SaaS Sales Training Program: Gap Selling for Enterprise Product Sales
Low win rates? Long sales cycles? Low average deal sizes? Missing growth goals? You’re not alone.
Why Risk-Based Selling Works for Cybersecurity
Low win rates? Long sales cycles? Shrinking deal sizes? Missed growth targets?
These problems are typically the result of a weak discovery process, canned product demos, or simply failing to understand the buyer’s business. They can lead to skyhigh CAC, reduced profitability, inaccurate forecasting, and more.
Diagnose your SaaS sales organization’s problems with a Gap Selling expert today
People We Work With:
SaaS Sales is Different
Enterprise SaaS deals involve multiple stakeholders, competing priorities, and complex technical requirements.
They move through long approval cycles where every decision is tied to business outcomes and measurable return.
Success depends on understanding the buyer’s business problem and connecting your solution to its technical, operational, and financial impact.
Key Challenges
Enterprise SaaS sales demand precision. Each deal moves through layered evaluations and competing priorities that test a team’s ability to manage complexity.
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Buying committees span IT, security, operations, finance, and the C-suite, each with unique goals and risk concerns.
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Technical reviews require detailed integration plans, security validation, and compatibility testing long before financial approval.
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ROI justification demands complete cost-benefit analysis, including implementation, training, total ownership cost, and measurable outcomes.
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Extended approval cycles stretch sales timelines through procurement, vendor comparison, and shifting budgets.
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Product-focused conversations stall progress when buyers are focused on workflow efficiency, cost reduction, and strategic outcomes.
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Skepticism builds around implementation, support, and whether the solution will solve the problem or add friction.
Gap Selling was built for this environment.
It trains SaaS sellers to diagnose business problems, quantify impact, and guide both technical and executive stakeholders toward confident decisions.
This guide is part of our Gap Selling Training system. Learn about the core methodology → Gap Selling Training Program: Problem Centric™ Sales Methodology
Better Discovery. Better Deals.
When sellers understand the business problem, everything changes — win rates, deal size, and forecast accuracy.
A Diagnostic Approach: Selling the Way SaaS Buyers Expect
Our SaaS sales training centers on a proven, data-driven framework designed for enterprise product markets.
Key Features:
The Problem Identification Chart (PIC) maps core business issues and traces the underlying operational, technical, and financial causes.
Buyer Input Data (BID) processes ensure every proposal is anchored by specific, verified information from IT, operations, finance, and executive stakeholders.
Training builds the skills to facilitate cross-functional stakeholder alignment and translate technical capabilities into clear business value for each buyer persona.
Teams learn to use evidence and workflow impact to structure compelling business cases that address implementation concerns and justify cost.
Gap Selling emphasizes evidence gathering, problem mapping, and consensus-building as essential skills for competitive SaaS sales, helping reps deliver solutions that buying committees can act on confidently.
SaaS Sales Training Program
This program equips your sales team with actionable Gap Selling skills tailored for complex enterprise buyers and SaaS deal cycles. All training is guided by your custom-built Problem Identification Chart (PIC), developed in partnership with your leadership.
What Your Reps Learn
Effective Discovery: Asking targeted questions to reveal genuine operational, technical, and financial challenges—and the business outcomes buyers care about.
Problem Diagnosis: Diagnosing root causes and business impacts so reps connect product capabilities to what matters most for each stakeholder (IT, ops, finance, exec).
Value Mapping: Aligning sales messaging and proposals to the buyer’s highest-priority problems, with clear evidence, ROI analysis, and implementation clarity.
Buyer Input Data (BID): Using verified buyer information and multi-stakeholder input in every conversation from initial outreach to final proposal.
Objection Handling & Stakeholder Alignment: Engaging technical buyers, operations teams, and finance with insights relevant to each—navigating committee-driven SaaS decisions.
Implementation Reality: Addressing integration concerns, timeline clarity, and support expectations that often derail enterprise SaaS deals.
Real-World Application: Practice scenarios, SaaS account role-plays, and personalized AI coaching.
Training Format
Fast-paced Gap Selling workshops, delivered live (virtual or on-site)
Tools and guides for reps to prepare, run, and recap SaaS sales conversations
Ongoing coaching and deal inspection using the PIC as a reference
Case Studies
Increased close rates and deal velocity through Problem Centric™ selling
Randy Ray, Chief Revenue Officer of Cart.com, recognized that despite exponential growth and relatively high win rates, his sales team was becoming “order takers” rather than consultative sellers. The team struggled with discovery and wasn’t commanding the value they should in enterprise SaaS deals. After implementing Gap Selling training Cart.com saw:
%
Increase in Average Deal Size
%
Increase in Win Rates
Time to Results
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Selling in a different industry? Gap Selling training adapts to all complex B2B sales processes. → Learn about Gap Selling Training
Struggling With Low Win Rates or Extended Sales Cycles?
We’ll help you uncover the hidden execution issues driving poor SaaS sales results before the next quarter slips away.
A Little Insight For Ya…
Here are a few tools to get you on the right path forward.
How Buyers Want to be Sold
This survey report shares direct input from buyers on how they prefer to be approached, engaged, and sold to. It highlights what buyers pay attention to, what gets ignored, and the reasons they move forward or walk away. You’ll see clear trends in messaging, outreach, and rep behavior that influence buying decisions.
Use this report to align your sales motion with how real buyers actually evaluate sellers.
Deal Review Framework
This resource outlines a nine-point deal review process anchored in buyer input. It helps sales leaders assess deal quality based on discovery, qualification, decision process, buying timeline, and urgency. Each criterion is designed to surface execution gaps and guide stronger coaching conversations.
Use it to bring structure, consistency, and focus to every deal review session.
Problem Centric™ OS Assessment
This self-assessment gives sales leaders a structured way to evaluate their team’s ability to execute. It breaks down your sales organization across three critical layers: Skills, Opportunity, and Forecasting. Each section contains targeted questions covering everything from methodology and coaching to pipeline visibility and forecast reliability.
Use this tool to inspect how well your systems support rep execution, deal quality, and leadership oversight. The assessment highlights gaps that stall performance and gives you a starting point to prioritize what needs to change first.