Checklist: Strategic Selling
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"With Weflow, we’re now capturing all relevant activities and have full transparency into the performance of each sales rep. It’s a game changer."
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"Weflow gives us better visibility and predictability of our business."
"Weflow eliminated the need for our VP to ask, ‘Did you follow up with that deal?’. It tracks customer interactions automatically, creating a framework that drives accountability across the team."
"None of the other tools gave us a solution like Weflow. From the beginning, we had a really smooth process."
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"I had a first introductory call with Weflow. I think I was sold after 15 minutes. There’s no question that the people at Weflow understood the problems that we were trying to solve."
"I’ve worked with Gong before, but Weflow’s simplicity and real-time sync are game-changing."
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"We use Weflow to auto-capture activity data, run deal reviews, and analyze our pipeline to inform our forecast. Being able to spot deal risks early has improved win rates and pipeline health."
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What's Inside
Buyer role mapping
- The four buying roles to identify on every deal: champion, user buyer, technical buyer, and economic buyer
- Position, goals, and day-to-day impact questions that qualify each contact against their role in the purchase
- How to surface decision criteria by asking what matters most to each contact and what they need to commit
Contact attitude assessment
- The four stakeholder mindsets that shape deal posture: growth, problem, everything is fine, and euphoria
- Discovery prompts to map current pain, existing workarounds, and the roadblocks each contact is hitting today
- Forward-looking questions that expose near-term risks and blind spots the contact has not yet recognized
Stakeholder influence planning
- How to combine buyer role and attitude into an individualized pitch for each stakeholder rather than one generic deck
- A method for pinning down the specific pain points that must be addressed to convert each contact
- Deal strategy prompts that assess persuasion effort required and when to pull in another team member
Daniel Schemmert
Daniel Schemmert is the Head of Growth at Weflow, where he's built the GTM engine from scratch. He spends valuable time talking to RevOps leaders about how they run pipeline, forecasting, and Salesforce. He's also the co-founder of RevOps Chat, the Slack community where 1,000+ RevOps practitioners share what's actually working inside their revenue orgs.
Go Deeper
Strategic Selling Framework: Map Buyers and Personalize Pitches
#88 Rolling Out SPICED across a 750-Person Sales Org
Sales Methodology Guide & Checklists
Frequently asked questions
What is strategic selling and how is it different from a standard sales process?
Strategic selling is a structured approach to complex, multi-stakeholder deals where you map each contact by role (Champion, User Buyer, Technical Buyer, Economic Buyer) and attitude (Growth, Problem, "Everything is Fine," Euphoria) before crafting your pitch. A standard sales process typically treats the account as a single entity and moves linearly through stages. Strategic selling forces you to treat each contact as a separate influence problem with its own logic.
What information do I need about my contacts before I can actually use this checklist?
At minimum, you need each contact's title, their stated goals, and some signal about how they currently view the status quo — whether they're feeling pain, chasing growth, or think things are fine. You can pull a lot of this from discovery calls, LinkedIn, and any notes in your CRM. If you're going into a deal cold with no contact intel, run discovery first — the checklist won't do much without raw material to work with.
How do I know if I've correctly categorized a contact's attitude, especially when they're hard to read?
The clearest signal is how they talk about current challenges: are they actively describing problems, or are they deflecting and saying things are under control? If a contact is unaware of a challenge that you can see clearly from the outside, the checklist flags that as a specific scenario — they may appear "Everything is Fine" but actually need a problem framed for them. When in doubt, treat the attitude as a hypothesis and update it after your next touchpoint.
Which of the three steps in this checklist should stay human-led versus something I could delegate or templatize?
Step 3 — crafting individualized pitches — needs to stay human-led because it requires judgment about how much persuasion each contact needs and whether to bring in another team member. Steps 1 and 2 can be partially templatized with a standard set of discovery questions, but the interpretation still requires a rep who actually knows the account. Don't hand this off to someone who hasn't been in the conversations.
How often should I revisit contact categories and attitudes during an active deal?
Revisit after every meaningful touchpoint — a call, a demo, a proposal review — because attitudes shift, especially once internal conversations start happening without you in the room. A contact who was "Everything is Fine" in week one can move to "Problem" after their boss asks a hard question. Treat your categorizations as live data, not a one-time exercise at deal open.
Can I use this checklist on smaller, single-stakeholder deals, or is it overkill?
For a true single-stakeholder deal, Steps 1 and 2 collapse into one quick mental check — you've got one contact, one attitude, done. Where reps get burned is assuming a deal is single-stakeholder when it isn't, so running through Step 1 quickly is worth the two minutes even on deals that look simple. If you genuinely have one decision-maker with no internal approvals, skip to Step 3 and focus your energy on the pitch.
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