Share this article

Learn from the brightest minds how to predictably and efficiently grow revenue.

Related Content

Lessons in Scaling Cybersecurity Sales with Dean Hickman-Smith

This week on the Revenue Insights Podcast, Guy Rubin, CEO of Ebsta, speaks with Dean Hickman-Smith, Chief Revenue Officer at HackerOne on Scaling Cybersecurity Sales. In this episode, Guy and Dean explore the evolution of sales leadership, the power of community in B2B sales, and how AI is transforming sales enablement and performance. Dean Hickman-Smith…

Building High-Converting Teams with Sean Murray of LeadIQ

This week on the Revenue Insights Podcast, Graham Smith speaks with Sean Murray, Senior Director of Sales and Sales Development at LeadIQ. In this episode, Sean shares his journey to tech sales, discusses his approach to building high-performing SDR teams, and explains why quality outreach trumps quantity in today’s sales landscape Sean Murray is Senior…

Transforming Productivity Metrics with Mike Perrone, Chief Operations Officer at Prodoscore

This week on the Revenue Insights Podcast, Guy Rubin, founder and CEO of Ebsta, speaks with Mike Perrone, Chief Operations Officer at Prodoscore.  In this episode, Guy and Mike discuss data-driven productivity scores, bridging employee flexibility with executive accountability, and how to empower sales teams through actionable insights and tailored coaching.  Mike Perrone is Chief…

 

Revenue Management Forecasting: Cailin Radcliffe of Loopio

Cailin Radcliffe jumped onto Sales Operations Demystified to share her knowledge and experience in Sales Operations and Revenue Management Forecasting. Check out all the other episodes of Sales Operations Demystified here.

You can learn more about:

Tools Mentioned:

Key Takeaways

Cailin’s first move when joining Loopio

When Cailin joined Loopio, one of the first things she did along with the VP of Marketing was to segregate the sales reps between SMB/mid-market/enterprise and between selected industries to focus their time.

This makes total sense… if there are certain industries that your product serves better than others, it makes sense to focus sales resources into these places to increase conversion rates.

Reducing “time to first deal”

Loopio recently hired a dedicated resource that reports into the sales director and is purely focussed on sales enablement. This person doesn’t report into Cailin though Cailin tasked this person with significantly reducing “time to first deal”.

By focussing in on ensuring that reps had enough pipeline to generate their first deal and ensuring they knew who they were selling too, the three most recent reps managed to close a deal within their first month whereas previously it would take up to three months.

What sales forecasting really tells you…

Cailin mentioned a quote that used to be repeated within Berkshire Hathaway: “Forecasting tells you very little about your business and a lot about the people forecasting.”

This is very true, and we have experienced this here at Ebsta also, some reps will consistently overstate their forecast and some will understate… you must understand the biases of your reps in order to forecast accurately.

Cailin’s favorite sales metric…

Cailin chooses two different sales metrics, the first was simply ARR. As obviously the best metric to explain how well your sales team is doing is the amount of revenue that the business is generating.

She also then went on to share a valuable insight when measuring the amount of pipeline Vs the number of opportunities in the pipeline. Cailin believes that amount of opportunities can be a more insightful metric as it isn’t skewed by abnormally large deals.

Cailin’s biggest influence…

Everyone.

Cailin says that she has learned from everyone on her journey from sales leaders to SDR’s and she urges people to learn from whoever they can (including from books!) during their career in sales operation.

Subscribe To Sales Ops Demystified:

Quote: