Course

The Billion-Dollar CFO Interview

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over 2,000+
Learners
Get inside the CFO decision process so you can speak the language of budget, risk, ROI, and executive approval when deals reach the finance desk.
Chris Orlob
Founder and CEO of Caliber (formerly pclub.io)
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Join learners mastering sales

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Brian McCarthy
Senior Vice President of Global Sales, Gloat
I've been through a lot of discovery trainings in my career, and this is easily at the top. The best part is how immediately actionable it is. My reps walked away with exact questions, tactics, and techniques they used to improve their next sales calls.
Smiling young man with slicked-back brown hair and green button-up shirt on a white background.
Alex Moffitt
Global Technical Sales Manager, Fusion 360 at Autodesk
We trained our teams on Discovery Masterclass, and we're already seeing an increase in opp conversion rates. Several reps said this was the most actionable sales training they've ever done.
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Jasi Johnson
Account Director at LinkedIn
Finished my quarter at 152%. Just wanted to send you a thank you note for the training and content. I finished my quarter at 152% and my half at 104% largely due to your teachings and learning from your experiences.
Smiling man with short dark hair wearing a black shirt against a black background.
Griffin Casey
Sales Manager at Drift
Best disco course - I'm seeing a ton of progress on my team - especially the Cause Analysis and Negative Implications - the problems we are talking about with prospects went from leads/pipeline to CAC, Attrition, etc so it's been huge getting higher in the org.
Portrait of a smiling middle-aged man with short brown hair and blue eyes against a beige background.
Brian McCarthy
Senior Vice President of Global Sales, Gloat
I've been through a lot of discovery trainings in my career, and this is easily at the top. The best part is how immediately actionable it is. My reps walked away with exact questions, tactics, and techniques they used to improve their next sales calls.
Smiling young man with slicked-back brown hair and green button-up shirt on a white background.
Alex Moffitt
Global Technical Sales Manager, Fusion 360 at Autodesk
We trained our teams on Discovery Masterclass, and we're already seeing an increase in opp conversion rates. Several reps said this was the most actionable sales training they've ever done.
Smiling woman with brown hair in a ponytail wearing gold hoop earrings and a sleeveless beige top standing in front of a green abstract background.
Jasi Johnson
Account Director at LinkedIn
Finished my quarter at 152%. Just wanted to send you a thank you note for the training and content. I finished my quarter at 152% and my half at 104% largely due to your teachings and learning from your experiences.
Smiling man with short dark hair wearing a black shirt against a black background.
Griffin Casey
Sales Manager at Drift
Best disco course - I'm seeing a ton of progress on my team - especially the Cause Analysis and Negative Implications - the problems we are talking about with prospects went from leads/pipeline to CAC, Attrition, etc so it's been huge getting higher in the org.
Portrait of a smiling middle-aged man with short brown hair and blue eyes against a beige background.
Brian McCarthy
Senior Vice President of Global Sales, Gloat
I've been through a lot of discovery trainings in my career, and this is easily at the top. The best part is how immediately actionable it is. My reps walked away with exact questions, tactics, and techniques they used to improve their next sales calls.
Smiling young man with slicked-back brown hair and green button-up shirt on a white background.
Alex Moffitt
Global Technical Sales Manager, Fusion 360 at Autodesk
We trained our teams on Discovery Masterclass, and we're already seeing an increase in opp conversion rates. Several reps said this was the most actionable sales training they've ever done.
Smiling woman with brown hair in a ponytail wearing gold hoop earrings and a sleeveless beige top standing in front of a green abstract background.
Jasi Johnson
Account Director at LinkedIn
Finished my quarter at 152%. Just wanted to send you a thank you note for the training and content. I finished my quarter at 152% and my half at 104% largely due to your teachings and learning from your experiences.
Smiling man with short dark hair wearing a black shirt against a black background.
Griffin Casey
Sales Manager at Drift
Best disco course - I'm seeing a ton of progress on my team - especially the Cause Analysis and Negative Implications - the problems we are talking about with prospects went from leads/pipeline to CAC, Attrition, etc so it's been huge getting higher in the org.

Stop guessing what CFOs care about and start building deals that can survive budget scrutiny

CFO approval is where vague value stories go to die. This course gives AEs direct perspective from three CFOs of billion-dollar businesses so they can understand what finance leaders fund, what they question, and what kind of business case earns serious consideration.

Before this course:

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You are unsure what CFOs actually look for when approving spend
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You struggle to translate product value into financial impact
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You rely on your champion without knowing how to prepare them for finance conversations
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Your business cases feel too seller-centered or too light on executive logic
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Your deals lose steam when budget approval becomes the next hurdle
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After this course:

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You understand the mindset CFOs bring to vendor decisions
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You know what finance leaders are willing to fund in tighter markets
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You equip your champion to sell the business case internally
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You connect your solution to risk, urgency, and measurable impact
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 You show up with more executive credibility when budget scrutiny increases
MEET YOUR MENTOR

Chris Orlob

Chris Orlob is the Founder and CEO of Caliber (formerly pclub.io), a revenue skill transformation platform built for modern revenue teams. Before founding Caliber, Chris helped Gong grow from $200K to $200M in revenue and reach a $7.2 billion valuation.

‍Across his career, Chris has studied the difference between sellers who explain value and sellers who make value financially undeniable. His work focuses on building the revenue skills required to navigate complex deals, win executive trust, and move opportunities through higher-stakes approval paths.

‍Inside The Billion-Dollar CFO Interview, Chris sits down with Jim Kelliher, CFO of Drift, Michael DiFilipo, CFO of Invoca, and Tim Riitters, CFO of Gong. Together, they reveal how CFOs think about spend, what makes a deal fundable, and how sellers can build business cases that stand up in the boardroom.

Course Overview

1
How to Sell to CFOs, According to Three Billion-Dollar CFOs
Agenda and Meet the Three CFOs
The Mindset of a CFO
What are CFOs Willing to Spend Money On
How to Empower Your Champion to Sell to Their CFO
Building a CFO-Worthy Business Case
Advice to Salespeople From Seasoned CFOs
CFO Interview Knowledge Check
Course info
Level
Expert
Topics
AEs
Run Time
59m 6s
Course Resources
The Billion-Dollar CFO Interview
Start Course
Start Course

Trusted by top performers at…

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Everything You Get to Become An Elite AE

Close More Deals, Grow Your Income, and Accelerate Your Career With the World’s #1 AE Performance Platform.

Quarterly Plan

What’s included

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Every Course & Transformation Path
Master every AE skill from discovery to negotiation.
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Certifications That Pay
Get credentials that increase earning power and promotion speed.
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New Courses, Every Month
Stay ahead of the market with fresh lessons, mini-paths, and frameworks released monthly from the world’s top revenue experts.
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AI-Powered Skill Practice (Full Library)
Turn learning into performance with AI deal simulations that let you rehearse real conversations, objections, and negotiations.
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Private Skill Stacker Community
Network with ambitious AEs who share strategies, wins, and playbooks — your new inner circle for accountability and opportunity.
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Live Group Coaching
Join bi-weekly live sessions with elite mentors and top AEs — get direct feedback, guidance, and accountability on your pipeline.
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Live Course Author Bonus Training Sessions
Learn directly from CROs, founders, and sales legends behind today’s fastest-growing companies.
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Annual Plan Exclusive Discount
Save 20% off when you join the annual plan.
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30-Day 100% Money-Back Guarantee
Not included in the monthly plan, though you are welcome to cancel any time.

Annual Plan

MOST POPULAR

What’s included

White check mark inside a black circle with a glowing green outline.
Every Course & Transformation Path
Master every AE skill from discovery to negotiation.
White check mark inside a black circle with a glowing green outline.
Certifications That Pay
Get credentials that increase earning power and promotion speed.
White check mark inside a black circle with a glowing green outline.
New Courses, Every Month
Stay ahead of the market with fresh lessons, mini-paths, and frameworks released monthly from the world’s top revenue experts.
White check mark inside a black circle with a glowing green outline.
AI-Powered Skill Practice (Full Library)
Turn learning into performance with AI deal simulations that let you rehearse real conversations, objections, and negotiations.
White check mark inside a black circle with a glowing green outline.
Private Skill Stacker Community
Network with ambitious AEs who share strategies, wins, and playbooks — your new inner circle for accountability and opportunity.
White check mark inside a black circle with a glowing green outline.
Live Group Coaching
Join bi-weekly live sessions with elite mentors and top AEs — get direct feedback, guidance, and accountability on your pipeline.
White check mark inside a black circle with a glowing green outline.
Live Course Author Bonus Training Sessions
Learn directly from CROs, founders, and sales legends behind today’s fastest-growing companies.
White check mark inside a black circle with a glowing green outline.
Annual Plan Exclusive Discount
Save 20% off when you join the annual plan.
White check mark inside a black circle with a glowing green outline.
30-Day 100% Money-Back Guarantee
Not included in the monthly plan, though you are welcome to cancel any time.
If you hired a top sales coach, invested in elite courses, and bought one-on-one mentorship, you’d spend over $10,000. Inside pclub.io, you get it all — for less than the cost of one dinner out per week.
REAL WORLD VALUE
$1,499 /qtr
YOUR INVESTMENT:
$299 /qtr
Sign Up For Quarterly
REAL WORLD VALUE
$10,000 /year
YOUR INVESTMENT:
$995 /year
Sign Up For Annual

Annual Plan

MOST POPULAR

What’s included

White check mark inside a black circle with a glowing green outline.
Every Course & Transformation Path
Master every AE skill from discovery to negotiation.
White check mark inside a black circle with a glowing green outline.
Certifications That Pay
Get credentials that increase earning power and promotion speed.
White check mark inside a black circle with a glowing green outline.
New Courses, Every Month
Stay ahead of the market with fresh lessons, mini-paths, and frameworks released monthly from the world’s top revenue experts.
White check mark inside a black circle with a glowing green outline.
AI-Powered Skill Practice (Full Library)
Turn learning into performance with AI deal simulations that let you rehearse real conversations, objections, and negotiations.
White check mark inside a black circle with a glowing green outline.
Private Skill Stacker Community
Network with ambitious AEs who share strategies, wins, and playbooks — your new inner circle for accountability and opportunity.
White check mark inside a black circle with a glowing green outline.
Live Group Coaching
Join bi-weekly live sessions with elite mentors and top AEs — get direct feedback, guidance, and accountability on your pipeline.
White check mark inside a black circle with a glowing green outline.
Live Course Author Bonus Training Sessions
Learn directly from CROs, founders, and sales legends behind today’s fastest-growing companies.
White check mark inside a black circle with a glowing green outline.
Annual Plan Exclusive Discount
Save 20% off when you join the annual plan.
White check mark inside a black circle with a glowing green outline.
30-Day 100% Money-Back Guarantee
Not included in the monthly plan, though you are welcome to cancel any time.
If you hired a top sales coach, invested in elite courses, and bought one-on-one mentorship, you’d spend over $10,000. Inside pclub.io, you get it all — for less than the cost of one dinner out per week.
REAL WORLD VALUE
$10,000 /year
YOUR INVESTMENT:
$995 /year
Sign Up For Annual

FAQ

Who is pclub built for, and what makes it different from other sales training?
pclub is built for every revenue role, from SDR to AE to CRO, and for the teams that lead them. If your performance depends on revenue skills, you belong here.What sets pclub apart is the system behind it. Most sales training is a one-time event taught by outdated trainers with no real-world credibility. pclub is a continuous Revenue Skill Transformation System, taught exclusively by the top 1% of revenue experts in the world, reinforced through AI-powered skill practice, and designed to compound over time. You are not just getting access to content. You are getting a flywheel that builds measurable skill capacity and drives real revenue outcomes.
Do I get instant access to all courses?
Yes. The moment you join, everything is unlocked. Start with whichever course or Transformation Path fits your most pressing goal and begin building skills you can apply right away. Every path is designed to move you forward fast.
How long will it take to apply what I learn?
Quickly. Every course is built for rapid, practical application, with templates, examples, and exercises designed around real-world scenarios. Most learners are putting new skills to work within their first week.
Will this work regardless of where I'm starting?
Yes. Every course and Transformation Path is built with a step-by-step structure that meets you where you are, whether you're closing your first deals or sharpening skills at the top of your game. The system is designed to compound, so every skill you build accelerates the next.
Are lessons live or recorded?
They are recorded. But pclub is not a video library you watch and forget. Each course is structured as a skill system, with instruction, homework, and AI-powered practice built in so you are actively building something repeatable, not just consuming content. Learn at your own pace, revisit modules anytime, and reinforce what you learn until the skill is yours.
Is access subscription-based?
Yes. Your subscription gives you full access to all courses and Transformation Paths, AI-powered skill practice, certifications, and the private Skill Stacker Community. Annual members also get live group coaching, live author bonus training sessions, and a 30-day money-back guarantee. Cancel anytime with no hidden terms or fine print.

Build CFO-ready deals that are easier to fund.

Use direct insight from billion-dollar CFOs to sharpen your business case, support your champion, and make your value easier for finance leaders to approve.

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