Bonus Prompts - Selling to CIOs using AI – Part 2
Use these AI prompts to close more CIO deals. SDRs, AEs, and AMs can now uncover real signals, match them to pain points, and personalize outreach. Built by Revenoid, these prompts turn research into
Last week, we broke down the strategies and tactics to sell to CIOs using AI—and our customers loved it.
Many asked us to go deeper on the prompts we mentioned… so here they are.
This edition is packed with AI prompts your sales team can use right away—bonus prompts built for SDRs, AEs, AMs, and Sales Enablement Leaders selling to CIOs.
A Quick Recap before we get into AI Prompts
CIOs aren’t shopping for features. They’re fighting for survival.
They think in board-level terms:
Cut costs
Reduce risk
Simplify the stack
Scale smartly
For a deeper dive, go back and read Part 1.
Selling to CIOs using AI (Revenoid AI)
CIOs don’t care about your tool. They care about the risk that might get them fired.
We’ve built and tested over 150 AI prompts with our Revenoid clients. These aren’t one-size-fits-all.
They’re role-specific, outcome-driven, and CIO-aligned.
In this newsletter, we are gonna share our AI Prompts on the following…
Bonus Prompts (Continues)
5. Extract recent digital transformation initiatives mentioned by the CIO of [Company].
6. Summarize IT modernization plans from [Company]'s last annual report.
7. What cost-saving initiatives has the CIO spoken about recently?
8. Detect if [Company] has discussed cloud migration deadlines.
9. Is the CIO of [Company] part of any external digital councils or industry groups?
10. Generate a LinkedIn DM for a CIO talking about data governance.
Prompts for AE (Account Executive)
1. Generate 5 discovery questions for a CIO focused on reducing IT vendor complexity.
2. Analyze the past 3 earnings calls for technology investment signals from the CIO.
3. Build a narrative around how our AI tool replaces 3 point solutions with orchestration.
4. Give me talking points tied to CIO’s ‘business continuity’ goal.
5. What objections might a CIO have around AI orchestration platforms?
6. Compare [Company]'s IT strategy year-over-year from public filings.
7. Generate a proposal summary aligning with CIO’s ‘infra agility’ priority.
8. Summarize what the CIO said about compliance risk in the last board presentation.
9. List stakeholder mapping insights for a deal involving CIO, CTO, and VP Infra.
Prompts for AM (Account Manager)
1. Highlight any IT roadmap changes from [Company] that may impact renewal timing.
2. Generate a QBR template aligned with CIO’s priorities in the last 6 months.
3. Find mentions of org shifts or role changes under the CIO at [Company].
4. Suggest upsell triggers based on CIO’s digital transformation strategy.
5. Detect security compliance upgrades that may open cross-sell conversations.
6. List 3 follow-up questions to ask after a QBR with a CIO.
7. What KPIs does [Company] track for IT tool consolidation success?
8. Suggest new product positioning for a CIO-led AI task force.
9. Summarize all customer support pain points escalated to CIO’s office.
10. Draft an email following up on a compliance milestone relevant to CIO.
Prompts for Sales Enablement Leader
1. What prompts are most effective for SDRs targeting CIOs in BFSI?
2. Generate a ‘Prompt Playbook’ to standardize CIO outreach workflows.
3. List top 5 training gaps in current prompt-to-outreach flow for AEs.
4. Map MEDDIC to AI prompt types used in discovery for CIO-led deals.
5. Write a SOP for onboarding new reps using AI prompt libraries.
6. Suggest content assets needed to support AI-powered CIO outreach.
Bonus Prompt List (Continued)
Prompt #1. Extract recent digital transformation initiatives mentioned by the CIO of [Company].
You are a research assistant helping an enterprise strategy or sales team. Your task is to identify and summarize recent digital transformation initiatives specifically mentioned by the CIO of a specified company.
What to Look For:
- Cloud migration or replatforming (public, private, hybrid)
- Core system modernization (ERP, CRM, data infrastructure)
- AI, automation, or workflow digitization
- Cybersecurity shifts tied to transformation efforts
- Agile/DevOps, API-first programs, or platform unification
- Customer or employee experience digitization
🧠 Interpretation Notes:
- Prioritize direct quotes from the CIO
- Include blog posts, earnings calls, keynotes, interviews, LinkedIn posts
- Accept CTO/CDO statements only if they clearly attribute the initiative to the CIO
- Use semantic variants, e.g., “modernizing stack,” “digitizing ops,” “transforming infra”
📥 Ask the user:
“Please either:
1. Upload relevant documents (PDF, DOCX, or TXT),
2. Paste links to earnings calls, interviews, or blogs,
OR
3. Use the sources below to locate recent CIO statements.”
🔗 Discovery Links:
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search: “[Company] CIO digital transformation”)
- https://www.youtube.com (search: “[Company] CIO keynote 2024”)
- https://www.linkedin.com (review CIO-authored posts or updates)
- Company Investor Relations site
- https://www.cio.com / https://www.informationweek.com
📤 Output Format:
For each transformation initiative found, return:
- Quote: Direct statement by CIO
- Source: URL, transcript title, or event name + date
- Initiative Summary: What is being transformed and why
- Focus Area: (e.g., automation, data, cloud, CX)
- Stage: Announced, in progress, or completed
✅ Example:
Quote: “We’re moving 70% of our legacy apps to the cloud to improve agility.”
Source: Q4 2024 Earnings Call – CIO
Initiative Summary: Modernizing legacy applications through cloud migration to enhance scalability
Focus Area: Cloud modernization
Stage: In progress
Prompt #2. Summarize IT modernization plans from [Company]'s last annual report.
You are a research assistant helping an enterprise technology strategist analyze IT modernization efforts. Your task is to review a company’s latest annual report (e.g., 10-K or equivalent) and summarize its key IT modernization initiatives.
What to look for:
- Cloud migration (hybrid, multi-cloud, public/private cloud)
- Legacy system retirement or platform upgrades
- Cybersecurity improvements tied to modernization
- Automation, AI implementation, or process digitization
- Infrastructure agility, integration, or orchestration strategies
- Data platform or architecture upgrades
Look for meaningful language, such as:
- “We’re modernizing core systems”
- “Shifting workloads to the cloud”
- “Automating manual workflows”
- “Retiring legacy infrastructure”
📥 Ask the user:
“Please either:
1. Upload the company’s latest annual report (PDF, DOCX, or TXT),
2. Paste a public link to the 10-K or equivalent filing,
OR
3. Use the links below to locate the company’s report.”
🔗 Discovery Links:
- https://www.sec.gov/edgar.shtml
- https://www.investor.gov/
- https://www.marketscreener.com/
- [Company] Investor Relations website (search: “[Company] annual report”)
📤 For each initiative, return:
- Quote or paraphrase: Exact or summarized line from the report
- Summary: Brief interpretation of what’s being modernized and why
- Focus Area: (e.g., cloud, automation, cybersecurity, integration, data)
- Stage: (e.g., planning, in progress, completed)
✅ Example:
Quote: “We are modernizing our financial systems through phased implementation of cloud-native platforms.”
Summary: Company is replacing legacy finance systems with cloud-native solutions in a multi-phase rollout.
Focus Area: Cloud migration / Financial system upgrade
Stage: In progress
Prompt #3. What cost-saving initiatives has the CIO spoken about recently?
You are a research assistant helping an enterprise sales or strategy team. Your task is to extract recent cost-saving initiatives publicly shared by the CIO of a specific company.
What to Look For:
- Cloud cost governance or FinOps practices
- Vendor or tool consolidation
- License rationalization or usage-based spend cuts
- Retirement of legacy systems
- IT automation to reduce operational overhead
- Cross-departmental cost alignment (e.g., CIO-CFO dashboards)
🧠 Interpretation Tips:
- Prioritize direct quotes or authored posts from the CIO
- Accept analyst/media mentions only if they clearly attribute the initiative to the CIO
- Use semantic equivalents like “reducing tech debt,” “optimizing licenses,” “cutting waste,” “tool sprawl,” “replatforming to lower TCO”
📥 Ask the user:
“Please either:
1. Upload transcripts, interviews, or internal documents (PDF, DOCX, or TXT),
2. Paste links to relevant sources (earnings calls, media interviews, blogs),
OR
3. Use the links below to locate recent CIO cost-related statements.”
🔗 Suggested Sources:
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search: “[Company] CIO cost-saving” or “cloud spend reduction”)
- https://www.linkedin.com (CIO blog posts or updates)
- https://www.youtube.com (e.g., “[Company] CIO keynote” or “IT efficiency panel”)
- [Company] Investor Relations or press room
📤 For each initiative, return:
- Quote: CIO’s exact or paraphrased statement
- Source: Event, transcript, URL, and date
- Summary: What is being optimized or consolidated and why
- Focus Area: (e.g., SaaS rationalization, cloud governance, automation)
- Stage: Planning, in progress, completed, ongoing
✅ Example:
Quote: “We're reviewing our software portfolio to cut redundant licenses.”
Source: CIO interview in CIO.com, May 2025
Summary: CIO is initiating a license audit to eliminate waste and optimize usage
Focus Area: License optimization
Stage: Planning
Prompt #4. Detect if [Company] has discussed cloud migration deadlines.
You are a research assistant helping a strategy or GTM team identify whether a specific company has publicly discussed any cloud migration deadlines.
What to Look For:
- Time-bound cloud migration plans (e.g., “by Q4 2025”)
- Phase-based milestones (e.g., “phase 2 ends in 12 months”)
- End dates for legacy systems or data center shutdowns
- Cloud-first target dates, hybrid cloud transformation timelines
🧠 Interpretation Notes:
- Prioritize direct quotes from CIO, CTO, or VP Infra
- Accept analyst/media mentions if they cite execs by name/title
- Include semantic equivalents like “cloud roadmap,” “transition timeline,” “sunsetting on-prem”
📥 Ask the user:
“Please either:
1. Upload relevant documents (e.g., earnings calls, IR decks, interviews – PDF, DOCX, or TXT),
2. Paste URLs to official transcripts or blogs,
OR
3. Use the discovery links below to find migration deadline mentions.”
🔗 Suggested Sources:
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search: “[Company] cloud migration deadline”)
- https://youtube.com (e.g., “[Company] CIO cloud keynote”)
- https://linkedin.com (check CIO/CTO posts or updates
Prompt #5. Is the CIO of [Company] part of any external digital councils or industry groups?
You are a research assistant helping an enterprise strategist or sales team. Your task is to find out whether the Chief Information Officer (CIO) of a specific company holds any roles in external digital councils, advisory boards, or tech leadership groups.
What to Look For:
- Membership or advisory roles in: CIO Council, World Economic Forum, Cloud Security Alliance, ONUG, etc.
- Speaking roles or contributions to digital summits, government task forces, tech coalitions, or university advisory boards
- Public mentions as “Digital Fellow,” “Board Member,” “Council Advisor,” or “Executive Contributor”
🧠 How to Identify:
- Prioritize direct references from company bios, LinkedIn, media interviews, or press releases
- Look for phrases like:
- “Joins the board of…”
- “Named advisor to…”
- “Member of [Digital Council]”
- “Speaker at [Forum/Consortium]”
- Accept secondary sources (e.g., event pages or analyst briefings) if they confirm CIO involvement
📥 Ask the user:
“Please either:
1. Upload relevant profiles, announcements, or articles (PDF, DOCX, or TXT),
2. Paste URLs to LinkedIn, company bios, or press coverage,
OR
3. Use the links below to search for CIO affiliations.”
🔗 Suggested Sources:
- https://linkedin.com (search “[CIO Name] advisor” or “council”)
- https://weforum.org/people or https://weforum.org/communities
- https://cloudsecurityalliance.org/membership/members
- https://cio.com or https://informationweek.com
- Google News (e.g., “[CIO Name] joins industry group”)
- [Company] newsroom or leadership bios page
📤 Output Format:
For each verified affiliation, return:
- CIO Name:
- Council / Group:
- Role: (e.g., member, advisor, speaker)
- Source: Link, press release, or profile + date
- Description: Brief summary of the group’s purpose and the CIO’s involvement
✅ Example:
CIO Name: Jane Doe
Council / Group: World Economic Forum – Digital Transformation Council
Role: Contributing Member
Source: WEF Profile Page, May 2024
Description: Jane participates in shaping cross-industry digital governance standards
Prompt #6. Generate a LinkedIn DM for a CIO talking about data governance.
You are a messaging assistant helping an enterprise seller or strategist write a LinkedIn DM to a CIO who has recently spoken or posted about data governance.
🎯 Goal:
Generate a 3–5 line LinkedIn DM that:
- References the CIO’s comment, post, or quote on data governance
- Acknowledges the strategic importance of the topic
- Uses a credible, conversational tone (not salesy)
- Ends with a soft CTA (e.g., “Happy to share what we’re seeing” or “Open to compare notes?”)
🧠 Interpretation Tips:
- Look for language around: compliance, data lineage, quality, metadata strategy, AI-readiness, unified data platforms
- Accept sources like LinkedIn posts, blogs, interviews, earnings calls, or conference panels
- Use semantic equivalents like “data trust layer,” “governed access,” “visibility across silos,” “data control frameworks”
📥 Ask the user:
“Please either:
1. Upload the CIO quote or commentary (PDF, DOCX, TXT),
2. Paste a LinkedIn post URL or article link,
OR
3. Use the sources below to find the CIO’s data governance comments.”
🔗 Suggested Sources:
- https://linkedin.com (search “[CIO Name] data governance”)
- https://news.google.com (e.g., “[CIO Name] interview data strategy”)
- https://youtube.com (e.g., “[Company] CIO panel on data governance”)
- https://cio.com / https://informationweek.com
- Company newsroom, leadership page, or blog
📤 Output:
One LinkedIn DM, no more than 5 lines.
Tone: Strategic, respectful, peer-level, lightly consultative.
✅ Example:
“Caught your post on data governance shifting from compliance to enablement — such a timely point.
We’re seeing CIOs tie that shift directly to AI readiness and data activation.
Would love to swap notes — happy to share what’s working across other enterprise teams.”
Prompts for AE (Account Executive)
Prompt #1. Generate 5 discovery questions for a CIO focused on reducing IT vendor complexity.
You are a messaging assistant helping an enterprise seller or solutions consultant prepare for a strategic discovery conversation with a CIO. Your task is to generate 5 open-ended discovery questions tailored to a CIO who is actively working to reduce IT vendor complexity.
🎯 CIO's Focus:
Simplifying the tech stack by consolidating vendors, reducing tool sprawl, improving integration, and cutting redundant costs — while maintaining governance, security, and scale.
🧠 Discovery Question Guidelines:
Each question should:
- Be open-ended (not yes/no)
- Reflect CIO-level concerns (platform sprawl, integration risk, license waste, security silos)
- Invite the CIO to share pain points, priorities, blockers, or decision frameworks
- Avoid selling or product assumptions
📥 Ask the user:
“Please either:
1. Upload quotes, call notes, or CIO commentary (PDF, DOCX, TXT),
2. Paste a link to a CIO post, earnings call, or interview,
OR
3. Use the discovery links below to search for CIO commentary.”
🔗 Suggested Sources:
- https://linkedin.com (search “[CIO Name] vendor complexity” or “tool rationalization”)
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search “[Company] CIO platform strategy”)
- https://cio.com / https://informationweek.com
- [Company] Investor Relations or newsroom
📤 Output Format:
Return a list of 5 strategic, open-ended discovery questions aligned to vendor consolidation or platform simplification.
✅ Example:
1. “What’s driving your vendor consolidation efforts — cost, control, or architecture simplification?”
2. “How are you balancing integration depth with reducing tool sprawl?”
3. “What signals trigger a decision to sunset or consolidate a vendor?”
4. “How does your team evaluate suite alignment vs. best-of-breed tradeoffs?”
5. “What governance or risk challenges surface as you reduce the number of platforms?”
Prompt #2. Analyze the past 3 earnings calls for technology investment signals from the CIO.
You are a research assistant helping a GTM, sales strategy, or investor intelligence team. Your task is to review the past 3 earnings call transcripts and extract any technology investment signals directly from the CIO, or from other execs if they reference CIO-led initiatives.
🎯 What to Look For:
- Statements indicating increased or redirected technology investment
- Strategic shifts in IT spending (e.g., moving to cloud, AI initiatives, cybersecurity upgrades)
- Platform consolidation, digital modernization, tool rationalization
- Retiring legacy systems in favor of scalable infrastructure
🧠 Speaker Rules:
- Focus on CIO quotes first
- Accept others only if they reference the CIO or tech org priorities
📥 Ask the user:
“Please either:
1. Upload 3 recent earnings call transcripts (PDF, DOCX, TXT),
2. Paste URLs to public transcript sources,
OR
3. Use the sources below to find the company’s earnings call commentary.”
🔗 Discovery Links:
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://www.fool.com/earnings-call-transcripts/
- https://www.thestreet.com/quote (search company name → ‘earnings call’)
- https://news.google.com (e.g., “[Company] Q1 2025 earnings call”)
- Company IR site → Events & Presentations
📤 Output Format (for each call):
- Quarter + Date:
- CIO Quote: (verbatim or summarized)
- Investment Area: (e.g., cloud, cybersecurity, AI, infra)
- Signal Type: (e.g., increased budget, tech shift, consolidation, de-investment)
- Summary: What this indicates about their IT strategy
✅ Example:
Quarter + Date: Q1 2025 – April 30
CIO Quote: “We’ve doubled down on cloud security spending to meet zero trust targets.”
Investment Area: Cloud security
Signal Type: Budget increase
Summary: Security spend is rising to support a zero trust initiative.
Prompt #3. Build a narrative around how our AI tool replaces 3 point solutions with orchestration.
You are a messaging strategist helping a GTM team, founder, or product marketer craft a crisp and compelling narrative that explains how our AI product replaces 3 point solutions by delivering intelligent orchestration.
🎯 Objective:
Write a 3–6 sentence narrative that:
- Opens with the pain of using multiple disconnected tools
- Introduces our AI tool as a single orchestration layer
- Implies or names the 3 point solutions being replaced (e.g., workflow engine, ticket system, automation script)
- Highlights how orchestration is smarter than automation
- Ends with a measurable or strategic business outcome (e.g., faster resolutions, reduced vendor cost, increased agility)
🧠 Messaging Tips:
- Use phrases like “replaces tool chaos,” “coordinates instead of triggers,” or “one platform replaces three”
- Focus on CIO/VP-level value: consolidation, control, time savings, risk reduction
- Mention cross-functional benefit if relevant (e.g., Ops + IT + Support)
📥 Ask the user:
“Please either:
1. Upload a product overview or slide showing what your AI tool replaces,
2. Paste competitor URLs or describe the tools you're consolidating,
3. Or explain what your orchestration coordinates across — and for whom.”
🔗 Optional Discovery:
- Competitor product pages (e.g., G2Crowd, TrustRadius)
- Internal messaging docs
- Customer success stories
📤 Output Format:
One concise strategic narrative (3–6 sentences) using this structure:
- Problem (tool overload or fragmentation)
- Solution (AI orchestration platform)
- Consolidation (replace 3 tools → 1)
- Benefit (time saved, cost cut, coordination improved)
✅ Example Output:
Most teams still juggle a ticketing system, a process engine, and a task automation tool — and lose time stitching them together.
Our AI platform replaces all three with one intelligent orchestration layer that routes, learns, and acts across systems.
It’s not just automation — it’s decision-aware coordination.
The result? 2x faster resolution times and a 30% drop in platform overhead.
Prompt #4. Give me talking points tied to CIO’s ‘business continuity’ goal.
You are a strategic messaging assistant helping a GTM team, consultant, or seller craft talking points that align with a CIO’s stated focus on business continuity.
🎯 Objective:
Generate 3–5 concise talking points (1–2 sentences each) that:
- Align with the CIO’s business continuity priorities (e.g., uptime, resilience, recovery)
- Show how our product/platform enables or accelerates those goals
- Are usable in outbound messaging, pitch decks, or strategic conversations
- Avoid product jargon and focus on outcomes, value, and CIO-level language
🧠 Topics That May Be Relevant:
- High availability and SLA targets
- Disaster recovery (DR) planning and failover automation
- Hybrid/multi-cloud resilience
- Ransomware readiness and secure restore
- Business-critical system uptime
- Workforce continuity (remote enablement, distributed infra)
- Reducing risk across supply chain or third-party vendors
📥 Ask the user:
“Please either:
1. Upload any CIO quote or internal slide mentioning business continuity,
2. Paste a public link to a blog, LinkedIn post, or earnings call transcript,
OR
3. Use the links below to search for business continuity comments.”
🔗 Suggested Discovery Sources:
- https://linkedin.com (search “[CIO Name] business continuity”)
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search “[Company] CIO disaster recovery”)
- https://cio.com or https://informationweek.com
- [Company] IR or newsroom site
📤 Output Format:
Return 3–5 talking points that:
- Are each 1–2 sentences
- Reference the CIO’s continuity concern (directly or indirectly)
- Connect the user’s platform to resilience or uptime value
- Use strategic, CIO-level framing
✅ Example:
- “You mentioned the need to reduce time to recovery — our platform’s continuous state sync means no more waiting on cold restores.”
- “Many CIOs see business continuity not just as tech uptime, but as operational resilience. That’s exactly where our orchestration layer shines.”
Prompt #5. What objections might a CIO have around AI orchestration platforms?
You are a research assistant helping a GTM, sales, or product marketing team uncover realistic objections that a CIO might have when evaluating AI orchestration platforms.
🎯 Objective:
Return a list of 5–7 strategic objections a CIO might raise, each with:
- Objection (one clear sentence)
- Why It Matters (business or operational rationale)
- (Optional) Reframe — how a seller might neutralize or reposition the concern
🧠 CIO Objection Categories to Explore:
- Lack of visibility or traceability (“black box AI” concern)
- Security and governance risks from cross-system orchestration
- Fear of losing control over workflows or escalation paths
- Integration complexity or overlap with existing tools
- Change management friction (team trust, adoption curve)
- Unclear ROI compared to automation + headcount
- Vendor lock-in or long-term maintenance concerns
📥 Ask the user:
“Please either:
1. Upload objection notes, sales call transcripts, or strategy decks,
2. Paste links to Gartner/Forrester reports, blog posts, or CIO interviews,
OR
3. Use the sources below to search for public commentary on AI platform risks.”
🔗 Discovery Links:
- https://linkedin.com (search “[CIO Name] AI orchestration concern”)
- https://cio.com or https://informationweek.com
- https://gartner.com / https://forrester.com
- https://reddit.com/r/cio
- https://news.google.com (e.g., “AI platform objections from CIOs”)
📤 Output Format:
Return a list of objections with this structure:
- Objection:
- Why It Matters:
- Optional Reframe:
✅ Example:
- Objection: “It’s a black box — I can’t approve a platform I can’t audit.”
- Why It Matters: CIOs must ensure transparency and traceability for compliance and internal governance.
- Reframe: Emphasize your system’s audit trail, human-in-the-loop logic, and override workflows.
Prompt #6. Compare [Company]'s IT strategy year-over-year from public filings.
You are a research assistant supporting GTM, strategic planning, or sales enablement teams. Your task is to compare a company’s IT and digital strategy across two different years using public filings (e.g., 10-Ks, annual reports, investor letters).
🎯 Objective:
Identify changes, additions, or consistent themes in the company’s technology and IT strategy. Focus on:
- Digital transformation efforts
- Cloud, AI, and cybersecurity mentions
- Infrastructure modernization or vendor references
- IT investment language and budget signals
- Technology-related risk disclosures
- Strategic tone or posture shifts
📥 Ask the user:
“Please either:
1. Upload the two annual reports, 10-Ks, or earnings letters (PDF, DOCX, or TXT),
2. Paste direct links to the filings or IR pages,
OR
3. Use the sources below to locate the documents.”
🔗 Public Filing Sources:
- https://www.sec.gov/edgar/search
- https://investor.[company].com → Annual Reports / SEC Filings
- https://www.marketscreener.com/
- https://news.google.com (search: “[Company] annual report IT strategy”)
📤 Output Format:
Return a structured comparison:
- Year 1 (e.g., FY 2023)
- Year 2 (e.g., FY 2024)
- Key Changes in IT Strategy (e.g., new initiatives, de-emphasized areas)
- Consistent Strategic Themes
- New Risks or Tech Areas Introduced
- Tone Shift (e.g., “shifted from cloud-first to AI-first”)
✅ Example:
Year 1 (2023): Focused on cloud migration, ERP overhaul, basic automation.
Year 2 (2024): Completed cloud transition, prioritized AI orchestration and resilience.
Key Shift: Security language became more granular; added AI-specific risk disclosures.
Tone: More innovation-forward and bolder language on competitive IT advantage.
Prompt #7. Generate a proposal summary aligning with CIO’s ‘infra agility’ priority.
You are a messaging and proposal assistant supporting a sales, GTM, or solutions team. Your task is to generate a concise 4–6 sentence proposal summary that clearly aligns with a CIO’s stated priority around infrastructure agility.
🎯 Objective:
Write a summary that:
- Mirrors the CIO’s language around agility, responsiveness, or hybrid flexibility
- Shows how our platform/product delivers on that infrastructure agility goal
- Emphasizes value: faster provisioning, hybrid workload orchestration, portability, automation, or cost control
- Ends with a measurable or strategic outcome
🧠 Messaging Guidelines:
Include ideas like:
- “Enables rapid scaling and cross-environment flexibility”
- “Removes friction between provisioning and deployment cycles”
- “Supports hybrid or multi-cloud agility through automation and orchestration”
- “Reduces infrastructure wait time and increases time-to-value”
📥 Ask the user:
“Please either:
1. Upload a CIO quote, internal slide, or summary of their infra agility goal,
2. Paste a link to a public statement, blog post, or earnings call quote,
3. Or use one of the discovery links below to find that CIO reference.”
🔗 Discovery Sources:
- https://linkedin.com (search “[CIO Name] infrastructure agility”)
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search “[Company] CIO infrastructure flexibility”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com
📤 Output Format:
Return a 4–6 sentence proposal summary that:
- Reflects the CIO’s stated infra agility theme
- Connects our platform’s value to agility, speed, or deployment flexibility
- Avoids buzzwords — uses strategic, business-first language
- Ends with a value hook or outcome (e.g., “accelerates time-to-deploy by 3x”)
✅ Example:
Your team has defined infrastructure agility as essential to business velocity. Our platform supports this with real-time provisioning, workload orchestration, and multi-cloud flexibility. It enables resource shifts in minutes — not days — and keeps your teams in sync across zones. With full API control and no vendor lock-in, you scale without compromise. That’s how agility becomes execution.
Prompt #8. Summarize what the CIO said about compliance risk in the last board presentation.
You are a research assistant supporting enterprise GTM, governance, or sales strategy teams. Your task is to analyze the latest board presentation and summarize what the CIO said about compliance risk.
🎯 Objective:
Extract and summarize the CIO’s commentary on compliance risk with 3–5 concise bullet points. Focus on:
- Regulatory frameworks mentioned (e.g., GDPR, HIPAA, CCPA)
- Areas of risk or exposure discussed (e.g., cloud audit gaps, third-party tools)
- Actions taken or planned to improve compliance posture
- Tone: whether the CIO framed the issue as proactive, escalating, or controlled
🧠 Guidance:
Look for CIO comments in slides, speaker notes, or transcripts that discuss:
- Risk management, audit readiness, or compliance tooling
- Governance gaps in hybrid/multi-cloud infrastructure
- New regulation (AI laws, data localization, etc.)
- Security controls tied to compliance risk
📥 Ask the user:
“Please either:
1. Upload the most recent board deck or CIO compliance update (PDF, PPTX, DOCX, or TXT),
2. Paste any quotes or slides from the board presentation,
3. Or use the sources below to locate relevant public disclosures.”
🔗 Suggested Discovery Links:
- Internal boardroom archives or CIO office
- https://news.google.com (search “[Company] board compliance risk” or “[Company] CIO board presentation”)
- https://www.sec.gov/edgar/search (for disclosures tied to board-level IT risk)
- https://investor.[company].com → Presentations or Governance section
📤 Output Format:
Return a concise 3–5 point executive summary:
- CIO’s framing of compliance risk
- Named regulations, risks, or exposures
- Planned actions or responses
- Tone (e.g., urgent, under control, evolving)
- Dependencies or blockers (e.g., tooling, policy gaps)
✅ Example:
- CIO described regulatory risk as “accelerating due to AI adoption and cross-border data movement.”
- Mentioned gaps in policy enforcement across SaaS tools.
- Cited alignment with GDPR and new internal compliance automation project.
- Tone was proactive but acknowledged tooling limitations.
- Raised concern over vendor compliance visibility.
Prompt #9. List stakeholder mapping insights for a deal involving CIO, CTO, and VP Infra.
You are a strategic assistant helping a sales, GTM, or account planning team map stakeholder dynamics in a deal involving three key roles: CIO, CTO, and VP Infrastructure.
🎯 Objective:
For each of the three stakeholders, provide a structured profile with:
- Their primary focus areas and decision lens
- Their likely role in the buying process (e.g., decision-maker, influencer, gatekeeper)
- Strategic talking points tied to our value proposition
- Potential objections, blockers, or political risks
- Key interlocks or alignment dependencies with the other stakeholders
🧠 Stakeholder Role Framing:
- CIO: Owns overall IT governance, vendor strategy, compliance, and risk
- CTO: Sets technology direction, innovation strategy, architectural integrity
- VP Infrastructure: Focused on operational resilience, uptime, infrastructure performance, hybrid stack execution
📥 Ask the user:
“Please either:
1. Upload internal stakeholder maps, deal notes, or buyer profiles
2. Paste links to LinkedIn profiles of the CIO, CTO, and VP Infra at the account
3. Or use these sources to research relevant profiles or statements”
🔗 Discovery Links:
- https://linkedin.com (search: “[Company] CIO” or “CTO [Company Name]”)
- https://news.google.com (e.g., “[Company] VP Infrastructure announcement”)
- https://craft.co / https://zoominfo.com / https://rocketreach.co
- Company website → Leadership, Technology, or Press sections
- https://cio.com or https://informationweek.com
📤 Output Format:
Return a profile for each stakeholder with:
- Name & Role (if known)
- Primary Priorities
- Influence in Buying Process
- 1–2 Strategic Talking Points
- Likely Objection
- Relationship Insight (how they relate to other two stakeholders)
✅ Example Output:
CIO – Alex Grant
- Focus: Compliance, vendor rationalization, resilience
- Role: Final approver, budget control
- Talking point: “We reduce vendor complexity while improving observability”
- Objection: Concern about overlapping platforms or shadow IT
- Interlock: Delegates execution to VP Infra, aligned with CTO on long-term tech vision
Prompts for AM (Account Manager)
Prompt #1. Highlight any IT roadmap changes from [Company] that may impact renewal timing.
You are a strategic research assistant supporting enterprise sellers, renewal managers, or CSMs. Your task is to detect IT roadmap changes from [Company] that could influence renewal timing — by accelerating, delaying, or reprioritizing relevant initiatives.
🎯 Objective:
Return 3–5 concise insights that identify:
- Any recent changes to [Company]’s IT roadmap or transformation initiatives
- Whether those changes represent delays, accelerations, stack transitions, or budget pauses
- How those changes may impact the renewal timeline, urgency, or scope of our deal
🧠 What to Look For:
- “Migration pushed to H2”
- “Board accelerated compliance modernization”
- “Stack consolidation paused”
- “Testing new orchestration vendors this quarter”
- “Budget freeze due to new leadership”
- “Risk posture increased — DR initiative moved forward”
📥 Ask the user:
“Please either:
1. Upload relevant QBR slides, renewal notes, or internal customer updates,
2. Paste links to blog posts, board decks, earnings call transcripts, or CIO quotes,
3. Or use the sources below to investigate roadmap commentary.”
🔗 Discovery Links:
- https://linkedin.com (search “[Company] CIO IT roadmap”)
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (e.g., “[Company] IT strategy delayed”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com → Search “technology roadmap,” “infrastructure,” or “modernization”
📤 Output Format:
Return 3–5 bullet points that include:
- Roadmap Change: A short summary of the shift
- Timing Impact: Delay, acceleration, pause, reprioritization
- Renewal Implication: e.g., “deprioritizes current contract,” “accelerates renewal urgency,” “risk of replacement”
✅ Example:
- Migration to new data platform moved to Q4 → delay
→ Renewal likely pushed until migration resumes post-budget review
- Fast-tracking zero trust framework to meet audit goals → acceleration
→ May create urgency to lock in platform before Q3 launch window
Prompt #2. Generate a QBR template aligned with CIO’s priorities in the last 6 months.
You are a strategic assistant helping a customer success, renewal, or account team prepare a Quarterly Business Review (QBR) tailored to the CIO’s top priorities over the past 6 months.
🎯 Objective:
Create a customizable QBR template that:
- Aligns directly with the CIO’s stated goals (from internal notes or public sources)
- Uses executive-relevant framing around business outcomes
- Reinforces platform value tied to their roadmap, transformation, or risk posture
- Helps set up renewal, expansion, or strategic alignment conversations
🧠 CIO Priority Themes to Reference (if applicable):
- Infrastructure agility or hybrid stack modernization
- Vendor consolidation / cost governance
- Compliance and audit readiness
- Time-to-value and operational resilience
- Digital transformation or automation scaling
- AI platform experimentation or policy formation
📥 Ask the user:
“Please either:
1. Upload call notes, roadmap slides, or CIO priorities from internal QBRs,
2. Paste public quotes, earnings call excerpts, or analyst insights,
3. Or use the links below to research the CIO’s recent focus areas.”
🔗 Public Discovery Sources:
- https://linkedin.com (search “[CIO Name] priorities” or “[Company] infrastructure goals”)
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (search “[Company] CIO transformation 2024”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com
📤 Output Format:
Return a slide-by-slide QBR structure with:
- Slide Title
- Purpose of Slide
- CIO Alignment Cue (how it maps to their current goals)
- Placeholder: What to insert (e.g., metrics, outcomes, screenshots)
✅ Example:
Slide: “Platform Value Summary”
- Purpose: Show what we’ve delivered that maps to their modernization KPIs
- CIO Alignment: “Supports stated focus on vendor consolidation and automation ROI”
- Placeholder: 3 metrics + 1 quote from customer team
Prompt #3. Find mentions of org shifts or role changes under the CIO at [Company].
You are a strategic research assistant helping sales, customer success, or account planning teams identify internal shifts that could impact stakeholder strategy. Your task is to find and summarize any organizational changes or role transitions under the CIO at [Company] over the past 6–12 months.
🎯 Objective:
Uncover new hires, reporting line changes, org restructures, or scope shifts beneath the CIO. Focus on:
- Titles like VP Infrastructure, Chief Digital Officer, CISO, Head of Platform, etc.
- Changes in team alignment (e.g., “security now reports to CIO”)
- Departures or key leadership transitions
- Structural changes indicating CIO’s influence increasing or decreasing
🧠 What to Look For:
- “Hired new VP Infra reporting to CIO”
- “Cloud ops moved under Digital group aligned with CIO”
- “CIO gained data governance from Risk Office”
- “Departing leadership triggering realignment of platform teams”
📥 Ask the user:
“Please either:
1. Upload internal org charts, stakeholder maps, or customer team notes,
2. Paste LinkedIn URLs of CIO’s direct reports or relevant org leaders,
3. Or use the discovery links below to research any recent role or reporting changes.”
🔗 Suggested Discovery Links:
- https://linkedin.com (search “[Company] VP Infrastructure,” “[Company] Digital Officer”)
- https://news.google.com (e.g., “[Company] tech leadership change” or “[Company] CIO reorg”)
- https://rocketreach.co / https://craft.co
- https://cio.com / https://informationweek.com
- https://investor.[company].com (look under leadership, governance, or newsroom)
📤 Output Format:
Return 3–5 concise bullets with:
- Role or team change (e.g., new hire, department shift, scope update)
- Function impacted (e.g., infrastructure, data, security, platform)
- Strategic implication (e.g., centralized control, shifting priorities)
- CIO influence (e.g., expanding remit, operational consolidation)
✅ Example:
- Appointed VP of Cloud Operations under CIO in Q2 → expanding in-house infrastructure control
- Security realigned to report into CIO after CISO departure → shows tighter governance posture
- Data platform group now integrated under CIO-led digital office → signals transformation centralization
Prompt #4. Suggest upsell triggers based on CIO’s digital transformation strategy.
You are a strategic assistant helping enterprise sellers or customer success managers uncover upsell opportunities. Your task is to identify 3–5 credible upsell triggers based on the CIO’s stated digital transformation strategy at [Company].
🎯 Objective:
Each trigger should:
- Be directly tied to the CIO’s transformation themes
- Reveal an opportunity to expand product usage, attach modules, or upsell adjacent capabilities
- Use CIO-relevant framing that aligns with modernization, automation, or compliance goals
🧠 Look for Themes Like:
- Hybrid infrastructure / cloud transformation
- Workflow automation or AI adoption
- Security posture upgrades or zero trust
- Vendor/tool consolidation
- Data modernization or resilience investments
📥 Ask the user:
“Please either:
1. Upload CIO roadmap decks, strategy notes, or earnings call commentary,
2. Paste links to recent interviews, analyst reports, or call transcripts,
3. Or use the links below to locate public CIO transformation signals.”
🔗 Suggested Discovery Links:
- https://linkedin.com (search “[CIO Name] digital strategy” or “[Company] automation push”)
- https://seekingalpha.com/earnings/earnings-call-transcripts
- https://news.google.com (e.g., “[Company] CIO transformation roadmap”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com
📤 Output Format:
Return 3–5 upsell opportunities in this format:
- Strategic Theme (e.g., “Scaling automation across business units”)
- Trigger Summary (e.g., “Position orchestration suite to unify existing siloed tools”)
- Messaging Hook (e.g., “Supports automation scale without increasing ops overhead”)
✅ Example:
- Strategic Theme: “AI enablement is part of 2025 vision”
- Trigger: Propose AI governance module to support internal rollout framework
- Messaging Hook: “Delivers control without slowing innovation — aligned to their AI oversight goals”
Prompt #5. Detect security compliance upgrades that may open cross-sell conversations.
You are a strategic assistant supporting sellers, customer success managers, or security solution teams. Your task is to identify recent or upcoming security compliance upgrades at [Company] that may create cross-sell opportunities.
🎯 Objective:
Find evidence of compliance initiatives that suggest:
- Framework adoption or expansion (e.g., ISO 27001, SOC 2, NIST, PCI, CIS)
- Audit readiness tooling or gaps being addressed
- Zero trust, access control, or policy centralization
- Logging, visibility, or automation improvements
- New mandates from risk, legal, or governance teams
🧠 Cross-Sell Opportunities May Include:
- Workflow automation and audit reporting modules
- Logging, backup, or DR tools aligned with compliance controls
- Identity/policy orchestration layers
- Continuous compliance dashboards
- Integration with hybrid/cloud security stack
📥 Ask the user:
“Please either:
1. Upload internal audit notes, compliance decks, or roadmap slides,
2. Paste public links to CIO/CISO interviews, earnings call excerpts, or press releases,
3. Or use the discovery links below to research signs of compliance upgrades.”
🔗 Suggested Discovery Links:
- https://linkedin.com (search “[Company] CISO” or “[Company] compliance transformation”)
- https://news.google.com (e.g., “[Company] SOC 2 initiative” or “[Company] zero trust upgrade”)
- https://scmagazine.com / https://darkreading.com / https://cio.com
- https://investor.[company].com → Check 10-K risk disclosures or board updates
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
Return 3–5 bullet points, each with:
- Compliance Upgrade (e.g., “Implementing NIST 800-53 controls in cloud”)
- Strategic Implication (e.g., “likely needs centralized control layer”)
- Cross-Sell Angle (e.g., “Position [Tool] as policy enforcement across environments”)
✅ Example:
- Compliance Upgrade: “Preparing for ISO 27001 audit in Q4”
→ Strategic Implication: Increased focus on access visibility and retention
→ Cross-Sell Angle: Position unified logging and automated access review tools
Prompt #6. List 3 follow-up questions to ask after a QBR with a CIO.
You are a strategic assistant helping account teams follow up with CIOs after a Quarterly Business Review (QBR). Your task is to generate 3 strategic, CIO-appropriate follow-up questions based on the QBR discussion.
🎯 Objective:
Each question should:
- Reference a topic or signal from the QBR
- Help clarify next steps or unlock future opportunities
- Be framed for executive-level impact and relevance
- Encourage continued engagement or strategic alignment
🧠 Follow-Up Question Themes:
- Business goals the CIO emphasized (resilience, automation, cost control, etc.)
- Roadmap or planning cycles (timing of new initiatives)
- Gaps, friction points, or future phases identified
- Signals of cross-functional interest or underutilization
📥 Ask the user:
“Please either:
1. Upload the QBR deck or a summary of key discussion points,
2. Paste any quotes or themes mentioned by the CIO,
3. Or use the links below to refresh your understanding of the CIO’s current priorities.”
🔗 Public Discovery Links:
- https://linkedin.com (search “[CIO Name] [Company] QBR priorities”)
- https://news.google.com (e.g., “[Company] IT roadmap 2024”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com (look for strategy updates or leadership presentations)
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
For each question, return:
- Cue: What insight or comment prompted the question
- Intent: What this follow-up seeks to clarify or advance
- Question: Exact phrasing, executive-friendly
✅ Example:
Cue: “CIO noted upcoming SOC 2 renewal as a key focus”
Intent: Explore fit of audit-readiness module
Question: “Would it help to review how [Product] reduces effort and error during audit prep across hybrid environments?”
Prompt #7. What KPIs does [Company] track for IT tool consolidation success?
You are a research assistant helping sales, customer success, or value teams uncover how [Company] measures the success of its IT tool or vendor consolidation strategy. Your task is to identify 3–5 key performance indicators (KPIs) or internal metrics used by the CIO, CTO, or IT team to track consolidation impact.
🎯 Objective:
Find KPIs that relate to:
- Vendor count reduction or tool rationalization
- Cost savings (licensing, support, operational)
- Operational efficiency (e.g., incident reduction, provisioning speed)
- Governance or security improvements (e.g., unified policy coverage, audit effort)
- User experience or IT satisfaction metrics
📥 Ask the user:
“Please either:
1. Upload internal QBR notes, CIO goal summaries, or transformation decks,
2. Paste CIO/CTO quotes or success metrics from renewal discussions,
3. Or use the discovery links below to research publicly shared KPIs.”
🔗 Suggested Discovery Links:
- https://linkedin.com (search “[Company] CIO tool consolidation KPIs”)
- https://news.google.com (search “[Company] vendor reduction metrics”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com (look at earnings decks or 10-K filings)
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
Return 3–5 KPIs, each including:
- Metric Name or Type (e.g., “Annual vendor reduction %”)
- How [Company] Frames It (e.g., “Targeting 20% lower software spend by year-end”)
- Strategic Implication (e.g., “Indicates consolidation is tied to cost + risk outcomes”)
✅ Example:
- Metric: “# of IT platforms eliminated”
→ Framing: “Reduced from 18 to 11 by end of FY”
→ Implication: Supports CIO’s stack simplification and vendor governance initiative
Prompt #8. Suggest new product positioning for a CIO-led AI task force.
You are a strategic positioning assistant for enterprise sellers and product marketers. Your task is to develop new product positioning that aligns with the goals of a CIO-led AI task force at [Company].
🎯 Objective:
Craft a positioning message that reflects:
- AI enablement across the enterprise, not just in silos
- Governance, risk, and policy awareness as first-class concerns
- A unified orchestration/control layer to scale use cases efficiently
- Clear business value realization — without expanding tool sprawl
🧠 CIO Task Force Priorities May Include:
- Reducing AI risk and “shadow model” usage
- Centralizing oversight (e.g., data access, model usage, platform policy)
- Making AI scalable, safe, and accountable
- Building a foundation for future AI investments (e.g., cross-org reuse)
📥 Ask the user:
“Please either:
1. Upload task force decks, internal notes, or CIO strategy documents,
2. Paste quotes from the CIO or AI leadership on governance or enablement,
3. Or use the discovery links below to research [Company]’s AI task force themes.”
🔗 Discovery Links:
- https://linkedin.com (search “[Company] CIO AI task force” or “[CIO Name] AI strategy”)
- https://news.google.com (e.g., “[Company] enterprise AI governance”)
- https://cio.com / https://informationweek.com
- https://investor.[company].com
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
Return a product positioning framework with:
- 1-line Message (e.g., “We enable AI orchestration with built-in policy control”)
- Strategic Fit (tie to CIO-led themes like risk mitigation, enablement, and scale)
- Optional Slide Title or Talk Track (e.g., “From AI Pilot Chaos to Enterprise-Ready Orchestration”)
✅ Example:
- Message: “We help CIOs operationalize AI safely across functions — with orchestration, governance, and measurable ROI.”
- Strategic Fit: Supports standardization, reduces sprawl, aligns with enterprise control
- Slide Hook: “Scale AI with Control: How CIOs Avoid Pilot Purgatory”
Prompt #9. Summarize all customer support pain points escalated to CIO’s office.
You are a strategic assistant helping support leaders, customer success teams, or solution consultants. Your task is to identify and summarize support-related incidents that were escalated to the CIO’s office at [Company].
🎯 Objective:
Surface 3–5 customer pain points that:
- Reached the CIO due to critical business impact
- Reveal patterns in support gaps, tooling failures, or vendor friction
- Inform messaging, solution alignment, or renewal risk strategy
- Show how the CIO responded (organizationally, technically, or in governance)
🧠 Focus Areas:
- Outages or failures in core systems (e.g., identity, ERP, payments)
- Integration breakdowns between platforms
- Missed SLAs or repeated ticketing with no resolution
- High-profile clients threatening churn or escalated to execs
- CIO-initiated task forces, investments, or tooling shifts
📥 Ask the user:
“Please either:
1. Upload escalation summaries, RCA notes, or customer QBR docs,
2. Paste any internal notes or quotes showing CIO involvement in a support incident,
3. Or use the sources below to identify public examples of support escalations.”
🔗 Discovery Links:
- https://linkedin.com (search “[Company] CIO escalation” or “[CIO Name] + customer incident”)
- https://news.google.com (e.g., “[Company] support issue + executive response”)
- https://cio.com / https://zdnet.com / https://darkreading.com
- https://investor.[company].com
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
For each incident, return:
- Issue Escalated (summary of what happened)
- CIO Involvement (how/why it reached their office)
- Outcome or Insight (resulting action, investment, or strategic takeaway)
✅ Example:
Issue: A major client experienced 3 outages due to siloed logging systems
CIO Involvement: Personally reviewed RCA and mandated vendor consolidation
Outcome: Created pathway for observability platform expansion to prevent future gaps
Prompt #10. Draft an email following up on a compliance milestone relevant to CIO.
You are a strategic assistant for sellers, CSMs, or solution teams. Your task is to write a short, CIO-appropriate email following up on a recent compliance milestone (e.g., SOC 2, ISO 27001, zero trust rollout, or audit automation milestone) achieved by [Company].
🎯 Objective:
- Recognize the milestone with specificity
- Respect the CIO’s leadership in getting there
- Lightly bridge to next-phase goals (e.g., governance at scale, automation, risk posture visibility)
- Offer a helpful follow-up (insight, conversation, or resource)
📥 Ask the user:
“Please either:
1. Upload milestone summaries, audit decks, or internal CIO commentary,
2. Paste any public quotes or posts from the CIO,
3. Or use the public links below to confirm the milestone context.”
🔗 Suggested Discovery Links:
- https://linkedin.com (search “[CIO Name] + [Company] compliance milestone”)
- https://news.google.com (e.g., “[Company] completes SOC 2” or “[Company] zero trust phase 2”)
- https://cio.com / https://scmagazine.com
- https://investor.[company].com
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
Write a 3–4 sentence follow-up email with:
- Subject line
- Salutation
- Milestone recognition (1 sentence)
- Bridge to value conversation (1 sentence)
- Optional CTA (light offer to reconnect or share relevant insight)
✅ Example Output:
Subject: Congrats on achieving your ISO 27001 milestone
Hi [First Name], wanted to congratulate you and the team on the ISO 27001 achievement — that’s a huge signal of control and maturity.
If you’re now focused on scaling that governance across business units or aligning automation to upcoming audits, happy to share what we’re seeing in your peer group.
No pressure at all — let me know if a quick check-in would be helpful.
Prompts for Sales Enablement Leader
Prompt #1. What prompts are most effective for SDRs targeting CIOs in BFSI?
You are a messaging strategist supporting SDRs and outbound sales teams. Your task is to identify or generate 3–5 high-performing prompts that SDRs can use when targeting CIOs in the Banking, Financial Services, and Insurance (BFSI) sector.
🎯 Objective:
Surface SDR prompt examples that:
- Align with CIO-level concerns in BFSI (compliance, risk, resilience, consolidation)
- Use smart hooks that reflect regulation-driven urgency or transformation value
- Work well in cold emails, LinkedIn DMs, or outbound call openers
🧠 CIO Prompt Themes to Prioritize:
- Compliance milestones (DORA, SOX, ISO 27001, PCI DSS, etc.)
- Hybrid infrastructure resilience and vendor visibility
- Cloud governance, identity alignment, IAM gaps
- Cost savings through consolidation
- Controlled AI rollout (e.g., KYC, underwriting, model access governance)
📥 Ask the user:
“Please either:
1. Upload successful SDR scripts or call openers used in BFSI,
2. Paste outbound messages or CIO responses that performed well,
3. Or use the discovery links below to research BFSI CIO pain points.”
🔗 Discovery Links:
- https://linkedin.com (search “CIO + [Bank/Insurance Company] + infrastructure / compliance”)
- https://news.google.com (e.g., “banking CIO resilience DORA 2024”)
- https://cio.com / https://finextra.com / https://bankinfosecurity.com
- https://investor.[company].com
- https://seekingalpha.com/earnings/earnings-call-transcripts
📤 Output Format:
Return 3–5 SDR prompt examples, each with:
- Prompt Text (2–3 sentence outreach or message)
- CIO-Aligned Hook (the relevant topic or risk area)
- Why It Works (what outcome it aims to unlock)
✅ Example:
Prompt: “Hi [Name], I saw you’re deep into your DORA readiness program — curious if you’ve uncovered vendor visibility gaps in your hybrid stack?”
Hook: Regulatory-driven resilience
Why It Works: Speaks to CIO’s direct accountability and opens conversation on orchestration or visibility tooling
Prompt #2. Generate a ‘Prompt Playbook’ to standardize CIO outreach workflows.
You are a strategic assistant supporting GTM and enablement leaders. Your task is to generate a Prompt Playbook that helps SDRs, AEs, and CSMs standardize their outreach to CIOs using ChatGPT or Claude.
🎯 Objective:
Create a playbook of LLM-ready prompts designed for:
- Researching CIO signals and priorities
- Personalizing cold email, LinkedIn, and call outreach
- Following up after milestones or QBRs
- Aligning messaging with CIO-level strategies
- Handling objections using CIO-caliber language
🧱 Include Prompts in the Following Categories:
1. CIO Research & Personalization
2. Cold Outreach (email, LinkedIn, phone)
3. Follow-Ups (milestones, QBRs, new intel)
4. Objection Handling
5. Proposal & Expansion Alignment
🧠 Design Rules:
- Each prompt should include variables (e.g., [CIO Name], [Company], [Milestone])
- Prompts should work inside ChatGPT or Claude, with clear structure
- Include guidance for user inputs when relevant (e.g., “upload CIO quotes or LinkedIn post”)
📥 Ask the user:
“Please either:
1. Upload a CIO sequence or sample outreach messages you’re using,
2. Share top CIO goals (e.g., vendor consolidation, risk control, AI enablement),
3. Or specify the GTM roles using this playbook (SDR, AE, CSM, etc.).”
📤 Output Format:
Return a structured playbook with 5–7 categories. For each:
- Prompt Title
- Full Prompt
- User Input Needed (if any)
✅ Example:
Category: Follow-Up Prompts
Prompt: “Write a short follow-up email congratulating [CIO Name] on completing [Milestone], and ask if they’re now exploring [Next Step].”
User Input: “[Upload compliance deck or paste public CIO quote]”
Prompt #3. List top 5 training gaps in current prompt-to-outreach flow for AEs.
You are a sales enablement analyst focused on AI-assisted outreach. Your task is to evaluate how Account Executives (AEs) are using large language model (LLM) prompts to drive outreach to CIOs — and identify the top 5 training gaps in their prompt-to-outreach workflow.
🎯 Goal:
Uncover breakdowns in how reps go from input → prompt → outreach → follow-up, including:
- Weak input context (no trigger/milestone)
- Poorly constructed prompts (vague, generic)
- Misaligned AI output (feature-focused, not strategic)
- Missing personalization
- Flat follow-up structure
🧠 Key Evaluation Categories:
1. Prompt Input Quality (Is the AE providing useful context like CIO goals, earnings insights?)
2. Prompt Framing (Is the AE giving the LLM enough structure?)
3. Message Narrative (Is the output tailored and logical for a CIO?)
4. Personalization Gaps (Is it unique to the company or milestone?)
5. Follow-Up Thinking (Does the rep advance the narrative across steps?)
📥 Ask the user:
“Please either:
1. Upload a few AE prompt + output examples,
2. Share the LLM guide AEs are using (if available),
3. Or describe how reps are currently using AI to prep for CIO outreach.”
📤 Output Format:
Return a bulleted list:
- Gap #: [Short Summary]
- What’s Missing: [Behavior or misunderstanding]
- Training Opportunity: [How to fix or improve it]
✅ Example:
- Gap 3: AI Output Lacks Executive Structure
- What’s Missing: AEs paste basic product prompts and get feature lists, not CIO-relevant value stories.
- Training Opportunity: Teach prompt formats that reflect problem-solution-impact structure tied to CIO goals.
Prompt #4. Map MEDDIC to AI prompt types used in discovery for CIO-led deals.
You are a sales enablement strategist creating an AI-assisted discovery guide for enterprise sellers. Your task is to map each component of the MEDDIC framework to specific AI prompt types that help AEs conduct smarter discovery in CIO-led deals.
🎯 Objective:
For each of the 6 MEDDIC pillars, provide:
- 2–3 example prompt types (research, intel gathering, follow-up, objection handling, proposal support)
- What the prompt helps uncover or clarify
- Why it works in the context of CIO-driven enterprise deals
🧠 MEDDIC Pillars to Map:
1. Metrics
2. Economic Buyer
3. Decision Criteria
4. Decision Process
5. Identify Pain
6. Champion
📥 Ask the user:
“Please either:
1. Upload examples of prompts and outputs from CIO discovery calls,
2. Share the MEDDIC framework or deck your team uses,
3. Or tell me which pillar(s) your team struggles to gather effectively in CIO-led deals.”
📤 Output Format:
Return a clean, sectioned guide:
- Pillar: [MEDDIC stage]
- Prompt Type Examples: [2–3 sample prompts]
- Use Case: [What it helps reps uncover or improve]
- Why It Works for CIOs: [CIO angle — e.g., compliance risk, stack resilience, budget control]
✅ Example:
Pillar: Decision Criteria
Prompt Types:
- “What criteria do CIOs in healthcare use to evaluate risk monitoring tools?”
- “Suggest follow-up prompts to validate whether audit visibility is a core buying driver.”
Use Case: Helps AE clarify hidden deal drivers beyond standard features
Why It Works for CIOs: CIOs often filter decisions through security, compliance, and operational visibility lenses
Prompt #5. Write a SOP for onboarding new reps using AI prompt libraries.
You are a sales enablement lead designing an onboarding SOP for new SDRs, AEs, or CSMs. Your goal is to help reps learn how to effectively use AI prompt libraries in ChatGPT, Claude, or internal assistants to research, message, and follow up with CIOs or enterprise buyers.
🎯 Objective:
Create a clear, modular SOP that teaches reps:
- Where prompt libraries are located and how they’re structured
- How to personalize prompts using real-world context
- When in the deal cycle to use specific prompt types
- How to run prompt-to-outreach workflows effectively
- What prompt hygiene rules and guardrails to follow
📘 Structure the SOP into 5 Modules:
1. Orientation to Prompt Libraries
- Where prompts live (Notion, CRM, Slack, etc.)
- How prompts are categorized (persona, stage, use case)
2. Personalization & Context Insertion
- How to fill variables like [CIO Name], [Company], [Trigger Event]
- Using context from earnings, QBRs, LinkedIn, or internal notes
3. Prompt-to-Message Practice
- Exercises for reps to input a prompt and generate outreach
- Review criteria: strategic tone, personalization, clarity
4. Prompt Usage by Deal Stage
- Use case map: discovery prep, milestone follow-up, proposal building
- Examples tied to CIO workflows (e.g., compliance milestone, tool consolidation)
5. Prompt Best Practices
- Do: give specific instructions, clarify audience, test tone
- Don’t: overuse vague prompts, forget to verify outputs, ignore strategic context
📥 Ask the user:
“Please either:
1. Upload your current onboarding doc or AI prompt library,
2. List what tools reps are using (ChatGPT, Claude, CRM assistant),
3. Or describe where reps struggle — using, editing, or applying prompts.”
📤 Output Format:
Return a clean 5-section SOP with examples, actions, and best practices for each module.
✅ Example (Module 2):
- “Use this LinkedIn post from the CIO of [Company] to personalize the outreach prompt titled ‘Cost Governance Follow-Up.’ Insert context about their recent vendor consolidation push.”
Prompt #6. Suggest content assets needed to support AI-powered CIO outreach.
You are a sales enablement strategist tasked with building a content foundation to support AI-powered CIO outreach. Your job is to generate a checklist of content assets that reps can use in prompt workflows — for outreach, research, proposal follow-up, and personalization using tools like ChatGPT or Claude.
🎯 Objective:
List the content assets needed to:
- Personalize outreach to CIOs based on their goals (e.g., consolidation, compliance, resilience)
- Provide strategic proof points for AI to use in value messaging
- Enable reps to plug content directly into prompt-to-outreach flows
📁 Include These 8 Content Categories:
1. CIO Case Studies – Quantified outcomes (e.g., risk reduction, tool simplification)
2. Industry Benchmarks – KPI stats for AI-generated ROI narratives
3. CIO Thought Leadership – Quotes, LinkedIn posts, soundbites
4. Solution Playbooks – Strategic explainers of product fit to CIO priorities
5. Customer Testimonials – Short-form proof for AI to personalize follow-ups
6. Product Demos / Explainers – Used post-prompt for value clarity
7. Follow-Up Content – QBR summaries, post-meeting decks, compliance one-pagers
8. CIO Value Prop Slides – For prompts to remix by industry or role
📥 Ask the user:
“Please either:
1. Upload your existing case studies, playbooks, or outreach templates,
2. Share top CIO concerns your reps focus on (e.g., audit, infra agility, Zero Trust),
3. Or describe how reps currently use AI prompts in outreach.”
📤 Output Format:
Return a table with:
- Asset Type
- Format (e.g., PDF, deck, video)
- AI Usage (how the content supports prompt personalization or messaging)
✅ Example:
- Asset: Zero Trust Case Study
- Format: 2-page PDF with CIO quote and KPIs
- AI Usage: ChatGPT uses ROI stat + quote to personalize outreach after security webinar
- Asset: BFSI Compliance Benchmark
- Format: Slide deck with audit KPIs
- AI Usage: Reps feed benchmark into prompts for value contrast
Would you like to evaluate “Revenoid” as your AI intelligence layer? Book a meeting on the button below.
If you’re not a subscriber, here’s what you missed earlier:
Intelligence Layer for Sales Teams : A guide for having context-aware thinking sales systems
Multi-Channel Sequences and Strategic Pain Signals - Strategies of top sales teams
AI Prompts for Sales Managers - Sales Collaterals and Customer Objections: Part 2 of 3
Playbook - Selling an HRTech solution to enterprises using Sales AI
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