Most $5–20M owners are their sales process: the relationships, the follow-up and the forecast all live in their head. Jason Cole ran business development for Schawk, LYFT Visual and Flipp. He explains how to get sales out of your head and into a process you can test.

Jason started in operations, as an on-site production manager at SGS, before leadership talked him into sales. Today he runs his own creative production shop, 3 Apples High. John Ling and Jason talk about:

• Why business is built on relationships, and why golf and lunches don't turn into sales

• Make the NDA your first small win, and watch who signs it

• Close the gap between sales and operations: your own team is your first customer

• From the production floor to sales: the bet that changed his career

• Run a process ten times before you judge it

• Work your pipeline math backwards: 20, 40, 60, 80, close

• What AI changes in sales, and why you should never go in cold

Three things to try this week:

1. Write down what success looks like and where you are today. The gap is your sales plan.

2. Break the path into five steps and run them ten times before you change them.

3. Make your first win small and concrete, like a signed NDA, and notice who signs it. That tells you who actually decides.

Disclosure: John and Jason worked together at LYFT Visual and then at Flipp. This episode isn't sponsored.

ABOUT OWNERS & EXPERTS

We scaled Flipp past $100M US by finding the best person in the market for each hard problem and learning from them. Owners & Experts brings that network to Canadian owners growing a $5–20M business: candid conversations, a new episode every week, from the team at CollectiveXP.

CHAPTERS

0:00 Intro

1:21 Business is built on relationships

3:12 How do you get a sales team to care?

4:41 Make the NDA your first small win

7:22 Whoever signs the NDA shows you who decides

8:40 Close the gap between sales and operations

13:14 Your own team is your first customer

15:22 From the production floor to sales

25:10 Sales is a numbers game. Process is how you win it

26:09 When your sales leader stops prospecting

29:43 Run a process ten times before you judge it

31:15 What great sales managers do differently

34:18 Work your pipeline math backwards

35:41 When relationship turns into pressure

40:03 What AI changes in sales

42:35 Never go in cold: three points per prospect

47:01 Your Monday move: define success, then five steps

50:03 What to do this week

LINKS

Watch on YouTube: youtu.be/xJtTX5Lixfo

Jason Cole on LinkedIn: linkedin.com/in/jasonvcole

3 Apples High: 3appleshigh.com

CollectiveXP: collectivexp.io

Demand is up, quality is slipping, and the reflex is to hire. John Rebello, former Director of Continuous Improvement at Flipp, explains why that takes about six months to pay off and still doesn't fix the process. He says to build a KPI tree first.

John learned continuous improvement on a GM assembly line and later built the continuous-improvement team on a Bombardier aircraft line, where, he says, moving inspections to where problems were caused cut defects by about 75%. Victor Wong and John talk about:

• Why adding headcount is a band-aid, and what to check before you open a job posting

• Bombardier: find where a problem is caused, not just where it's caught

• Why leaders stop at the top-line number, and how KPIs should link up and across teams

• When the top number lies: two regions that cancel each other out

• 30,000 support tickets, and the team only ever saw 3,000

• The dashboard nobody looks at, and how fast your business really moves

• How to build your first KPI tree in 10 minutes

Three things to try this week:

1. Before you hire to fix a quality problem, find where it's caught and where it's caused, then move the check upstream.

2. Break revenue into price × volume, then one level further for your business. That's your first KPI tree.

3. Put one scoreboard where every team can see it, and look at it on a set rhythm.

Disclosure: Victor and John worked together at Flipp. This episode isn't sponsored.

CHAPTERS

0:00 Cold open

0:24 Welcome to Owners & Experts

1:39 Why hiring won't fix your quality problem

3:55 From The Goal to the GM assembly line

7:56 Why fast growth leaves so much to fix

9:13 Bombardier: 1,000 snags per aircraft

16:40 Why leaders stop at the top-line number

20:50 When the top number lies: Arizona vs Ontario

24:27 Your first KPI tree will be wrong

25:26 30,000 tickets, and the team saw 3,000

28:03 The dashboard nobody looks at

31:52 How fast does your business really move?

33:16 Build your first KPI tree in 10 minutes

37:00 Find what changed, then share what you learn

39:28 Give your team a scoreboard

LINKS

Watch on YouTube: youtu.be/kOAKzkRejlc

John Rebello on LinkedIn: linkedin.com/in/johnrebello

CollectiveXP: collectivexp.io

Last episode, Justin Wood told $5–20M owners to just build a product. Chris Chae has spent 15 years building them, and he's watched owners hire engineers, hand them "what to build" a couple of hours a week, and stall.

Chris ran product inside a venture studio, ran Sportsbook Review after it was acquired, and led product at Neo Financial. Today he's a fractional chief product officer. In this episode of Owners & Experts he covers:

• Why every product person should own a number

• Rebuilding an acquired business for a new market: picking a new customer and turning the old community into evangelists

• Growing a new line without cannibalizing the core

• Why the customers you turn away tell you what to build next

• Whether every $5–20M business should build a product

• What product is for now that AI has made building cheap

• Why owners stall, and when to bring in product help

Three things to try this week:

1. Look at the customers you're turning away. They're telling you what to build next.

2. Build something small yourself, even in a tool like Lovable, to learn how product works.

3. If you hire engineers, don't give "what to build" two hours a week. That's where owners stall.

Disclosure: Chris and I worked together at Flipp, and he's been advising us at CollectiveXP this year. This episode isn't sponsored.

CHAPTERS

0:00 Cold open: just build it?

0:25 Welcome to Owners & Experts

0:54 Every product person should own a number

3:01 Sportsbook Review: rebuilding an acquired business for a new market

6:58 The first big call: pick a new customer

8:02 Turning the old community into evangelists

10:26 Grow without cannibalizing the core

12:39 Neo: adding product lines around the customer

15:20 Listen to the customers you turn away

19:45 Should every $5–20M business build a product?

22:37 AI made building cheap. So what's product for?

26:31 Never touched AI? Start by building

31:04 Where to start: get in the ring

34:55 Why owners stall, and when to bring in product help

39:43 The question owners should ask: what's possible?

42:26 What to do this week

LINKS

Watch on YouTube: https://youtu.be/1GZQmQ4Iza4

Episode 1, Justin Wood: https://www.collectivexp.io/cxplive/owners-and-experts/justin-wood?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep02

Chris on LinkedIn: https://www.linkedin.com/in/chrischae/

Owners & Experts is a weekly podcast for Canadian business owners growing a $5–20M company, hosted by John Ling and Victor Wong of CollectiveXP, part of the team that built Flipp.

CollectiveXP: https://www.collectivexp.io/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep02

AI just made your expertise cheaper. So what's left for a $5–20M business? Justin Wood, founder of Produktiv, says it's trust, and that owners should build a product around it.

Justin has spent 16 years building marketing engines in-house, at agencies and at startups. He says his own podcast, The Katalog, brought in about 20% of his agency's revenue in one year. We talk about:

• Why the $2–5M stage is a "valley of death", and the difference between a business owner and an entrepreneur

• How a podcast built his sales pipeline, and why it only works if you're curious rather than selling

• The Wealthsimple test: why a $5–20M firm needs a product, and why the product is the marketing

• How to tie every dollar of marketing spend to a dollar of revenue

• Why "boring" AI is good news for owners

Three things to try this week:

1. Write down the five questions clients ask you every week. That's your content, and maybe your first product.

2. Tag every link and QR code so you can tie a dollar spent to a dollar made.

3. Record one real conversation with a client or a peer, and put it out.

Disclosure: Justin and I worked together back in his KRFTWRK days, and we've traded notes on our businesses ever since. This episode isn't sponsored.

CHAPTERS

0:00 Cold open

0:36 Welcome to Owners & Experts

1:26 The playbook changed: from craftsperson to director

6:03 The $2–5M "valley of death": owner vs entrepreneur

9:45 AI can outthink you. It can't out-trust you

12:18 How a podcast built his pipeline

19:45 Two kinds of owners on AI

27:39 Why a $5–20M firm needs a product

29:49 The product is the marketing (the Wealthsimple test)

32:58 Tie every dollar spent to a dollar made

38:32 Turn the questions you answer every week into a product

41:57 Why "boring" AI is good news

47:30 The fundamentals haven't changed

50:30 Build the audience, then the product

53:17 What to do this week

LINKS

Watch on YouTube: https://youtu.be/c3fTQK1bs04

Produktiv: https://produktiv.agency/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01

Trakt: https://trakt.pro/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01

The Katalog (Justin's podcast): https://thekatalog.co/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01

Justin on LinkedIn: https://ca.linkedin.com/in/jwoodisgood

Owners & Experts is a weekly podcast for Canadian business owners growing a $5–20M company, hosted by John Ling and Victor Wong of CollectiveXP, part of the team that built Flipp.

CollectiveXP: https://collectivexp.ai/?utm_source=podcast&utm_medium=shownotes&utm_campaign=owners-experts-ep01