Private Sales Coaching

Fixing the gap between knowing and doing.

1:1 private coaching, group workshops, and community sessions — for sales reps and leaders who want help turning what they know into what they consistently do.

See how it works
36k+LinkedIn followers
2#1 bestselling books
15+Years in B2B sales
Rich Smith
Two-time #1 bestselling author & 15+ years in B2B sales

Built in the trenches. Refined through coaching.

I'm Rich Smith — a sales practitioner, leader, and coach with over 15 years in B2B sales. I've carried a bag, built and scaled regional teams for a global Sales Enablement SaaS company, founded and exited a B2B SaaS business (Refract), and now lead growth at MySalesCoach.

Most salespeople think they need better skills. Usually it’s something else — a mindset, a belief, or an execution pattern that no amount of training will ever touch. That’s the gap I work in.

I work privately with founders, sales leaders, and individual contributors who are serious about change — not a programme they’ll forget in a week, but real, sustained improvement in how they think, sell, and lead.

  • Sales leader — built & scaled a regional team for a global Sales Enablement SaaS company
  • Founder — built & exited Refract, a B2B SaaS company
  • Head of Growth — MySalesCoach, the Sales Coaching Operating System™
  • Author — two #1 bestselling books on sales
  • 36,000+ followers on LinkedIn
My philosophy

Most salespeople think they have a skills problem. They don’t. The real blocker is almost always a mindset, a belief, or an execution pattern — something no training programme will ever fix.

Skills can be taught in a day. Changing how someone thinks, what they believe, and how they actually behave under pressure? That takes coaching. Real coaching. Done consistently, over time, grounded in what’s actually happening — not what people think is happening.

That’s what I do. And it’s why I built everything around fixing the gap between knowing and doing.

Three ways to work together

Every engagement starts with a conversation. No programmes. No templates. Just the work that actually moves the needle for you.

01

1:1 Private Coaching

The highest-impact way to work together. Ongoing private coaching tailored entirely to you — whether you're a rep, manager, or leader. Weekly sessions, deal support, and real accountability between calls.

Most popular Learn more →
02

Group Workshops

Focused, bespoke sessions built around your team’s specific challenges. Not off-the-shelf training — designed around your context, your gaps, and the behaviours that are costing you deals.

For sales teams Learn more →
03

Tactical Programmes

Curriculum-based programmes built for tactical mastery. A structured series of modules designed to develop specific skills, knowledge, and behaviours over a number of weeks — with frameworks, tools, and live practice built into every session.

For reps & AEs Learn more →

From the blog

Real coaching dilemmas. Honest thinking. Published on LinkedIn — no fluff, no playbook recycling.

Episode 01

The Deal Is Already Done Before You Show Up

Why the most important part of winning a deal happens before the first meeting — and what great sales coaching...

Read on LinkedIn
Episode 02

You Can't Coach Commitment

Coaching can sharpen skills and shift beliefs — but it can't manufacture the will to do the work. What to do w...

Read on LinkedIn
Episode 03

You Can't Script Away Cold Call Reluctance

A better talk track doesn't fix call reluctance. The root is always a belief problem — and that's where the co...

Read on LinkedIn

What people say

"From our first meeting he gave me very actionable advice and feedback I could put to use immediately. In each of our meetings he was fully engaged and ensured I was getting the most of my time with him while also challenging me to explore my own process and creative ideas."

Riley Higgins

Riley Higgins

BDR

ZOOM

"I never left a session just knowing what I needed to focus on — I always left knowing HOW to focus on a certain area; what exactly I needed to do. I hit my goals and ended up the highest performer in my segment."

Lucy Limberis

Lucy Limberis

Account Executive

HUBSPOT

"Coaching with Rich is probably the best career decision I’ve made. His methods are never pushy — he focuses on creating real value. That perspective has completely changed the way I think about sales."

Sophie Potton

Sophie Potton

Account Executive

TRUSTPILOT

"Rich offers a vital sounding board backed by years of in-the-trenches sales experience. While Rich consistently challenged my thinking, he did so in a non-judgmental way that built trust and led to a more honest reckoning of the problems at hand."

Russell Isaacson

Russell Isaacson

MM Sales Manager

ZIP.CO

"The best coaches don’t give you answers. They ask the right questions. Rich does that better than anyone I’ve worked with. When I moved into sales management at HubSpot, I had the experience of a top rep and none of the skills of a leader. Rich helped me close that gap."

Kieran Krohn

Kieran Krohn

Head of Growth

SCALESTATION

"Rich has been an incredible mentor to me. He is hands-on, always available and someone who truly leads by example. I’ve had the privilege of working with him through two major career milestones — from stepping into leadership to growing into a director role."

Karina Clifford

Karina Clifford

Sales Director, ANZ

HUBSPOT

"It’s rare to find someone who can impact both leadership effectiveness and frontline execution — Rich does both exceptionally well. He helped me operate at a higher level as a leader and became a trusted sounding board on high-stakes decisions."

Jordan Smith

Jordan Smith

Sales Director

HUBSPOT

"Working with Rich far surpassed my expectations. He helped me shift my focus toward strategic coaching and aligning with my team’s core purpose. He’s deeply empathetic to the challenges of the role but isn’t afraid to challenge your beliefs when needed. My team’s pipe cover jumped from 2x to over 3x, and we’re now one of the top-performing teams in ANZ for 2026."

Ben Revitt

Ben Revitt

Sales Manager

HUBSPOT

The writing

Two #1 bestselling books written for salespeople serious about their craft — not looking for hacks or quick wins.

Problem Prospecting?! book cover
#1 Bestseller

Problem Prospecting?!

Most salespeople were never taught how to prospect. They were just thrown in at the deep end and left to figure it out. This is the actionable pipeline generation playbook that fixes that — packed with practical frameworks, scripts, and how-to guides written by three sales leaders who still prospect every single day.

Get the book →
Deconstructing Discovery book cover
#1 Bestseller

Deconstructing Discovery

The quality of your discovery calls makes or breaks your pipeline — yet most reps stumble through them. Built from thousands of hours of frontline coaching and real call transcripts, this is the tactical playbook for running high-impact conversations that actually convert. Less guesswork. More clarity. Better outcomes.

Get the book →

Ready to close the gap?

Start with a 30-minute conversation. No pitch. No pressure. Just an honest chat about where you are and what’s possible.

Let's talk

Limited spots available for 1:1 engagements.

Ongoing series

Sales Coaching Conundrums

Real dilemmas from the coaching room. Each episode explores a specific situation where the right coaching move isn't obvious — and works through what good actually looks like.

Published on LinkedIn — follow the series

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The blog is free. Private coaching is where the real work happens. If you're ready to talk, let's do it.

Let's talk
Rich Smith

The highest‑impact way to close the gap

Private coaching tailored entirely to you. Not a programme. Not a course. A genuine partnership built around your specific gaps, your deals, and your growth — with real accountability at every step.

How it works

Every engagement is structured, intentional, and built around evidence — not guesswork.

01

Diagnostic assessment

We start by evaluating your competencies and identifying your real gaps — not the ones you think you have. This builds a clear profile of where coaching will make the biggest impact, so we spend our time on what actually matters.

02

A shareable coaching plan

Before we begin, I build a structured coaching plan covering everything we'll work on across the lifecycle of our engagement. It's yours to keep, share with your manager if relevant, and refer back to — so there's always a clear north star.

03

Coaching on reality — not opinion

I'll ask you to share recordings of your real sales calls — your own, or your team's. This means coaching is grounded in what's actually happening, not what we think is happening. It's the most honest and highest-impact form of coaching there is.

04

Recorded sessions, logged against your plan

Every coaching session is recorded and logged against your coaching plan, so you can revisit key moments, track your own development over time, and never lose the thread of where we are and where we're going.

05

Action plans & accountability

After every session, we log clear action plans so progress is trackable and visible. I take accountability seriously — which means I'll follow up, call it out if it hasn't happened, and help you understand why.

06

Tools & frameworks

Throughout our engagement, you'll get access to a range of tools and frameworks I've developed and refined over 15+ years — practical resources that reinforce what we're working on and give you something concrete to apply immediately.

Is this for you?

Private coaching works best for people who are serious about change — not just looking for a quick fix.

Sales reps & AEs

You're performing but you know there's another level. You want honest feedback on your calls, your deals, and your thinking — and someone to hold you to it.

Sales managers

You were a great rep. Leading is different. You want to build a coaching culture, not just manage a pipeline — and you need support making that transition properly.

Sales leaders & VPs

You're operating at a high level but facing complex challenges — team performance, organisational dynamics, high-stakes decisions. You need a sounding board who's been there.

“It’s rare to find someone who can impact both leadership effectiveness and frontline execution.”
Jordan Smith — Sales Director, HubSpot

Let's talk

A free 30-minute conversation to understand where you are, what's getting in the way, and whether we're the right fit.

Let's talk

Limited spots available.

Rich Smith

Built around your team. Not off the shelf.

Every workshop is designed around your team’s specific challenges, your context, and the behaviours that are costing you deals. Interactive, practical, and built to translate into real change — not just a day out of the office.

Workshop programmes

Four core programmes — each battle-tested, practically grounded, and built from real experience in the field.

01

Prospecting & Pipeline Building

The content that directly influenced Problem Prospecting?! — and the same methodology I used to build outbound sales teams across three separate companies. This isn’t theory. It’s a proven, practical approach to generating consistent pipeline from scratch.

Cold callingEmail outreachSocial sellingPipeline generation
02

Discovery

The quality of your team’s discovery calls makes or breaks your pipeline. Built from thousands of hours of coaching and reviewing real recorded calls, this workshop closes the gap between knowing what great discovery looks like — and actually doing it in the room.

Uncovering real painLayered questioningBuilding credibilityDriving momentum
03

MEDDPICC & Complex Deal Cycles

For teams working larger, more complex opportunities. This workshop goes beyond the framework itself — it focuses on how to apply MEDDPICC in live deals, navigate multi-threaded buying committees, and run deals with discipline and clarity from first meeting to close.

MEDDPICCChampion buildingMulti-threadingDeal qualification
04

Custom Programmes

Not every team needs an off-the-shelf programme. If you have a specific challenge — a new team ramping up, a capability gap, a product pivot — I’ll build something around your brief. We start with a conversation about where you are and where you need to get to.

Built to your briefAny stage or teamFully bespoke

How it's delivered

Flexible by design — built to fit your team, your schedule, and how you work best.

In person

Full-day or half-day sessions delivered on-site with your team. The highest-impact format — real energy, real conversation, real output.

Virtual

Fully interactive remote sessions for distributed teams. Same quality, same engagement — no travel required.

Hybrid

Mix of in-person and virtual sessions — ideal for teams spread across locations or for programmes running over multiple weeks.

From knowing to doing

Most training fails because it stops at the workshop. People leave energised, go back to their desks, and within a week they’re doing exactly what they were doing before.

Every workshop I run can be paired with 1:1 coaching as reinforcement — individual sessions to help each person apply what they’ve learned in their real deals, on their real calls, with their real customers.

That’s how you close the gap between knowing and doing.

Group workshop

Shared frameworks, skills, and thinking. Builds team-wide language and capability.

1:1 coaching reinforcement

Individual sessions to apply the learning in real deals. This is where behaviour change actually happens.

Real, lasting change

“We brought Rich in for a team session and it reset how our whole team thinks about discovery.”
Mark P. — VP Sales, B2B Services

Ready to level up your team?

Tell me about your team, your challenges, and what you’re trying to achieve. We’ll work out the right programme together.

Let's talk

All workshops are tailored — no two are the same.

Curriculum-based.
Skill-focused.
Built to stick.

These aren't one-off workshops. Tactical Programmes are structured, module-based courses designed to build specific skills over a series of sessions — with frameworks, live practice, and tools built in throughout. The kind of development that actually changes what happens on calls.

Programme 01 — Account Executives

From Discovery
to Close

A complete curriculum for AEs who want to win more deals, at higher value, with less discounting. Built around the skills that separate elite salespeople from everyone else.

5 Modules Live + Recorded For AEs
Session 1

Diagnostic & Goal Setting

Framework: The Sales Diagnostic ("a Sales Blood Test")
  • Complete a behavioural sales diagnostic and review the results live — not to judge, but to find blind spots and superpowers
  • Set tangible, personal goals that everything else in the programme connects back to
Behavioural Diagnostic Personal Goal Canvas Baseline Review
Session 2

Discovery Beyond the Surface

Framework: The Inverted Pyramid of Pain
  • Move discovery from process pain ("we're on spreadsheets") down to real business and personal impact
  • Handle the prospect who just wants to see the platform, without abandoning discovery altogether
  • Practise the exact questions that get to the emotional and financial cost of staying with the status quo
Pain Ladder Questions Objection-to-Discovery Redirect Live Discovery Practice
Session 3

Bringing the Right People In Early

Framework: Multithreading Before, During & After the Call
  • Build a stakeholder map before the first call, not after a deal has already gone quiet
  • Learn language for bringing in additional people that feels natural, not transactional or forced
  • Practise surfacing a prospect's decision-making structure early, while it's still easy to ask
Stakeholder Map Multithreading Language Bank Decision-Maker Questions
Session 4

Value Selling & ROI

Framework: Realisation Over Convincing
  • Reframe from convincing a prospect to helping them realise it themselves — the same shift that makes discovery work
  • Build a repeatable way to tie your value to a prospect's specific cost of inaction
  • Apply the framework live against a deal currently sitting in your pipeline
Cost-of-Inaction Calculator Value Narrative Script Live Pipeline Review
Session 5

Demo — Show the Problem, Not the Product

Framework: WIHYS/IWSYT — What I Heard You Say / I Will Show You Today
  • Fix the most common demo mistakes: the tour bus experience, taking too long to reach the money shot, presenting instead of conversing
  • Tie every feature you show directly back to something the prospect already told you, so nothing feels generic
  • Build a more exciting, memorable demo experience that keeps the prospect leaning in, not checking their phone
WIHYS/IWSYT Framing Conversational Demo Questions Closing Questions
Session 6

Bigger Deals, Higher ASP

Framework: The ASP Expansion Framework
  • Diagnose the habits that quietly cap deal size — anchoring on price too early, under-scoping the need
  • Learn how to expand scope naturally within a deal, not as an awkward upsell bolted on at the end
  • Use what surfaced in the demo to widen the conversation to the full size of the opportunity
Deal Sizing Checklist Expansion Question Bank Scope Widening Practice
Session 7

Maintaining Momentum & Urgency

Framework: Behind-the-Scenes Selling + Consequence-Based Urgency
  • Move out of on-screen selling into the work that actually keeps a deal alive between meetings
  • Build genuine urgency tied to the prospect's own timeline, not artificial deadlines
  • Recognise where people-pleasing habits let deals quietly drift, and what to do instead
WIHYS Follow-Up Email Decision Map Consequence-Based Follow-Up
Session 8

Objection Handling

Framework: Acknowledge · Explore · Respond (LAER)
  • Learn one flexible framework for handling any objection, rather than a different script for each one
  • Reframe objections as buying signals rather than roadblocks to push through
  • Practise live against the specific objections you're hearing most right now
LAER Framework Objection Reframe Bank Live Objection Practice
Session 9

Negotiation

Framework: The Give-Get Model
  • Build the language to hold firm on price and terms without it feeling like conflict
  • Practise creating healthy friction — the kind that makes a prospect respect you more, not less
  • Work directly on saying no to a request without damaging the relationship, especially for natural people-pleasers
Negotiation Language Bank Give-Get Practice Walk-Away Price Exercise
Session 10

Re-Engaging Stalled Deals

Framework: Stall Diagnosis & Re-Engagement Plays
  • Diagnose why a specific deal actually went quiet, rather than guessing
  • Use re-engagement plays that reconnect a prospect to their own original business case — not a generic "just checking in"
  • Work through two or three real stalled deals from your pipeline live
Stall Reason Checklist Re-Engagement Email Bank Live Pipeline Triage
Session 11

Consolidation & Forward Plan

Framework: The Personal Sales Playbook
  • Pull discovery, multithreading, demos, momentum, objection handling, and negotiation into a single personal playbook
  • Set concrete targets and habits for the next quarter that keep the progress going after the programme ends
  • Leave with a clear plan for applying everything to the deals sitting in your pipeline right now
90-Day Action Plan Habit Tracker Personal Playbook Document
How it runs

Format

  • Weekly through the first month, then fortnightly
  • Delivered live over video — sessions recorded and shared
  • Direct access between sessions via WhatsApp or LinkedIn
  • Call recordings reviewed on request ahead of any session

What you'll walk away with

  • Personal behavioural diagnostic & goal canvas
  • Stakeholder map & multithreading language bank
  • LAER objection framework & give-get negotiation language
  • A personal sales playbook and 90-day action plan

Interested in this programme or want to discuss a bespoke version for your team?

Let's talk
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