Skip to content
Scalewise
  • For Clients
    • Book Call
    • GTM solutions
    • GTM ScaleAudit
    • Permanent Hiring
    • Fractional Leadership
  • For Investors
  • For GTM Experts
  • About Us
  • Resources
  • Case Studies
Contact us
Login
Scalewise
Scalewise
Back
  • Podcast
  • Tom Glason
  • 17 Sep 2026

The Coaching Relationship That Changed Everything – Alex Olley on building Go-To-Market rigour at Reachdesk

Toggle Share Icons Menu

What happens when the investor everyone expects to say ‘yes’ tears your Go-To-Market plan apart in front of 15 people?

For Alex Olley, Co-Founder and CRO of Reachdesk, that moment at his Series B in 2021 became the inflexion point of his career as a Revenue Leader. 

 

In this episode, Alex tells us the full story from that shocking investor meeting to the coaching relationship that changed his career and Reachdesk forever. We also touch on how Alex is deploying AI today – from surfacing high-intent accounts to using outbound and business cases and why he believes efficiency without accuracy is a trap. 

 

It’s a conversation about the line between the art and the science of selling, and what it actually takes to go from good to great as a CRO. 

📚 Episode Chapters:

04:00 – The Series B wake-up call
13:00 – Lessons on Sales Rigour
23:30 – Art vs Science in Sales
25:00 – Applying AI without losing creativity
29:00 – The importance of unit economics for CROs

🎧 Continue listening…

Make sure you listen to Season 2 with Sam Jacobs on building for efficient growth

Want to listen to the full episode with Alex?

 Listen here: 

🎙️ Apple Podcasts 

🎙️ Spotify 

🎙️ Simplecast

 

Or watch below…

Enjoyed this episode or have a guest suggestion for us?

We’d love to hear any feedback you have for us and any suggestions or guest recommendations you may have. Simply get in touch with our production team at [email protected]

Patrick Coleman

Patrick Coleman

Co-founder & CEO, QStory

“ScaleWise has transformed our go-to-market approach enabling us to implement best in class Account Based Sales Marketing strategies that deliver high-quality pipeline consistency”

Matt Jones

Matt Jones

Head of Go-To-Market, EvaluAgent

“Having valuable expertise ‘on tap’ from ScaleWise has been pivotal in accelerating the growth of Evaluagent”

Placeholder image

Tatjana Hayward

Communications & Business Operations Lead Senseforce

“ScaleWise coaching had a big impact right from the start, helping us to execute a much more effective marketing strategy whilst implementing best practices throughout our sales & marketing funnel. ”

Related Articles

Read now
Making The Grade with Laura Moniz de Aragão
  • 29 Oct 2026
  • Podcast

Laura Moniz de Aragão on the 5 Human Skills AI Can't Replace

Laura Moniz de Aragão on why AI is making the human side of enterprise selling more valuable.
Read now
Read now
  • 22 Oct 2026
  • Podcast

Shabri Lakhani on separating real bets from AI hype in your 2027 planning

Tom Castley on the sales methodology he built around a simple idea: that prospects' questions reveal more truth than their answers.
Read now
Read now
Making the Grade with Shabri Lakhani
  • 15 Oct 2026
  • Podcast

Shabri Lakhani on separating real bets from AI hype in your 2027 planning

Shabri Lakhani on why she refused to bake unproven AI productivity gains into her FY27 plan and the case for investing in enablement.
Read now

Unsure what you need?

Book a 30-minute call with our Growth Advisor.

Book now

Scaling Solutions

  • GTM ScaleAudit
  • Permanent Hiring
  • Fractional Leadership
  • GTM ScaleAudit
  • Permanent Hiring
  • Fractional Leadership

GTM Experts

  • Why work with ScaleWise
  • Become a GTM Expert
  • Terms of Service
  • Why work with ScaleWise
  • Become a GTM Expert
  • Terms of Service

Knowledge

  • Resources
  • Case Studies
  • Pearls of Wisdom
  • Resources
  • Case Studies
  • Pearls of Wisdom

Company

  • About Us
  • Contact Us
  • For Investors
  • About Us
  • Contact Us
  • For Investors

Subscribe

We don’t spam! Join our newsletter to receive resources & insights to help you scale.

© 2026 ScaleWise. All right reserved.

  • Privacy Policy
  • Privacy Policy
Linkedin

Latest research:

How to scale from Series A to B

Read now
Our site uses cookies to distinguish you from other users of our site. This helps us to provide you with a good experience when you browse our site and also allows us to improve our site. A cookie is a small file of letters and numbers that we store on your browser or the hard drive of your computer. We only use (and store) non-essential cookies on your computer's browser or hard drive if you provide your consent. You can block cookies by activating the setting on your browser that allows you to refuse the setting of all or some cookies. However, if you use your browser settings to block all cookies (including essential cookies) you may not be able to access all or parts of our site.