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The Dirty Side Of Sales

Forget the textbook BS—here’s how enterprise deals REALLY get closed.

Enterprise Sales Is Where the Real Money Lives

Here’s How to Get Your Share

Enterprise Sales vs. B2B vs. B2C: Where the Real Money Is

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Role Type
AVG Commission
Top Performers
Enterprise (B2E)
$260K+
$1M+
B2B
$150K-$300K
Up to $500K
B2C
$54K-$70K
Up To $150K

RepVue (repvue.com) - The gold standard for sales compensation data, especially for tech/enterprise roles
Payscale (payscale.com) - Compensation reports filtered by sales role and industry
Glassdoor Salaries (glassdoor.com/Salaries) - Crowdsourced salary data

Sales Type
Typical Deal Size
Sales Cycle Length
Enterprise (B2E)
$100K-$5M
6-18 months
Mid-Market B2B
$25K-$250K
3-9 months
SMB B2B
$5K-$50K
1-6 months
B2C
$100-$5K
0-30 days

Why Enterprise Deals Are Your Startup’s Fastest Path to Profitability

Forget chasing hundreds of small customers. Enterprise clients deliver 10-100X the revenue per deal while requiring only 2-3X the effort. 

  • Hit $1M ARR faster with just 5-10 key deals (vs. 200+ SMB contracts)

  • Build strategic partnerships that lock out competitors for years

  • Turn one signature into recurring revenue through multi-year enterprise contracts

Selling to enterprises isn’t about shiny brochures or scripted pitches

  • Navigating bureaucratic mazes where ‘no’ is the default answer

  • Finding the REAL decision-maker (hint: it’s never who you think)

  • Getting ghosted after months of work (and how to prevent it)

  • Competing when price isn’t your advantage

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The Dirty Truths of Enterprise Sales You Won’t Learn Anywhere Else

This isn’t your typical sales training. Here’s the unfiltered, behind-the-scenes playbook that enterprise sales veterans use to close six- and seven-figure deals – the stuff they don’t teach in business school or corporate training programs.

Content

Lecture 1: The B2E Goldmine
Why enterprise sales delivers 10X revenue with less effort than SMB sales, and how to spot whale clients before competitors do.
 
Lecture 2: Pipeline for Giants
The 5-stage enterprise deal flow most reps miss, and how to qualify leads without wasting months.
 
Lecture 3: Product-Market Fit at Scale
Reframing your product as a board-level solution through strategic customization.
 
Lecture 4: Trigger-Based Lead Hunting
Finding enterprise buyers through hidden signals rather than cold outreach.
 
Lecture 5: Ugly Presentations That Win
Why polished decks fail with executives, and the 3 slides that decide all enterprise deals.
 
Lecture 6: First Meeting Alchemy
Transforming initial conversations into urgent next steps using power silence and budget-revealing questions.
 
Lecture 7: Champion Cultivation
Identifying and weaponizing internal advocates who will sell for you behind closed doors.
 
Lecture 8: Bureaucracy Hacking
Shortcutting 18-month decision cycles by decoding real vs. stated procurement processes.
 
Lecture 9: POC Warfare
Designing pilot projects that become impossible to cancel or reject.
 
Lecture 10: Closing on Your Terms
Structuring deals for automatic renewals and using walkaway tactics that work on enterprises.

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