48 ChatGPT Prompts for Sales Outreach

Write a cold email to a [job title] at a [company type] for [product/service]. Open with a specific observation about their company, identify the pain point in one sentence, present value without jargon, and close with a low-friction CTA (not 'book a demo'). Under 100 words.

Tip: Cold emails under 100 words with a question CTA get 2-3x more replies.

Create a 4-email cold outreach sequence for [product/service] targeting [persona]. Email 1: initial outreach. Email 2 (day 3): different angle. Email 3 (day 7): value-add (case study/insight). Email 4 (day 14): breakup. Different subject lines, under 80 words each.

Tip: Most deals come from emails 2-4. The sequence matters more than any single message.

Write 5 cold email opening lines for [job title] about [pain point]. Reference something specific about their company, demonstrate research, and connect to the problem you solve. No generic openers.

Tip: The opening line is where 90% of cold emails fail. Reference something specific.

Create a cold email for a warm trigger: [visited pricing page / downloaded whitepaper / attended webinar / referral]. Reference the trigger event, connect to a relevant insight, and suggest a next step. Natural, not surveillance-like.

Tip: Warm triggers make cold emails feel timely. Reference the trigger in the first sentence.

Write 5 cold email subject lines for each approach: curiosity, value, question, social proof, and personalization. Product: [describe]. Target: [persona]. Under 40 characters. No clickbait or caps.

Tip: Subject lines under 40 characters have the highest open rates for cold email.

Create a multi-channel sequence combining email and LinkedIn. Day 1: connection request. Day 2: cold email. Day 5: LinkedIn comment. Day 7: follow-up email. Day 10: LinkedIn voice message. Day 14: final email. Full copy for each.

Tip: Multi-channel sequences get 2-3x the response rate of single-channel.

Write a cold email for re-engaging a prospect who went dark. They [describe what happened] [X weeks] ago. Reignite interest without being pushy. Offer new value or changed circumstance.

Tip: Re-engagement emails with new value work better than 'just checking in.'

Rewrite this cold email to be shorter, more personal, and compelling. Current: [paste]. Recipient is [job title] at [company type]. Make it feel like a helpful peer, not a salesperson. Cut anything that doesn't earn the right to ask for their time.

Tip: Read your cold email out loud. If it sounds like a press release, rewrite it.

Write 5 LinkedIn connection request messages for [job title] in [industry]. Under 300 characters, reference a specific reason for connecting, provide value or shared interest. No sales pitch.

Tip: Connection requests should never sell. Get accepted first, build rapport, then introduce what you do.

Create a LinkedIn DM sequence after acceptance. Message 1: thank and ask a genuine question. Message 2 (3 days): share something relevant. Message 3 (1 week): offer insight and mention how your company helps. No hard pitch until they show interest.

Tip: Treat LinkedIn DMs like a networking event: build rapport before you pitch.

Write 5 LinkedIn InMail messages for [job title] at [company type] about [product]. Personalized opener referencing their activity, concise value prop, low-pressure CTA. Under 200 words each.

Tip: InMails with questions in the subject line and under 200 words get more responses.

Create 5 LinkedIn comments for prospects' posts that add genuine value and subtly position expertise. 2-4 sentences, add new perspective or data, never mention your product.

Tip: Thoughtful comments on prospects' posts build recognition before outreach.

Write a LinkedIn voice message script (30 seconds) for following up with a prospect who accepted but hasn't responded. Conversational, reference their profile, suggest a brief call.

Tip: LinkedIn voice messages have dramatically higher response rates because they're personal and rare.

Create a LinkedIn post designed to attract inbound interest from [target persona]. Share a genuine insight about [problem you solve], tell a brief story or share data, provide actionable advice. Don't mention your product.

Tip: Inbound LinkedIn posts that teach attract more qualified leads than product pitches.

Write a framework for engaging with prospect content over 4 weeks before outreach. Week 1: like and comment on 2 posts. Week 2: share their post with commentary. Week 3: engage in a thread. Week 4: send DM referencing the engagement.

Tip: Four weeks of engagement makes your DM feel like the natural next step.

Create a LinkedIn recommendation for a prospect or customer to strengthen the relationship. Genuine, specific about their professional qualities. Plus a recommendation request message making it easy to say yes.

Tip: Writing unsolicited recommendations is an underrated relationship-building tactic.

Write 8 follow-up email variations: after sending proposal, after demo, after 'need to think about it', after no-show, after pricing objection, after 'check back next quarter', after champion leaves, and after competitor wins. Under 80 words each.

Tip: Each scenario requires a different emotional approach. Adapt tone to where the prospect is mentally.

Create a breakup email for a prospect who stopped responding after [X] touchpoints. Respectful, slightly humorous, clear about closing the loop, includes easy one-click re-engage option.

Tip: Breakup emails often have the highest reply rate because they trigger loss aversion.

Write a follow-up after a discovery call with [prospect]. Reference: key pain points discussed, solution proposed, and agreed next step. Brief summary, clear CTA for next meeting. Professional but warm.

Tip: Post-call follow-ups sent within 1 hour have significantly higher engagement.

Create 5 value-add follow-up emails sharing something useful instead of asking 'any update?' Each: relevant article/case study/insight, brief explanation of relevance, and soft CTA.

Tip: Every follow-up should provide value, not just request an update.

Write a follow-up for 'timing isn't right' / 'check back in Q[X].' Acknowledge their timeline, set a future touchpoint, provide value in the meantime. Calendar link for future date and a useful resource.

Tip: When prospects say 'not now,' respect their timeline but stay visible with periodic value.

Create a re-engagement sequence for a closed-lost deal from [X] months ago. Reason for loss: [reason]. 3 emails: 'what's changed' product update, relevant industry case study, and direct ask about evolved situation.

Tip: 30% of closed-lost deals reopen within 12 months with relevant value touches.

Write a follow-up after prospect attended our webinar about [topic]. Reference the event, highlight a key insight, connect to their business challenge, and suggest a conversation.

Tip: Event follow-ups within 24 hours referencing specific content get 3x more responses.

Create a champion enablement email for a contact who needs internal approval. Provide: one-pager summary to forward, talking points for internal objections, ROI template, and offer to join an internal presentation.

Tip: Make it easy for your champion to sell internally. Provide all materials in one email.

Write a discovery call script for a first meeting with a [job title] about [pain point]. Include: opening (agenda + time expectation), 10 open-ended questions from broad to specific, transition phrases, and closing with next steps. 30 minutes.

Tip: Great discovery calls follow 80/20: the prospect talks 80% of the time.

Create 15 discovery questions following SPIN: Situation (current state), Problem (pain), Implication (cost of the problem), and Need-payoff (envisioning the solution). For selling [product] to [persona].

Tip: SPIN leads the prospect to articulate why they need a solution.

Write a demo script for [product] to a [persona] who cares about [concerns]. Structure: brief agenda (30s), pain recap (1min), 3 features mapped to pain (15min), ROI discussion (5min), Q&A and next steps (5min).

Tip: Never demo features the prospect didn't ask about. Map every feature to their pain.

Create a mutual action plan email after a successful demo. Include: agreed timeline, decision makers and roles, evaluation criteria, next steps with owners and dates, potential blockers, and projected go-live date.

Tip: Mutual action plans increase close rates by creating shared accountability.

Write talk tracks for 5 common objections: 'too expensive', 'already using [competitor]', 'need other stakeholders', 'send me more info', and 'no budget right now.' Response framework and 2 example scripts each.

Tip: Best objection handling: acknowledge, clarify, reframe. Never argue with the objection.

Create a voicemail script for cold calling a [job title] about [product]. Under 30 seconds. Name, company, specific reason for calling, value teaser, and CTA to expect your email.

Tip: Voicemails should create enough curiosity to get them to open your follow-up email.

Write a negotiation prep document for a deal with [company] worth ~$[amount]. Cover: their priorities, our walk-away, 3 low-cost high-value concessions, responses to negotiation tactics, and ideal vs acceptable outcome.

Tip: Prepare 3 concessions that cost you little but the buyer values highly.

Create a post-close onboarding handoff email from sales to customer. Include: partnership celebration, CSM introduction, first 30 days overview, milestones and timeline, getting-started resources, and contact directory.

Tip: The handoff from sales to success is where many relationships falter. Make it seamless.

Write a proposal executive summary for [company] needing [solution]. Cover: business problem, cost of not solving it, proposed solution, expected outcomes with metrics, investment summary, and timeline. One page.

Tip: The executive summary should stand alone as a complete pitch.

Create a pricing justification comparing our $[amount] solution to their current $[amount] spend. Include: direct costs, hidden costs of current approach, ROI calculation, and payback period.

Tip: Frame pricing as investment vs return, not as a cost.

Write a case study for a proposal featuring a customer similar to the prospect: same industry, similar size, similar challenge. Structure: challenge, solution, results with metrics, and customer quote. Half a page.

Tip: Case studies with a similar customer are the most persuasive proposal element.

Draft a scope of work for a [service type] proposal. Define: objectives, deliverables, timeline with milestones, responsibilities (ours vs theirs), assumptions, and out-of-scope items.

Tip: Clearly defined out-of-scope items prevent the most common friction: scope creep.

Create 3 pricing tiers using the Goldilocks principle: basic (core problem), recommended (best value), premium (everything). For each: name, features, price, and who it's best for. Highlight recommended.

Tip: Three options with a highlighted recommendation converts better than a single price.

Write a proposal cover letter to [prospect name, title, company]. Reference conversations, demonstrate understanding, and explain what makes this proposal different. Under 250 words.

Tip: The cover letter should feel like a personal message from someone who deeply understands their problem.

Create an ROI calculator framework for [product]. Include: input variables (current costs, time, error rates), calculation formulas, output metrics (time saved, cost reduced, revenue gained), and visual presentation format.

Tip: An interactive ROI calculator where the prospect inputs their own numbers is more convincing than your projections.

Write a proposal follow-up strategy: 5 emails over 3 weeks. Day 1: confirm receipt. Day 4: additional case study. Day 8: proactive concern. Day 14: timeline check. Day 21: decision framework or comparison worksheet.

Tip: Proposal follow-ups should add new value each time.