Takeaways (With AI Prompts) from “Future of Prospecting” Webinar Series : Part 1 of 2
This edition unpacks high-impact strategies from champions like Ashley Zagst, Jason Bay, Saad Khan etc —covering AI-powered sales workflows, cold calling techniques, and LinkedIn prospecting playbooks
Last year, we hosted a high-impact webinar series on the “Future of Prospecting” featuring sales champions — Jason Bay, Ashley Zagst, Saad Khan etc.
Each session was crafted to help SDRs, AEs, and Sales Leaders leverage AI for prospecting outcomes that move the pipeline.
With over 4200+ sales professionals impacted, this newsletter covers the takeaways from these sessions.
We have also added ready-to-use prompts for each takeaway so that your team can implement it today.
In this newsletter, we are covering takeaways along with prompts for 3 of the webinars from our series.
We are gonna cover the takeaways from other webinars in the next newsletter.
Takeaways from Webinar #1 - AI-Powered Sales for hitting quota
For SDRs
Takeaway 1. Intent-Based Account Research
“Signals alone aren’t enough. You need to layer them to find timing + intent.”
Experts recommended:
Use job postings and funding news as opening signals.
Enrich with LinkedIn activity, hiring volume, or category-level growth.
Combine 3–4 signals to confidently identify buying windows.
Prompt:
"Act as a business intelligence and GTM strategy analyst focused on uncovering high-intent, high-fit companies for targeted outreach or partnership development.
Your task is to identify 10 recently funded companies that meet all the following criteria:
1. Hiring for [Persona] roles — e.g. 'Head of [Function]', 'VP of [Function]', or equivalent — as indicated by job listings, LinkedIn, or careers pages.
2. Expanding or actively operating in [Target Region], based on hiring activity, press releases, regional office launches, or leadership movements.
3. Recently funded — raised a Seed to Series C round within the past 6–9 months.
For each company, provide:
- Company Name
- Funding Round: Round, amount, and date (e.g., “Series B – $22M – Feb 2025”)
- Open [Persona] Role(s): Job title(s) and source link(s)
- Expansion Activity in [Target Region]: Evidence such as job locations, press, or exec posts
- Top Strategic Initiative: Inferred from public data (e.g. “Building enterprise GTM in EMEA”, “Launching AI infrastructure product”, “Scaling data pipeline for healthcare customers”)
- Source(s): List of URLs or citations (e.g., Crunchbase, TechCrunch, LinkedIn, company blog)
Format as a clean, scannable table or bullet list.
If common trends or strategic themes emerge across companies (e.g. “AI-led GTM expansion”, “Mid-market motion ramp-up”), summarize them at the end to inform positioning or narrative development."Takeaway 2. Mapping Triggers to Pains
“Most reps just reference the trigger. The best reps map it to a business pain.”
Example:
Trigger = “Hiring Sales Enablement”
Great reps = “You’re hiring enablement—are you trying to ramp reps faster due to missed Q targets?”
Prompt:
“Write a 2-sentence outreach hook that connects a recent trigger (e.g. [Trigger]) to a likely strategic goal or business pain (e.g. [Challenge or Priority]), and positions [Your Solution] as the timely, low-friction way to address it. Avoid buzzwords. Make it sound observant and relevant — not salesy. Hook should feel like a helpful insight from someone who ‘gets it.’”
Personalization Framework for Scaling This Hook:
Trigger → Use a sales intelligence tool or news monitor to spot:
New hires (esp. VPs or C-levels)
Fundraising announcements
Tech adoption (LinkedIn Tech Stack, BuiltWith)
Job postings (open roles = gaps)
Product launches or pricing page changes
Translate Trigger into Pain or Priority:
New VP = mandate to fix/improve/scale
Job role = internal bottleneck they’re trying to solve
Tech adoption = integration, ROI justification, or workflow change
Funding = urgency to show traction, operational scale
Launch = need for better GTM, onboarding, or support system
Plug into Hook Template:
Keep it human. Think “a smart friend DM’d this,” not “cold outreach.”
Example Using Placeholders:
“Saw you’re hiring a [Role] — usually means [Company] is either growing fast or trying to fix [problem]. We help teams at this exact stage with [Your Product] so they can [benefit] without [common pain].”Takeaway 3. Personalization That Drives Replies
“AI lets you personalize relevance, not just surface details.”
Instead of:
“Saw you raised funding. Congratulations!!”
Try:
“I saw you raised $12M and are hiring SDRs. Are you investing in scaling outbound? We help teams like X ramp 30% faster.”
Prompt:
You are a B2B SaaS founder and expert in sales messaging. Write 3 concise and personalized cold outreach messages for a [Job Title] in [Industry] who has recently shown activity on LinkedIn such as [LinkedIn Signal – e.g., hiring, posting about a trend, sharing company news, etc.]. The goal of the outreach is to [Goal – e.g., book a discovery call, explore a fit, pitch a solution].
Each message should:
- Reference the LinkedIn signal naturally in the opening
- Include a relevant and valuable insight or offer based on your product/service
- Use soft, non-pushy language for the CTA (15-min call, quick chat, etc.)
- Be short (50–90 words max) and conversational in tone
- Position the sender as a peer or problem-solver, not a salesperson
Include:
- 3 different message variations using different angles: one based on hiring, one on thought leadership or industry trend, and one on a company milestone or event
- Refined subject lines for each
Use placeholder tokens so the messages are easy to personalize later:
[First Name], [Role], [Company], [Industry], [Topic], [Product/Service], [Result], etc.Takeaway 4. Automating the SDR Workflow
“AI isn’t replacing reps. It’s removing grunt work.”
The new loop:
Prospect → Research → Signal → Prompt → Message
Experts shared how AI tools now help write the first draft of outreach, suggest who to reach out to, and even score ICP fit.
Prompt:
Act as a seasoned GTM operator and growth strategist. Create a 4-step outreach sequence targeting [GTM Leaders] (e.g., VP of Sales, CRO, Head of Growth) to inform them that [Company] is expanding its GTM team. The sequence will run across LinkedIn and email, with the goal of sparking high-signal conversations—not just transactional recruiting.
# Sequence Objective:
- Build brand awareness for [Company] as a high-performance GTM org
- Start meaningful conversations with top-tier GTM leaders about the expansion
- Attract interest from potential hires, collaborators, or connectors in the GTM space
- Signal thought leadership and forward momentum in the market
# Sequence Structure:
Step 1 – LinkedIn DM (Friendly & Insightful)
Personalized hook: reference a recent post, podcast, or shared interest
Brief mention of [Company]’s GTM expansion
Casual, peer-to-peer tone — “We’re building something cool, thought you’d appreciate it”
CTA: “Would love to swap thoughts on what makes world-class GTM teams tick.”
Step 2 – Email Follow-Up (Credible & Contextual)
Short re-intro + quick company snapshot (growth stage, traction, new markets)
Mention GTM team expansion, type of talent or mindset being sought
Signal culture: fast-moving, collaborative, results-driven
CTA: “Open to a quick chat this week? Happy to share more.”
Step 3 – LinkedIn Engagement or Post Mention (Soft Touch)
Comment insightfully on their recent post or tag them in a relevant GTM-focused post from [Company]
Goal: stay visible, build rapport, and show shared perspective
Step 4 – Final Email Nudge (Direct but Warm)
Reiterate why their background stood out (highlight a specific project, company, or GTM approach)
Reference previous messages lightly
CTA: “If this isn't a fit right now, no pressure — but would genuinely enjoy trading notes if you're up for it.”
# Messaging Principles:
Conversational over corporate
Show that this is about mutual signal and peer respect, not just pipeline or hiring quotas
Use GTM-native language: growth loops, segmentation strategy, PLG motions, RevOps alignment, etc., where appropriateFor AEs and AMs (Account Executives)
Takeaway 5. AI-Powered Call Intelligence
“I don’t want another transcript—I want what matters.”
Summarizes discovery calls.
Flags objections and emotional tone.
Logs follow-ups automatically and connects to CRM.
Prompt:
Summarize all recent updates, news, and CRM notes for [Company X] to prepare for a discovery call. Include strategic initiatives and suggested discovery questions.Takeaway 6. Strategic Initiative Discovery
“Executives don’t care about tools. They care about transformation.”
Top AEs use:
Company’s OKRs
Recent board-level statements
Strategic bets (e.g. market entry, cost reduction)
They frame conversations around these initiatives, and AI helps identify such initiatives from public/private data.
Prompt:
Help me uncover potential transformation goals for this company (cost-cutting, revenue growth, efficiency). Suggest 5 discovery questions to surface those goals.Takeaway 7. Proposal and Mutual Action Plan Automation
“Writing proposals that get buy-in takes hours. AI can cut that by 70%.”
AI co-pilots suggest proposal structure based on persona and industry.
Integrates objection counters and stakeholder priorities.
Takeaway 8. Multi-threading with Context
“Buying teams are bigger. AI helps map and message everyone differently.”
Co-pilot identifies influencers vs. blockers.
Drafts separate messages for each, aligned to their stake.
Additional Prompts for SDRs and AEs
#1 Deal Acceleration Prompt
“This account is stuck in stage [X]. Analyze internal notes + external signals. Recommend 3 moves to re-engage stakeholders and align to a strategic priority.”#2 Proposal Co-pilot Prompt
“Draft a proposal email for [persona], connecting our use case to their initiative of [expansion, compliance, efficiency, etc.]. Include 3 proof points and a suggested mutual action plan.#3. Multi-threading Prompt
“Create 3 custom messages for different personas at [Company X] (CFO, Director, End-user). Align each message with their likely concerns.”#4. Objection Handling Prompt
“This AE call had pricing concerns. Summarize the objections and suggest 3 trust-building follow-ups aligned to their goals.”#5. Playbook Generator Prompt
“Create a 5-step outbound playbook for [industry] targeting [persona] using insights from recent win stories and top-performing reps.”#6. Win-Loss Analysis Prompt
“Based on lost deals in [segment], identify patterns in objections and missing signals. Recommend 3 improvements to the sales motion.”#7. Cross-Channel Strategy Prompt
“Design a 7-day multichannel outreach strategy for [vertical] with 2 emails, 2 LinkedIn touches, and 1 Linkedin Comment per prospect.”Revenoid’s Unique Advantage
Advantage 1. Internal + External + Proprietary Data Visibility
“I want one place that tells me what’s going on—internal convos, Slack, CRM notes, external triggers, everything.”
Revenoid wins by:
Syncing all data touchpoints.
Giving unified insight across what reps know, what’s public, and what you’ve learned before.
Advantage 2. Beyond Triggers: Strategic Pain Mapping
“Don’t just say why now. Say why this matters in Q3 vs. Q4.”
Revenoid enables reps to:
Spot real business initiatives.
Tailor pitch based on C-suite concerns—not just a signal.
Takeaways - Cold calling tips by sales champions
Takeaway 1. “Start with the why before you dial.”
“Too many reps call without clarity. Before I call, I ask:
What change is happening at this company?
Why now?
Why me?
Signals like hiring, funding, or reorgs give me that entry point.”
Tactic:
Build an “intent layer” before outreach using job boards, hiring trends, growth initiatives, or new market entry.
Prompt:
“Create a multi-step cold outreach sequence (Email + LinkedIn + WhatsApp) for a [persona] at [company], considering they just [signal: e.g., hired a new VP Sales / raised funding / announced layoffs]. Tie the message to a likely strategic initiative.”Takeaway 2. “You’ve got 7 seconds to earn permission.”
“Cold calls are like walking into a CEO’s office uninvited. Be honest and low-pressure. I always lead with:
‘This is a cold call—can I take 27 seconds to explain why I called?’
90% say yes because I’m being upfront.”
Tactic:
Use a disarming opener to humanize the interaction and flip control to the buyer.
Prompt:
This company [trigger: e.g., opened 3 new job roles in RevOps]. What strategic initiative does this suggest? Recommend 3 ways to position our solution in outreach.Takeaway 3. “Talk about their boardroom, not your dashboard.”
“I don’t pitch features. I anchor to strategic priorities—like revenue growth, compliance, or cost reduction.
I’ll say: ‘Saw you're hiring enablement leaders. Are you ramping a new sales team?’ That ties to their internal shift.”
Tactic:
Use public signals + strategic pain templates. Go from “we help do X” to “you’re trying to achieve Y.”
Prompt:
Write a 30-second cold call intro for [persona] at [company] based on this insight: [insert insight]. Include a curiosity hook, a strategic pain reference, and a no-pressure CTATakeaway 4. “Objections = Curiosity Triggers”
“When someone says, ‘Not interested’—I don’t push. I lean in.
‘That makes sense. What would make this relevant next quarter?’
That opens the door to understanding their roadmap.”
Tactic:
Teach reps objection reframing. AI can analyze common objections and recommend curiosity-driven responses.
Prompt:
I received this objection on a call: ‘We already have a vendor for this.’ Craft 3 curiosity-driven responses that reframe the conversation and open up a strategic discussionTakeaway 5. “Cold calling is multi-threading in real-time.”
“If the person I’m calling isn’t the buyer, I use that moment to pivot:
‘Totally get it—would it help to include [Ops Head] who owns this problem?’
AI helps surface those contacts fast.”
Tactic:
Don’t let a “not me” end the call—pivot to related stakeholders. Use AI agents to fetch internal mapping instantly.
Prompt:
Based on [company]’s hiring and leadership structure, identify 3 personas likely involved in the buying decision for [solution]. Suggest personalized message angles for each.Takeaway 6. “Don’t end with ‘Does this time work?’”
“My close is never a time—it’s a reason.
‘Let’s see if what you’re doing on [X initiative] lines up with how we helped [Company Y].’
Now they’re not booking a call, they’re continuing a strategy convo.”
Tactic:
Reframe your CTA. Use AI to generate “next step” framing tied to peer proof and strategic value.
Takeaways from Webinar 2 - Learn linkedin outreach from Champions
Takeaway 1. Make Your Profile a Magnet Before You Message
“I treat my LinkedIn profile like my best-performing landing page. If someone clicks through after I comment or send a request, and they don’t immediately understand who I help and why I’m credible, I’ve lost them.”
Tactic:
Write a results-driven headline.
Add proof and credibility above the fold.
Use your banner space to show social proof.
Prompt:
Analyze this LinkedIn profile [insert link or summary]. Recommend changes to the headline, about section, and banner to attract [ICP: e.g., SaaS Founders looking to scale sales]Takeaway 2. Connection Request ≠ Cold Pitch
“Don’t be that person who pitches in the connection message. I delete those instantly. Instead, reference something relevant and just connect like a human.”
Tactic:
Mention something specific to the prospect’s role, company, or content.
Example:
“Saw you’re hiring SDRs at [company]. I love connecting with folks building GTM teams.”
Prompt:
Write 3 non-pitchy connection requests for [persona] who recently [signal: e.g., got promoted, joined a new company, posted about GTM]. Each should be under 30 words and signal relevanceTakeaway 3. Commenting Is Pre-Warming Your Lead
“If you're not commenting, you’re invisible. Cold DMs get cold responses. I comment for 2-3 days before I reach out—that way, they’ve seen my name, my value, my intent.”
Tactic:
Follow target buyers, engage with their posts intelligently.
Add a POV or question to their post instead of empty praise.
This builds name recognition and familiarity before the first DM.
Prompt:
Give me 5 high-signal comments to leave on posts made by [persona]. The goal is to build familiarity before outreach. Focus on adding POV or insight to their topic.Takeaway 4. First Message = Context + Curiosity
“Your first message should say why you’re relevant—not why they should care. That comes later. And end with a question that’s easy to reply to.”
Tactic:
Reference something recent they posted or announced.
Tie it to a potential strategic initiative.
Ask something specific:
“How are you thinking about scaling enablement with your current headcount?”
Prompt:
Draft a first LinkedIn message for [persona] at [company] who recently [trigger]. Tie it to a strategic initiative and end with a curiosity-building questionTakeaway 5. Follow-Up = Fresh Value, Not Reminder
“The worst follow-up is ‘bumping this up’. Instead, bring something new—a trend, a case study, a relevant shift in the market. Make every touch worth reading.”
Tactic:
Don’t repeat yourself. Advance the narrative.
Example follow-up:
“Noticed [competitor] rolled out [new strategy]. We’ve seen that open up [pain point]. Curious to know if that’s surfaced for you yet?”
Prompt:
“Write 2 follow-up messages for a prospect who didn’t reply to the first LinkedIn message. Each follow-up should include a new angle: use case, insight, industry trend, or competitor move.Takeaway 6. Your Content Is Your Best SDR
“Every post is a touchpoint. I’ve had prospects binge 5 of my posts, then reply to my DM with ‘Saw your piece on onboarding efficiency—let’s talk.”
Tactic:
Post 1–2x per week on topics your buyers care about.
Use frameworks:
Problem > Mistake > Story > Outcome
“One thing I keep hearing from [persona] is...”
Pin your best post so it’s visible to every profile viewer.
Conclusion
This is just the first half of what we uncovered. In Part 2, we’ll dive into advanced strategies from the remaining webinars — covering deal acceleration, 2X meeting booking frameworks, and AI-powered account insights.
Would you like to evaluate “Revenoid” for surfacing strategic pains, mapping them to your value prop, and executing complex, human-sounding playbooks across every channel? Book a meeting on the button below.
If you’re not a subscriber, here’s what you missed earlier:
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
Playbook for selling a "Cyber Security" solution to enterprises - Using AI Co-pilot
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