David Rajakovich

SETsquared Partnership

Provide strategic and practical guidance to build the next great company.

Entrepreneur in Residence

David Rajakovich Inc.

Founder & CEO

Skill Dynamics

Key achievements include transforming senior management by adding high-calibre talent, turning strategy into operational reality and developing a trust-based, high performance culture positioning the company for rapid growth. Thrived in a private equity-backed, SaaS environment with an imperative for value creation.

Owned the product with full P&L responsibility - focussing on solving customer business problems through the content and technology components of our product. Created the content function from its inception using the latest in learning technology and developing a framework for how we write content. Built the world-class, highly-rated supply chain content from scratch and created the entire advanced elements of procurement content from its inception. Oversaw the overhaul of our systems including the development of an innovative, multi-tenant Skills Gap Assessment system that greatly improved its intuitiveness from the user's perspective and resulted in a step-change in operational efficiency. Facilitated the transition from one content delivery system to a new Learning Management System which significantly improved engagement. Added a state-of-the-art advanced analytics module that demonstrated client ROI.

Managing Director - Product & Operations

Positive Purchasing

Led the design, development and maintenance of the online academy offering. Implemented IT infrastructure including back-up, security and optimization. Transformed client and internal ideas for applications, enhancements and functionality into reality. Managed in-house and external web development resource. Project managed the development of and created academy multi-media content. Recruited and trained new academy team members. Managed costs to the budget and responsible for overall profitability of the academy offering. 

Led category management, negotiation, Supplier Relationship Management training and consultancy workshops. Developed course material for workshops for all of the above.

Vice President of Online Operations

Led procurement training in category management, Strategic Relationship Management and Negotiation for many global organizations. Created purchasing tools, workbooks, e-learning, and other content. Facilitated the creation of creative strategies across many purchasing categories. Project managed online academy product.

Lead Consultant

Alcoa

Responsible for problem solving, process auditing, restoring production flow, correct usage and problem resolution of Oracle ERP system, and resolving personnel issues in the finishing department of the Downingtown Flexible Packaging Plant. Responsible for meeting production goals, and for ensuring that Environment, Health, and Safety standards are upheld. Also, identified strengths and weaknesses in the finishing process and implemented solutions. Drafted and received approval for multiple major process changes resulting in greater productivity and less waste within 3 months of starting work and continuing throughout time of employment.

Production Supervisor

US Army

Highlights include:
- Chosen above over 50 lieutenants to work directly for the Brigade Commander

- Rated in the “Top 1%” of officers on final Officer Evaluation Report by Brigade Commander

- Selected to represent the Brigade as the Brigade Liaison Officer to 32nd Air and Missile Defense Command during March 2005 Roving Sands/Red Flag Joint Exercise

Air Defense Officer

Co-Founder of REKREATE | Accelerating the pace of office space leasing

I have guided two successful Private Equity exits. My experience spans nine years at the executive level and more than fourteen years in the corporate L&D training sector. I have lived and worked on three continents, speak Spanish fluently, and enjoy working with people across all different cultures and backgrounds. I have led a SaaS private equity-backed organisation as CEO, delivering procurement and supply chain digital training to over 250 blue-chip clients around the world. 

I started with Skill Dynamics - then known as SiPM - in 2013 as Managing Director – building our product from very early in its development. I created the Content function from its inception using the latest in learning technology. I have overseen the development of our technology to assess, deliver and demonstrate ROI through advanced analytics to our L&D clients. As CEO of Skills Dynamics, we disrupted the procurement and supply chain training industry, opening people’s eyes to the effectiveness of training practitioners digitally.

Co-Founder

ReKreate accelerates the leasing of office space for landlords by creating and displaying elegant, realistic 3D visualisations on the web. 3D visualisations allow landlords to market their properties without having to rely on physical visits. We design the offices of tenants’ dreams together with those tenants on a video call saving time, the cost of speculative refits and their associated embodied carbon. ReKreate further accelerates the reduction in voids by providing a Bill of Materials and their costing based on the design the client has chosen, thus quickening the pace of the work to prepare the space. We were created by commercial real estate experts and powered by intuitive technology to grow landlords’ yield exponentially. ReKreate accelerates leasing, saves cost and enables landlords to obtain financing, insurance and continued rental income by proving their dedication to achieving a carbon net zero world.

Exit Planning isn’t synonymous with replacing people.

As a CEO, my philosophy is simple:

Transform, not replace.

So here’s how I transform teams.

(without a full overhaul)

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PE Exits: Succeeding Without Team Overhaul

Duolingo is the king of EdTech.

It’s the #1 most downloaded language learning app in the world…

with a user base of more than 500m.

Here’s how Duolingo built a $9 billion public EdTech company:

(and revolutionised language learning)

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Duolingo's Strategy: $9.58B Valuation & IPO.

Private Equity needs an entirely new model of value creation.

Here’s the problem:

Portfolio companies face intense demands from PE investors for significant returns in 3-5 years.

This urgency puts even the most competent of leaders under strain, leading to either:

— high turnover or internal conflict

— underinvestment in leadership development (i.e. people skills)

As a result, leadership strength and human capital investments are often deprioritised.

(since returns are harder to quantify)

The default route then involves installing new CEOs who can execute quickly:

by aggressively cutting costs and eliminating overhead.

The result?

A high turnover of key leaders at all levels.

(and even customer defection)

While this is financially advantageous in the short-term…

This approach fails to foster a culture of leadership at all levels.

It also erodes long-term investment returns.

Successful companies need strong leaders at ALL levels, not just at the top.

Leadership is a team sport—not a lone man’s miracle.

PE must pivot from focusing solely on operations to valuing human capital more. 

Today’s PE model (focused on quick buys, fast profit, debt leverage) is threatened by stiff competition and surging interest rates.

Financial engineering alone makes it much harder to deliver strong returns.

Rather, cultural transformation and leadership effectiveness need to be accounted for.

Investing in human capital is what creates valuable, competitive companies in the long term.

Who’s with me?

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Remote work isn’t the enemy.

It’s the lack of trust and communication within your team.

Yes, it’s easy to take advantage of remote working.

But that doesn’t mean remote work is obsolete.

At Skill Dynamics, our team was entirely remote at least in its inception. 

Yet we still scaled the company to a lucrative exit.

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Building a Strong Remote Team Culture

Anyone can build an EdTech business. 

But steering one towards an 8-figure exit is a mastery of its own.

Here are 5 data-driven tips to build your EdTech company with an exit in mind:  

(From an EdTech CEO with an 8 figure exit)

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5 Tips to build an EdTech company for a Profitable Exit

Most companies misunderstand what high-performing cultures are.

(Hint: It’s not an ‘anything goes’ culture)

Neither is it a culture where there’s no diversity of thought.

Or a ruthless culture where every team member is out for one another. 

A high-performing culture is when your team is productive, efficient and motivated to achieve business goals.

It’s an environment rooted in mutual trust, transparency and collaboration.

So here’s what high-performing culture is, and isn’t:

(From a CEO who’s built one) 

P.S. What are your thoughts?

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Exit planning is an exhilarating time. 

High stakes? Absolutely.

But that doesn’t mean your company should face unexpected financial setbacks. 

Here are 3 of the most common financial missteps companies make when exit planning

(and how to avoid them):

3 Financial Mistakes companies make when Exit Planning

Digital learners struggle to be motivated.

But Generative AI will change this forever.

Here’s how Generative AI will democratise education:

(and create a class of attentive and motivated learners)

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How Generative AI will revolutionise EdTech?

Your CEO can make or break your Exit. 

You need best-in-class governance to create stability, direction and focus. 

Here’s the impact the right CEO can have on your Exit strategy:

Turning Vision to Reality:

A good CEO translates strategy into measurable outcomes. They identify and drive KPIs that are crucial for the company’s growth. 

Navigating Change:

An adept CEO manages transitions smoothly, maintaining focus on the company’s objectives while minimising disruptions and uncertainty. 

Making Data-Driven Decisions:

A standout CEO relies on empirical evidence to make critical and accurate decisions, rather than intuition. This reduces the risk of errors and instills stakeholder confidence. 

Assembling a High-Performing Team:

The right CEO understands how to build and retain a high-performing team of A-players, who are capable of advancing the company’s mission. 

Maintaining Effective Communication:

A successful CEO maintains open and transparent communication across the company. 

They’re capable of articulating the overall vision, managing expectations and building trust amongst stakeholders. 

Strategic Negotiation and Deal-Making:

A skilled CEO understands how to maximise the company’s valuation and secure favourable exit terms. 

They advocate effectively for the interests of the company and bridge the expectations of all parties 
involved.

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Most EdTech businesses will become obsolete in 10 years.

And this is why:

E-learning that simply digitises traditional education isn’t competitive enough.

Rehashing classroom materials into online videos isn’t “innovation”.

How you leverage technology to transform pedagogical approaches—that’s true innovation. 

Learners today desire on-demand, contextual and hyper-personalised learning.

Generative AI is catalysing this shift— It relates the content specifically to the learner’s needs.

It also shows how learners can apply their lessons practically.

These are all elements that traditional e-learning companies lack:

→ The ability to contextualise what they’ve learned in real-world applications.

Think DuoLingo:
The app adjusts the difficulty and content of lessons based on a user’s performance.

It gamifies learning to maximise motivation levels and morale to learn.

(And improves learning retention)

But it also caters to a range of learning pathways.

Your EdTech business needs to think about how accessibility and diversity in learning styles can be achieved with technology.

Put pedagogy first. 

And technology serving pedagogical intentions second.

That’s how you stay competitive.

Which innovation in EdTech excites you? 

Leave a comment below.

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Exited companies have 1 theme in common: 

A high-performance workplace culture.

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Building a High-Performance Team.

EdTech should never be purely digital.

Here’s what I mean:

At my previous companies, we used to implement fully digital learning pathways. 

This was brilliant for profit margins and scaling…

But less than ideal for retention and motivation.

No human contact meant learners didn’t get the support they needed.

It’s one reason why EdTech platforms struggle with high churn.

Users are fed with learning material and are expected to get on with them.

(with no access to support…)

(all of which leads to demotivation)

This could’ve been resolved in 2 ways:

1. Instructor-led training

(where an expert onboards you to your program)

2. Collaborative learning

(where users directly engage with each other)

A human touch brings relevance and depth to the learning experience.

(which automated systems struggle to replicate)

Scalability isn’t the only metric we should be concerned about in EdTech.

It’s learning effectiveness, which directly impacts user satisfaction and retention.

Put humans at the forefront of everything.

When you do so, scalability will naturally follow.

This means:
— Caring about user satisfaction
— Adding human touchpoints

Afterall…

A learning platform is only truly scalable when churn is addressed. 

P.S. Which side of the debate are you on? Purely digital, or digital with some human touchpoints?

Want to know the key ingredient behind Skill Dynamics’ 8-figure exit?

It’s hiring A-Players.

Look, it’s impossible to scale without having top performers.

(Especially in the C-Suite)

Attracting A-Players requires cultivating a strong organisational culture.

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Hiring A-Players: Key to Skill Dynamics' 8-Figure Success

“David, how did you create such a high-performing culture at Skill Dynamics?”

My answer has always been the same.

→ It’s creating a conducive, healthy work environment.

One where every employee feels empowered to thrive in their role.

I take great pride in how I structured and trained the Skill Dynamics’ team.

Every employee had clarity over their responsibilities and expectations.

We embraced a culture of ownership, accountability and transparency from all levels.

This was how the Skill Dynamics’ team has always been empowered to:

— ask questions
— voice dissenting opinions
— be honest about where they were struggling
— challenge C-level assumptions

— excel in their fields

But more importantly, every member was heard and valued for their views and contributions. 

Feedback wasn’t just given top-down, but also bottom-up.

We embraced multi-directional feedback pathways, not a unilateral one.

Fluid leadership underpinned our management:

Leaders adjusted their approach to specific contexts, needs and people.

(No 2 employees were the same, so why should our leadership stay rigid?)

Importantly, Our C-level leaders led by example—

demonstrating the behaviours and qualities they expect from their own teams.

Look, your company will struggle to accomplish much if you don’t have a harmonious team.

After all, a happy and well-adjusted team is a productive, resilient business.

Your team is your greatest organisational asset.

Invest in and prioritise their well-being first.

And you’ll never have to worry about talent retention or poor performance again.

Do you agree?

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Exit Planning isn’t just about optimising financial metrics.

It’s easy to have a myopic focus on finances.

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Expert Leadership Key for Successful Exits.

Your company culture is the biggest driver influencing your success. 

Here are 7 ways to improve your company culture:

(From a CEO who’s built a high-performing one)

1) Make people feel heard

Value your employees’ contributions and opinions.

Involve them in conversations. 

Make them feel integral to the company dialogue.

This is how you’ll get employees to start taking pride in their work.

They’ll feel a sense of ownership:

becoming more vested in the company’s success.

And they’ll proactively think of ways to improve the business.

2) Team Building

Spending quality time together as a team builds trust and improves communication.

It also allows your team to better understand one another, mitigating conflict.

Organising occasional team social activities should be your priority.

At Skill Dynamics, we’d organise virtual cocktail nights and step challenges.

This enabled us to build a sense of community and camaraderie in the company.

3) Learn how to manage different personalities

Get to know your employees on a deeper level.

No 2 employees are the same:

So your management style shouldn’t be either.

Adapt your leadership style to who you’re managing. 

Be empathetic and understand why various personality types react differently to situations.

Instead of jumping to conclusions… 

take a step back and identify how best to approach the situation.

4) Encourage Transparency and Honesty

Keep your employees in the loop, welcome honest feedback and share both good and bad news.

Being a transparent leader requires vulnerability:

But it invites respect and trust from your team members.

5) Hire people who are humble

Egoistical employees can be a burden to the entire company.

They can quickly damage your company culture and fuel interpersonal conflict.

This makes it difficult for the rest of the team to excel in their jobs.

Look for people who’re humble, selfless and willing to learn.

Don’t be afraid to axe toxic personalities. 

6) Be involved in the nitty gritty

Employees aren’t daft.

They can pick up on leaders who are unclear about what’s going on.

Refrain from making uninformed decisions as a leader:

It’ll simply make you look less credible.

Instead, immerse yourself in the specifics of every project you’re involved with. 

7) Be clear and direct on guidelines

Eliminate ambiguity and ensure that your teams know exactly what’s expected of them.

When instructions are straightforward…

Your team can execute their tasks without constant clarification.

Clarity empowers your team to be more streamlined, efficient and productive with their work.

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99% of Private Equity’s decision-making is driven by data alone.

Here’s where I might ruffle some feathers: 

An over-reliance on data creates limits.

1) Data isn’t objective reality

Data reflects our framing of reality rather than an unbiased truth.

2) Data can be incomplete

Data contains gaps in information.

There’s always missing context.

3) Data can be a poor predictor of future growth

Data reflects past occurrences.

But the future is fluid:

it’s subject to unforeseen variables and trends.

Future growth stems from creativity and applying innovative solutions.

So here’s what Private Equity should do:

— Test hypotheses and leverage this to drive their strategy

— Stop collecting even more data: This causes inertia. Focus on executing instead

— Stop seeking a ‘magic’ insight from excessive analysis. It’s never going to come

— Forget spreadsheets: They don’t provide the same insight as qualitative knowledge

— Focus on qualitative insights just as much as quantitative: understanding consumer behaviour is critical (relationship quality can be hard to quantify)

More importantly…

Once a decision is made:

Own it, look forward and measure its success.

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