The Challenger Sale – developed by Matthew Dixon and Brent Adamson through research on thousands of B2B salespeople – identifies five rep profiles (Hard Worker, Relationship Builder, Lone Wolf, Reactive Problem Solver, Challenger) and finds that Challengers consistently outperform the others, especially in complex sales. The Challenger rep teaches prospects something new about their business, tailors the message to the specific stakeholder, and takes constructive control of the conversation rather than yielding to every objection. CRM doesn’t teach the Challenger approach – that’s training – but CRM provides the data infrastructure that makes Challenger behaviours possible at scale: research, stakeholder mapping, insight delivery, and commercial tension tracking. This guide covers how to configure CRM to support Challenger selling.
That means the CRM has to do more than hold a pipeline stage. It should help the rep build a commercial point of view, track the stakeholders involved, and keep the storyline of the deal visible as the conversation evolves.
Challenger sales works best when the CRM supports research, account insight, and follow-up discipline rather than just storing contact details. The method depends on reps understanding the customer’s business well enough to teach something useful, tailor the message, and keep control of the conversation.
The Three Challenger Behaviours and Their CRM Requirements
| Challenger Behaviour | What It Requires | CRM’s Role |
|---|---|---|
| Teach | A commercial insight – something the prospect doesn’t know about their business that creates urgency for change. Must be tailored to their industry and role. | Account research fields, industry context, enrichment data, competitor positioning notes |
| Tailor | Understanding which stakeholders care about what. The CFO cares about cost; the Sales VP cares about revenue; IT cares about integration. | Multi-contact tracking, stakeholder role fields, influence/decision authority mapping |
| Take Control | Ability to handle objections by reframing, not conceding. Requires knowing common objections by persona and having prepared responses. | Objection fields on contact/deal records, competitive intelligence notes, deal coaching properties |
Setting Up CRM for Challenger Research (the “Teach” Phase)
Challengers lead with insight, not product. The insight has to be grounded in the prospect’s business context. CRM preparation for the Teach phase:
Account-level research fields – add custom properties to your Company/Account object:
- Industry vertical (dropdown – precise, not generic)
- Business model (SaaS / transactional / services / manufacturing etc.)
- Current growth phase (startup / scaling / mature / declining)
- Known strategic initiative (text – e.g., “expanding into EMEA”, “launching new product line”)
- Primary business challenge (text – your assessment based on research)
These fields are populated by reps during account research and by enrichment tools (Clearbit, ZoomInfo, Apollo). The insight a rep delivers in the Teach phase should be informed by these fields – not generic industry claims, but something tied to this company’s specific growth phase and initiative.
Insight library – some teams build a CRM-linked knowledge base of commercial insights by vertical and persona. This doesn’t live in the core CRM properties but can be stored in a linked document library, a HubSpot knowledge base article, or a Salesforce content library. Reps pull the relevant insight for this account’s profile and customise it for the call.
Stakeholder Mapping for the “Tailor” Phase
Most enterprise B2B deals involve multiple stakeholders. The Challenger’s Tailor behaviour requires knowing who influences the decision and what each person cares about. Standard CRM contact records aren’t designed for this – they capture individual contact data but not the relationship map. Fix this with:
Contact-level fields on each stakeholder:
- Buying role (dropdown): Economic Buyer / Technical Buyer / Champion / Blocker / End User / Influencer
- Decision authority (dropdown): Final decision / Veto / Recommends / Informed only
- Primary business concern (text – what this person cares about)
- Engagement level (dropdown): Actively engaged / Occasionally responsive / Not engaged / Unresponsive
- Relationship strength (1-5 scale – rep’s assessment)
With multiple contacts per deal each assigned a buying role, the rep can see at a glance: do we have access to the Economic Buyer? Is the Champion engaged enough to navigate internal politics? Is there a Blocker we haven’t addressed?
In HubSpot, use the deal’s Contacts association panel and custom contact properties. In Salesforce, use the native Opportunity Contact Roles object – it has built-in role fields designed for exactly this purpose.
Tracking Commercial Tension (the “Take Control” Phase)
Challengers maintain constructive tension – they don’t concede every objection, they reframe. CRM can support this by tracking where tension exists and how it’s being managed:
Deal-level objection tracking:
- Primary objection raised (dropdown – standard taxonomy: price / timing / competitor preference / no budget / internal politics / not convinced of ROI)
- Objection status (dropdown): Active / Addressed / Resolved
- Reframe approach used (text – note how the rep reframed rather than conceded)
These fields serve two purposes: they help the rep track deal health, and they generate data across many deals about which objections appear most often at which stages, which reframes are most effective, and which objections correlate with deal loss. That’s Challenger coaching data.
Using CRM Data to Build Commercial Insights
The strongest Challenger insights are built from patterns your company sees across many customers – because you’ve sold to hundreds of companies in this space, you can see things the prospect can’t. CRM data is the source of these insights:
- Which companies in this vertical typically have a hidden cost in their current process that they’re not measuring? (Look at your closed-won deals – what problem did they all share?)
- What does the onboarding data show about time-to-value for companies at this growth stage?
- What do renewal/expansion patterns tell you about which early-stage choices drive long-term success?
This kind of insight is built by analysing CRM data at the portfolio level – not just reviewing individual records. Revenue operations teams can extract this from CRM reporting and package it as insight frameworks reps use in discovery and presentations.
“Our reps understand Challenger in training but go back to relationship selling on real calls”
The regression to relationship selling happens because Challenger requires preparation, confidence, and a clear insight – all of which take time and skill. Relationship selling is easier under call pressure. CRM can counter this by making preparation mandatory in the workflow: (1) build a pre-call checklist as a CRM task that must be completed before a discovery call is logged – it includes “What insight are you leading with? What is this stakeholder’s primary concern? What objection are you anticipating?” (2) Use call recording tools (Gong, Chorus) to review whether reps are actually teaching rather than pitching and build coaching feedback directly to deal records. The goal is to make Challenger behaviours measurable so managers can coach to them.
“We don’t have multi-stakeholder visibility – we only track one contact per deal”
Single-contact tracking is a structural CRM problem that makes Challenger impossible to support. Fix: enforce the practice of adding all known stakeholders to each deal with their buying roles. In HubSpot, this means using the Contact associations on a Deal and adding the custom buying role/authority fields. In Salesforce, use Opportunity Contact Roles (standard object – no configuration needed, just enforcement). Without multi-contact visibility, the Tailor behaviour has no data foundation.
“We can’t tell which deals have an active blocker until they stall”
Blockers show up as stalled deals – late-stage no-decision losses. CRM can flag deals at risk of this pattern: build a deal health view that surfaces deals where (a) there’s no Economic Buyer contact in the deal, (b) there’s a contact tagged as Blocker with Objection Status = Active, or (c) the deal has been in the same stage for more than your average stage duration. These are the deals that need Challenger reframing, not just follow-up.
Sources
Dixon, M. and Adamson, B., The Challenger Sale (original research)
Gartner, B2B Buying Behaviour and Stakeholder Complexity (2025)
Salesforce, Opportunity Contact Roles Documentation (2025)
HubSpot, Multi-Contact Deal Management Best Practices (2026)
Supporting the Challenger Sale Approach Through CRM Configuration
The Challenger Sale methodology requires reps to teach prospects something new about their business, tailor the message to the specific stakeholder, and take control of the sale. This is fundamentally a rep skill set and coaching challenge, but CRM configuration can support each of the three components. A CRM that captures stakeholder insight data, stores approved teaching materials linked to buyer profiles, and tracks whether reps are following the Challenger conversation structure makes the methodology operationally sustainable rather than dependent on individual rep talent.
What types of sales roles benefit most from the Challenger Sale methodology?
The Challenger Sale methodology is most effective for reps selling complex B2B solutions where the customer has multiple options, a long evaluation process, and genuine uncertainty about what the best solution looks like. It is particularly well-suited to technology, professional services, and financial services sales where the rep can credibly deliver a commercial insight based on industry knowledge. It is less appropriate for transactional sales with short cycles and commoditised products, where the relationship and responsiveness aspects of the Rep Performer profile (also from the CEB research that produced Challenger) may be more relevant. The research found that Challenger-style reps significantly outperform other profiles in complex B2B sales but not in simple transactional sales.
How is the Challenger Sale different from consultative selling?
Consultative selling asks questions to understand the customer’s needs and then proposes a solution. The Challenger Sale begins by teaching the customer something new about their situation before discovering their needs. The distinction is in who leads the problem definition: in consultative selling, the customer articulates their problem and the rep proposes a solution; in the Challenger Sale, the rep introduces a new way of looking at the problem that the customer may not have considered. In CRM terms, this means Challenger reps often create or reframe the Problem Statements field rather than simply recording what the customer said their problem was. The most effective approach combines elements of both: use Challenger teaching to establish credibility and reframe thinking, then use SPIN-style discovery to understand the implications.
Can the Challenger Sale methodology be used for inbound leads?
Yes, but the emphasis shifts. For outbound prospecting, the rep leads with the commercial insight because there is no existing relationship or expressed need. For inbound leads where the prospect has already identified a problem and is evaluating solutions, the Teach component is less about introducing a new problem and more about reframing the evaluation criteria. Instead of teaching the customer that they have a problem they did not know about, the Challenger rep teaches the customer that they are evaluating solutions using the wrong criteria, leading to a new framework that favours the rep’s solution. In the CRM, inbound deals should still have a Teaching Material field populated with the content used to reframe the evaluation.
How should sales managers coach Challenger Sale behaviours using CRM data?
CRM data provides three coaching levers for the Challenger Sale. First, content usage: review which teaching materials the rep is using and whether they are being used with the right buyer personas. Second, stakeholder engagement: check whether the rep has engaged all relevant stakeholders and tailored the message by reviewing the stakeholder priorities and tailoring notes fields. Third, deal control: review whether next steps, decision timelines, and champion briefing activities are being logged consistently. When a deal stalls, the manager can diagnose whether the stall is a teaching failure (the customer has not been given a reason to change), a tailoring failure (the message is not resonating with the decision-maker), or a control failure (the buying process has drifted without a clear next step).
Embedding Challenger Sale Principles Into Your CRM System
Building a Challenger Insight Library Inside Your CRM
The Challenger approach centres on delivering commercial insight that reframes how buyers think about their problem. Create a CRM content library with insight assets tagged by industry, persona, and deal stage. Reps can pull the right insight before each call and log which insights were used in deal notes. Over time you identify which insights consistently open doors and advance deals.
Tracking Teach-Tailor-Take Control Steps in CRM Deal Records
Map the three Challenger steps to CRM deal properties: Teach – insight delivered and logged; Tailor – economic impact calculated for this account; Take Control – consensus plan agreed. Require each property to be populated by the Proposal stage. Pipeline reviews become a qualitative check on Challenger execution, not just a numbers review.
Measuring Challenger Methodology Effectiveness with CRM Win Rate Data
After 90 days of Challenger adoption, pull a win rate comparison: deals where all three Challenger steps are logged vs. deals where they are missing. Most teams see a 10-20 percent win rate improvement in Challenger-complete deals. This data makes the business case for continued Challenger training investment.
A CRM that supports Challenger selling gives the rep structure without flattening the message. The system should make it easier to prepare and debrief, not force every account into the same generic template.
Common Problems and Fixes
Problem: Teaching Content Is Not Stored or Tracked in the CRM
The Teach component of the Challenger Sale requires reps to lead with a commercial insight: a piece of information the customer does not know about their industry, their competitors, or their own business that reframes their thinking. Most organisations create this content in marketing, but reps often cannot find it when they need it, use outdated versions, or choose to skip the teaching component and jump straight to product demonstration.
Fix: Create a CRM content library (available in HubSpot Sales Hub, Salesforce CRM Content, and Zoho CRM Documents) that organises teaching materials by buyer role, industry, and deal stage. For each piece of content, include metadata: the buyer persona it is designed for, the commercial insight it delivers, and the problem it reframes. Train reps to retrieve and attach content from the library to deal records when they use it, creating a record of which materials were shared with which accounts. Track content engagement in HubSpot to see which teaching materials generate the most follow-on activity. Review and update the content library quarterly to ensure insights remain current.
Problem: Tailoring Is Inconsistent Because Stakeholder Profiles Are Not Captured
The Tailor component of the Challenger Sale requires reps to adjust the commercial insight and the value message based on the specific priorities and concerns of the individual stakeholder they are addressing. A CFO cares about risk and total cost of ownership. A VP of Sales cares about revenue impact and quota attainment. A CTO cares about integration and security. Reps who deliver the same message to every stakeholder are not executing the Challenger methodology; they are delivering a product pitch with a Challenger-style opening.
Fix: Add a stakeholder priorities field to CRM contact records for key deal contacts. The field should capture the individual’s stated business priorities, their preferred decision-making criteria, and any objections or concerns expressed. When preparing for a stakeholder meeting, the rep reviews this field and selects the appropriate content and message angle. In the deal record, create a Tailoring Notes field that captures how the rep adapted the commercial insight for each stakeholder. This field is reviewed in deal coaching conversations to assess whether the rep is genuinely tailoring or delivering a generic pitch with minor adjustments.
Problem: Taking Control Is Confused With Being Pushy
The Take Control component of the Challenger Sale is the most frequently misapplied. Taking control means driving the buying process proactively: proposing next steps, setting clear decision timelines, and redirecting conversations that are drifting away from the business case. Some reps interpret this as applying high-pressure tactics, which damages relationships and produces the opposite outcome. Others are uncomfortable with any form of assertiveness and interpret the component as optional.
Fix: Define taking control behaviours in CRM deal activity requirements. At each pipeline stage, specify the actions that represent appropriate control of the buying process: next steps agreed and recorded in the CRM, decision timeline confirmed and entered in the Target Decision Date field, champion briefed on how to present the business case internally. Make these activity records required for stage advancement. This translates the abstract concept of taking control into specific, measurable behaviours that managers can coach to and reps can execute consistently. The difference between taking control and being pushy is whether the rep is advancing the customer’s decision process or bypassing it: the former is Challenger, the latter is pressure selling.