Oren Klaff, bestselling author of Pitch Anything

I’ve had a lot of roles in digital agencies and consultancies. I’ve been a frontend developer, a UX Designer, an Art Director, a Project Manager, an Interaction Designer, a Researcher, a Service Designer…the list goes on. I tried everything with gusto and enthusiasm, always hoping that I’d find a role where I could say “Yes, this is me.” One of the roles that I never expected to find myself in was sales – in fact when an old boss asked me to try it, I laughed, and then flatly refused. But, just like any good story, the call to adventure was too strong and pulled me in eventually.

I began sales reluctantly. Between us friends, the only thing that really excited me was the dangling carrot of commission. For me, salespeople were all the same; something largely synonymous with the stereotype of a ‘used-car salesman’ from ‘days gone by’. Salespeople talked their way into getting people to reluctantly part with their money. They used tricks and cons for short-term gain. They were dishonest, conniving, scheming, slimy.

Well, I now know that this isn’t true. Sure, there are people like that somewhere, but there are a far greater proportion of salespeople who genuinely believe in their product or service and want to improve their customer’s lives in one way or another. It took me a while, but eventually, I learned the following:

1. Sales can be one of the most exciting and creative parts of any business
2. There is an art to sales and pitching, but that’s not a negative thing
3. There is also a science to sales and pitching – also not a negative thing
4. You can be honest, and moral, and genuine, and be hugely successful in sales
5. The answers are all out there if you’re prepared to put in the work to educate yourself

Yes, I realise that this is a blog post about Oren Klaff, but that stuff is important – you see when I started in sales, I was terrible. For the most part, in previous roles, I’d picked things up pretty quickly – I’d followed the instructions, I’d practiced, I’d got gradually better. In sales, at first there don’t appear to be any instructions. On closer look, there are too many: thousands of books that all pertain to have the best method, the winning formula, but are often in direct conflict with one another!

I mean, shiiiiiit. Creating a winning pitch seemed like a cross-between alchemy, a college degree and total luck. And then amongst the swathes of texts, I found Oren Klaff and his book Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal. Along with a couple of other books, this changed everything for me. It cut through the fluff and told me “Do this, then do this, then do this”, and for a guy who likes instructions, it was exactly what I needed. I’ve read that book over and over and I use its teachings every single day to win real pitches.

With that in mind, when I started the podcast, Oren Klaff was the name at the top of my list. In my very first wave of hopeful emails in 2022, I poured out my heart and my gratitude to Oren and humbly asked him if he’d consider being a guest on the show.

No response.

I followed up a couple of weeks later, and then a couple of weeks after that. I got creative with the requests – some were like essays, some were one-liners, some attempted to be funny or provocative, and some aimed to show off my own knowledge and expertise in pitching. I emailed Oren twice a month for 8 months, and every email was unique, personal, and had a new spin. It was pretty soul destroying, until one day, I received an email back. It was entitled:

Persistence pays off.

And the rest, as they say, is history. I hope you enjoy the episode.