Win the deals that
define your year.

A six-move strategy to choose the right opportunities, build them around business improvements that justify investment, and win commitment from executives accountable for the company’s financial results.

Watch3 MIN
The Big Bet Method by Dan Wiedmann — hardcover book
Field record
15 yearsin enterprise technology sales Salesforceenterprise sales veteran ServiceNowstrategic platform deals 200+new logos won Sandlercertified in professional selling CFIfinancial valuation certification
The big idea
The Strategy

The game has changed.
Here's how to win it.

The Activity Playbook Is Dead

Activity-based selling thrived when software demand was high. Today, outreach without a compelling value hypothesis struggles to create enough qualified opportunities to exceed quota.

SalesRevenue Opportunity Volume Where the bet starts Sales Activity Value Hypothesis Win Rate Qualification Rigor Deal Execution Average Deal Size Business Impact Value Capture

Exceeding Quota Requires the Right Portfolio

To exceed quota, we need to build a portfolio of qualified opportunities whose combined expected value can carry our number within the selling time available.

Expected value: A $1.10M, Deal B $1.00M, Deal C $1.00M, stacking to $3.1M against a $3.0M quota. Win rates 70%, 65%, 60%; hours 700, 650, 650; total 2,000. EV EV EV

Expected Value (EV) = deal value × probability of winning.

Three Challenges Stand in the Way

Poor opportunity selection consumes selling time without adding enough expected value. Reliance on existing demand limits qualified opportunity volume. Without executive ownership, win probability and deal size suffer.

Time
Selling hours
Creation
Opportunity volume
Altitude
Win rate
Net effectEV < Quota

Choose. Create. Win.

To overcome these challenges, we choose opportunities based on expected value relative to selling time, create reasons to invest tied to leadership’s financial objectives, and win executive commitment early.

CHOOSE CREATE WIN PORTFOLIO EV > QUOTA
ChooseRight opportunities
CreateCompelling investment
WinExecutive commitment

Execute the Strategy with the Big Bet Method

The Big Bet Method translates this strategy into six coordinated moves, guiding sellers from opportunity selection through executive engagement, evaluation, and investment approval.

ChooseCreateWin
BBet on the Right Opportunity
IInvestigate the Business
GGet in the Room
BBuild Buy-In
EEngineer the Evaluation
TTake the Deal Down
Dan Wiedmann
About

The Experience Behind the Method

I’ve spent 15 years selling enterprise technology, from startups to nearly a decade at Salesforce.

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