Selling to CHROs using AI - Bonus Prompts

This newsletter covers actionable AI prompts that help sales teams engage CHROs faster—covering research, messaging, and follow-up sequences that turn HR signals into booked meetings.

Last week we covered seven big pieces as a part of “Selling to CHROs using AI” first part:

1. CHRO Buying Behavior. Why results beat discounts.

2. Account Research. Pull pain from 10-Ks, job ads, and LinkedIn.

3. Hyper-Personalized Sequences. Trigger → Pain → Value → CTA.

4. Multi-Channel Cadence. Five touches that boost reply rates.

5. AI Deal Coordination. SDR, AE, AM stay on the same page.

6. Copy-Paste Toolbox. Emails, LI scripts, SOC-2 trust lines.

7. Final Push. Close fast or lose ground to AI-ready rivals.

In case you missed it, here is the link:

The last issue was heavy on the content side. Today you get sharp and specific prompts.

Paste a prompt into your sales co-pilot or use Revenoid to directly get these in your workflow.

In seconds you’ll see fresh research, clear copy, and the next step to take.

It works like a cheat code for winning CHRO deals.

Scroll down, copy the prompts, and put them to work.

We are gonna cover following prompts below:

1. Prompts for SDRs

• SDR Prompt #1 – Extract Strategic HR Signals and Craft Personalized Outreach Hooks for [Company]

• SDR Prompt #2 – Create First-Touch & Peer-Led Outreach Emails Based on a CHRO’s DEI Pledge

• SDR Prompt #3 – Craft Personalized LinkedIn DMs Based on a CHRO’s AI Literacy Academy Post

• SDR Prompt #4 – Frontline AttritionVoice Message Generator (≤ 30 sec)

• SDR Prompt #5 – Extract and Personalize Cold Outreach Using HR Initiatives from [Company]’s Latest Earnings Call

2. Prompts for AEs

• AE Prompt #1 – Identify HR Pain Points from Attrition & DEI Mandates, and Quantify the ROI Impact

• AE Prompt #2 – Handle HRIS Integration Objections with Strategic and Conversational Follow-Up Questions

• AE Prompt #3 – Create a One-Page Demo Brief + Slide Headlines Framing AI Outcomes for CHROs

• AE Prompt #4 – Write a Discovery Follow-Up Email That Recaps Pains, Outlines Next Steps, and Adds Relevant Social Proof

• AE Prompt #5 – Probe AI ROI Expectations Using Direct and Consultative Peer-Framed Questions

3. Prompts for Sales Enablement Leaders

• Sales Enablement Prompt #1 – Train Sales Reps to Distinguish Signals from Intent + Provide Good & Bad Examples

• Sales Enablement Prompt #2 – Train Reps to Navigate AI Risk Concerns in Discovery Conversations

• Sales Enablement Prompt #3 – Turn 3 Buyer Signals into a Strategic Value Story, Then Refine for ROI Logic

• Sales Enablement Prompt #4 – Create a Knowledge-Check Quiz on Top AI Objections + Provide Sample Answers

• Sales Enablement Prompt #5 – Train Reps to Spot Strategic Hiring Signals vs. Noise Using Flashcards + Usage Tip

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Prompts for SDRs

SDR Prompt #1 – Extract Strategic HR Signals and Craft Personalized Outreach Hooks for [Company]

Prompt:
You are a highly skilled SDR, Sales Leader, or RevOps Analyst creating account-level insight to drive intelligent outreach. Your task is to identify 3 strategic HR signals for [Company] that can inform compelling and timely outreach to the CHRO or senior HR leadership. Use publicly available sources to extract signals from three channels:

1. Earnings Calls – Look for forward-looking HR-related statements (e.g., hiring plans, workforce transformation, retention goals, DEI initiatives).

Resources:
https://www.sec.gov/edgar.shtml

https://www.alphastreet.com
https://seekingalpha.com/earnings/earnings-call-transcripts

2. LinkedIn Posts – Analyze the company page, leadership content (especially CHRO), hiring announcements, EVP messaging, or HR trends mentioned.
Start here:
https://www.linkedin.com/company/[company]/
https://www.linkedin.com/in/[CHRO-name]/ (if known)

3. CHRO Interviews – Find recent interviews, podcast appearances, or media features involving the CHRO or HR leadership to surface top-of-mind priorities.
Try:
Google search: “CHRO [Company] interview”
https://www.hrexecutive.com

https://www.hrotoday.com

https://www.workforce.com

For each signal, return two versions:

## Version 1:

1/ Signal — Brief summary of insight
2/ Pain Point — One-line that implies what’s broken, risky, or in flux
3/ Outreach Angle — One-liner that subtly frames how your solution aligns

## Version 2:

Everything above +: • Hook Sentence — A soft, insight-led opener (suitable for LinkedIn DM or cold email)

Should demonstrate listening and relevance
Avoid hard selling
Use human tone (e.g., “Noticed... Curious...”)

Example:

Signal: CHRO said on a podcast that upskilling frontline teams is the 2025 HR priority. Pain Point: Traditional LMS adoption has stalled with frontline employees.
Outreach Angle: Our mobile-first learning tools help frontline workers engage with upskilling at scale.
Hook Sentence: “Caught your CHRO’s note on 2025 upskilling for frontline teams—how are you thinking about driving adoption at the last mile?”

At the beginning of the task, prompt the user to provide:

– Target company name
– Optional: Known CHRO name (if available)

SDR Prompt #2 – Create First-Touch & Peer-Led Outreach Emails Based on a CHRO’s DEI Pledge

Prompt:
You are a seasoned SDR, Sales Leader, or RevOps Analyst crafting personalized outbound emails to senior HR leaders. Your task is to draft two outreach-ready messages based on a recent DEI pledge or public statement made by the CHRO at [Company].

# Part 1: Research Prep

Ask the user to provide the following (or instruct them where to find it):

1. Target Company Name
2. Target CHRO’s Name (if known)
3. Link or quote from the CHRO’s recent DEI statement or initiative

If this is not readily available, prompt them to explore:

1/ LinkedIn:
https://www.linkedin.com/in/[CHRO-name]/
https://www.linkedin.com/company/[company]/posts/

2/ Google search:
"CHRO [Company Name] DEI pledge"
Or search with: site:prnewswire.com, site:businesswire.com, or site:[companydomain.com]

3/ HR Media Sources:
- https://www.hrexecutive.com
- https://www.hrotoday.com
- https://www.workforce.com

# Part 2: Output Structure

Once the DEI statement is sourced, generate the following:

## Version 1 — First-Touch Email (Max 70 words)

- Reference the CHRO’s DEI pledge or quote with genuine acknowledgment
- Tie it to a relevant challenge, question, or priority HR leaders face
- Keep it professional but conversational
- Soft close (e.g., “Would love to hear how you're approaching...”)

## Version 2 — Peer-Share Rewrite

- Simplify the language
- Remove any CTA or structured pitch
- Make it sound like a peer sharing a relevant idea or article
- Use a natural tone like:
“Saw your recent post on DEI—reminded me of this piece on how orgs are embedding that into onboarding. Thought you might find it interesting.”

# Example Output

## Version 1 – Email

Subject: DEI as a foundation, not an initiative

I saw your recent DEI pledge about embedding equity into leadership culture at [Company] — a powerful shift. Many HR leaders are now rethinking how they measure progress beyond hiring metrics. Curious how you’re approaching that internally.

## Version 2 – Peer Rewrite

Noticed your DEI note around embedding equity in leadership — such an important direction.

Came across a framework a few other teams are using to connect inclusion with leadership behavior tracking — ping me if you'd like the link.

SDR Prompt #3 – Craft Personalized LinkedIn DMs Based on a CHRO’s AI Literacy Academy Post

Prompt:
You are a senior SDR, sales leader, or RevOps analyst writing LinkedIn messages that convert thought leadership signals into warm, peer-style conversations. Your task is to generate two versions of a direct message (DM) based on a LinkedIn post by a CHRO or HR leader about launching an AI Literacy Academy at [Company].

## Step 1: Collect Signal Input

Prompt the user to provide one of the following:

- A direct link to the LinkedIn post

- OR the text excerpt from the post

- OR the company/CHRO name so you can help find it via LinkedIn

Search guidance if needed:

- https://www.linkedin.com/company/[company]/posts/
- https://www.linkedin.com/in/[CHRO-name]/recent-activity/

## Step 2: Output Structure

### Version 1 – Signal-Based DM

- Max 40 words
- Reference the post directly (e.g., “saw your note on launching the AI academy…”)
- Acknowledge the initiative insightfully
- End with a soft, relevant curiosity

### Version 2 – Tightened DM + Asset Offer

- Compress the first message further
- Include a link or mention of a relevant resource
Example: “quick read on keeping adoption momentum going post-launch”
- Still under 40 words total
- Tone must remain peer-like and non-salesy

# Sample Output

## Version 1 – DM

Saw your note on launching the AI Literacy Academy — such a timely initiative. Curious how you’re planning to keep momentum high after the initial rollout. Have you gotten early feedback yet?

## Version 2 – DM + Asset

Loved your AI Academy post. If helpful, here’s a 2-min read on driving post-launch adoption — seen a few orgs use it to keep engagement up. LMK if useful.

SDR Prompt #4 – Frontline AttritionVoice Message Generator (≤ 30 sec)

Prompt

# Context:
You’re speaking as a blend of:
- results-driven SDR (concise)

- seasoned frontline manager (empathy)

- leadership coach (consultative authority).

Fixed signal
- Frontline attrition jumped from 14 % to 26 %.

# Tasks
## A. Version 1 (V1 script)
- Draft a voicemail that fits a 30-second slot (≈ 60–75 words).
- Lead with the 14 → 26 % attrition spike.
- Spark curiosity with one open question about impact.
- Signal urgency (cost, customer hit, or quarter-end).
- Close with one clear CTA: a quick callback to [Callback_Number].

## B. Version 2 (V2 warmer script)
- Rewrite V1 so it feels warmer and more human—name use, brief empathy line (“I know floors are stretched”), thankful close.
- Keep urgency cue and stay within 30 seconds.

Style Rules
- Plain language—no jargon.
- One ask only; no multiple CTAs.
- End with gratitude rather than a hard sell.

SDR Prompt #5 – Extract and Personalize Cold Outreach Using HR Initiatives from [Company]’s Latest Earnings Call

Prompt:
You are a senior SDR, Sales Leader, or RevOps Analyst researching target accounts for personalized outbound. Your task is to review the latest earnings call transcript for [Company], identify the #1 HR-linked strategic initiative, and then create a personalized cold outreach setup that links your AI-based solution to that initiative.

## Step 1: Request Input from the User

Prompt the user to provide:

- Target Company Name
- (Optional) Link to the earnings call transcript if already sourced

If not provided, suggest searching for the latest earnings transcript via:

Earnings Transcript Sources

- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://www.alphastreet.com
- https://ir.[companydomain].com
- https://www.sec.gov/edgar.shtml

Use keywords like:

- “talent,” “skills,” “hiring,” “workforce transformation,” “AI enablement,” “employee productivity,” etc.

# Step 2: Output Structure

## Version 1 – Strategic Initiative Summary

- One-sentence summary of the most relevant HR initiative mentioned in the transcript
- Stay close to the exec’s original language if possible
- Format:
“[Company] emphasized [HR initiative] in their latest earnings call, citing [goal/reason].”

## Version 2 – Initiative + Solution Mapping + Subject Line

- Add one sentence mapping the initiative to the pain point your AI product solves
- Finish with a subject line that includes both the initiative and the AI value
- Format:
“[Company] emphasized [HR initiative] in their latest earnings call, citing [goal]. This links directly to [problem your AI solves], which we address through [solution type].
Subject line: ‘[Company]’s [initiative] ↔ [AI capability]’”

# Example Output

## Version 1 – Summary

Unilever highlighted its shift toward skills-based hiring in the latest earnings call, citing the need to unlock internal mobility and fill roles faster amid global talent constraints.

## Version 2 – With Mapping + Subject Line

Unilever highlighted its shift toward skills-based hiring in the latest earnings call, citing the need to unlock internal mobility and fill roles faster. That directly aligns with the friction we help solve using AI-based skill-matching and internal talent discovery.
Subject line: ‘Unilever’s mobility push ↔ AI for skill-matching’

Auto run this in REVENOID (or manual run in ChatGPT for every account) before your next email, and you’ll never send a generic pitch again.

Prompts for AEs

AE Prompt #1 – Identify HR Pain Points from Attrition & DEI Mandates, and Quantify the ROI Impact

Prompt:

You are an Account Executive preparing for strategic outreach or discovery with HR or DEI leadership at [Company]. Your task is to analyze two key live signals:

1. +12% attrition
2. A newly announced DEI mandate

From these, extract the top three HR pain points that are likely blocking progress toward the company’s people goals (e.g., retention, DEI pipeline, onboarding, internal mobility, manager capability).

Then, quantify each pain with an ROI-related metric to strengthen your business case.

# Step 1: Ask the User for Input

Ask the user to provide:

- Target Company name
- (Optional) Known attrition reference (e.g., earnings call quote, layoff note, Glassdoor trend)
- (Optional) Link or quote from the company’s DEI initiative or statement

If not provided, guide them to research using:

For Attrition:

- Google: "attrition at [Company] 2024"
- https://www.glassdoor.com/Reviews
- https://www.alphastreet.com
- LinkedIn layoffs or exec-level comments

For DEI Mandate:

- LinkedIn:
https://www.linkedin.com/company/[company]/posts/

- HR media:

https://www.hrexecutive.com

https://www.prnewswire.com

- Company ESG or DEI report (check investor relations or newsroom)

# Step 2: Output Structure

## Version 1 – Pains Only

List 3 HR pain points created or exacerbated by the attrition + DEI mandate combination
Focus on blockers like DEI ramp failure, manager burden, onboarding inconsistency, etc.

Format:

• Pain 1: [Short, specific pain]
• Pain 2: [...]
• Pain 3: [...]

## Version 2 – Pains + ROI Metrics

- Re-list the 3 pains and attach an estimated financial, efficiency, or talent risk metric to each
- Use benchmarks if exact data is unavailable (e.g., average cost of attrition, productivity impact from churn)

Format:

• Pain 1: [Description] → [ROI metric]
• Example: “DEI onboarding breakdown → Each drop-off costs ~$58K in lost ramp + future diversity pipeline compounding effect”

# Sample Output

## Version 1 – Pains

• High early-tenure attrition undermines DEI cohort momentum
• Overloaded managers lack tools to support diverse new hires
• Skills gaps are growing due to lack of re-onboarding post-attrition

## Version 2 – With ROI Metrics

• DEI hires are churning early → ~$50K avg cost per failed onboarding cycle
• Managers stretched thin → 12% productivity dip across teams in exit-heavy orgs
• DEI progress reset by churn → Up to 9 months delay in pipeline diversity metrics

AE Prompt #2 – Handle HRIS Integration Objections with Strategic and Conversational Follow-Up Questions

Prompt:

You are an Account Executive responding to a concern from [Buyer] — likely a CHRO, Director of People Tech, or HR stakeholder — about integrating your AI solution with their existing HRIS (e.g., Workday, SAP SuccessFactors, UKG, Oracle HCM).

Your task is to draft two versions of follow-up questions:

# Step 1: Ask the User to Provide

1. The buyer’s role/title (e.g., CHRO, Director of HR Tech)
2. Target Company name (optional, but useful)
3. Known or suspected HRIS platform (e.g., Workday, Oracle HCM, SAP)

If unknown, suggest they search via:

- Job posts on https://www.linkedin.com/company/[company]/jobs
- Tools like

https://www.g2.com

or

https://www.slintel.com
- Public RFPs, ESG reports, or HR tech stack references in earnings calls

# Step 2: Output Structure

## Version 1 – Strategic Follow-Up Questions

Draft three questions aimed at uncovering the root of the integration concern.

– Keep questions focused and structured
– Target potential pain points: security, change management, vendor fatigue, IT bottlenecks

Format:

• What’s the core integration friction you're anticipating with [HRIS]?
• Are there specific data flows or existing workflows you're looking to protect?
• Has [Company] attempted to integrate other AI tools with [HRIS] before?

## Version 2 – Conversational Rewrite

Rewrite those same questions in a more natural, collaborative tone.

- Use phrasing that reduces tension
- Encourage co-exploration
- Signal empathy and openness to adapt

Format:

• Totally get it — what kind of friction have you seen before when plugging something into [HRIS]?
• Is it more about avoiding disruption to what’s working, or just not wanting to open another IT ticket?
• Have you all looked at layering AI into [HRIS] yet, or is that something you’re still evaluating?

# Example Output

## Version 1 – Strategic Questions

• What’s the biggest blocker you anticipate in integrating this with Workday?
• Are there specific approval layers or IT dependencies we should be aware of?
• Have you tried layering analytics or AI into Workday previously — and if so, how did it go?

## Version 2 – Conversational Rewrite

• Totally fair — where do you usually see things jam up with Workday integrations?
• Is this more about internal bandwidth or guarding the current workflows?
• Curious — have you already explored any AI add-ons for Workday, or still feeling that out?

AE Prompt #3 – Create a One-Page Demo Brief + Slide Headlines Framing AI Outcomes for CHROs

Prompt:
You are an Account Executive preparing for a CHRO-level sales conversation. Your task is to:

1. Write a 1-page demo brief that highlights the three most strategic outcomes your AI product delivers to CHROs.
2. Add three corresponding slide headlines that could anchor a sales deck or discovery narrative.

Your output should be clear, executive-level, and tightly aligned with what CHROs care about: workforce transformation, retention, DEI, onboarding speed, skill development, or HR cost reduction.

# Step 1: Ask the User to Provide

Prompt the user for:

1. A short description of what their AI product does
- e.g., “AI-powered onboarding personalization”
- or “AI for mapping and activating workforce skills”

2. Who their target HR persona is
- e.g., CHRO, VP of Talent, Head of L&D

If not known, offer to help categorize it based on function or goal.

Also offer optional links to research CHRO priorities:

– https://www.hrexecutive.com
– https://www.mckinsey.com/capabilities/people-and-organizational-performance
– https://www.gartner.com/en/human-resources

# Step 2 – Output Structure

## Version 1 – Demo Brief: 3 Outcomes

List three strategic outcomes delivered by the AI solution. Each should include:

- The outcome (headline-style)
- A short sentence or clause explaining it or providing a real-world example

Format:

• Outcome 1: Accelerated onboarding → Personalized ramp plans cut time-to-productivity by 30%
• Outcome 2: Reduced early attrition → Adaptive nudges help managers support at-risk new hires
• Outcome 3: DEI ramp success → Real-time insights flag drop-offs across diverse cohorts

## Version 2 – Add 3 Slide Headlines

Create three slide titles (1 per outcome) that summarize the core narrative of your demo:

- Use short, powerful language
- Make the value obvious at a glance
- Match each slide title to its respective outcome

Format:

• Slide 1: “Onboarding in half the time — personalized from Day 1”
• Slide 2: “Stop early attrition before it starts”
• Slide 3: “DEI onboarding that scales — and sticks”

AE Prompt #4 – Write a Discovery Follow-Up Email That Recaps Pains, Outlines Next Steps, and Adds Relevant Social Proof

Prompt:

You are an Account Executive following up after a discovery call with a buyer (e.g., CHRO, VP of Talent, People Ops Lead). Your task is to write a follow-up email that does the following:

1. Recaps the 2–3 core pain points discussed — use their language wherever possible
2. Outlines the agreed-upon next steps in clear, friendly terms
3. In a second version, adds a relevant case study, benchmark, or customer story link to reinforce credibility and alignment

# Step 1: Ask the User to Provide

Prompt the user for:

– 2–3 short pain points from the discovery call (phrased in buyer language if possible)
– The agreed next step(s)
– A relevant case study, benchmark, or customer proof link
OR offer to help them find one using:

Case Study / Benchmark Sources:

Internal sales enablement docs
Public customer pages or PDF decks

https://www.forrester.com

https://www.gartner.com
https://www.linkedin.com/company/[yourcompany]/posts

https://www.hrexecutive.com

# Step 2 – Output Structure

## Version 1 – Follow-Up Email (Recap + Next Steps)

- Friendly subject line (optional)
- Opening line of thanks
- Three bullets listing the key pain points
- One line confirming next step(s)
- Close with light invitation to reach out if priorities shift

Format:

Hi [Name],

Thanks again for the time today — great to hear where [Company] is focusing. Here’s what stood out from our conversation:
• [Pain 1]
• [Pain 2]
• [Pain 3]

Next step: [insert action or meeting]. Let me know if anything shifts in the meantime — happy to stay close.

## Version 2 – Enriched Email (Add Social Proof)

- Add 1–2 lines pointing to a case study, customer win, or benchmark stat
- Keep tone helpful, not promotional

- Link to the asset if possible

Format:

PS — Sharing this in case it's helpful: how [Similar Company] tackled [similar pain] and saw [result] → [link]

Always happy to unpack how this could apply to [Company] when the time’s right.

# Sample Output

## Version 1 — Recap Email

Hi Jamie,

Really enjoyed the conversation today — appreciate the transparency around what you’re tackling. From our discussion, I captured:
• Managers struggling to onboard new hires consistently
• Early attrition spiking in frontline teams
• HR team overloaded with manual onboarding touchpoints

Next step: loop in your HRIT partner for feasibility review. Let me know if anything changes on your end.

## Version 2 — With Case Study

PS — Thought this might resonate: how Acme Co. cut new hire ramp time by 30% and boosted 90-day retention by 22% using a similar flow → [link]

Happy to share more if helpful.

AE Prompt #5 – Probe AI ROI Expectations Using Direct and Consultative Peer-Framed Questions

Prompt:

You are an Account Executive engaging with a buyer (e.g., CHRO, VP of Talent, People Analytics Lead) who is evaluating your AI solution. Your task is to:

1. Write a direct but respectful question that probes the buyer’s expectations around AI ROI (return on investment or impact).

2. Reframe that same intent as a consultative, peer-informed question, using a quote or anecdote from a similar customer or company.

This helps you understand what success looks like for the buyer — without sounding transactional — and positions you as a trusted, insight-led partner.

# Step 1: Ask the User to Provide

Prompt the user for:

- Buyer’s title/role (e.g., CHRO, VP of People, Director of L&D)
- (Optional) A real or paraphrased quote from a similar buyer (from case study, call, or testimonial) that speaks to how they defined AI ROI or impact
If no quote is available, offer a few templates (below)

Example Peer Quote Templates:

- “We were just looking to prove AI worked — not solve everything at once.”
- “If it moved the needle on onboarding time, that was enough to justify it.”
- “ROI for us meant time back for HR and better retention in month one.”

# Step 2 – Output Structure

## Version 1 – Direct ROI Question

Craft a straight, respectful question that helps uncover how the buyer will evaluate success.

Format examples:

— What does success look like to you if you move forward with this?
— Are there specific outcomes or ROI metrics that matter most in making this work for your team?
— What kind of win would you need to see for this to feel worth it?

## Version 2 – Reframed Peer-Led Question

Take the same core idea and reframe it as a consultative conversation using a peer quote or customer insight.

Format examples:

— One People Ops lead we spoke to said, “We didn’t need AI to solve everything — we just needed to see some ramp-time reduction in 30 days.” Curious what a meaningful win looks like for you?

— I’ve heard from a few HR teams that ROI here usually means time savings or attrition reduction — not hard dollars right away. Is that the case for your team, or something else?

NOTE: Revenoid will do this automatically for all your target accounts.

Prompts for Sales Enablement Leader

Sales Enablement Prompt #1 – Train Sales Reps to Distinguish Signals from Intent + Provide Good & Bad Examples

Prompt:

You are a Sales Enablement Lead (or RevOps leader) training SDRs and AEs to become sharper, insight-led sellers. Your task is to:

1. Draft a training prompt that helps reps clearly distinguish between signals (surface-level public clues) and intent (real indicators of buying motion).

2. Add examples — good and bad — that show how reps might confuse or correctly interpret these inputs in real GTM scenarios.

The focus should be on helping reps use signals to guide research and personalization, but rely on intent to qualify engagement or action.

# Step 1: Ask the User to Provide

Prompt the user for:

1. A list of signal types reps typically track (e.g., CHRO LinkedIn post, job posting, earnings call insight)
2. A working definition of intent in their GTM motion (e.g., AI-readiness, onboarding pain, manager enablement)
3. The tools reps use to gather signal/intent (e.g., LinkedIn, job boards, 6sense, Gong, CRM)

If not provided, suggest default examples like:

– Signal: “Hiring a Head of People Analytics”
– Intent: “CHRO states in podcast they’re rethinking onboarding tech in Q3”

# Step 2 – Output Structure

## Version 1 – Training Prompt

Write a short, realistic training scenario that reps can react to.

Format:

Scenario: You’re researching [Company]. You notice they’ve posted a job for [“VP, Talent Intelligence”] and their CHRO recently shared an article about reskilling.

• Is this a signal or intent?
• What makes it either?
• What additional info would help you determine whether this is worth reaching out?

Encourage reps to identify:

- What’s merely informational (signal)
- What shows readiness, ownership, or urgency (intent)

## Version 2 – Add Good and Bad Examples

Good Examples (correct interpretation):

- Signal: “They posted for a DEI Program Manager” → May indicate priority, but not necessarily buying motion.
- Intent: “CHRO said on a podcast, ‘We’re overhauling onboarding this quarter.’” → Specific, time-bound, buyer-owned.

Bad Examples (confused signal as intent):

- “They just raised funding — so they’re buying something.” → Broad signal, not specific to your problem.

- “They shared an article about AI on LinkedIn — must be ready to talk.” → Interest ≠ buying motion

Add a note:

Reps should pair signals with context to infer intent — not assume one equals the other. Ask: Who said it? Is there urgency? Is it aligned to our solution space?

Sales Enablement Prompt #2 – Train Reps to Navigate AI Risk Concerns in Discovery Conversations

Prompt:

You are a Sales Enablement Lead or Account Executive building training materials for reps who are selling AI products into HR, IT, or operations. Your task is to:

1. Generate a mock call scenario where a prospect raises a concern about AI risk (bias, data handling, compliance, explainability, or trust).
2. Append three strong follow-up questions that a skilled rep would ask to explore the objection — not dismiss it or over-pitch.

This helps reps build confidence handling objections rooted in risk, while learning to listen, clarify, and align with how the buyer defines “safe” AI.

# Step 1: Ask the User to Provide

Prompt the user for:

- The persona who would raise the objection (e.g., CHRO, VP People Analytics, IT Security Lead)
- The type of AI risk to simulate (e.g., bias, privacy, data exposure, explainability, trust)

- (Optional) A real or paraphrased quote from a previous call or deal loss tied to risk

If not provided, default to a commonly heard risk like:

“We’re nervous about bias in AI, especially in anything related to hiring or promotion decisions.”

You can also help the user source realistic risk quotes from:

https://www.hrexecutive.com
https://www.gartner.com/en/artificial-intelligence
https://www.linkedin.com/search/results/content/?keywords=ai%20risk%20bias

# Step 2 – Output Structure

## Version 1 – Mock Call Prompt

Create a short role-play prompt to simulate the objection.

Format:

Scenario: You’re on a discovery call with the CHRO at [Company].
Midway through, they pause and say:

“Look, we’re intrigued by the AI — but we’ve also seen these models reinforce bias, especially around promotion or performance feedback. That’s a big red flag internally.”

Prompt: How do you respond?

## Version 2 – Add Follow-Up Questions

Append three thoughtful follow-up questions the rep could ask to explore the concern.

Format:

• Have you had a specific experience with that in the past — either at [Company] or somewhere else you’ve worked?
• What kind of safeguards or transparency would give your team more confidence?
• Is there someone internally (IT, Legal, DEI) who usually reviews AI tools from a compliance or risk lens?

Sales Enablement Prompt #3 – Turn 3 Buyer Signals into a Strategic Value Story, Then Refine for ROI Logic

Prompt:

You are an Account Executive preparing for outbound, a follow-up email, or a discovery recap. Your task is to turn three observed signals from a target account into a strategic value story — and then tighten that story using ROI framing.

This will help you frame urgency and connect your AI solution to a business outcome that resonates with decision-makers.

# Step 1: Ask the User to Provide

Prompt the user for:

- Target Company Name
- The three buyer signals they’ve observed (e.g., job post, exec quote, earnings call note)
- A short description of their AI product and what outcome it enables (e.g., onboarding speed, retention, DEI hiring)

If needed, guide them to find signals via:

1. LinkedIn posts:
https://www.linkedin.com/company/[company]/posts/

2. Job listings:
https://www.linkedin.com/jobs,

https://www.indeed.com

3. Earnings call transcripts:
https://www.seekingalpha.com/earnings/earnings-call-transcripts

4. Google News + "site:[company].com"

# Step 2 – Output Structure

## Version 1 – Value Story Prompt

Write a short narrative (2–3 sentences) that weaves together the three signals and positions your solution as the timely next step.

Format Example:

[Company] is clearly gearing up for change — they’ve launched an AI skills academy, are hiring a Head of People Analytics, and just announced a DEI ramp initiative. That signals serious focus on talent agility, data-driven decision-making, and equity. They’re likely looking for ways to accelerate impact and prove outcomes fast — which is where [your AI solution] fits.

## Version 2 – ROI-Tightened Version

Refine that story into a concise statement that anchors in metrics, business risk, or financial impact.

Format Example:

With a DEI ramp, people analytics hire, and AI academy launch, [Company] stands to shorten time-to-impact by 30% and reduce talent churn costs by 6–7 figures — if they deploy the right AI-powered enablement layer now.

Sales Enablement Prompt #4 – Create a Knowledge-Check Quiz on Top AI Objections + Provide Sample Answers

Prompt:
You are a Sales Enablement Lead building a training module to help AEs or SDRs navigate the most common AI objections they face from HR, IT, or Finance buyers. Your task is to:

1. Write a quiz with 3–5 short scenarios where a prospect raises a common objection to AI tools (e.g., bias, explainability, integration lift, ROI uncertainty).

2. For each question, provide a multiple-choice or open-ended format.

3. Then, provide sample answers that explain the correct reasoning and offer a brief, talk-track style response.

# Step 1: Ask the User to Provide

Prompt the user for:

1. 3–5 objections their team hears most (optional — use defaults if not provided)
2. The AI product category their team sells into (e.g., HR tech, onboarding, workforce analytics)
3. The buyer persona(s) most likely to raise those objections (e.g., CHRO, CIO, CFO, Head of People Analytics)

If not provided, use this default list of objections:

1. Bias or fairness concerns
2. Lack of explainability
3. IT lift or integration burden
4. HRIS redundancy
5. Unclear ROI

# Step 2 – Output Structure

## Version 1 – Quiz

Example format:

Scenario: The CHRO says, “We’ve been burned by AI tools that introduced bias in how candidates were ranked.”

Q1: What’s the root concern here?
a) Cost
b) DEI risk and brand exposure
c) Onboarding workflows
d) Feature depth

Q2: What would you ask next to keep the conversation open?

## Version 2 – Sample Answers

Provide:

- Correct answer from multiple-choice (with explanation)
- Suggested follow-up response (1–2 sentence talk track)

Example:

Correct answer: b) DEI risk and brand exposure

✔ Sample follow-up: “Totally fair. More teams are building AI into their DEI review process — curious how you’ve handled fairness audits in the past, or who owns that on your team?”

Sales Enablement Prompt #5 – Train Reps to Spot Strategic Hiring Signals vs. Noise Using Flashcards + Usage Tip

Prompt:
You are a Sales Enablement Lead training SDRs and AEs to distinguish between strategic hiring signals (which warrant outreach) and hiring noise (which doesn’t). Your task is to:

1. Generate 4–6 flashcards that contrast job posts or hiring events.
- On the front of each card: show a realistic job post or description.
- On the back: label it as either “Hiring Noise” or “Strategic Signal”, with a short explanation.

2. Then, add a usage tip that helps reps apply this knowledge when reviewing job boards or company LinkedIn pages.

# Step 1: Ask the User to Provide

Prompt the user for:

- The AI product category or solution their reps are selling (to tailor the relevance of signals)
- Common roles or hiring patterns they’ve seen misused by reps
- Any titles or language that typically indicate transformation (e.g., “building,” “scaling,” “stand up a new function”)

If not provided, default to examples from HR tech and people analytics, and suggest reviewing:

https://www.linkedin.com/company/[company]/jobs

https://www.indeed.com
https://builtin.com/jobs

# Step 2 – Output Structure

## Version 1 – Flashcards

Create flashcards in this format:

Front: “Now hiring: 10 Customer Success Associates – seasonal roles”
Back: ❌ Hiring Noise — volume-based hiring, no indication of new program or strategic shift

Front: “VP, People Analytics – build centralized reporting for skills strategy”
Back: ✅ Strategic Signal — implies new executive function tied to skills transformation

Front: “We’re growing fast — hiring a Recruiter in every region!”
Back: ❌ Hiring Noise — growth message, but no direct link to transformation or buyer pain

Front: “Director of EX Enablement — own onboarding redesign in 2024”
Back: ✅ Strategic Signal — shows clear initiative, buyer alignment, and executive support

## Version 2 – Add Usage Tip

End with a concise, practical tip for reps to apply.

Example:

💡 Usage Tip: Prioritize roles that include phrases like “own,” “build,” “lead,” or “reimagine” — especially in HR, EX, DEI, or analytics. These often signal transformation aligned to buying behavior.

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If you’re not a subscriber, here’s what you missed earlier:

1. Bonus Prompts - Selling to CIOs using AI – Part 2

2. Intelligence Layer for Sales Teams : A guide for having context-aware thinking sales systems

3. The Ultimate Messaging Framework (with AI Prompts) Playbook for High-Performance Sales Teams : Part 1 of 2

4. Multi-Channel Sequences and Strategic Pain Signals - Strategies of top sales teams

5. AI Prompts for Sales Managers - Sales Collaterals and Customer Objections: Part 2 of 3

6. AI Prompts for Sales Managers - Part 1 of 3

7. Playbook - Selling an HRTech solution to enterprises using Sales AI

8. Playbook for selling a "Cyber Security" solution to enterprises - Using AI Co-pilot

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