger brand relationships.

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Tags: CRM, Digital Disruption, Marketing

1 Article/Blog
MarTech Biggest Challenges in 2026
Blossom by Things TT
February 12, 2026

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Tags: CRM, Digital Transformation, Marketing

1 Bachelors Degree
Bsc Management
University of the West Indies
June 01, 2011
Activities and societies: Management Society,
Caribbean Reasonings (Chair of Religious Series)

Strategic Business Management, International Marketing Management, International Marketing Communication, Professional Ethics, Intermediate Macro-Economics, Caribbean Economy.

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Tags: Leadership, Management, Marketing

1 Masters Degree
Marketing Analytics
Berkley
March 31, 2020
MicroMasters. Covers an analytical approach to marketing. Competitive analysis, business strategy, market segmentation, targeting

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Tags: Analytics, Leadership, Marketing

4 Media Interviews
TTT Interview - Things TT
TTT News
October 06, 2019

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Tags: Business Strategy, Marketing

Things TT Market covered by A Millien Concepts
A Millien Concepts
October 17, 2018

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Tags: Business Strategy, Marketing

Interview with Things TT Founder
A Big Box Of Crayons
November 30, 2017

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Tags: Business Strategy, Marketing, Retail

Things TT Media Coverage
CTV News
May 25, 2017
This interview highlights the challenges of entrepreneurship and how the Things TT brand creates a platform for small business owners to sell their products and build their brand. As the founder, my focus was to build a community and encourage progress.

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Tags: Business Strategy, Marketing

2 Memberships
Customer Success Collective
Customer Success Collective
February 01, 2026
The Customer Success Collective’s mission is to enable people in the customer success profession to provide nothing less than pocket aces performances.

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Tags: Business Strategy, CRM, Marketing

AI Accelerator Institute
AI Accelerator Institute
February 01, 2026
The AI Accelerator Institute's mission is to help develop the next generation of machine intelligence specifically focusing on accelerating AI at the edge.

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Tags: Business Strategy, CRM, Marketing

1 Panel
Media Trends That Will Shape Consumer Behaviour
Media Insite
January 22, 2026

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Tags: AI, AI Ethics, Marketing

1 Speaking Engagement
Mastering Omnichannel
Exco
October 25, 2024
Mark Corrigan & Rhesa Lessey

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Tags: CRM, Marketing

Thinkers360 Certifications

1 Certification

Thinkers360 Credentials

8 Badges

Radar

Blog

2 Article/Blogs
What are some of the challenges in MarTech?
Thinkers360
March 27, 2026

One of the most common challenges that companies face is that they operate with multiple tools in their marketing stack, each fulfilling a specific task, often with significant overlap. According to Salesforce, the average company uses eight marketing tools in 2026. Beyond the challenges of managing these tools, their presence often creates fragmented processes, which can ultimately be counterproductive.

Consequently, another major challenge emerges: messy data. When data is sourced from different systems with different data structures, unification becomes difficult. This often leads to data quality issues and inconsistencies which result in trust issues. Marketers have cited this as a major pain point.

Data integration proves to be another common challenge among MarTech teams. Connecting systems isn’t just about APIs, true integration means structuring and harmonising data. When data is presented, it must mean the same thing to everyone. For example, “revenue” can mean very different things across platforms. In one system, it may represent the purchase value, before goods are delivered, while in another, revenue is only recognised upon receipt of the goods. Aligning data definitions is critical to successful data unification and should never be underestimated.

Underpinning successful integration is strong governance and defined ownership. Without clarity, even the best solutions fail. Governance sometimes comes as an after-thought, only after there is confusion and loss.

As companies grow, so does their reliance on data. While scalability is a positive sign of growth, it comes at a cost. Larger data volumes increase infrastructure and processing requirements, driving up the investment required to support them.

While technology plays a critical role; people and processes are just as important. Many organisations struggle to find the right resources and programs to upskill existing teams. Success in modern marketing requires greater cross-functional collaboration and more well-rounded teams. Whether in marketing, IT, analytics, or operations, teams need a basic understanding of each other’s roles to perform effectively. When teams lack a basic understanding of each other’s roles, silos form, and productivity suffers.

Beyond skills, change management is often underestimated. Resistance happens when the organization is fearful of change because it is perceived to bring obsoletion, misalignment and loss. In fact, according to WTW 2023, only 43% of employees believe their organization is effective at managing change. This mistrust is perpetuated in MarTech, with some employees citing poor usability, malfunctions and overuse as concerns.

So how do martech professionals navigate these challenges?

MarTech projects don’t fail because of the technology, it fails because of a lack of clarity and team dynamics. The mission must be clear and defined for all stakeholders, so that each team knows what they’re working toward. It’s also important to assess the current state of marketing. What is the current marketing stack? What are the gaps between the strategy and execution? These questions form the basis of a meaningful audit which helps to define a realistic way forward.

Stakeholder engagement across Marketing, Operations, IT, Finance and Human Resources are critical as success is hardly achieved in isolation. Equally important is the perspective of the customer, which guides decision-making and prioritisation. Some organisations use the Balanced Scorecard framework to translate their goals into a comprehensive set of performance measures which guides their path forward. Having a holistic perspective ensures alignment and improves the speed and quality of the end result. Failure to have clear protocols for resolution, escalation and decision-making, MarTech teams experience frustration or stagnation.

Data unification and consistency is every marketer’s kryptonite. It’s not enough to simply integrate data sources, there must be alignment and clarity around each entity, whether it’s a customer, product, or transaction. Stakeholders must agree on the business definitions- that job is not just IT’s responsibility, and failure to capture the perspective of the business is one of the most common reasons for delay and poor results.

The business needs to qualify each metric: what is considered an “active customer”? How is revenue attributed? What constitutes a conversion? Without this alignment, there are conflicting sources of truth, leading to poor decisions, inefficient targeting and poorcustomer experiences. A single, trusted view requires more than technology, it requires governance. This includes naming conventions, data validation rules, ownership and processes for ongoing monitoring and reconciliation. 

It’s also important to recognise that data unification is not a one-time activity, rather it evolves as the business grows and new data sources are introduced. The goal isn’t perfection, but it is agility. The organization must build flexibility and continuous improvement into its workflow.

Finally, on the topic of cost controls and budget, the reality is that you must plan for them. SaaS expenses can escalate quickly, especially as new components and services are added. While platforms may promote every new capability, the reality is that not every service is necessary. Each addition should be evaluated as a business case. The costs that should naturally scale are processing, core platform upgrades, and human resources, as functions mature, specialise, and see broader adoption across the organisation.

MarTech enables organisations to deliver personalized communication and experiences at scale, however it is not a magic wand. These outcomes don’t happen by default, it takes deliberate effort and continuous improvement. Treating your MarTech stack like a quick fix can lead to expensive decisions and disappointing results. Therefore Marketing’s digital transformation must be approached with a clear understanding of the goal, stakeholder engagement, structure and a discipline to overcome the challenges that will arise. The path may not always be straightforward, however it is possible, and rewarding.

See blog

Tags: Digital Transformation, Marketing, Retail

The Role of Memory in Modern-day Business
Thinkers360
February 27, 2026

How many times have you had to repeat your issue to a customer service representative? It’s frustrating and it’s revealing. When customers are forced to repeat themselves, it signals gaps in your CRM strategy, and it’s likely costing you in both reputation and revenue.

A Customer Relationship Management (CRM) system should function like the hippocampus, the part of the brain responsible for memory and learning. It should maintain a complete view of the customer, allowing every interaction to be informed, consistent, and service-driven.

The challenge is that this level of continuity isn’t always straightforward, especially for large, long-established organisations with deep roots and vast amounts of data. This data is often siloed across platforms, making it difficult to access and connect with context. Customers expect organisations to remember as people do, and this expectation is exacerbated in the age of AI.

So what do customers actually want you to remember, and what does “memory” mean in a business context?

Beyond order details and past purchases, customer expectations run much deeper. Customers anticipate that organisations will use insights to create value. This is where memory comes into play - recalling information in isolation offers little benefit. What customers want is something more meaningful. They expect organisations to recognise patterns and offer value through proactive replenishment, relevant reminders, or an understanding of natural buying cycles.

Failure to create these experiences results in a disjointed customer journey. Over time, disappointment sets in, trust erodes, and churn rates increase. In more advanced cases, market share diminishes as customers migrate to organisations that feel more customer-centric.

It is therefore critical for businesses to remember. Good memory is reflected across the entire customer journey. It shows up in how an organisation communicates, the channels it chooses, the products it offers, and how well it respects customer preferences. At its best, it feels like a good friend checking in at the end of the day. 

Customers want organisations to remember what helps them move forward in the most frictionless way possible. Preferences, past interactions, appointments, order history, and relevant moments, like birthdays, should not be repeated. However, at the same time, they expect restraint and intermittent privacy check-ups. Customers want their data to be used with intention, not intrusion or surveillance and the difference lies in respect and consent. In modern CRM systems, memory creates relevance, but discretion is what sustains the relationship.

The organisation must collect data, but there must be governance to guide this collection, retention and deletion. The most effective CRM strategies are supported by governance and infrastructure that protects customers. Boundaries must also be honoured so connection feels genuine rather than calculated. 

In a landscape where CRM tools are more accessible than ever, it is the experience they create that truly differentiates organisations. In a world saturated with messaging and automation, the businesses that stand out are not the loudest, but the most attentive. Customers don’t want to be known in every detail, rather they want to be understood in the moments that matter. CRM, when designed as a memory system, enables that understanding by carrying context forward while respecting privacy. Ultimately, memory is not just a technical capability; it is a signal of care. And in modern customer relationships, care is what keeps people coming back.

See blog

Tags: Business Strategy, CRM, Leadership

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