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AI campaigns undetected by spam filters

Jason Lemkin breaks down how Marc Benioff and SaaStr prove AI SDRs can work effectively when treated exactly like their human counterparts, and not just magic bots:

Salesforce’s 100M-lead challenge

➔ Salesforce had 100M untouched prospects for 26 years.

➔ Even 15,000 salespeople couldn’t handle doing everything.

➔ AI agents solved it by:

✔ Calling back uncontacted leads

✔ Running business conversations

✔ Identifying complex problems

Example: Instead of ignoring 4M leads/year, AI now begins re-engaging frozen prospects and passes hot opportunities directly to your Salesforce’s CRM processes

Omni-channel tracked supervisions

❖ Salesforce built orchestrations deciding when AI or humans lead.

❖ The system does:

➤ Automated outreach → AI sends first message or call invitations

➤ Conversation management → AI handles FAQs and basic objections

➤ Further escalation → Human SDRs are involved for custom solutions

Example: If a prospect asks about integrations with unusual ERP systems, AI flags potential complexity in the problem and looks for a human SDR rep immediately.

Economics behind scaling upgrade

📌 If only 1% of 100M leads convert, that equals millions in sales revenue.

📌 Redeploy SDR headcount to various higher-value positions.

Example: Support staff were moved to enterprise accounts while AI covered low-level lead follow-up.

SaaStr’s realistic-world tutorials

↳ SaaStr achieved #1 responses using customized AI messages in 2 weeks.

↳ How founders trained systems:

🔑 2 weeks of heavy onboarding (90 minutes mornings, 1 hour evenings)

🔑 Daily auditing practice routine for 60 continuous days (30–45 minutes)

🔑 Continuous process improvement based on feedback responses

↳ Example: A bad AI email said:

“Hey [First Name], I did some research on [Company] and thought you might be interested…”

↳ A good AI email said:

“Hi John, saw you attended SaaStr London last year - congrats on your move to Acme Corp! Given Acme’s push into AI security, you might be interested in our 2025 London VC track.”

Personalization workflow systems

❖ Generic mail-merge = ignored.

❖ Specific context = responses.

❖ Examples of what works:

➤ Reference previous event attendance

➤ Mention LinkedIn job position changes

➤ Link messages with company priorities

Human-in-the-loop orchestration

❌ Neither Salesforce nor SaaStr lets AI run unsupervised.

SaaStr’s system:

🎤 Humans answer when AI gets a reply

🎤 Daily audits catch weak responses

🎤 Onboarding teaches AI from mistakes

Salesforce’s system:

💬 Omni-channel supervisor routes conversations

💬 Keeps context across AI + human interactions

💬 Escalates when problem-solving gets required

Example: If AI schedules a call, human SDR’s must show up prepared with context from recent AI conversations.

Data structure as your foundation

❖ AI only works effectively with organized data.

❖ Salesforce: Harmonized everything in their Data Cloud.

❖ SaaStr: Pulled from 10 years of CRM + 20M words of content + event history.

Example: SaaStr found old opportunities that were never logged properly. AI could now surface these missed opportunities for re-engagement.

Segmentation for performance

⇒ AI SDRs work best with warm or semi-warm prospects.

High-performing segments:

📌 Past attendees

📌 Existing customers

📌 Website visitors

Low-performing segments:

⚠️ Cold outbound to generic lists

Example: SaaStr had success with reviving ex-customers, but unsatisfactory returns from blasting cold email list sequences.

Build customers into your sales process

Mark Hunter continues outlining behaviors defining what a true sales leader really is. Frame questions and benefits in ways that get your prospect to commit to next steps:

Challenge the status quo

🔑 Your competition isn’t another vendor - it’s no decision.

🔑 Too many sellers avoid asking difficult questions early on.

🔑 Leadership forces prospects out of their comfort zones.

Example: A rep might begin by saying:“If you continue with your current system, what does that cost you each month in wasted time?”

Reach for accountability

❖ Sales leaders own their customers’ success.

❖ Accountability builds trust and prevents fraud.

Example: If you sell equipment that promises efficiency gains, remain involved to ensure your customer actually reaches those gains.

Serve your constituents

✅ Serving comes before selling in everything.

✅ By helping customers, you build relationships.

✅ Transforms from getting money to connections.

Example: Offer valuable insights, learning resources, or personal introductions that help your customers - even if they don’t instantly buy.

The urgency controls for breakout growth

Scott Leese points out different characteristics in business startups that end up with successful finishes. Know what separates winners from the average seller population:

1. Move with ridiculous urgency

👉 Winning companies shrink the gap between idea and action to hours, not weeks.

Example: Scott provided candidate names in the evening. By midnight, the VP had already reached out and booked calls. That speed compounds progress day after day.

2. Seek feedback - apply learning

🎤 Struggling businesses debate advice or dismiss things as “not for us.”

🎤 Successful ones act on everything immediately:

✱ They instantly ask feedback on their systems

✱ They admit what they don’t really know YET

✱ They change feedback into action right away

Example: Instead of explaining why a business strategy isn’t working, top business founders test everthing first, adapt to consequences, and move forward.

3. Build process management layers

👉 Exits come from developing stages of leadership.

✔ Promote SDRs → AEs → Managers → VPs

✔ Invest in sales managers who’ll increase revenues

✔ Build talent instead of relying on constant hires

Example: The companies succeeding already have future VPs growing inside their org, ready to take ownership of bigger revenue targets.

TO-GO

Matt Green: Shorter cycles are killing your deal quality

Koen Stam: Required pillars of lasting market expansion

Todd Busler: AI unlocks hidden revenue in missing deals

Gabe Lullo: Pressure drives busywork, not selling growth