Deal Coaching

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Why Deal coaching?

I believe sales training doesn't work. At least, in isolation it doesn't.

Real learning is done on the job. That learning can be accelerated with the help of guidance from an experienced coach.

Rather than having content being pushed at your team, they'll get weekly conversations that extract some of what they already know, get expert advice on real deals and build new capabilities that let them accelerate their performance.

Deal Coaching

This is not generic sales training or coaching – it's 100% focused on offering both strategic and tactical counsel on deals that are active in your pipeline. I work with your team weekly to increase deal value, accelerate deal velocity and lift your win rate.


I work with teams in 3 month sprints. We set a consistent time and day and connect to discuss sales challenges, real deals and new skills reps or their managers are looking to build.

This is typically in small groups of 2-3 (see FAQ) but can be 1:1 should budgets allow.

I will also join your team Slack or MS Teams instance (if requested) and provide feedback or advice on client facing assets and communication.


  • Your team build new skills faster and solidify those they have
  • Your get an external voice bringing new ideas to your deals
  • Expect to increase win-rates and accelerate sales
  • Your team feel invested in and grow confidence


Pricing is fixed at A$5,500/quarter + GST (or $4250 USD for international clients).

This includes:

  • 10 sessions in total. One with leaders—typically 9 with the rep(s), and one review session with the team
  • A 1-page end of engagement report with recommended internal follow-on actions
  • Limited support, feedback and review of sales communication (emails, proposals, call recordings) with a 12 hour or next business day SLA.

Answering a few questions you might have

What kind of companies and teams do you work with?

I specialise in B2B technology sales. Particularly early-stage SaaS business still discovering a repeatable sales process. I do some work with Sales Development teams but mostly focus on full-cycle sales (Account Executives) Note: I don’t work with cybersecurity companies to avoid any conflicts of interest.

When do small group engagements work?

Coaching in this format can work with small groups where each rep is of similar experience level and working on deals that often resemble one-another. Shared experience, conversation and guidance on sales opportunities in this context can actually help with cross-pollinating skills and scaling the learning.

Do you offer in-person sessions?

In instances where your team is located in Sydney and is happy to work with early mornings, limited availability is possible for in-person coaching.

What times are available?

For Australian clients this is typically at beginning or end of a day – most teams prefer this as it does not take away from normal business hours dealing with prospects and customers. USA: Your afternoons work well with my early morning, so we work to that overlap.

Asia: Late afternoon/end of day in Asia can often work well. Depending on your buyer and audience I may or may not be the best solution for you–I am more than happy to discuss this with you first.

Europe: Frankly, Europe can be difficult and I may be able to refer you to someone in your timezone.

How do I book sessions?

At the beginning of the engagement we'll work to find a suitable repeating time that works for everyone and schedule this ahead of time.

What do you mean by review of sales communication?

Many times throughout the sales process reps would like input on collateral, proposals and emails with their prospects. I'll provide short, in-the-moment feedback.

Shouldn't we be able to do this internally?

Some companies can, others either don't have the resources or simply don't have the experience. I have the vantage point of having seen many, many sales processes and teams and you get to take advantage of that.

By the time we've worked together you should also have improved your own internal capability or have a blueprint for ongoing development for your team.

Will you sign an NDA?

Absolutely. I will work with you in any way to ensure your complete confidence and trust in confidentiality, including signing an NDA.

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