Senior Commercial & Growth Leader · Strategic Deal Navigator

Jackie
du Plooy

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

FCMA, CGMA MSc Behavioural Economics BCom I&O Psych
$150M+
Career Contract Value
$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. $150M+ in career contract 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. $150M+ in contract 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 IT S&S
$150M+Career Contract Value
$33MARR
25+Years Experience
6Countries
120Team Led · BFSI
3Continents
Career defining moments

Proof Points
That Matter.

T-Systems (now Gijima) · Financial Services & Insurance
$136M
Largest single engagement secured

The defining deal of the T-Systems years. A $136M IT Outsourcing and infrastructure engagement with one of Africa's largest financial services and insurance groups. End-to-end IT managed services, infrastructure transformation, and application delivery across the enterprise.

South Africa & UK · 2009 to 2015BFSIT-Systems
HCLTech · Guidewire
$5M
Insurance platform deal won from scratch

Joined HCLTech SA in 2019 and secured a $5M Guidewire claims system implementation from a standing start, with an offshore delivery centre built in Madurai - closed on sector depth and commercial precision.

South Africa · 2019InsuranceHCLTech
Monstarlab · MENA
3 M&A
Acquisitions led end to end (Saudi Arabia & Dubai)

As VP Operations and Commercial at Monstarlab, led three MENA acquisitions (Saudi Arabia and Dubai) end to end that repositioned the firm's regional footprint - alongside securing a $5M strategic deal through applied behavioural economics.

Prague · 2024M&AMonstarlab
HCLTech · Energy
$33M ARR
Renewed at $158M multi-year · Current

Managing the $33M ARR strategic energy engagement for HCLTech in Stavanger - driving 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 problem, 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.
A signature capability

Executive Briefings
& Innovation Experiences

Some of the most decisive moments in a complex deal happen in the room - when senior stakeholders experience a capability rather than read about it. I design and lead executive briefing and immersion programmes that turn technology and delivery capability into executive confidence.

01

Architect the experience

Shape high-profile executive briefings that align an organisation's priorities and industry insight with each account's specific objectives - memorable, consistent, and commercially purposeful.

02

Curate the expert network

Build and orchestrate cross-functional networks of leaders and subject-matter experts, matching the right expertise to each engagement so every conversation lands with authority.

03

Accelerate deal velocity

Use briefings and innovation engagements as strategic levers - strengthening executive relationships, matching each engagement to where a customer sits in their journey, and moving decisions forward.

04

Measure the outcome

Define success across every engagement - from relationship depth to measurable adoption - and turn program impact into clear, data-driven stories that justify continued investment.

In practice

From offshore delivery-centre immersions to C-suite roundtables across six countries - designing the executive experiences that de-risk major decisions and build the trust complex deals depend on.

Where I have lived and worked

6 Countries.
3 Continents.

🇿🇦
Home · Siemens IT S&S 2000–2009 · T-Systems 2009–2015 · Wipro 2015–2019 · HCLTech 2019
South Africa
Cape Town

Where it all began. BCom in Industrial and Organisational Psychology at UNISA, completed 2021. The $136M Financial Services & Insurance engagement at T-Systems, and the BFSI leadership at Wipro both have their roots here.

🇬🇧
Siemens IT Solutions & Services (now Atos) · 2000 to 2009
United Kingdom
London

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

🇸🇬
Concentrix Tigerspike · 2020
Singapore
Singapore

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

🇦🇪
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.

🇨🇿
Monstarlab · 2024
Czechia
Prague

VP Operations and Commercial at Monstarlab, leading MENA deal strategy. $5M strategic contract, closed zero to signature in six months. Three MENA acquisitions led end to end. Prague sharpened the ability to build commercial momentum where trust is the currency.

🇳🇴
HCLTech · November 2024 to Present
Norway
Stavanger

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

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: A2 completed at the Goethe-Institut, currently progressing through B1 intensive, targeting B2 to C1 by Q4 2026.
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 IT Solutions & Services - delivering IT Outsourcing, infrastructure managed services, AI and digital transformation, and enterprise technology strategy at C-suite level across three continents.

HCLTechWiproMonstarlabConcentrixT-SystemsSiemens IT Solutions & ServicesIT OutsourcingInfrastructureAI & Digital Transformation
$150M+
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 behavioural insight, AI adoption, 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 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 succeed with transformation are not the ones with the best technology, but the ones that understand how their people will actually respond to it.

2024
🇨🇿 Prague & Dubai · 2021 to 2024

Monstarlab - Vice President, Operations and Insurance Commercial Growth

Led commercial strategy and enterprise deal-making across Europe. Secured a $5M contract by understanding the cognitive patterns behind complex B2B procurement decisions. Led three MENA acquisitions (Saudi Arabia and Dubai) end to end that repositioned the firm's regional footprint.

2021
🇦🇪 Dubai, UAE · 2021 to 2023

Monstarlab - VP Engagement, Insurance

VP Engagement managing insurance platform engagements across the Gulf, concurrent with the Prague 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.

2020
🇸🇬 Singapore · 2020

Concentrix Tigerspike - Commercial Director, 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.

2019
🇿🇦 South Africa · 2019 to 2020

HCLTech - Regional Commercial Director

Joined HCLTech SA and secured a $5M Guidewire implementation from a standing start. New enterprise relationships, new market - closed on the strength of insurance platform depth and commercial precision.

2015
🇿🇦 Cape Town, South Africa · 2015 to 2019

Wipro - Head of BFSI Sales and Commercial

Based in Cape Town, built the BFSI vertical from zero to a 120-person operation with full P&L ownership against a $50M operating budget. Drove $12M in annual growth and won the Oracle Health Insurance engagement. The pattern was consistent: organisations designing for systems while ignoring the people who had to use them.

2009
🇿🇦 South Africa · 2009 to 2015

T-Systems (now Gijima) - Head of Finance and Strategic Accounts

Led the $136M Old Mutual engagement - the largest IT services contract signed in South Africa at the time - a ZAR 2.6bn, four-tower IT Outsourcing programme (network, workplace, data centre, cloud) on a seven-year renewal cycle. Turned account profitability around by 50%. Deep exposure to large-scale outsourcing and infrastructure managed services across South Africa and the UK.

2000
🇿🇦🇬🇧 South Africa & United Kingdom · 2000 to 2009

Siemens IT Solutions & Services (now Atos) - Commercial Manager

Nine years across South Africa and the UK at Siemens IT Solutions & 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.

Professional profile

The CV,
Condensed

"$136M Financial Services & Insurance. $5M 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 strategic energy account for HCLTech. Driving transformation at CxO level. Applying behavioural economics to close complex, multi-stakeholder enterprise deals. November 2024 to present.
Credentials
FCMA, CGMA · MSc · BCom
MSc Behavioural Economics and Game Theory. BCom I&O Psychology, UNISA, 2021. PG Diploma Innovation and Design Thinking. FCMA, CGMA Fellowship. 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 IT Solutions & Services (SA & UK). IT Outsourcing and infrastructure managed services across Siemens IT S&S, 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)
  • 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
Behavioural insight in change adoption and deal-making. Decision-making 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.

Behavioural Science7 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 - AI, digital, 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 navigating change will need someone who understands the human and cognitive drivers of how people respond to change.

June 2026Read
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. 25 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 behavioural insight, AI transformation, and commercial growth - for executives who want to lead with evidence, not assumption.

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Jackie du Plooy
Jackie du Plooy
Senior Commercial & Growth Leader
Stavanger, Norway
JdP
Jackie du Plooy
FCMA, CGMA · MSc Behavioural Economics | Senior Commercial & Growth Leader · Strategic Deal Maker · Behavioural Insight
6,200+
Connections
6
Countries
25+
Yrs Exp
  • Writing on the neuroscience of enterprise deal-making and how cognitive bias shapes B2B procurement decisions
  • Publishing on 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 senior commercial and growth leadership from BFSI, energy, and insurance across three continents
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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
    New article: Decision architecture in the boardroom - what the science of decision-making tells us about how leaders actually decide.
  • NOV
    2024
    HCLTech, Stavanger: Joined as Regional Commercial Director, managing the $33M ARR strategic 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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Stavanger, Norway
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© 2026 Jackie du Plooy · FCMA, CGMA · MSc Behavioural Economics Senior Commercial & Growth Leader · Strategic Deal Navigator · Behavioural Insight