Convertive Consultancy
Strategic clarity for decision-makers
Monthly strategic sparring for leaders who can't afford to make the wrong call.
As an executive, founder, or senior leader, you make decisions with far-reaching consequences every day. Digital investments, platform choices, commercial strategies. Each decision can cost or generate millions. Yet an independent voice that asks the right questions before you commit is often missing.
The Executive Sparring Retainer gives you ongoing access to strategic clarity. No agenda, no sales pitch, no weekly reports that nobody reads.
Why executives choose this form of sparring
You're stuck between competing truths
IT flags risks. Sales wants speed. Finance demands business cases. You need to make the call, but every internal voice has a different agenda. What's missing is an independent thinker who doesn't play politics and does challenge assumptions.
Digital investments are spiralling
A new platform. A marketplace strategy. A customer data infrastructure. The business case seemed sound, but halfway through the complexity turns out to be underestimated. You need someone who has navigated these minefields before and knows where the real pitfalls are.
Growth has stalled and nobody knows why
The numbers are flattening. Teams point fingers. Everyone has an opinion but nobody has the full picture. You're looking for someone who recognises patterns, uncovers root causes, and helps you prioritise without further politicising your organisation.
You don't need another consultant with templates
You don't want a 47-slide presentation deck. No frameworks that fit everywhere and work nowhere. No junior consultants thinking up your strategy for you. You want someone who thinks at your level, asks sharp questions, and helps you reach better conclusions faster.
Why I'm the right sparring partner
You're not looking for a yes-man. You need someone who understands the dynamics at the intersection of leadership, commercial strategy, and technology. Someone who has been in the trenches and knows from experience why digital investments fail, or succeed spectacularly. My track record rests on four pillars:
1. I speak the language of the boardroom and of tech
The biggest failure costs in organisations occur where IT and commercial teams don't understand each other. I've spent years acting as the translator between these worlds. I understand the board's business case, the CCO's revenue targets, and IT's architecture concerns. This allows me to cut through assumptions at speed.
2. Battle-tested in digital growth
From stalled replatforming projects and complex e-commerce transformations to SaaS go-to-market launches: I've navigated these minefields before. Where theory stops, I see the practical obstacles ahead. I recognise the patterns behind stagnating growth and know which levers actually move the needle.
3. Radically independent
My only agenda is your success. I don't sell development hours, I have no hidden partnerships with software vendors, and I don't engage in internal politics. This gives me the freedom to ask the sharp, uncomfortable questions that are often avoided internally.
4. A proven sounding board for senior leaders
I regularly sit across the table from CEOs, CDOs, CCOs, and founders. I know from experience how lonely it can be when you're the one who has to make the call on budgets ranging from hundreds of thousands to millions. I'm not a junior consultant throwing a framework at you. I'm an experienced peer who keeps you strategically sharp.
How the Executive Sparring Retainer works
- Dedicated contact, flexible engagement. You get a fixed number of strategic sparring hours each month. No mandatory meetings, no fixed agenda. You decide when you need sharpness.
- Focus on breakthroughs, not paperwork. No intake forms, no monthly reports, no status updates. Just direct conversations about choices, assumptions, and risks.
- Independent and agenda-free. No upselling of follow-up projects. No platform or vendor preferences.
- Discretion as standard. Everything stays within this collaboration. No documentation that could be used internally.
Where you gain clarity
Loneliness at the top
You can't share every doubt, scenario, or concern with your management team or shareholders. You're looking for a safe space to think out loud without it immediately causing unrest across the organisation.
From founder to CEO
What got you here won't get you further. You need to shift from seeing and solving everything to letting go and delegating. How do you prevent yourself from becoming the biggest bottleneck to your own growth?
Structure versus speed
You need to professionalise but worry about killing the start-up mentality. How do you build processes that don't slow things down but actually enable scalability? Balancing culture with ambition.
The impostor feeling
Sometimes your company grows faster than your comfort zone. The question "Am I still the right person for this stage?" lingers. We turn uncertainty into sharp leadership so you don't freeze, you decide.
Escaping the day-to-day
Operations constantly pull at your sleeve. Before you know it, weeks have passed without any strategic progress. We force you out of the operational tunnel vision: are you just busy, or are you actually effective?
Your personal sustainability
You're always on and the weight of responsibility is heavy. How do you stay sharp and energised without burning out? We ensure that not just the company, but the leader behind it, grows sustainably.
Who this is for
This type of engagement is designed for leaders with ultimate accountability: CEOs and managing directors, CCOs, CDOs, e-commerce directors, and founders responsible for growth.
You're looking for strategic sparring if you:
- Bear ultimate responsibility for digital growth or transformation
- Make decisions involving budgets ranging from hundreds of thousands to millions
- Have no patience for internal politics or theoretical advice
- Want a regular sparring partner who speaks your language and understands technology
What it delivers
- Faster, better decisions. Less deliberation, less delay, more confidence in your direction.
- Lower cost of failure. Avoiding expensive missteps by asking the right questions sooner.
- Greater focus. Priorities sharpened, teams aligned on what matters.
- Less friction. IT and commercial teams get on the same page faster.
- Peace of mind. Structural clarity without hidden agendas.
What this is not
- Not coaching (no personal development plans or reflective exercises)
- Not a traditional consultancy subscription (no juniors, no standard methodologies, no reports)
- Not interim management (you remain at the helm)
- Not a technical consultancy (no blueprints, but clarity on the value of technology)
How an engagement begins
- Introductory call. A no-obligation conversation (approx. 1 hour) about your situation and objectives.
- High-level intake. A discussion about ambitions, challenges, and decision-making.
- Monthly retainer. A fixed number of hours per month, deployed flexibly.
- Review and continuation. After a few months, we evaluate whether it's delivering the value you expect.
Next step
Want to explore whether the Executive Sparring Retainer is right for your situation? Schedule a no-obligation introductory call. We'll discuss your challenges and determine together whether this form of strategic sparring adds value.
Executive Sparring Retainer is a service by Convertive Consultancy, independent strategic consultancy for digital growth and transformation.