Hey there Croners!
Welcome back to The Prospecting Masterclass, the original Crono column where we bring you insights and tips from the brightest minds in sales.
In today’s B2B SaaS world, prospecting is harder than ever. Buyers are flooded with automated messages, generic outreach, and AI-generated content. Standing out doesn’t come from sending more messages, it comes from sending better ones.
In this episode of The Prospecting Masterclass, we talk with David Wilkins, sales leader and SDR expert, about what truly makes prospecting effective today.
From his journey into sales to his views on human-first outreach in the age of AI, David explains why the best reps constantly ask themselves one simple question: “So what?”
We explore the mindset that separates great SDRs from average ones, the role generative AI will play in the next 12–18 months, and why the future of prospecting isn’t about more tools, but about giving reps the right signals, the right context, and the space to think creatively.
Can you tell us a bit about your journey in sales and how you got into prospecting?
As most people do, i fell into sales.
I wanted to be a sports teacher, so after a semi distinguished career as a semi pro rugby player in the Netherlands, i decided to move back to the UK.
I never settled back at home, so decided to move back to the Netherlands and started working in a mayonnaise factory, then i got the phone call that changed my life, i was asked to interview for a business development rep role.
I had no idea what it was, but i found quickly that all the skills i had learnt from sport and teaching made it the perfect fit.
What do you think makes a prospecting approach truly effective today?
Reps need to take a step back and consider: is what I’m saying actually valuable?
The ‘So what’ question should be ringing through the reps ears every time they start writing an email or beginning a pitch on the call.
Those that act the most human in those interactions with reps are the ones who will be successful.
Looking back, what’s one lesson you wish you’d learned earlier in your sales career?
It would have been to assume positive intent more, and not think that people were out to ‘get me’.
Humans naturally are selfish and are not going to be willing to give you help or support unless they truly do care about you.
So embrace it when people are willing to give their guidance and leadership to you.
What role do you see generative AI playing in prospecting over the next 12-18 months?
Human to human prospecting is critical in the age of AI.
Where the best organisations will win over the coming 12-18 months is giving their reps a signal of information about the pains the prospect is currently facing and how their product can help them solve those pains.
Thats where AI will be truly successful in helping reps.
Then we need humans to convey that message. We are a long way from having a bot talking to a human and being able to interpret speech, sarcasm or quick fire objections.
From your perspective, which soft skills separate a good SDR from a great one?
It’s their growth mindset.
Too many SDRs think that if they hit their KPIs they are automatically deserving of a promotion.
Your KPI are the base, how you show up in the organisaton, testing out new ways of outbound, setting up marketing campaigns, failing fast and learning quick, thats the separator.
If you could give one piece of advice to SaaS leaders on rethinking their prospecting process for 2026, what would it be?
Do you really need all of these tools for your teams?
What if you can create one pane of glass for your reps to go to each and every day for their prospecting?
What would be the time save for them?
How much more productivity would you get out of the team?
Can you save money?
That is the one thing i would ask them.
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