Sales Kick-Off Speaker
Equipping Your Team for a Year of Sales Focus, Clarity and Confident Execution
Caspar Craven is a sales kick-off speaker known for delivering highly engaging, thought-provoking, story-driven keynotes that help teams reset, refocus and align at the most important moment in the commercial calendar. His talks bring together real-world commercial experience, behavioural insights and practical tools that help people think clearly, stay motivated and work together with greater consistency throughout the year.
He helps sales teams at all levels build the mindset, habits, and collaboration needed to meet ambitious targets, navigate uncertainty, and deliver strong performance.
Caspar’s approach has been shaped by a life of unconventional experience: twice sailing around the world (once competitively, once with his wife and their three children under ten), serving as a CFO of a business sold to Private Equity, working as an Associate Director at KPMG, and building, scaling, and selling his own technology business.
These contrasting worlds of high-performance business and high-pressure adventure form the foundation of the practical, grounded insights he brings to organisations at their annual sales kick-off.
“You truly inspired our people to think and act differently!”
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Sales Kick-Offs at a Glance
Caspar Craven brings together experience from three distinct worlds that shape how he approaches sales kick-offs and annual kick-off events.
Extreme environments & high-pressure moments
Twice sailing around the world: once competitively, once with his wife and their three children under ten - Caspar learned how to keep people focused when conditions change fast, pressure is high, and the next decision really matters. Those same principles apply when you are asking a sales or leadership team to commit to ambitious goals at the start of a demanding year.
Corporate leadership at scale
As CFO of a business sold to Private Equity and a former Associate Director at KPMG, Caspar has led teams through restructuring, shifting strategies and high-stakes targets. He understands the realities leaders face when they are trying to align multiple functions, manage pressure from above and still keep their teams motivated and engaged.
Entrepreneurial growth & reinvention
Caspar built, scaled and sold a technology company, working closely with fast-growing teams where clear communication, rapid learning loops and shared ownership were essential. He knows what it takes to keep people energised when expectations are high, and the landscape keeps moving.
This combination of extreme environments, senior leadership and entrepreneurial growth shapes the practical, human-centred approach he brings to sales kick-offs and annual kick-off events. Caspar is a bestselling Bloomsbury-published author and the author of The Big Bold Mindset®. He speaks regularly at global leadership, teamwork and resilience events for organisations including Johnson & Johnson, Intuit, ABB, Boston Consulting Group and Ashurst.
Organisations bring Caspar in when they want their kick-off to create a lasting shift in how people think, work together and deliver results, and not just a short-lived burst of motivation.
Why World Class Teams Book Caspar as Their Sales Kick-Off Speaker
Caspar’s sales kick-off keynotes create a shift in how people think about the year ahead, not just how they feel on the day. Organisations trust him at their most important internal event because he delivers more than motivation. He delivers clarity, alignment and a renewed sense of purpose.
Teams don’t just leave energised. They leave with the tools, focus and mindset they need to approach ambitious targets with confidence and consistency. Every session is crafted to the specific commercial context, challenges and outcomes your organisation is driving towards.
His talks draw on:
The Big Bold Mindset®: 20 principles for creating clarity and consistent action
The latest behavioural insights and research
High-impact, story-led teaching
Practical tools teams can apply immediately
And he delivers it all with humility, humour and a relatable style that stays with audiences long after the kick-off finishes.
The Science Behind Caspar’s Approach
Caspar’s work focuses on closing the gaps that hold commercial teams back: clarity, motivation, collaboration and consistent execution. Recent research reinforces this:
MIT Sloan: teams with clear goals and strong communication are significantly more likely to achieve sustained high performance.
Deloitte: 87% of organisations report internal misalignment and unclear priorities as the biggest barriers to commercial results.
Harvard Business Review: more than 70% of employees say they lack the skills or clarity needed to prioritise effectively — a critical issue for sales teams operating under pressure.
Caspar’s sales kick-off keynotes give teams the mindset, tools and behaviours to bridge these gaps immediately.
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The feedback from the team was amazing. We loved the provocation and all felt super inspired. Thank you!
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The Outcomes You Can Expect from Hiring Caspar as Your Sales Kick-Off Speaker
Hiring Caspar as your sales kick-off speaker helps teams move from noise, uncertainty and fragmented focus to clarity, ownership and consistent execution across the year. Typical outcomes include:
Create clarity around goals, priorities and expectations
Teams gain a firm understanding of what matters most, how success will be measured and how their individual roles contribute to shared commercial results. This clarity helps reduce confusion, misalignment and wasted effort in the months ahead.
Strengthen motivation and energy for the year ahead
Caspar helps teams reconnect with purpose, renew their focus and build the mindset needed to stay engaged when targets are ambitious and the pace is high. The kick-off becomes a genuine reset point, not just another meeting.
Improve collaboration across the commercial, product and operational functions
Sales performance is never a single-team effort. Caspar equips people with practical tools to communicate better, break silos and work more effectively across boundaries so the entire revenue engine moves in sync.
Build resilience and ensure teams stay effective under pressure
Caspar teaches commercial teams how to stay steady when challenges arise replacing firefighting with structured thinking, practical habits and tools that protect focus, wellbeing and performance throughout the sales cycle.
Increase speed and quality of decision-making
With improved clarity, alignment and communication, teams avoid bottlenecks, reduce rework and make smarter, faster decisions which are essential in complex or fast-moving markets.
Foster ownership and accountability throughout the sales cycle
Caspar helps teams shift from “I hope someone fixes this” to “Here’s what I can own.” This mindset reduces blame, increases responsibility and drives more consistent follow-through on actions that matter.
Reinforce ambition and build confidence around bold commercial targets
By removing blockers and “why nots”, people approach ambitious goals with more confidence and creative thinking. Teams feel equipped and not intimidated by the scale of what they’re aiming to achieve.
Improve self-leadership and personal performance habits
Caspar helps individuals build the mindset, routines and clarity needed to stay focused, energised and effective. These are the foundations of consistent, high-quality sales execution.
Ideal for:
Sales kick-offs
Annual kick-off events
Commercial strategy sessions
Leadership and sales enablement programmes
Cross-functional revenue teams
All-hands and culture events
Offsites and planning retreats
“An amazing, inspiring experience for our leadership team that left them fired up to really deliver big goals”
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Sales Kick-Off Speaker FAQs
What makes Caspar Craven a distinctive sales kick-off speaker?
Caspar combines three rare domains: senior corporate leadership, entrepreneurial growth and extreme high-pressure environments. This gives commercial teams practical insights they can use immediately, delivered through relatable stories, bold ideas and grounded commercial experience.
What topics does Caspar Craven specialise in at sales kick-offs?
Caspar speaks on mindset, alignment, resilience, collaboration, decision-making and the habits that drive consistent sales execution. His frameworks include The Big Bold Mindset®, The Big Bold Circle and principles from his Bloomsbury-published books.
Who does Caspar typically speak to at sales kick-offs?
He works with sales teams, commercial leaders, cross-functional revenue teams and wider organisational groups involved in delivering commercial results especially those navigating change, complexity or ambitious targets.
What outcomes can we expect from Caspar’s sales kick-off keynote?
Teams leave with clarity, renewed motivation, stronger collaboration and a mindset that helps them stay focused and effective under pressure. They gain practical tools they can use immediately throughout the sales cycle.
How does Caspar tailor his sales kick-off keynotes?
Every engagement begins with a discovery call to understand your goals, commercial context and desired outcomes. Caspar then designs a keynote aligned to your strategy, culture and the specific behaviours you want to reinforce across the year.
Does Caspar speak at global sales kick-offs?
Yes. Caspar regularly speaks at global commercial conferences and kick-offs for organisations including Johnson & Johnson, Intuit, ABB, GSK, Boston Consulting Group and Standard Life.
Does Caspar deliver both virtual and in-person sales kick-off keynotes?
Yes. Caspar speaks at in-person, hybrid and fully virtual events worldwide, ensuring the same level of engagement, clarity and impact across all formats.
Does Caspar offer workshops as well as keynotes?
Yes. Alongside keynotes, Caspar delivers signature workshop, The Big Bold Goals Leadership Experience focused on mindset, collaboration, communication, resilience and aligning teams around bold commercial goals.
How do we book Caspar as our sales kick-off speaker?
Simply click Check Availability to begin the process. Caspar and his team will share options aligned to your goals and guide you through the preparation, design and delivery stages.
Current Sales Kick-Off Topics Caspar Tackles
Organisations bring Caspar in when they need their teams to align around ambitious commercial goals, think more clearly under pressure and work together with greater consistency across the sales cycle. The most in-demand sales kick-off topics include:
How do we create clarity and focus at the start of the year?
Most sales organisations are not short of ambition. They’re short of clear priorities and shared understanding. Caspar helps teams simplify what matters, align around core goals and remove the noise that derails execution. The result: stronger focus from day one.
How do we build the mindset needed to hit ambitious sales targets?
Big targets require clear thinking, resilience and consistent behaviour. Caspar helps teams understand the mindset shifts that reduce overwhelm, lower reactivity and build the confidence to pursue goals others see as unrealistic.
How do we improve cross-functional collaboration for better commercial outcomes?
Sales performance depends on marketing, product, operations and customer success. Caspar gives teams practical tools to communicate across boundaries, strengthen trust and break silos so that deals progress faster and customers receive a unified experience.
How do we maintain motivation and energy throughout the sales cycle?
Peaks and troughs are common in sales environments. Caspar teaches teams how to manage energy, build sustainable habits and stay steady under pressure so they perform at a consistently high level without burning out.
How do we make faster, smarter decisions in complex markets?
When uncertainty rises, poor decision-making slows everything down. Caspar helps teams cut through noise, simplify choices and act with greater confidence and alignment; a key advantage in fast-moving markets.
How do we create accountability and ownership across commercial teams?
Caspar helps teams shift from reactive thinking (“someone needs to fix this”) to ownership (“here’s what I can take responsibility for”). This mindset reduces blame, increases trust and accelerates progress throughout the revenue engine.
How do we raise ambition and unlock bold commercial thinking?
Many teams underestimate what they can achieve. Caspar shows people how to remove the limiting beliefs and “why nots” that cap performance. Teams leave with the courage and clarity to pursue more ambitious commercial outcomes.
““Caspar has been exceptional to work with for our Sales Kick Off. We were blown away by his charismatic presentation and experience achieving Big Bold Goals with a human touch. He ensured that he fully understood the purpose and objectives of our kick-off conference so he could tailor and adapt his speech. He hit the perfect balance between strategy and making it real for the team. The feedback was energising — people were fascinated by his experience in both the corporate world and his family expeditions. The tools and techniques were tangible, relevant and immediately applicable.”
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About Caspar Craven
Caspar Craven is a sales kick-off speaker based in London who works with sales, commercial and cross-functional teams around the world. He is a best-selling Bloomsbury-published author and the author of The Big Bold Mindset®, his latest work on how people think clearly, act boldly and deliver results in uncertain and fast-moving environments. He regularly speaks at global kick-offs and commercial conferences for organisations including Johnson & Johnson, Intuit, ABB, GSK, Boston Consulting Group and Standard Life.
His work focuses on helping teams create clarity, build high-performance habits and deliver ambitious commercial goals with consistency. Caspar blends real-world senior leadership experience with story-led teaching, behavioural science and practical tools teams can apply immediately across the sales cycle.
For event organisers searching for sales kick-off speakers who combine human-centred storytelling with real-world commercial experience, Caspar offers a practical, research-backed approach that creates lasting shifts in how people think, collaborate and execute.
What It’s Like to Work With Caspar
Event organisers value Caspar for his preparation, adaptability and partnership mentality before, during and after the event.
He listens, adapts and designs the talk around your exact commercial goals, audience and desired outcomes for the year ahead.
The process is simple:
Discovery call: understand your context, targets and outcomes for the kick-off
Talk design: tailored to your audience, messages and commercial priorities
Refinement: you receive a clear summary and proposed direction
Delivery: high-impact keynote with strong alignment to your goals
Ongoing support : reinforcement of key messages, Q&A, attendee engagement
Every sales kick-off is built around your team, your culture and the commercial results you want to drive.
Caspar’s speaking services include: