Senior Commercial & Growth Leader · Strategic Deal Navigator

Jackie
du Plooy

Unlocking complex deals,
strategic accounts & growth
through behavioural insight.

CGMA FMA MSc Behavioural Economics BCom I&O Psych
$300M+
Infra Outsourcing TCV
$33M
ARR
25+
Yrs Experience
My Journey Get in touch
The Deal Navigator Method
"Complex deals rarely fail on the solution. They fail on the human, political and commercial layers no one mapped."
The Deal Navigator
A senior commercial and growth leader who navigates the human, political, financial and cognitive layers of complex enterprise deals. My work sits where commercial strategy, behavioural insight and C-suite alignment meet — helping organisations find what is really blocking momentum and build a clear path to yes. $300M+ in enterprise value, built on trust, not just terms.
01
Decode the human layer
Map the decision-makers, motivations, incentives, fears and blockers behind every deal. The layer others skip is the one that decides the outcome.
02
Build executive consensus
Align C-suite, finance, delivery, operations and partners around a shared commercial outcome. $300M+ in enterprise value closed across financial services, energy and insurance.
03
Shape the commercial case
Connect value, risk, pricing, ROI and business outcomes into a deal structure that can actually be signed. Commercial rigour and financial discipline, applied where it matters most.
04
Accelerate growth decisions
Create the conditions for renewal, expansion, transformation and long-term partnership value. Twenty-five years turning complex enterprise relationships into lasting growth.
Experience at
HCLTech
Wipro
Monstarlab
Concentrix
T-Systems
Siemens
$300M+Infra Outsourcing TCV
$33MARR
25+Years Experience
6Countries
120Team Led · BFSI
4Continents
Career defining moments

Proof Points
That Matter.

Wipro · Major Financial Services Group
$136M
Largest single engagement secured

The defining deal of the Wipro decade. A $136M IT Outsourcing and infrastructure engagement with Major Financial Services Group — one of Africa's largest financial services groups. End-to-end IT managed services, infrastructure transformation, and application delivery across the enterprise.

Cape Town · 2015 to 2019BFSIWipro
HCLTech · Guidewire
$15M
Insurance platform deal won from scratch

Joined HCLTech SA in 2019 and secured a $15M Guidewire insurance platform implementation from a standing start. IT Outsourcing deal encompassing infrastructure, application managed services, and platform delivery — closed on sector depth and commercial precision.

South Africa · 2019InsuranceHCLTech
Monstarlab · Europe
$20M
M&A strategy developed and executed

As VP Operations and Commercial at Monstarlab, developed and executed $20M in M&A strategy that repositioned the firm's European footprint — alongside securing a $5M strategic deal through applied behavioural economics.

Prague · 2020 to 2024M&AMonstarlab
HCLTech · Energy
$33M ARR
Strategic energy account · Current

Managing the $33M ARR strategic energy engagement for HCLTech in Stavanger — AI and digital transformation at CxO level in one of the world's most strategically significant energy companies.

Stavanger · Nov 2024 to PresentEnergyHCLTech
Where I create value

Problems I
Help Solve

The commercial and growth challenges where behavioural insight, commercial rigour and C-suite alignment make the difference.

01
Complex deals are stalling despite a strong solution.
02
C-suite stakeholders are not aligned around the value case.
03
Strategic accounts are underperforming or at risk.
04
Growth depends on multiple decision-makers with competing priorities.
05
AI or digital transformation is struggling because adoption was treated as a technical issue, not a human one.
06
Commercial teams need sharper deal strategy, stakeholder mapping and executive influence.
07
Partnerships are not translating into measurable revenue growth.
08
Customers need trust, confidence and a clearer path to value.
Where I have lived and worked

6 Countries.
3 Continents.

🇿🇦
Home · Siemens 2000–2009 · Wipro 2015–2019
South Africa
Cape Town

Where it all began. BCom in Industrial and Organisational Psychology at UNISA, completed 2021. The $136M Major Financial Services Group engagement and the 120-person BFSI team at Wipro both have their roots here.

Siemens Business ServicesWiproUNISA 2021
🇬🇧
Siemens Business Services · 2000 to 2009
United Kingdom
London

Part of the Siemens Business Services chapter, working in London alongside the South Africa base. The UK raised the commercial standard — faster, more competitive, less forgiving.

Siemens Business Services2000 to 2009
🇸🇬
Concentrix · 2020
Singapore
Singapore

Asia Pacific chapter at Concentrix. Applied gamification, nudge theory, and choice architecture to digital product development for Telco and Airline clients. Behaviour is not universal.

ConcentrixAPAC2020
🇨🇿
Monstarlab · 2024
Czechia
Prague

VP Operations and Commercial at Monstarlab, leading European deal strategy. $5M strategic contract. $20M M&A strategy developed and executed. Prague sharpened the ability to build commercial momentum where trust is the currency.

MonstarlabVP Operations & Commercial2024
🇦🇪
Monstarlab · VP Engagement · 2021 to 2023
United Arab Emirates
Dubai

VP Engagement at Monstarlab managing insurance platform engagements across the Gulf. Guidewire, Sapiens, and Oracle Health Insurance at enterprise scale. Dubai: scale is assumed, relationships are non-negotiable.

MonstarlabVP EngagementGuidewire2021 to 2023
🇳🇴
HCLTech · November 2024 to Present
Norway
Stavanger

Regional Commercial Director at HCLTech, managing a $33M ARR strategic energy account — the strategic energy engagement — in Stavanger. Working at CxO level on AI and digital transformation.

HCLTech$33M ARREnergy SectorNov 2024 to Present
Communication

Languages &
Cultural Fluency

English
Native
Primary language across all commercial roles, negotiations, and written work. Board level across six countries and three continents over 25 years.
Afrikaans
Native
Home language. Germanic roots create a natural bridge to Dutch comprehension — a practical advantage in Netherlands and Benelux markets.
German
In Progress · A2
English fluent · Afrikaans native · German developing. Currently studying at the Goethe Institut toward professional proficiency.
Cultural fluency
6 Countries · 3 Continents
Navigated high-stakes commercial engagements across Arabic, Czech, Norwegian, Malay, and Singlish business cultures. In complex enterprise deals, it is often the deciding factor.
Sector expertise

Industries &
Domain Depth

Technology has been the constant thread through every chapter. 25 years, six countries — and a real depth in the industries and people it has served.

Foundation
Technology & IT Services

The through-line across every role, every country, every deal. 25 years operating inside the world's leading IT services firms — HCLTech, Wipro, Monstarlab, Concentrix, T-Systems, Siemens Business Services — delivering IT Outsourcing, infrastructure managed services, AI transformation, and enterprise technology strategy at C-suite level across three continents.

HCLTechWiproMonstarlabConcentrixT-SystemsSiemens Business ServicesIT OutsourcingInfrastructureAI Transformation
$300M+
Infra Outsourcing TCV
$33M
ARR Current
Banking & Financial Services
Deep Expertise

Extensive client executive experience across retail banking, investment banking, and financial services transformation. Applied behavioural economics to complex B2B deal cycles.

Retail BankingFinTechRisk & Compliance
Insurance
Deep Expertise

Led insurance platform transformations across the Gulf, Europe, and beyond. Specialist knowledge of Guidewire, Sapiens, and Oracle Health Insurance.

GuidewireSapiensOracle Health Insurance
Energy & Utilities
Current Focus

Currently managing the $33M ARR strategic energy account at HCLTech in Stavanger. Helping make AI and digital transformation commercially adoptable — connecting technology ambition to executive confidence, commercial value and real adoption.

$33M ARREnergy SectorAI in EnergyNordics
Telecommunications
Sector Experience

Applied gamification, nudge theory, and behavioural science to Telco product development at Concentrix in Singapore across APAC markets.

Telco APACGamificationCX Strategy
HR & People Technology
Sector Experience

BCom in Industrial and Organisational Psychology and CBT Certification. Built and led a 120-person BFSI team at Wipro applying I&O Psychology principles at scale.

I&O PsychologyChange ManagementProsci
Neuroscience & Decision Science
Emerging Focus

Applying 25 years of enterprise commercial experience at the intersection of cognitive neuroscience, AI decision-making, and enterprise strategy. Completing MIT Neuroscience for Business.

NeuroeconomicsDecision ScienceMIT Neuroscience for Business
Career chapters

The Journey
So Far

"Every country. Every deal. Every stakeholder. The pattern was the same: the strategy was rarely the problem. The human layer always was."
2024
🇳🇴 Stavanger, Norway · November 2024 to Present

HCLTech — Regional Commercial Director

Managing a $33M ARR strategic energy account — the strategic energy engagement — for HCLTech in Stavanger. Working at CxO level to drive AI and digital transformation in one of the world's most sustainability-focused energy markets. The organisations that will win with AI are not the ones with the best models, but the ones that understand how their people will actually respond to them.

Nov 2024 to PresentHCLTech$33M ARREnergy · Norway
2021
🇦🇪 Dubai, UAE · 2021 to 2023

Monstarlab — VP Engagement, Insurance

VP Engagement managing insurance platform engagements across the Gulf, concurrent with the European VP Operations role. Guidewire, Sapiens, and Oracle Health Insurance at enterprise scale. Dubai operates on different commercial logic: scale is expected, relationships are non-negotiable.

2021 to 2023Guidewire · Sapiens · Oracle HIGulf BFSI
2020
🇨🇿 Prague, Czechia · 2020 to 2024

Monstarlab — VP Operations & Commercial, Europe

Led commercial strategy and enterprise deal-making across Europe. Secured a $5M contract by understanding the cognitive patterns behind complex B2B procurement decisions. Spearheaded $20M M&A strategies that repositioned the firm's European footprint.

2020 to 2024Monstarlab$5M Strategic Deal$20M M&A
2020
🇸🇬 Singapore · 2020

Concentrix — Client Executive, Digital & Innovation

Singapore sharpened a different kind of commercial thinking. Working across Telco and Airline clients in the APAC market, applied gamification, nudge theory, and choice architecture to digital product development. Behaviour is not universal — context shapes cognition.

2020ConcentrixTelco & AirlinesSingapore · APAC
2019
🇿🇦 South Africa · 2019

HCLTech — Client Executive, Insurance

Joined HCLTech SA and secured a $15M Guidewire implementation from a standing start. New enterprise relationships, new market — closed on the strength of insurance platform depth and commercial precision.

2019HCLTech$15M GuidewireInsurance
2015
🇿🇦 Cape Town, South Africa · 2015 to 2019

Wipro — BFSI Practice Lead & Client Executive

Based in Cape Town, built and led a 120-person BFSI delivery team. The defining commercial win: a $136M engagement with Major Financial Services Group. Every failed transformation confirmed the same pattern: organisations designing for systems while ignoring the humans who had to use them.

2015 to 2019Wipro$136M Major Financial Services Group120-person BFSI team
2009
🇿🇦🇬🇧 South Africa & United Kingdom · 2009 to 2015

T-Systems — Commercial Manager

Following Siemens Business Services, continued at T-Systems across South Africa and the UK. Deep exposure to large-scale IT Outsourcing, infrastructure managed services, and technology transformation engagements — working with major corporate and public sector clients on complex, multi-year IT services contracts.

2009 to 2015T-SystemsSA & UKManaged Services
2000
🇿🇦🇬🇧 South Africa & United Kingdom · 2000 to 2009

Siemens Business Services — Commercial Manager

Nine years across South Africa and the UK at Siemens Business Services. Commercial management of large-scale IT Outsourcing and infrastructure services contracts. Engaging at senior stakeholder level in one of the world's most process-driven organisations — where structured deal management and client governance are not just disciplines but survival skills.

2000 to 2009Siemens Business ServicesSA & UK
Professional profile

The CV,
Condensed

"$136M Major Financial Services Group. $15M Guidewire. $33M ARR energy account. The edge was never the product. It was understanding how the person across the table actually decides."
Current Role
Regional Commercial Director — HCLTech, Stavanger
Managing the $33M ARR energy account energy account for HCLTech. Driving AI transformation at CxO level. Applying behavioural economics to close complex, multi-stakeholder enterprise deals. November 2024 to present.
Credentials
CGMA · FMA · MSc · BCom
MSc Behavioural Economics and Game Theory. BCom I&O Psychology, UNISA, 2021. PG Diploma Innovation and Design Thinking. CGMA Fellowship. FMA. CBT Certified. Prosci Change Management.
Career Span
2000 to Present
HCLTech (Stavanger) · Monstarlab (Prague and Dubai) · Concentrix (Singapore) · HCLTech SA · Wipro (Cape Town) · T-Systems (SA & UK) · Siemens Business Services (SA & UK). IT Outsourcing and infrastructure managed services across Siemens, T-Systems, Wipro, and HCLTech. Insurance platforms: Guidewire, Sapiens, Oracle Health Insurance.
Research Direction
Behavioural Science × Commercial Growth
Bringing 25 years of commercial experience together with a deep curiosity about how people think, decide, and lead. A lasting interest in why people — not technology — remain the deciding factor in every strategy.
Core Expertise
What I Bring
  • Strategic enterprise deal-making ($5M to $136M)
  • AI and digital transformation advisory
  • Behavioural economics in commercial strategy
  • CxO and C-suite stakeholder engagement
  • Insurance platforms: Guidewire, Sapiens, Oracle HI
  • Cross-cultural leadership · 6 countries · 3 continents
Research Focus
Behavioural Economics & Growth
Cognitive biases in AI adoption and deal-making. Decision neuroscience in digital transformation. Neurological drivers of organisational change resistance. 25 years of evidence that the human layer determines commercial outcomes.
Where I fit

Roles I'm
Best Aligned To

Best suited to senior commercial and growth mandates where organisations need to unlock complex revenue, expand strategic accounts, strengthen executive relationships, or reposition transformation value.

Chief Growth Officer
Chief Commercial Officer
Commercial Director
Strategic Growth Director
Strategic Client Engagement Director
Strategic Deals Director
Enterprise Account Director
Partnerships & Growth Director
Customer Transformation Lead
Where I create the most value

Complex, high-trust commercial environments where growth depends on more than a sales target — enterprise B2B organisations across insurance, BFSI, technology and transformation-led businesses, with strong technical, delivery and finance teams that need a commercial leader to translate capability into customer value.

Thought leadership

Insights on
Growth & Deals

"The best strategies are not the cleverest ones. They are the ones people actually believe in."

Writing about leadership, decision-making, and the human side of business — for leaders who want to build things that last and make a genuine difference.

Neuroscience & AI7 min read

Why the Smartest Companies Are Finally Taking Behavioural Science Seriously

The best commercial strategies are not built on better products or lower prices. They are built on a precise understanding of how the people on the other side of the table actually make decisions. Behavioural science is no longer a nice-to-have — it is a competitive edge.

April 2026Read on LinkedIn
Behavioural Economics6 min read

The Human Layer — Why Every Transformation Fails at the Same Place

Every major transformation programme — digital, AI, operational — fails at adoption. Not at design. Not at build. At adoption. The reason is always the same: organisations plan for systems and forget to plan for the humans who have to change with them.

May 2026Read on LinkedIn
Decision Science

The Chief Behavioural Officer — The C-Suite Role Nobody Is Talking About Yet

Every major enterprise deploying AI will need someone who understands the cognitive and neurological drivers of how humans respond to AI systems.

Coming April 2026Upcoming
Decision Science

Decision Architecture in the Boardroom — What Neuroscience Says About How Leaders Actually Decide

We teach leaders strategy frameworks and financial models. We almost never teach them how their own brain shapes every decision they make.

January 2026Read
Behavioural Economics

What Insurance Can Teach Every Industry About Behavioural Economics

Insurance products are built on neurological contradictions. The organisations redesigning around how customers actually process risk are gaining measurable commercial advantage.

December 2025Read
Change Management

6 Countries. 15 Years. One Consistent Pattern in How Organisations Fail at Change

From Johannesburg to Singapore to Oslo, the failure pattern in change management is identical everywhere. It is never the strategy. It is always the human layer.

November 2025Read
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New thinking, every two weeks.

Practical insights at the intersection of cognitive science, AI strategy, and commercial leadership — for executives who want to lead with evidence, not assumption.

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Jackie du Plooy
Jackie du Plooy
Client Executive · Behavioural Scientist
Stavanger, Norway
JdP
Jackie du Plooy
CGMA · FMA · MSc Behavioural Economics | Client Executive · Strategic Deal Maker · Neuroscience and AI
500+
Connections
6
Countries
25+
Yrs Exp
  • Writing on the neuroscience of enterprise deal-making and how cognitive bias shapes B2B procurement decisions
  • Publishing on AI transformation strategy and why most programmes fail at the human layer
  • Building the case for the Chief Behavioural Officer — the most important C-suite role organisations have not created yet
  • Sharing 25 years of client executive experience from BFSI, energy, and insurance across three continents
Connect on LinkedIn
Latest
  • APR
    2026
    Published: The neuroscience of why digital transformation projects fail, and what to do about it.
  • MAR
    2026
    New article: 25 years applying behavioural economics at enterprise scale — what I have actually learned.
  • JAN
    2026
    MIT edX: Completing Neuroscience for Business — adding formal credential to 25 years of applied practice.
  • NOV
    2024
    HCLTech, Stavanger: Joined as Regional Commercial Director, managing the $33M ARR energy account energy account.
Work with me

Let's Talk
Growth.

Whether you are shaping what comes next, navigating a complex deal, or looking for a leader who understands that lasting results are built with people — I would love to hear from you.

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Based in
Stavanger, Norway
Available for
Senior commercial & growth mandates
Advisory & consulting engagements
Speaking & keynotes
LinkedIn
linkedin.com/in/jackieduplooy
© 2026 Jackie du Plooy · CGMA · FMA · MSc Behavioural Economics Client Executive · Strategic Deal Maker · Neuroscience and AI