Stop "Just Checking In": How to Build Sales Plays That Actually Convert
Brute-force follow-up is not a sales strategy — it's noise. Here's how to build deliberate sales plays that address every dimension of the buying decision and win complex B2B deals.
Stop "Just Checking In": How to Build Sales Plays That Actually Convert
By Simplyfyd | GTM Strategy · Sales Playbook
TL;DR — Key takeaways
"Just checking in" is not a sales strategy — it's noise that your prospect filters out automatically. Winning complex B2B deals requires deliberate sales plays that address five dimensions simultaneously: domain authority, proof of competence, political navigation, relationship depth, and competitive differentiation. This article gives you the framework, the plays, and a sample sequence you can deploy this week.
Table of Contents
- Why Brute-Force Follow-Up Fails
- The Sales Play Framework: Five Dimensions of a Deal
- Dimension 1 — Domain Authority
- Dimension 2 — Proof of Competence
- Dimension 3 — Political Navigation
- Dimension 4 — Relationship Depth
- Dimension 5 — Competitive Differentiation
- Putting It Together: A Sample Sales Play Sequence
- The Plays Your Team Needs to Build Right Now
- Building Your Play Library: A Practical Starting Point
- The Bottom Line
There's a sales email sitting in your prospect's inbox right now.
It says: "Hi [Name], just checking in to see if you've had a chance to review our proposal. Happy to answer any questions!"
Your prospect has seen it 11 times from 11 different vendors this month. They haven't replied to any of them. They won't reply to yours either.
Brute-force follow-up — the "just checking in," the "circling back," the "bumping this to the top of your inbox" — is not a sales strategy. It's noise. And in today's B2B environment, where the average enterprise deal involves 6 to 10 decision-makers, 3 to 6 competing vendors, and a buying committee that meets once a fortnight, noise is the fastest way to lose.
The companies winning complex B2B deals aren't sending more emails. They're running smarter plays.
This article lays out a framework for building sales plays that work — not by pestering your prospect into submission, but by systematically addressing every dimension of the buying decision: the rational, the emotional, the political, and the competitive.
1. Why Brute-Force Follow-Up Fails
Before building the solution, it's worth understanding why the status quo fails so spectacularly.
The "just checking in" email makes one enormous assumption: that the only thing standing between you and a closed deal is the prospect's memory. That they simply forgot you existed, and a gentle nudge will snap them back into action.
In reality, deals stall for entirely different reasons:
- Internal misalignment — the champion loves you, but the CFO is skeptical
- Competitive pressure — a competitor has been schmoozing the economic buyer directly
- Risk aversion — the prospect needs more proof before sticking their neck out internally
- Priority shift — a new initiative has consumed the budget conversation
- Relationship gap — you only know one person in a six-person committee
None of these problems are solved by another "checking in" email. Each requires a specific, targeted response — a play designed to address that exact obstacle.
The best sales organizations treat an active deal like a chess board, not a waiting room. They read the position, identify the vulnerabilities, and make deliberate moves.
2. The Sales Play Framework: Five Dimensions of a Deal
A sales play is a deliberate, coordinated sequence of actions designed to advance a specific deal by addressing a specific obstacle. Unlike generic outreach, a play has a clear diagnosis, a clear objective, and a clear set of moves.
Great sales plays operate across five dimensions simultaneously. Think of them as five levers — and the best reps pull multiple levers at once.
| Dimension | The Question Your Prospect Is Asking |
|---|---|
| Domain Authority | "Do these people actually understand my world?" |
| Proof of Competence | "Can they actually deliver what they're promising?" |
| Political Navigation | "Who in my organisation needs to be comfortable with this?" |
| Relationship Depth | "Do I actually trust these people enough to bring them into my business?" |
| Competitive Differentiation | "Why you over everyone else?" |
3. Dimension 1: Domain Authority
The question your prospect is asking: "Do these people actually understand my world?"
Buyers aren't just evaluating your product. They're evaluating whether you understand their industry, their competitive pressures, their internal dynamics, and their specific problem deeply enough to be trusted with their money and their reputation.
The "just checking in" email signals the opposite of domain authority. It says: I have nothing new to bring you. I'm just here because I need to close this quarter.
Plays that build domain authority
The Insight Drop — Send a piece of original thinking (your own or curated) that is hyper-relevant to a challenge they mentioned in a discovery call. Not a generic industry report. Something specific: "You mentioned your team is struggling with MQL-to-SQL conversion. We just published a breakdown of the 3 pipeline leakage points we see most often in Series B SaaS companies — thought it might be useful." This play positions you as a thinking partner, not a vendor.
The Competitive Intelligence Brief — If you know who you're competing against, prepare a short, honest landscape brief. Not a feature comparison table (those are self-serving and everyone knows it). A genuine read on the market: where each approach is strong, where it breaks down, and why the choice matters given their specific situation. Buyers respect candour. It builds trust faster than any pitch deck.
The Relevant Case Study Drop — Not a generic customer logo. A story that mirrors their situation: same industry, same company stage, same problem, same objection they're wrestling with. The closer the mirror, the more powerful the play.
4. Dimension 2: Proof of Competence
The question your prospect is asking: "Can they actually deliver what they're promising?"
This is different from domain authority. A firm can understand your world deeply and still fail to execute. Proof of competence answers the "but can you do it?" question — and it needs to be addressed proactively, not defensively.
Most reps wait until a prospect raises a competence objection before responding to it. By then, doubt has already set in. The best reps get ahead of it.
Plays that establish proof of competence
The Reference Play — Don't just offer references as a late-stage checkbox. Proactively connect your prospect with a customer who faced the same situation, at the same stage, in the same industry. Better yet, make the introduction before they ask. It signals confidence and removes friction from the buying process simultaneously.
The Work Sample — If your engagement involves a methodology, a framework, or a deliverable, show a version of it. A sanitised strategy document, a sample RevOps audit, a redacted GTM plan. Seeing the work product reduces the abstraction of buying professional services significantly.
The Mini-Win — If possible, identify a small, scoped piece of work you can do before the contract is signed — a workshop, a diagnostic, a 2-hour session. Getting paid isn't the goal; getting in the room and demonstrating your thinking is. Prospects who experience your work close at dramatically higher rates than those who only hear about it.
The Metrics Play — Translate your value into numbers that live on your prospect's scorecard. Not generic ROI percentages — specific projections tied to their business model: "Based on your current pipeline velocity and average deal size, closing 2 more deals per quarter would represent $1.2M in incremental ARR. Here's how we've driven that outcome for companies at your stage."
5. Dimension 3: Political Navigation
The question your prospect is asking (internally): "Who in my organisation needs to be comfortable with this before I can move forward?"
This is the dimension most reps ignore entirely — and it's often the single biggest reason deals stall or die.
In most B2B deals, the person you're talking to is not the only person who matters. There's an economic buyer controlling the budget. There's a technical evaluator who will raise procurement concerns. There's a sceptic on the committee who has been burned before. There's an executive sponsor who needs to feel ownership of the decision.
If your sales play doesn't account for the political landscape of the buying committee, you're building a house on sand.
Plays that address political dynamics
The Multi-Thread Play — Identify every stakeholder involved in or adjacent to the decision. Build a relationship map. Then deliberately initiate contact with each thread — not to sell, but to understand their perspective and serve their specific interest. The CFO needs a cost-benefit narrative. The CTO needs a technical integration story. The VP of Sales needs to know you won't disrupt their team. Each conversation is different.
The Champion Enablement Play — Your internal champion wants to say yes. But they have to sell this internally without you in the room. Give them the tools to do it: a one-page internal brief, a business case template, talking points for the budget conversation, answers to the objections they'll face. The easier you make it for your champion to champion you, the faster the deal moves.
The Executive Alignment Play — If the deal is significant enough, activate your own executive. A peer-to-peer call between your CEO/CRO and their executive sponsor changes the conversation. It signals commitment, elevates the relationship, and gives both sides a chance to discuss strategic fit rather than procurement details.
The Sceptic Play — Every committee has one. Rather than avoiding the sceptic, seek them out. Request a direct conversation: "I understand you have some reservations — I'd actually love to hear them directly. I'd rather address your concerns now than have them surface later." Sceptics who feel heard become allies. Sceptics who feel ignored become deal-killers.
6. Dimension 4: Relationship Depth
The question your prospect is asking: "Do I actually trust these people enough to bring them into my business?"
In B2B services and complex technology sales, trust is not a nice-to-have. It is the product. Buyers are not just purchasing a capability — they're purchasing confidence that the people delivering it will behave well when things get complicated, which they always do.
Relationships are built through accumulated interactions of genuine value. Not "quick calls to catch up." Not "coffee to stay in touch." Deliberate touchpoints that demonstrate you're thinking about them when there's nothing in it for you.
Plays that build relationship depth
The Unsolicited Value Play — Send something useful with zero agenda. An article relevant to a challenge they mentioned. An introduction to someone in your network who could help them. A heads-up about a competitor move. The "I was thinking of you when I saw this" play, when genuine, is more powerful than any pitch. It creates reciprocity without asking for it.
The Personal Milestone Play — Note anniversaries, promotions, company milestones, published articles. Acknowledge them briefly and genuinely. Not as a CRM checkbox — as a human interaction. "Saw your company announced the Series B — congratulations, that's a significant milestone. Hope the team gets a moment to celebrate before the next sprint."
The Joint Event Play — Invite your prospect to something that isn't a sales pitch — a roundtable with their peers, an industry panel, a small executive dinner. Shared experiences build relationships faster than any email sequence. And placing your prospect in a room with customers who love you is the most credible proof of value you can provide.
The Long Game Play — Some relationships take 18 months to become deals. The reps who win those deals are the ones who showed up consistently over that entire period without expectation. A quarterly touchpoint with genuine value — a relevant insight, a market update, a check-in on a strategic initiative they mentioned — keeps you top of mind without being pushy.
7. Dimension 5: Competitive Differentiation
The question your prospect is asking: "Why you over everyone else?"
In most contested B2B deals, the difference between the winner and the runner-up is not the product — it's the story. How clearly and credibly a vendor communicates why their approach is uniquely suited to this buyer's situation.
Generic differentiation ("we're more flexible," "we have better support," "our platform is more intuitive") is indistinguishable from what every competitor says. Specific, situation-anchored differentiation cuts through.
Plays that sharpen competitive positioning
The Situation-Specific Wedge — Identify the one dimension of this deal where your approach is genuinely, demonstrably superior for this specific buyer. Not in general — for them. Anchor every conversation around that wedge. "For a company at your stage, with your go-to-market motion, the most important thing is X. Here's how we approach X differently — and why that matters in your context."
The Reframe Play — If a competitor is winning on a dimension you can't match (price, features, brand), don't fight that battle. Reframe the decision criteria. "A lot of companies focus on feature count at this stage. What we've found is that the companies who scale fastest focus on adoption speed and time-to-first-result. On that dimension, here's how we compare."
The FUD Inoculation Play — If you know a competitor is going to raise a specific concern about your firm — size, experience, pricing model, integration capability — address it before they do. "You'll probably hear from [Competitor] that [concern]. Here's our honest answer to that." Getting ahead of the FUD removes its power.
The Vision Play — Paint a picture of what the working relationship looks like 12 months from now. What will have changed? What will they have built? What does success look like? This shifts the conversation from feature comparison to partnership aspiration — and it's a dimension most competitors never address.
8. Putting It Together: A Sample Sales Play Sequence
Here's what a real multi-dimensional sales play looks like for a deal that has gone quiet after a proposal submission.
Week 1 — Domain Authority + Relationship
Your champion receives a one-page "market intelligence brief" you've prepared: three things happening in their competitive landscape right now that are relevant to the decision they're making. No ask. Just value. A follow-up note: "Happy to walk through this on a 20-minute call if it would be useful."
Week 2 — Proof of Competence + Political
You send a sanitised work sample from a similar engagement — a strategy document or framework output — with a note: "Thought this might help your team visualise what the first 90 days looks like." You also send a one-page internal brief your champion can use for the budget conversation.
Week 3 — Competitive Differentiation
You request a direct call with the sceptic on the committee. You acknowledge their concern directly, share your honest answer, and ask what it would take to address it. You leave with a specific action item.
Week 4 — Executive Alignment + Relationship
Your CEO or CRO sends a brief, personal note to their executive sponsor — not a sales pitch, a genuine expression of interest in the strategic challenge they're solving. Offers a peer-level conversation.
Week 5 — Synthesis
You bring everything together in a revised proposal that reflects everything you've learned about the political landscape, the competitive situation, and the individual priorities of each stakeholder. It's not the same proposal with a new cover page. It's a document that shows you've been listening.
This is not brute force. This is chess.
9. The Plays Your Team Needs to Build Right Now
Every sales organisation should have a library of plays — not email templates, but strategic responses to specific deal situations. Start with these:
The Stalled Deal Play — For deals that have gone quiet post-proposal. Diagnose why (champion disengaged? competitor moved in? internal priority shift?) and activate the appropriate response.
The Multi-Stakeholder Play — For deals where you only have one thread into the organisation. Systematically build relationships with every relevant decision-maker.
The Competitive Displacement Play — For deals where a competitor has the incumbent relationship. Focus on the dimension where the incumbent is most vulnerable and the prospect is most frustrated.
The Late-Stage Risk Play — For deals that are close but stalling on procurement, legal, or final approval. Identify the specific blocker and address it with precision — whether that's a revised commercial structure, an executive conversation, or a phased implementation option.
The Reactivation Play — For deals that were lost or went cold 6–12 months ago. Circumstances change. Budgets reopen. Champions move companies. A well-timed, value-first reactivation play converts lost deals at a surprising rate.
10. Building Your Play Library: A Practical Starting Point
You don't need 50 plays. You need the right 10 — deeply understood, consistently executed, and continuously refined based on what's working.
For each play, define:
| Element | Question to Answer |
|---|---|
| Trigger | What deal situation activates this play? |
| Objective | What specific outcome does this play achieve? |
| Moves | What are the 3–5 specific actions in the sequence, in order? |
| Owner | Who executes each move? (Rep, manager, executive, marketing?) |
| Assets | What materials are needed? (Case study, brief, insight, introduction?) |
| Success Metric | How do you know the play worked? |
Document your plays. Train your team on them. Review them quarterly. The companies with the best sales play libraries don't just have better reps — they have better systems.
11. The Bottom Line
The buyers you're pursuing are smart, busy, and bombarded. They've developed a highly refined filter for vendor noise — and "just checking in" goes straight through it.
What cuts through is relevance. Specificity. Genuine understanding of their situation. Proof that you've thought harder about their problem than your competitors have. A relationship that feels like a partnership before the contract is signed.
The difference between a rep who sends follow-up emails and a rep who runs sales plays is the difference between hoping and strategising. One waits for the prospect to make a decision. The other shapes the conditions under which the decision gets made.
Stop checking in. Start playing chess.
Simplyfyd helps B2B technology companies build and execute sales plays as part of a Unified Revenue Engine — combining Fractional CRO/CMO leadership, onshore sales support, and GTM strategy into a single, integrated growth motion. Book a strategy call to see how we can help your team close more of the deals already in your pipeline.