Most sales teams wait for the economy to “settle down” before they change how they sell. By then, it is usually too late.
If you believe tougher trading conditions are either here or on the way, you need more than optimism and more activity. You need a proactive Challenger Sales Play; a deliberate campaign that reframes how customers see their problems and creates momentum where none exists.
This article is about designing that play: who to target, what to say, and how to run it so your team is not simply reacting to shrinking budgets.
What This Topic Really Means
This is not a general introduction to Challenger selling or a theory piece about recessions. It is about building a specific, time-bound sales play your team can run:
- You pick a clearly defined segment and challenge.
- You build a sharp, insight-led narrative around that challenge.
- You equip your team with questions, proof points and metrics to run a consistent conversation.
- You set a cadence (who we contact, how often, with what next step).
Think of it as a campaign in the pipeline, not a training course. The aim is to put structure on proactive selling when the market feels hostile.
You are not asking for budget “because times are hard”. You are showing that standing still is commercially dangerous, and that there is a rational case for acting now.
Why This Matters for Irish and United Kingdom Businesses
In Ireland and the United Kingdom:
- Many sectors are relatively small; when demand softens, there is nowhere to hide.
- Buyers are under pressure to freeze or delay projects, even when they know there is risk.
- Traditional relationship or solution selling easily stalls at “call us again next quarter”.
A Challenger Sales Play helps you to:
- Put structure and discipline around proactive outreach.
- Give salespeople a clear story to take to market, not just “check-ins”.
- Generate opportunities that would not appear through inbound or tender processes alone.
Key Principles / Framework / Breakdown
1. Define the Play: Who and What
Before you script anything, decide:
- Which customers or prospects?
One vertical, role, or problem type. Narrow is better. - What specific challenge?
A risk, inefficiency, or missed opportunity that is becoming more painful as conditions tighten. - What change do you want?
A diagnostic workshop, a pilot, a switch from a legacy approach – be clear.
Write this down in one paragraph. If it is fuzzy on paper, it will be fuzzier in the field.
2. Build the Challenger Conversation Path
Now design the conversation your reps will lead.
A practical Challenger path for this play might look like:
- Hook question or observation
Open with a non-obvious insight about their environment: something that makes them stop and think rather than say “we know”. - Explore the overlooked impact
Use prepared questions to uncover where this issue is showing up in their numbers, operations or people. - Share concise proof points
Bring two or three examples, benchmarks or anecdotes that show this is a real, solvable problem not a theory. - Contrast action vs inaction
Help the buyer quantify, even roughly, what it costs to leave things as they are versus tackling the issue. - Offer a low-risk next step
Suggest something concrete and manageable: a short workshop, a pilot, a narrow test. The next step is the outcome of the play, not the full sale.
Document this as a one-page talk track so everyone runs broadly the same pattern while still sounding like themselves.
3. Use Metrics to Anchor the Business Case
In tougher markets, opinions are not enough. Your play needs numbers, even if they are ranges or scenarios.
For your chosen challenge, decide:
- Which 2–3 metrics matter most to this buyer?
(e.g. churn rate, rework costs, delayed revenue, compliance risk, overtime spend.)
Recent research also shows that how salespeople structure their thinking has a direct impact on complex deals. Brontén and Cabrera’s 2025 paper, “Structured Thinking Structures Sales Opportunities that Win,” argues that win rates actually peak when 4–5 stakeholders are involved, and that performance drops only when complexity is unmanaged. Using their DSRP-483 framework, they show how mapping stakeholders, perspectives and relationships helps sales teams co-create a shared mental model of the opportunity and focus on the few high-leverage actions that matter most. It is a useful reminder that a Challenger Sales Play is not just about a strong story; it also needs structured thinking behind the scenes to navigate multiple decision makers and move the opportunity forward.
- What typical ranges you see in your client base.
- How your solution realistically shifts those metrics.
You are not trying to build a 40-page ROI model. You are giving reps simple levers they can use in conversation: “even a 10–15% improvement here is worth €X–€Y for teams like yours”.
4. Agree a Clear Outreach Cadence
A Challenger play fails if it lives only in a slide deck. You need a cadence:
- Targets: Named accounts, by owner.
- Channels: Phone first, supported by email and LinkedIn where relevant.
- Sequence: How many touches, over what period, before we disqualify or recycle.
- Success definition: For this play, what counts as a win? (e.g. number of discovery workshops booked.)
Keep it simple enough that you can see, week by week, whether the play is being run or not.
5. Treat It as a Team Sport, Not Lone-Wolf Selling
Because this is a proactive play, it needs:
- Marketing support: a short explainer, a follow-up email template, maybe one simple visual to back up the story.
- Leadership attention: pipeline reviews that specifically ask, “how is the Challenger play performing?”
- Peer sharing: short huddles where reps share what is landing, what questions work, and what objections are emerging.
When everyone works from the same spine of insight and structure, the whole team learns faster.
How Leaders Should Approach This
As a leader, your job is to sponsor and simplify.
- Choose one play, not five.
Start with a single, tightly defined Challenger play. Prove it works before spinning up variants. - Be involved in shaping the story.
Bring your view of the market, your board-level conversations, and your experience of previous downturns. - Remove unnecessary friction.
Make sure your CRM, reporting and targets reflect the play: reward the right behaviours, not just end-of-quarter heroics. - Coach to the framework.
When reviewing calls or meetings, listen for the Challenger elements: the hook, the insight, the contrast, the next step.
Common Mistakes (and How to Avoid Them)
- Re-labelling old decks as “Challenger”
Nothing changes except the title slide.
Fix: Build a new narrative around a specific challenge, not generic product messaging. - Making the play too broad
“This works for everyone.” It will not.
Fix: Start with one segment where your insight is strongest. - Over-engineering the business case
Reps get lost in spreadsheets.
Fix: Focus on a small set of simple, credible metrics. - No clear end state
Calls end with “we will send you some information”.
Fix: Define the next step the play is designed to achieve and coach towards that.
What Good Looks Like
When a Challenger Sales Play is working, you will see:
- A noticeable increase in pipeline created from proactive outreach, not just inbound.
- Prospects referencing your insight and metrics in their internal discussions.
- Short, focused follow-up cycles built around workshops, pilots or trials.
- A team that can clearly explain why this challenge matters now, without sliding back into generic product talk.
Importantly, you will also see clear data on how the play is performing, which helps you decide whether to scale, tweak or retire it.
How Jordan Wolf Associates Helps
At Jordan Wolf Associates, we help organisations design and run a practical Challenger Sales Play that fit their markets and teams.
We support clients through:
- Play design workshops
Defining the target segment, challenge and desired outcomes for your Challenger play. - Narrative and talk-track creation
Building the hook, questions, proof points and simple metrics your team can use immediately. - Enablement and training
Equipping your salespeople to run the conversations confidently across phone, video and face-to-face meetings. - Live deal and cadence coaching
Working with sales leaders to review activity, sharpen messaging and iterate the play based on real feedback.
The objective is always the same: a repeatable, insight-led play that keeps sales momentum going, even when the market is difficult.
Get Your Free Consultation
If you want to explore what a Challenger Sales Play could look like for your organisation, we are always happy to talk.
Email: gerard@jordanwolf.ie
Phone: +353 (1) 556 3049
Frequently Asked Questions on a Challenger Sales Play
1. How is a Challenger Sales Play different from general Challenger selling?
A play is a specific campaign for a defined segment and problem, with clear messaging and cadence. Challenger selling is the broader methodology behind it.
2. How long should a play run?
Typically 9–12 weeks is enough to see whether it generates meaningful opportunities and where it needs refinement.
3. Can we run multiple plays at once?
Eventually yes, but start with one. Too many plays at launch just dilute focus and data.
4. Do we need new technology to do this?
Usually not. Most teams can run a Challenger play using their existing CRM and communication tools, the key change is in design and discipline.
5. Will this work if our team is mostly account managers, not hunters?
Yes, provided they are willing to initiate new kinds of conversations with existing customers about overlooked risks or opportunities.
