ON AIR: With Owen Episode 37 Featuring Benjamin Dennehy ‘The UK’s Most Hated Sales Trainer’

Introducing our 37th episode of ON AIR: With Owen – our latest interview video series with honest conversation about scaling revenue, hosted by our Founder & CEO, Owen Richards.

Our 37th guest is Benjamin Dennehy (The UK’s Most Hated Sales Trainer®).

Owen and Benjamin are talking all things telephone prospecting – why are so many sales people bad at it, and can anybody train to become good at it? 


  • The reasons so many sales people are bad at telephone prospecting and whether anybody can train to become good at it
  • Behaviours of sales people
  • The transition to a change in mindset and how long that can take
  • Whether you should or shouldn’t charge for a proposal
  • Call Tips from Benjamin

ON AIR: With Owen Episode 36 Featuring Lisa Ansell – Business Development Geek at Sales Geek

Introducing our 36th episode of ON AIR: With Owen – our latest interview video series with honest conversation about scaling revenue, hosted by our Founder & CEO, Owen Richards.

Our 36th guest is Lisa Ansell, Business Development Geek at Sales Geek. Owen and Lisa discuss having purpose in a sales role – what do you believe in and what drives you.


  • Tips for Founders that are starting a business venture with no sales background
  • Why people dislike and don’t enjoy sales
  • Why personality makes a high-performing sales professional over process
  • The first steps to developing a graduate starting a sales career
  • The big questions sales professionals should be asking
  • What having purpose means in a sales role and why it’s important

ON AIR: With Owen Episode 35 Featuring Lisa Dempster – Company Director at Sales Consult

Introducing our 35th episode of ON AIR: With Owen – our latest interview video series with honest conversation about scaling revenue, hosted by our Founder & CEO, Owen Richards.

Our 35th guest is Lisa Dempster, Company Director at Sales Consult. Owen and Lisa discuss a broad range of sales topics such as discounting, pipeline management, how to recruit great sales people, and much more

  • The dos and don’ts when it comes to discounting
  • Why you shouldn’t build discounting into your sales cadence
  • When you should provide discount and for what reasons
  • The difference between a reduction and a discount
  • The definition of pipeline management
  • The dos and don’ts when it comes to pipeline management
  • How to identify if somebody is or isn’t your buyer
  • Why bravery is a key skill for a successful salesperson
  • Why curiosity is such a powerful tool in sales
  • The current state of recruitment in sales

Predicting Ramp Time And Quarterly Measuring: Why Tolerance For Failure Is Vital

Striking the right balance between healthy optimism and being necessarily realistic is crucial when it comes to predicting accurate ramp times and setting appropriate targets within a business. 

One of the most common mistakes when it comes to building and managing an outbound sales team is vastly overestimating what’s going to happen in a short space of time, and underestimating the challenges that come with the process before it becomes successful. 

Nothing in sales has ever happened overnight, and that sentiment rings even truer when discussing the hurdles that come with outbound. In this scenario, more than most, possessing a tolerance for failure, in terms of both the process and the individuals involved within it, is absolutely crucial for both short and long-term success. 

This idea—one that is still unfortunately very prevalent within our industry—that you can hire an SDR and have them ramp up to 100%, to perform at their absolute optimum in the space of just three months, is naive at best. Realistically, it’s going to take at least six months to get close to that highest level, in many cases it can take up to a full year. 

The lack of education and understanding surrounding the length of sales cycles is a major factor in these misconceptions. For instance, and this is hardly an uncommon scenario for a newly hired SDR: they book their first meeting in month two, they meet two weeks later, the prospective client takes a further two weeks to mull it over, then they hold a second meeting, then the client takes it to their next board meeting but doesn’t get time to discuss it, eventually it gets brought up in the next board meeting and finally, it gets signed off. 

Before you know it, and this is through no fault of your SDR, that whole sign-off process has turned into a three month operation, and could even be a whole six months on from the SDR actually joining the business.  

On top of that, you need to factor in further variables that can affect sales, such as seasonality, regulatory changes, economic shifts and even something as simple, but hugely disruptive, as a key person leaving the business. It’s never stagnant, it’s a constant process of improvement and it definitely doesn’t just peak after three months, then flatline from that point onwards. 

Outbound is one of, if not the hardest channel to find success with, especially in the short-term. It takes the longest time to generate a return, often has the longest sales cycles and generally offers the lowest conversion rates. The issue with all of that, is if you’re a small business attempting to scale, and something doesn’t work out the way you’d hoped, you don’t achieve the revenue you’d predicted, you really feel it and that experience sticks with you for a long time. 

These kinds of situations are a massive factor in many people’s attitude towards using outbound as a channel, and again, much of it comes down to a lack of education surrounding the time and resources that actually need to be pumped in to make it succeed. 

All of this means you have to modify the way in which you measure your team and business’ success. 

When deciding upon quarterly KPIs, these ramp times must be factored in accordingly. Don’t just make targets solely revenue-focused, it isn’t an accurate reflection of the work that might be going on behind the scenes and it’ll just appear that you’re failing, when in reality, things aren’t as black and white as that. 

Naturally, stakeholder alignment will come into play throughout this target-setting process, and ensuring the relevant figures are informed and supporting your approach is absolutely crucial. Getting everyone on the same page and forging this understanding early will save a lot of headaches further down the line when it comes to feeding back the numbers. 

Devise and agree on a series of ambitious, but realistic milestones throughout the year, again, ones that aren’t just focused on revenue. Month one could be useful learnings, month three for pipelines, six months for opportunities that look like they could close and then solid revenue targets at 12 months. Of course, these timelines will differ on a business-by-business basis and will fluctuate depending on the length of your own average sales cycles. 

With all that being said, the great thing about outbound sales in comparison to other channels, is once you do hit a point where you ramp to 100%, you can take those vital learnings to shape your future operations and the scope for growth becomes colossal.

Things will begin to snowball and it becomes extremely scalable. Once you evaluate and understand the metrics behind the success, you can begin to layer in more SDRs, or you introduce better technology that allows those SDRs to flourish. 

It’s a massive contrast to inbound sales, where once you’ve maximised your budget and reached everyone in your network – you hit a ceiling. With outbound, when you approach it in the right way, with the right mindset and with that tolerance for failure, that ceiling doesn’t exist. 

For more information on truly understanding how to predict ramp time and adjusting your quarterly measurements accordingly, tune into our Founder & CEO, Owen Richards appearance on The SaaS Sales Performance Podcast. 

Alternatively, we’d be happy to chat through any queries you have in evaluating your outbound sales approach, get in touch now.  

ON AIR: With Owen Episode 34 Featuring Kristofer Bunker – Founder & CEO at Hapi Health

Introducing our 34th episode of ON AIR: With Owen – our latest interview video series with honest conversation about scaling revenue, hosted by our Founder & CEO, Owen Richards.

Our 34th guest is Kristofer Bunker, Founder & CEO at Hapi Health. Owen and Kris discuss the challenges you have when growing out an outbound sales team aligned with growing revenue


  • The strategies that helped Hapi Health grow from 0 – 200 clients
  • The challenge Kris and Hapi Health faced and how they overcame them
  • Growing backwards – How to align growing sales and resource
  • How Kris created trust around the brand
  • How trust plays and key role in internal and external growth
  • Kris looks at the big challenges coming up in the next 12 months for Hapi Health

LIVE Roundtable: How To Structure A Killer B2B Cold Call

We’re hosting our seventh live roundtable as part of our NEW annual content series, around setting up an outbound sales function.

Get ideas, inspiration and advice from our panel of experts, who will share and discuss their own experiences and open the floor to questions from the audience.

In April we announced that we will be going live every month for the next 12 months, chatting about all topics relating to outbound sales and the stages of building a team.

We’ll be answering your questions around (but not limited to) how to:
1. Introduction – Your first impression and the way you start the call is critical
2. Pitch – Telling your prospect why you’re calling and what you have to offer
3. Transition to questioning/discovery – Often a missed part of the cold call
4. Discovery/questions – The part where you uncover whether there is a good fit between your offering and your prospect’s situation
5. Objection handling – How you respond to questions and objections will define your success, so how do you overcome these?
6. Close/wrap up – If you don’t ask, you don’t get. So how do you close for the meeting?

Owen Richards – Founder & CEO at Air Marketing

Marco Alfano-Rogers – Sales Director at Air Marketing
Jonathan Finch – Director of Group Sales at Sales Geek
Alex Shrimpton – Enterprise Sales Manager at Infinity

Who is it for?
Sales Professionals (BDEs, BDRs, SDRs, Sales Leaders/Managers)
Revenue Leaders